I’ve written about 250 book reviews on The Simple Dollar since I started the site in late 2006. Along the way, I’ve found a few books that I just immediately recommend for certain topics. My general personal finance recommendation is Joe Dominguez and Vicki Robin’s Your Money or Your Life. My regular debt management recommendation is Dave Ramsey’s The Total Money Makeover. For investing, I usually recommend Larimore, Lindauer, and LeBoeuf’s The Bogleheads’ Guide to Investing. Time management? I’ll point to David Allen’s Getting Things Done.

Throughout all of those books, though, I’ve never really found a single book I could recommend about entrepreneurship. There’s not been one book that really talks about the process of taking an idea you have in your head, investing your spare time and effort into it, and building it into something sustainable that can earn you significant money over time. The closest book I’ve found to that goal is Michael Masterson’s Ready, Fire, Aim, which does a very good job covering the topic, but feels incredibly rushed in places.

That’s why I felt pretty optimistic about reading Dave Ramsey’s latest, EntreLeadership. Ramsey is very good at hammering home the basic ideas you’ll need on a topic and pairing it with enough motivation to get you to go out there and try it yourself.

EntreLeadership Defined
In order to be successful, an entrepreneur has to be a leader. Even at the very start, when a business is nothing more than a side gig or the germ of an idea, it will never get started if you don’t step up to the plate and say that things need to happen. Even then, you’ll have to communicate with people and likely delegate some of the tasks that have to be done. Without some leadership skills, it will never happen. Entrepreneurship and leadership are intrinsically connected, and the principles of leadership help even the nascent entrepreneur.

Start with a Dream, End with a Goal
A lot of us have dreams of what we’d like to do with our lives. I’ve made no secret of my dream to be a writer. Others dream of other things. The difference between a dreamer and an entrepreneur is whether or not they can convert that dream into a goal, particularly a goal with a plan to get there. A dream is a fun indulgence, but it doesn’t come true if you don’t set it as your destination and focus on how exactly to achieve it.

Flavor Your Day with Steak Sauce
A big key of entrepreneurship is good time management. In order to have the time each day you’re going to need to make your business work, you’ve got to have a great grip on your time. Ramsey advocates using to-do lists, but also reflecting on Covey’s four quadrants (important and urgent, not important and urgent, important and not urgent, and not important and not urgent), where, obviously, important should always trump urgent.

“Spineless Leader” Is an Oxymoron
The best thing you can do as a leader is to make decisions quickly based on the information you have and be able to explain why you made those decisions. “Leaders” who don’t make decisions tend to lead organizations that fall apart. Leaders who make decisions without basing them on information tend to make horrible decisions. Leaders who make decisions based on information but can’t explain them tend to sow mistrust with their team.

No Magic, No Mystery
This chapter is most of the key ideas of a “business 101″ class wrapped up into a single chapter. Ramsey covers the life cycle of a product (introduction, growth, peak, decline) and how to start over again. There’s also a deep look at marketing a product, with basic ideas such as scarcity and appeal covered in the discussion. Almost any business you get into will involve some level of marketing, so it’s important to understand the basics of it.

Don’t Flop Whoppers
Here, Ramsey discusses the process of turning a detailed idea or a small side business into a larger entity. There are two keys to this, in Ramsey’s eyes: passion and calling. Passion is something that gets you excited to get out of bed in the morning. You can’t wait to get started on the activities at hand. Calling is what you want to achieve in your life. I’m passionate about writing, but my calling is using my words to change people’s lives.

Business Is Easy… Until People Get Involved
One of the biggest challenges in growing a business beyond a solo gig is the people. I can speak to this from experience: it was dealing with employees (interviewing, training, cleaning up their mistakes, etc.) that was the single worst experience of running The Simple Dollar, in my eyes. Ramsey offers a lot of good material that covers the entire life cycle of an employee, from the hiring process to maintaining good work to letting go of problematic employees.

Death of a Salesman
The best thing a good salesman can do is to focus on the customer and come up with solutions for that customer in mind. Sometimes, that means doing things that aren’t directly beneficial for your business, such as helping with things that are outside of your business or suggesting products and services that you don’t sell. If a customer walks away from you happy with the exchange and in a better place because of it, you’ve succeeded in your goal.

Financial Peace for Business
Businesses need to manage their finances well and, yes, be frugal. Owning a business isn’t a ticket to spending like a madman. Here, Dave takes the personal finance advice from Financial Peace Revisited and applies the advice to small business management. It actually works quite well, because the basic principles of personal finance – spend less than you earn, avoid debt, etc. – work very well for small businesses.

The Map to the Party
When a business grows into a multi-person outfit, the key to success is communication. The more people feel that they’re able to communicate and that their ideas are of value, the more they actually do communicate, the more involved they are, and the better decisions you can make for the business as a whole. Good communication feeds on itself, as does bad, so the best thing a leader can do is be candid and open.

People Matter Most
The people in your business matter more than anything else. If you can’t do right by them, you can’t do right by the rest of your business, and if you can’t do right by that, your business will eventually fall apart. Treat the people who work for you well. Respect what they need and work with it. Listen to what they’re telling you and don’t brush it off. The more you do that, the more they’ll respect you (if they’re good people that you want working for your business).

Caught in the Act
One key way to build your business is to make sure your business is recognized, particularly when you’re doing good things. Little steps, such as your email signature or your stationery, makes a difference. Mentions in the media also help. The more little pieces of positive recognition you have floating around out there, the more likely it is you’re going to draw in a random customer off the street.

Three Things Successful People Never Skip
Contracts, collections, and vendors. Dealing with each of these is the kind of detail work that can drive a person mad, but it’s the details of these things that can make or break a small business. Being detail-oriented in these areas almost always pays off.

Show Me the Money!
Be generous to the people that cause you to win. There are a lot of ways to do this – bonuses, higher salary, and so forth. Keep in mind, however, that the reason to do this is to reward the people that are showing good performance – and good performance is demonstrated in the form of happy customers.

Mastering “the Rope”
At some point, you eventually have to start delegating decisions to others as your business grows. The key to that is to make sure you’re surrounded by people you trust who you know will make decisions that are good for the business as a whole, people who share your perspective on how the business should be run. Your immediate team should consist of these people.

Is EntreLeadership Worth Reading?
This is the best single book on entrepreneurship that I’ve yet read.

Most of my problem with other entrepreneurship books is that they give short shrift to the early growth of a business, when it grows from an idea to a side business to perhaps a full time solo endeavor or one with one or two employees. They skip this part and move on to the point where a business has a handful of employees.

While that latter part is important to understand, so is the infancy of the business. It’s often that infancy that makes or breaks potential entrepreneurs, and Ramsey spends a good half of the book talking about issues at that level before moving on to growth issues.

Ramsey maintains the friendly tone that has worked well for him in personal finance books, and it works well here with entrepreneurship. There’s just the right level of detail in the information, mixed with great anecdotes.

If you’ve ever thought about launching your own business, this is a great book to start with.

Check out additional reviews and notes of EntreLeadership on Amazon.com.

Spend less than you earn.

Often, I’ll break this down into two methods you can use to earn more money. You can either increase your earnings (through a better job, better investments, and so on) or you can decrease your spending (through frugality).

The other day, I was having a discussion with an old friend who reads The Simple Dollar. He mentioned that I often repeated that statement and he suggested that I was actually just talking about two different kinds of success and that what differentiated the two types of success was how accessible the action was.

He said something that really left me thinking. “Anyone can get rich,” he said, “but the ability of a lot of people to multiply their earnings is extremely limited. Simply saying ‘earn more’ doesn’t mean a whole lot to an awful lot of people. What you’re telling many of your readers is just to ‘spend less.’ That’s a success, of course, but that’s not very clear from your statement.”

In other words, personal finance success boils down to two main avenues.

Success in the Margins
Simply put, finding financial success in the margins means that you’re finding financial success through ordinary actions. Frugality is, of course, one of these, as are most methods of passive investing (putting money in savings accounts, putting money into 401(k)s, and so on).

These methods bring one to riches, but they require a continuous input of small successes. However, these small successes are available to everyone and aren’t that hard to achieve by themselves. The biggest components needed here are willpower and a good work ethic.

Frugality, as mentioned above, is a key component of this. Seeking out ways to reduce your spending is vital in this process, as it is that reduction in spending that provides the extra money that you’ll use to build your wealth.

Steady income, ideally with a steady increase over time, is another essential part of success in the margins. You have to have enough income coming in that you can cover your bills with a bit left over. Ideally, frugality will serve mostly to increase the size of that “bit left over.” A typical career falls into this category and getting steady raises over a period of time certainly falls into this category.

A savings plan That “bit left over” needs to be saved for the future. You have to have the willpower to save it and the willpower to leave it alone once you do start saving it.

Patience is a necessary component. Because the components here are so straightforward and available to everyone, they don’t magically work overnight.

Anyone can follow this path to financial success. The reason many people decry it as impossible is that they don’t have the patience to plan for the long term and they don’t have the willpower to overcome short-term temptations.

Success in the Mainstream
On the other hand, finding financial success in the mainstream means that you’re finding financial success through extraordinary actions. Think of Bill Gates or Mark Zuckerberg when you think of these things.

Success in the mainstream means that you’re able to build wealth through enormous leaps in income. Through some mechanism or another, you’re able to earn a significant amount of money quickly. Often, some components of success in the margins (like living frugally and continuing to earn a steady income) are essential at the early stages of success in the mainstream.

There are several methods and components for mainstream financial success.

Entrepreneurship is certainly one path to this type of success. Controlling the entirety of a business so that the profits from that business flow to you is a path many people have followed to wealth, but the vast majority of businesses fail within the first few years of existence. It’s risky and it’s incredibly challenging.

Exceptional talent, usually built through a lot of uncompensated or lightly-compensated practice and sometimes mixed in with natural physical or mental gifts, can also earn a person exceptional wealth. Whenever you think of a top athlete in a mainstream professional sport, you’re usually looking at this category. They usually have some physical gifts that they’ve immaculately refined through a ton of work.

Blind luck also plays a role. People win lotteries (though this is a pretty poor strategy). People get windfalls and are included in estates. People find themselves in the right place at the right time. This is a completely unreliable path to financial success, almost completely devoid of planning or effort.

Anyone can try to follow this path to financial success. However, it is far from a guarantee, and the road is littered with people who fail along this path. It also often sacrifices success in the margin along the way.

What’s Your Success?
As mentioned above, anyone can find financial success in the margins. All it really takes is willpower and patience, traits that virtually everyone has or can cultivate within themselves.

At the same time, success in the mainstream is available for anyone to try, but is much more difficult to succeed in. Anyone can be an entrepreneur. It takes exceptional work, more than a bit of luck, and some skill to make it in an entrepreneurial path. Anyone can also be lucky, but there’s little you can do for that. Exceptional talent requires a lot of work to refine (work without compensation) and often also requires some physical gifts that not everyone has.

In other words, success in the mainstream is not a guarantee. However, many of the avenues in it provide a challenge and a pathway for those who wish to take it on.

Good luck, whichever route to success you choose to take.

One of the biggest reasons that people fail in their entrepreneurial ambitions is that they simply didn’t lay the groundwork for their business venture. They didn’t ask themselves hard questions about what they were ready for, what their best skills were, what skills needed boosting from others, and what they needed to actually accomplish to make things happen. Often, entrepreneurs believe that they’re Superman. They’re not.

The premise of The Entrepreneur Equation by Carol Roth, then, is to guide you through that very process. Instead of asking “Are you really ready for entrepreneurship?” as almost an affront to someone’s skill, Roth is asking it in the sense of saying “Have you laid the groundwork to maximize your skills, cover the things you’re not strong at, and maximize your chances to actually make this work?”

It’s a powerful question and one that potentially separates Roth’s book from many other entrepreneurial books out there.

The Issue – The Assumptions, Myths, and Realities of Entrepreneurship
Many people associate entrepreneurship with some sort of fulfillment of the American dream. Everyone’s supposed to be a big success in business, right? The truth is that most businesses fail and the only people that see entrepreneurial success are either extremely lucky or have been hardened by repeated failure. The most important thing for a first-time entrepreneur to know is that you have a huge chance of failure and the most valuable thing you’ll get out of it is what you learn from the failure.

(Now that’s a rah-rah way to open a book!)

Simply put, not everyone is meant to enter into that grindhouse. Some people function best in an environment where they’re given straightforward tasks. Other people simply can’t handle the stress involved. Still others have a skill set that’s best designed for technical and specialty work.

Assessing Your Fit with Entrepreneurship
Is entrepreneurship the right situation for you? The book is divided into two major sections (with two smaller ones bookending it), the first of which addresses whether or not you have the mindset that works for entrepreneurial endeavors – and if so, whether it works best in a partnership and so on.

Much of the writing here comes in the form of imploring you to evaluate yourself and offering up a lot of ideas on how to really figure out whether entrepreneurship is right for you. Mostly, Roth seems to be trying to persuade you that it’s not right for you, which, again, is an interesting tack to take. The big difference seems to be that a true entrepreneur is willing to take on these problems and flaws and seek ways to correct them, either through partnership or self-improvement.

Assessing the Business’s Fit with You
The flip side of that coin is the question of whether or not the business idea you have really fits with you. Much of this section really comes down to a complete re-write of your business plan, because that is what it amounts to. Roth pushes you to look for every possible flaw in your plan (particularly ones that match up with flaws in your entrepreneurial style), then seeks out ways to correct those flaws.

My feeling, after reading this section, is that it should lead to a serious re-write of almost any entrepreneur’s business plan, particularly that of a first-timer. If a business doesn’t fit with your skill set or your style, it’s not going to work and it has an extreme likelihood of failure, so the key is to take what you know of yourself and make sure that the business you want to start matches it.

Assembling Your Entrepreneur Equation
Roth’s term “entrepreneur equation” mostly refers to your entrepreneurial elements and the things you’re going to need (mentors, partners, etc.) to make this business idea succeed. Assembling those elements and getting them in place as early as possible will pave your road to the level of success that you want to achieve.

Is The Entrepreneur Equation Worth Reading?
If you’ve ever considered starting your own business in even a halfway serious manner, Roth’s book will be a worthwhile read for you. For most of it, it will make you feel as though you’re completely not ready for this leap, but at the same time, it’ll also point you in the direction of what you need to do to be ready for the leap.

If you read it and actually follow through with the ideas within, you’ll find yourself in a much better place to succeed with your entrepreneurial plans.

Because of that, I would almost always encourage people to read this as one of their very first reads on entrepreneurship. Rather than jumping into a “rah rah everyone can do this” book on entrepreneurship, this one gets you ready so that when you read the cheerleading-type books, you’ll know there’s actually something behind the cheerleading.

I loved this book because it felt genuinely challenging, as if Roth wasn’t there to just cheerlead you and tell you everything was going to be okay. We all need that dose of reality sometimes.

Check out additional reviews and notes of The Entrepreneur Equation on Amazon.com.

Tammy on Facebook wants to know about “How to know when your part-time small business can transition into your full-time income.”

This is an experience I went through in 2007 and 2008 and an experience I’ve discussed privately with several other small business owners. It’s a scary transition indeed.

For me, there were five real factors I looked at before deciding to make the transition.

First, could I do the work consistently over a long period of time? In other words, would I still want to be doing this in, say, five years? I asked myself this question in 2007 and it’s now 2011, so I think I got the answer here right.

This is basically a passion gut check. It takes… something to be able to write two personal finance articles a day every day for years. Whatever it is that you’re doing, can you see yourself doing it every single day for years? Is this something that excites you from the moment you wake up?

For me, I often start my days with such relish that I can’t wait to get started with the writing. I’ll write my posts (an average of about three per weekday all year long), plus other contracted writing, plus additional things I’m writing for my own enjoyment (like my sometimes-mentioned fantasy novel). I love to write.

Second, is there a way to consistently earn money from this work? As long as I can consistently write content of a reasonably high quality, I’ll be able to earn enough money to get by with my work. The Simple Dollar earns money from ad revenue, but I have several outstanding offers to write for other sources.

Unless the environment of writing online drastically changes, I should be able to earn at least a limited income from my writing online. This gives me a route to consistently earn money.

What’s your pathway to consistent income? Do you have an abundance of prospects for earning money, or are those prospects limited?

Third, are you able to market yourself effectively to find more work? Are you able to find new clients for your work? Are you able to reach an audience for your work? Are you able to grow both of these things?

This likely involves the use of things like social media, effective emailing strategies, and so on. Without clients, fans, or customers, you can’t make it. Without tools with which to contact them, you can’t build them up.

I had the advantage of already having a large audience for The Simple Dollar when I chose to play it full time, and the site itself incorporates a lot of tools for audience members to share the content, which further expands the audience. For many people, social media (like a Facebook fan page or a Twitter account) is the tool with which they reach and expand their audience of readers, followers, clients, and employers.

Fourth, do you have an extremely healthy emergency fund? Do not dive into a side business, freelancing, or any form of self-employment without some sort of significant financial safety net. If you can’t live for a few months without any income, you’re not ready to make that jump.

Going solo means that you don’t have the reliability of a regular paycheck to rest your head upon. Instead, you will be going through periods with a lot of income and other periods with little income. The only real way to survive that is to have cash on hand to supplement your income during the dry periods.

When I walked away from my previous job, we had enough cash in savings to survive for several months even if I didn’t earn a dime in income. I would not have walked away without that support in hand.

Finally, do you have a sensible grasp of your accounting needs? Paying taxes, continuing to save for future goals, and maintaining a working household budget are tricky things to juggle when you’re self-employed (welcome to quarterly taxes!). You’ve got to have a plan for keeping things in order or else you’re going to wind up not getting financially ahead or, even worse, finding Uncle Sam on your tail.

You’ll find a lot of solutions out there for this. For me, the best approach was to take every dollar I earned and split it in half. Half of it went into a “tax” account and the other half went into our normal household account. Each quarter, I would pay income taxes out of the “tax” account, and I’d make up any shortfalls at the end of the year out of that account. Anything left would be rolled back into our household money.

You may find a different solution that works well for you. However, if you don’t have a clear plan in place for all of this, you’re going to run into some serious problems down the road. This must be in place before your business is large enough for you to seriously consider making the leap.

Cover these bases thoroughly and you’ll be in a much better position to transition from side business to full time concern.

Julia on Facebook asks about “Good ways to make money on the side or as a stay at home mom.”

There is essentially infinite ways to make money on the side. The only way to really narrow down that list is to start putting some restrictions on it, which Julia does very quickly with the second part of her question. So, for starters, let’s look at the requirements of a stay-at-home parent.

SAHM Requirements
Here are some of the requirements that tighten down the options for a typical stay-at-home parent to earn money on the side.

Flexible time This is the biggest reason why people choose to become stay-at-home parents: the time flexibility. They want to be there for their children during the day and engaged with them. However, there are naptimes and there are times after spouses come home from their jobs where they can engage in “me” time or in employment time.

Limited space Typically, stay-at-home parents have at least some tightness on the space available in their home environment and usually can’t afford storefront space or even significant storage space.

Limited startup budget Most stay-at-home parents face limited cash resources that they can invest in getting a side business going. After all, stay-at-home parenting inherently means a single-income family.

Income Options Meeting Those Requirements
Even with these restrictions, there are still a multitude of options for stay-at-home parents who wish to earn a side income. Here are some of the more popular options that I’ve actually seen stay-at-home parents have success with.

Blogging and/or freelance writing There’s a reason that you can easily find an army of “mommy blogs” out there. Blogging about parenting concerns is a perfect business for a stay-at-home parent which works particularly well because you can directly involve the children in the typical article creation process. To do this successfully requires a bit of a business approach, however, and will definitely take some startup time. Another approach that can scratch the same itch and provide more immediate (but less long-lasting) income is simply engaging in freelance writing. One good place to start is freelancewritinggigs.com.

Child care Multiple stay-at-home parents I know engage in some degree of child care. They take in the children of a neighbor or friend for some fee during the day. In other situations, a small group of stay-at-home parents will rotate their children among different households during the week, giving the stay-at-home parents a free day or two a week to have a limited part time job.

Home economizing I know several stay-at-home parents that focus their energies on home economizing, which minimizes every dime of income actually spent. They’ll maintain a garden, engage in projects like air-sealing their home, prepare and freeze meals in advance, carefully plan their grocery shopping trips, and search for great free activities for their families to enjoy. They’ll research all product purchases to find the best bang for the buck and put effort into making handmade gifts as well. These actions can shave a tremendous amount from the monthly spending for a family.

Social media representative Two different stay-at-home parents I know work as social media representatives for local businesses. They’ll set up Twitter and Facebook accounts for these businesses and maintain them for a small fee, making the customer interaction as easy as possible for the harried small business owner. In exchange, they’re often paid a small fee or sometimes paid in discounts or coupons for the business.

Freelancing Two other stay-at-home parents I know engage in part-time freelance work in their previous career path (one in graphic design and one in computer programming). Most of these gigs are standalone projects that they’ve found by developing their own online resume of their work and seeking out opportunities on their own using the contacts from their previous career and within their community.

A few things to avoid If you see a system advertised that will help you make great money from your kitchen table, avoid it. Often, it simply places you in the middle of a multi-level marketing scheme that’s difficult for a person without extensive networking skills to make a lot of money at. Alternatively, the plan requires a ton of time investment to earn significant money, time that is better invested elsewhere. If someone is going to set you up with a moneymaking opportunity, they’re the ones that are going to make the money here, not you.

On Facebook, Patsy asked about “Spouses with disabilities… how can you help your spouse by earning extra income? Also, when you have funds for bills only, should you invest in starting a home business by not paying on a bill that month?”

Patsy is asking a number of interrelated questions here. However, the situation she describes is not an uncommon one. Many households involve one disabled spouse while the other spouse works outside the home. Their finances are often challenging, and the disabled spouse often has a big desire to do something to contribute to the income level of the household.

This brings us to the first question implied here.

How can a disabled person earn extra income?
There are several key factors to consider when thinking about this question.

First, is the disabled person able to earn an income? Some disabilities enable a wide variety of activities, while other activities may be completely out of the realm of the disabled person. A realistic assessment of what work can be done is a vital first step.

Second, how much additional income can be earned? Many disabled households have deep restrictions on additional income lest their disability benefits be cut. Before you start engaging in an income-earning activity, know exactly what your limits are on additional earning.

Often, disabled individuals have a hard time finding suitable employment because of their disability, but that doesn’t necessarily mean that they can’t produce useful work. A great option for individuals in this situation is piecework at home, where they can produce up to their physical or income limits with great control.

One option for this is Amazon’s Mechanical Turk. This is piecework broken down to a very simple level, with quick tasks to perform, but you don’t tend to earn a strong hourly rate (you’ll earn less than minimum wage). However, you can do it whenever you want at whatever rate you’re comfortable with.

Another option, particularly if you have writing skills, is freelance writing jobs. Usually, you’ll be asked to write an article (or a number of articles) for a website and are paid a small amount per article. Many such services exist, including freelancewritinggigs.com. Again, you won’t earn a mint from this, but it has incredible flexibility with time and energy restraints, which are often chief concerns with disabled individuals. If you are successful with this, you may eventually reach a point where you will want to launch your own website.

Of course, some of these options inherently have startup costs. For starters, many of these options require a home computer and internet access. For many households with a disabled person, finances are tight. How can you make that transition? That really hits on the second part of Patsy’s question.

Should you skip bills to fund a microbusiness?
No. Do not skip bills in order to fund a microbusiness. If you do this, you are putting yourself and the rest of your family in a very precarious financial position because, if you’re in this situation, you don’t have enough resources to keep the bills paid.

You shouldn’t start a microbusiness on credit, either. Don’t use a credit card to buy a newer computer because you dream of using it to make money. Again, you’re putting yourself in a more precarious financial position than you were before because of the dream of making money, not the reality of it.

The solution, as always, is frugality. Shave your spending in every way you can. If you need money for a basic piece of equipment to make this happen, start by cutting back spending every chance you can. Each time you do that, put away some of what you saved for that purchase. Even if it just means putting a dollar in a jar, that’s still a positive move.

Also, don’t invest in high-end equipment unless you’re upgrading low-end equipment that you’ve used to death. For starters, never overinvest in starting a business in an area where you don’t have a proven track record. If you’re trying to start an online business, don’t buy a top-end piece of equipment. Buy a low-end piece of equipment, as it can do most of the things you’ll need to do. Always minimize your startup expenses in every way you can.

Similarly, this is a perfect situation to ask for help with. If your financial reality is this tight, consider asking your church for help or look for help with other community groups. Many people would be happy to donate older equipment to you for just this type of use.

Very rarely will you improve your situation by buying something, particularly when you can’t really afford it. If you’re in a state where you’re deciding between a purchase and paying your monthly bills, you can’t really afford it.

In other words, I had about two weeks of vacation coming to me. I wasn’t really sure what to do with that time, though. I didn’t have children. My wife didn’t have any vacation time coming. So I asked him what I should do with the time. He looked at me thoughtfully and simply said, “Why don’t you just take a sabbatical?”

A sabbatical means a period in which you choose not to work in order to achieve something else that will improve your life. If you take a week off of work in order to re-pave your driveway, that’s a sabbatical. If you take two weeks off in order to take a class, that’s a sabbatical.

So what did I do during that week? I drafted a novel. It was the second novel-length work of fiction that I’ve completed in my life (and, like the first one, I now think it’s pretty awful). It was also a great learning experience for me. It taught me how to organize the threads of a complex story. It showed me that I had the capacity to write such a lengthy thing. It gave me the experience that I can build on with better stories later on.

Since that first experience in 2004, I’ve tried to take a sabbatical once a year or so. I’ll take a week off of work in order to work on some project or increase some personal skill of mine. One year, I used the sabbatical to take a Photoshop course. Another year, I spent the sabbatical working on my finances and, eventually, laying the foundations for The Simple Dollar. I plan to use a sabbatical in the fall of this year to “woodshed” on the piano, focusing squarely on mastering a couple of piano pieces.

What can you do on your sabbatical? Complete a personal project that needs a lot of focused time. Teach yourself a new skill that you know will be valuable in the future. Take a compressed course to pick up a skill.

The specifics depend entirely on you and what things you wish to accomplish and learn in your own life. Building a skill that you can use professionally is almost always a strong idea, as is a class that leads directly to a professionally useful skill. Completing a large personal project is also quite valuable, as is setting up the infrastructure for a side business or a larger personal project.

I could write a very long list of such ideas. Learn how to use a particular computer program like Photoshop. Learn a computer programming language like Scheme. Start an online business. Write a novel. Clean out every closet and nook and cranny in your home. Re-shingle your roof. Give a number of speeches and presentations to improve your public speaking skills. Take a compressed course on a topic valuable to your career at the local college. The list goes on and on.

The key is to make sure that you’re either doing something to improve your skill set or doing something that improves the value of the things in your life, particularly something that you can’t quite accomplish while working.

Why not just take a vacation? For starters, sabbaticals are easier to propose to supervisors. My experience – and the shared experience of others – is that it’s much easier to sell a supervisor on using vacation time for a skill-building exercise than it is for an actual vacation. Why? When you take normal vacation time, you’re not really increasing your value to the company during that time spent. If you’re building skills during that time, then you typically do increase your value. Even if you don’t build a skill that’s of value to the workplace, knowing that you’re local in case of an emergency can again make vacation time easier to sell to a tough supervisor.

For another, after a sabbatical, you have a genuine accomplishment. You learned a new skill or you took care of something significant that needed finishing. That sense of accomplishment is incredibly valuable, as it fills you with confidence as well as the rewards of whatever it is that you’ve accomplished.

After a sabbatical, you’re in a better place. That in itself is a tremendous reward and a strong source of good feeling which you can use to fuel your return to work. Good luck.

For example, I notice that, often, personal finance bloggers are either wholeheartedly about frugality or they’re all about entrepreneurship and earning more money. They’ll write only about their ideas and sometimes even take swipes at other perspectives (I often see entrepreneurship blogs making fun of frugality).

Frankly, I find this completely silly.

There are times when frugality is the best option. There are times when focusing on increasing earnings is the best option. Most of the time, there’s no reason not to try and do both.

For example, the effects of frugality are more immediate than the effects of building your income. When you make a choice to not buy something or to find a less expensive way of doing something, you start reaping the rewards from that choice immediately. That money goes from being spent to residing in your pocket right now. Thus, if you need immediate relief, frugality is the superior tactic.

On the other hand, frugality has a limit. There’s only so much you can cut before you start having to make seriously life-altering choices.

At the same time, the ability to earn more is limitless. There are always potential avenues to earn more money. You can get a second job, start a business, ask for a raise, and so on and so forth. Unlike frugality, there is no cap. You can always earn more. You can’t always cut more.

However, the value of your actions isn’t always clear when you’re trying to earn more money. Yes, it’s clear how much more you’re going to earn if you take a second job, but what about a decision to start a business? What about raising your skill set? It’s essentially impossible to interpret what those actions will earn for you. They might earn nothing. They might earn a lot. With frugality, you can almost always calculate how much you’ll save.

I tend to think that the biggest differences between frugality and increasing earnings come with your perspective and focus on life.

In my eyes, frugality shines best in the short term. If you’re in a financial panic after, say, a major car repair, frugality will help you. If you’re saving for a goal that’s a year or two down the road, frugality will make that goal possible.

Similarly, frugality is superior when you need precise numbers. For example, if you’re trying to figure out how to come up with a car payment, building your skill set for a better job is irrelevant. On the other hand, eating every meal at home can quickly provide the money you need for that car payment.

On the other hand, increasing earnings shines over the long term. Building your skill set doesn’t pay off today or tomorrow. Neither does networking, nor does starting your own business. These types of things need consistent effort and time to grow into earnings in your pocket, but the rewards they reap often greatly exceed those earned by frugality.

Increasing earnings is all about growth. Growth is often unpredictable, but the rewards of growth are tremendous, pushing you upwards to new heights.

What’s better? My take is that tactics from each side are useful in a successful life. Poor spending choices, for example, make it harder for you to make challenging decisions that can increase your earnings. It’s very hard to make an entrepreneurial leap, after all, if you’re not frugal.

The destination of financial independence is the same no matter which path you take.

Fried’s “six easy steps” are as follows:

1. Understanding the buyer is the key to being a strong seller
2. It’s all about passion
3. Charge real money for real products
4. There are different pathways to the same dollar
5. Bootstrapping
6. Practice

This actually turned out to be one of the few articles from the ‘net that I actually print out, because I wanted to jot down some of my own notes on the margins. I realized, after I was finished, that these notes actually made for the backbone of a pretty compelling article in its own right.

So, without further ado, here’s my own “five easy steps for making money.”

1. Practice
This underlines everything that a person can do to make money. The greater your skill, the more money you’ll make by plying that skill. How do you improve your skills? Practice, preferably in a deliberate fashion. Break down what you’re doing into little pieces, and practice those pieces.

For me, that often means doing writing drills. Yep, I do writing drills pretty often. I’ll do little drills like “write a complete story in fifty words or less” or “compress this document as much as possible without losing any meaning” all the time, just for the sake of practice. It’s a skill builder.

I usually don’t find actual writing tasks to be that strong in terms of practicing. Many people assume that if they do the task professionally, they must be good at it. That’s akin to a professional basketball player believing they’ll stay on top if all they do is play games of basketball. The truth is that the best basketball players are constantly doing drills and never leave the gym.

So how do you practice things like selling? The article offers a good suggestion:

Go buy something on Craigslist or eBay. Find something that’s a bit of a commodity, so you know there’s always plenty of supply and demand. An iPod is a good test. Buy it, and then immediately resell it. Then buy it again. Each time, try selling it for more than you paid for it. See how far you can push it. See how much profit you can make off 10 transactions.

Start tweaking the headline. Then start fiddling with the product description. Vary the photographs. Take some pictures of the thing for sale; use other photos with other items, or people, in them. Shoot really high-quality shots, and also post crappy ones from your cell-phone camera. Try every variation you can think of.

I think it’s useful for almost everyone to practice transferable skills – like selling. Written communication is one type of transferable skill, as is public speaking.

If you want to be great, practice.

2. Care
What do I mean by care? You have to want to do the things you’re doing – and want to do them well. If you don’t care about it, you won’t be able to go the extra mile to stand out from the crowd.

This goes hand-in-hand with practice, of course. If you don’t care about the field you’re in, you’re not going to practice and you’re not going to rise to the top. Caring about your performance and what you’re doing is what will bring you to the top, and practice is a key component of that.

Quite often, this is intermingled with the idea of passion. In the end, they both point to the same thing. If you don’t have an emotional involvement and a drive to always move forward in this field, you’re not going to succeed.

3. Know what people want (or need)
You might think that the particular skill you have or the particular item you want to sell is a great thing. The question really is whether or not anyone else thinks that item or skill is a great thing (and thus worth paying for).

Something is only worth what someone else is willing to pay for it with their time, money, or effort. In my case, what I sell is generally paid for with the reader’s time (through ad space sold to banks and financial institutions on my website), though I do sell other items as well (such as my books).

How does it “sell”? People find value in reading what I write, whether it’s because they find it useful for their own personal growth or because they find it entertaining. There’s enough value there that people are willing to pay for it with their time (and occasionally their money).

People want to have a sense of control over their lives. My site attempts to fulfill that want, at least in part.

4. Make something distinctive that people will want (or need)
In order for that “sale” to continue, I have to continue writing worthwhile stuff that’s useful enough or entertaining enough for it to stand out from the crowd of sites that talk about personal finance and other topics. How do I do that? I talk about my own story in depth. I post very regularly so that there’s always fresh content to read. I use conversational language in my writing rather than the drier tones often found in financial writing.

It is those factors that make up the “special sauce” – the distinctive element – of The Simple Dollar. If I didn’t do those things, my site would be one of many personal finance blogs looking for an audience. It’s the distinctive things that makes The Simple Dollar stand out a bit, and I keep them in mind with everything that I do.

What do you have that’s distinctive? Don’t just look at your advantages – quite often, your disadvantages make you distinctive. I’ve seen the work of a blind painter. It’s stunning, but part of that overall picture comes from the disadvantage of the artist. Because he has overcome that disadvantage, it contributes something more to the finished product.

5. Create multiple revenue streams
Regardless of what you’re doing in life, there’s a big benefit to creating multiple income streams. Many people make their life more difficult by focusing only on one income stream – their primary job – and avoid creating more. Then, when that primary stream falls apart through a job loss, they’re in dire straits.

The solution is to find ways to create more than one revenue stream in your life. This requires some sort of investment on your part – money, time, energy, ideas, or some combination of them. The proceeds come in a fairly regular income. Sometimes, this income can be active (like a side business), which requires continuous work for more proceeds. At other times, it’s passive (like an investment), which does not require additional work.

This is going to be a significant theme of The Simple Dollar moving forward. As I write this, I’m working on developing a few additional income streams for the future, and I plan on writing about them once they’re in place.

Here’s the flat-out truth about running a small business: you, the business owner, are where the buck stops. Period. Small businesses are a great way to start earning more money, but they’re not easy.

When something goes wrong, it’s up to you to clean it up. Yes, you may have employees who will take care of it, but those employees are far from perfectly reliable – and often, when you’re in startup mode, you don’t have employees to take care of the problem.

You’ve also got the demands of needing a certain level of income, either to survive off of the business or to earn enough to jump into the business full time, which means that when something does go wrong, you’ve got a powerful motivator to drop everything and fix it.

The end result? Sometimes, starting and running a small business can inject complete chaos into your life. A server goes down and you’re forced to choose between that and your child’s first soccer game. An employee fails to show up and you have to fill in, ditching a date night with your wife. Or, you choose to forget about the business and it begins to fail because of unmet customer expectations. Either way, you lose. (I have to make choices like this sometimes – I decided a long time ago to sacrifice the long term health of The Simple Dollar at the altar of my family’s needs when the choice comes to that.)

How do you manage all of the chaos of a small business without going crazy? That’s the topic of Clate Mask and Scott Martineau’s book Conquer the Chaos. Small business really is a juggling act, particularly during the startup era. Does this book have solid advice for dealing with this? Let’s find out.

1 – The Entrepreneurial Revolution
Why do people become entrepreneurs and start their own businesses? Time. Control. Freedom. Running your own business gives you these things in a way that being an employee simply cannot. You also, of course, have the direct relationship between your work and your income, which means that you aren’t merely a cog in someone else’s machine. All of this can be incredibly tempting. But…

2 – Enter, Chaos
When you make the choice to dig into entrepreneurship, you find yourself constantly have to make very difficult choices between your small business and your personal life. Do you choose to spend this evening watching a movie with your wife or building a better website? Do you meet with this great potential customer or do you make it to your daughter’s recital? No matter what you choose, you’ll have some regret about missing the other choice. Even worse, you’re often making these types of choices – the things that form a huge part of the foundation of your life – on the complete spur of the moment. It’s stressful and chaotic.

3 – Grow or Die
Making the challenge more difficult is that your business has a very simple imperative, especially during the startup phase: grow or die. Most businesses don’t open the doors with the ability to pay the bills. They have to grow to make it. In order to grow the business, you’re going to be pushed strongly towards the “business” choices instead of the “personal” choices, especially at first.

4 – Emotional Capital
What you begin to find is that you have only so much passion inside of you. How are you going to use that passion? Are you going to channel that passion into your personal life and view the business as merely a support structure (one that probably won’t survive over the long term)? Or are you going to channel that passion into the business, growing something tremendous? Alternately, you can try to split the two, but this will deal a lot of difficult choices onto your plate.

5 – Disciplined Optimism
The solution? Discipline. Spend some time figuring out what the priorities are well in advance so that you’re not stressed out and torn when a challenging decision comes before you. Better yet, resolve those priorities to the point that you feel good about your choice and you feel optimistic about what you’re building, whether it’s your family or your business or whatever you decide.

6 – Entrepreneurial Independence
Another challenging factor is the double-edged sword of independence. Independence means you get to make your own decisions, but it also means that you don’t have the guidelines, advice, and parameters that a typical job has. My best solution for this is to find a mentor who can guide you through some of this difficult transition.

The rest of the book really focuses on some of the resolutions for these problems, after the authors made clear what the challenges are.

7 – Centralize
One thing that many harried small business owners do is that they keep tossing in “solutions” for specific problems. While this can help in the short term, eventually there are so many “solutions” in place that the regular operation of the business can be confusing. You’re far better off centralizing things with only one system for handling everything – much like GTD handles everything for your personal tasks.

8 – Follow-Up
Another thing that often happens with small businesses is that you find yourself with tons and tons of loose ends, all of which need to be followed up on. While it’s often tempting to just go start new initiatives, it’s usually more rewarding in the long run to devote time to tying up all of the loose ends in front of you before moving on. If you don’t do this, the sheer weight of all of the loose ends will crush any forward progress you want to make because so many of the things you need in order to move forward will simply be undone.

9 – Automate
This chapter doesn’t refer so much to automation as it does to having a series of very standardized procedures for various things you’ll be doing as a small business owner: customer follow-up, inventory, and things like that. Part of that standardized procedure relies on having a reliable calendar that reminds you of when specific steps of that procedure needs to be done. An example: if you would ideally like to follow up with a new customer three times at certain intervals after their initial purchase, these can be entered into your calendar immediately after the purchase. Then, on that day, you just look at your calendar and boom there’s the reminder of the follow-up you need to do.

10 – Avoiding the Backslide
Once you get things rolling well, it’s easy to sometimes fall back into chaotic situations. One easy way to tell whether or not you’re falling back or you’re about to run into trouble is to ask yourself if your business would survive if you disappeared for a few weeks. If you can’t say yes, then you’re on the verge of backsliding – your systems aren’t up to snuff to avoid potential chaos.

Is Conquer the Chaos Worth Reading?
I would highly recommend this book to anyone who is in the planning stages of running a small business or is having difficulty with their current business. Conquer the Chaos really isolates what most of the common problems are for a small business owner and provides at least the outline of some solutions for those problems.

I would probably couple this book with a great book on time and information management, like GTD, which focuses heavily on implementing a centralized system that can deal with a lot of the challenges in this book.

This book works best when it’s applied during the “thinking” and “planning” part of small business preparation – once the ship has started to sail, much of what’s in this book is harder to implement and consider. In other words, if you’re looking at entrepreneurship in the future, particularly the short term, give this book a read.

A few days ago, a college student I know was talking about his upcoming graduation. His plans mostly revolved around getting a good paying job, but he also talked about how he might go back to school some day and study a particular branch of philosophy that he truly loved studying and reading about.

I asked him why he was choosing to put a good paying job over a path that he was deeply personally passioante about that might not necessarily earn a great deal in the near future. He pretty much exploded, offering up a rant about how the world revolves around money and the only way he would ever be able to chase the dreams he has is if he has lots of income.

I couldn’t disagree more. Let me explain why.

First, the need for money in the bank comes down to what you’re responsible for. If you’re fresh out of college with nothing to your name but a car, you really don’t have that much that you’re responsible for. You don’t have a house. You don’t have a partner. You don’t have children. You don’t have an established career to protect.

You just have you, your dreams, your skills, and your potential. Nothing else.

Second, you don’t actually have a lot of day-to-day financial need, either. It’s perfectly normal and acceptable for a new graduate to live in a small apartment or a room in a house. Why? The rent is cheap. You can eat really cheap, too – just stock up on whatever fresh produce is on sale at the grocery store.

The big money that many people often believe they need is for stuff that they actually merely want, and it’s those wants that stand in the way of taking a leap towards a dream.

Thus, your income requirements are very low. You’re responsible for yourself. Just you. All you really need is a place to lay your head at night and food in your belly.

If you can’t find a job doing what you want to do, take on an internship. If you can’t find an internship, ask for one directly from the place you dream of working. If that doesn’t work, just start doing and sharing. Whatever it is you dream of doing, there’s an avenue out there to explore it and throw yourself in with your whole heart.

Since you don’t need much income, get a job sitting behind a counter at a gas station at night. Earn minimum wage and sit there with your notebook open, collecting your ideas and thoughts about whatever it is you want to do. Spend your mental and physical energy building the life you want.

There is no better time in your life to just throw caution to the wind and see where your passion will carry you than when you’re young and free of many responsiblities. If it doesn’t work, you’re not out anything much – maybe a few years, at worst. If it does work, you’ve opened the door to a lifetime of doing what you want to do.

What do you really have to lose? Not much. What do you have to gain? The life you dream of.

I’m in my mid twenties, worked doing tech support all through college, and worked out of college as the IT director for a political campaign of 120 staffers. I now have left to a job that fits my interests a little bit better, but clearly still have a lot of IT skills.

I haven’t been doing any IT work on the side, but the friend of a coworker of mine needs some computer help. I’m perfectly happy to help her. What I really want is money, but I feel awkward asking for it. I’m not in debt, I’m pretty healthy financially, but money is preferred just because I want to spend it on what I want, rather than just asking for a general category of gift (bottle of scotch, etc). Any advice on how best to explain that I charge a certain rate and not feel bad about it? (Her fix is pretty easy for someone with my background, hence the guilt)

The best approach in this situation is to decide what you want in advance, then be up front and clear about it. Communication never fails to be a winner in any situation and the earlier you communicate your needs, the better. You should communicate what you want at the earliest possible juncture in this so that there’s never any chance of there being a misunderstanding of the arrangement.

The secondary question, of course, is whether or not you should feel guilty about doing this.

There’s one big thing to keep in mind whenever you provide this kind of service or any kind of service: people are paying you to provide a service they can’t – or are unwilling to – do for themselves. You are providing some sort of expertise or trait that they’re not bringing to the table, whether it’s knowledge of leverage for moving a piano, arm strength for digging a lily pool, or IT skills for solving a computer problem.

To them, the skill you have has value. Quite often, it has significant value.

What value? It doesn’t matter what you think that skill is worth. It matters what they think the skill is worth. That amount is what the person receiving that service is willing to play. In other words, it’s set by the marketplace – if there are fifty plumbers in a city, they all charge similar rates, for example.

Another factor to remember is that you are selling your spare time. That time has significant value – you have a limited quantity of it and it’s often the only time you have for leisure and recreation. When you fill that time with tasks that you don’t want to be doing, you deserve some sort of compensation for it.

Thus, I would check around in the community and find out what the going rate for the type of service you’re going to provide is, then provide the service at that rate or a slightly lower one. After all, that is the price they would pay for that service in the broader marketplace.

You may decide that a lower rate for family and friends is appropriate and, if that’s the case, reduce the rate you charge to benefit that person. Should you provide that kind of rate reduction? That’s up to you, but if you are providing that rate, make it clear up front and on any receipts or invoices you provide just to keep matters clear for the future.

On the other hand, there is some value in providing the service pro bono, particularly if the service isn’t too stressful for you. This can have an enormous social benefit – it often opens the door to a long exchange of value on both sides of the coin, from work opportunities to assistance with tasks and advice. There is a great deal of value in following this path and, quite honestly, it’s probably the path I would follow in this case.

Good luck in whatever you choose.

Several months ago, I wandered upon Pamela Slim’s excellent blog, Escape from Cubicle Nation. In a nutshell, the blog covers the transition from working in a cubicle (i.e., a traditional job) to self-employment – and all of the issues in between.

Slim packaged up many of the best ideas into a guide to this transition, also titled Escape from Cubicle Nation. And, since I enjoyed the blog so much, I picked up the book, looking forward to reading what Slim had to say, especially since this is a journey I’ve gone through over the last couple of years.

Here’s the entire thing in a nutshell: if you’re thinking of quitting your office job and doing something on your own, this is your handbook. It’s thorough, detailed, and heavy on the applicable ideas. Let’s dig in.

I Have a Fancy Title, Steady Paycheck, and Good Benefits. Why Am I So Miserable?
Many jobs involve sacrificing one’s core values – you might not necessarily be doing work that you dislike or object to, but the work isn’t in line with what you want out of life. Many jobs are also filled with trifling details that are simply not fulfilling. Work also often involves jumping through hoops for a boss – a process that isn’t clear on how it helps you (or helps anyone). Adding these factors together, it’s not entirely surprising that people are unhappy with their work, even if it’s a “good” job.

If It Is So Bad, Then Why Am I Afraid to Leave?
Slim points toward status, routine, and recognition as big factors, but I think an even bigger factor is a fear of the financial unknown. Many, many people are out there living paycheck to paycheck, deeply fearing the idea that the job might go away. I know that this was my biggest roadblock against taking the leap into being a self-employed writer – I was afraid that the steady money would go away. Security was my biggest fear and it held me in place for a long time.

Detox from Corporate Life
Slim offers six steps that can help a person “detox” from corporate life – in other words, the steps a person should take to reduce and eliminate some of the mental holds that their job puts on their mind. Clear your plate of as many tasks as you can (leaving you some breathing space in your day). Start writing down and tracking your ideas. Get creative and expose yourself to new ideas.

What’s Really Involved in Moving from Employee to Entrepreneur?
This chapter outlines a step-by-step process for making that leap. It’s not a be-all end-all guide, but instead it just outlines a framework that the rest of the book fills in in detail. I think her framework might be too specific – what I’ve found is that often people try out lots of different things, something takes off, and they hop onto the rocket ship. Thus, it’s often useful to look at some of the prep as generally useful – like getting your finances in order – but some of the others are a bit more specific than might be necessary. Instead, just try to seek out your own rocket ship – and the way to do that is to follow your passions.

What Are All the Ways to Be Self-Employed?
It’s really impossible to make such a list, so what Slim does instead is to break it down into a big handful of different factors worth considering. What will you do? Why will you do it? Who will consume it? How will they pay? Who will you do it with? Those factors are very different in different self-employment and entrepreneurship positions.

How Do I Choose a Good Business Idea?
After that chapter, a person’s mind might be loaded down with ideas. How do you choose the right one? Slim argues that a person benefits from figuring out their sweet spot – the point where your talents (what you’re genetically encoded to do), your passions (what you love to do), and what’s marketable (what people will pay you to do) intersect. You can even do it by making a list for each of these three categories and figure out where they overlap. Once you start getting a vague sense of where you’re going, start doing research. What’s possible in that area?

Recruit Your Tribe
The next step to success is to surround yourself with the right people – peers who are doing similar things and mentors who have already found success. Slim addresses how to do this in detail, encouraging you largely to just go where the conversation is, join in, and listen. People are already out there talking about your area and it’s worth your while to start participating, building relationships, and growing.

Rethink Your Life: Options for Scaling Back, Downsizing, and Relocating
What? Frugality? Minimizing your stuff? That’s for losers, right? Actually, frugality is for winners. It’s much, much easier to take a challenging leap if you’ve got a healthy bank account and don’t have a pile of bills coming in every week. If you want to give self-employment a try, minimize. Save some money. Get rid of as many bills as you can. Learn how to live a little leaner. It’s really a choice: do what makes you happy all the time or have stuff that makes you happy during the hours you’re not working.

Do I Really Have to Do a Business Plan?
Many people look at a business plan as some sort of dry, formal step – a pointless document that doesn’t really help anyone and is best avoided. In truth, a business plan’s purpose is simply to guide you through the thought process of making sure all of your bases are covered. Have you thought about your customers? Have you thought about likely what-ifs? A business plan is just a way to push you to think about these vital questions. So, don’t worry about the formality of your document at the end – but think a lot about the questions involved.

Define the Spirit of Your Brand
What are you going to do to stand out from the pack? What’s different about your business, particularly in a field full of competitors? That’s a difficult question for a lot of people. You cannot find success by just copying something that’s already successful. At most, you’ll be mediocre. What did I do different to build The Simple Dollar? I decided not to be snarky or wholly fact-based, but instead to be earnest, something that wasn’t really done in a blog form too much at that point.

Test Often and Fail Fast: The Art of Prototypes and Samples
Once you have your idea in place, try it. Don’t spend lots of time making it perfect before trying it. Instead, throw it out there, share it, get some feedback, and use it to improve. That’s what I’m doing with my podcast. The first few episodes weren’t all that good, but if I hadn’t shared them anyway, the later episodes wouldn’t have improved at all. I wouldn’t have had a good idea of what was wrong.

Look Your Finances in the Eye
What about the money? It’s all about the money, in the end. You need to get a real grip on your financial state – and that means real numbers. Know what you owe. Know what your bills are. Know what you bring in now. Then plan ahead – get rid of those debts as soon as you can, minimize your bills, improve your credit rating, and build a big fat emergency fund. This is all personal finance 101, but it’s worthwhile stuff.

How to Shop for Benefits
The biggest fear when it comes to self-employment for many folks is health insurance. What will I do without employer health insurance? Slim covers options for people in the United States here, but in the end, this area changes so much that you should do your own research. I think the real solution over the long run will probably be a national health care plan – if this is easily accessible and actually decent, people will sign up in droves and take the leap, I think.

Dealing with Your Friends and Family
Many people find a lot of resistance in their lives if they suggest making a major change in their career. Why? In the end, most people resist change in their lives, and your major career change is often a change in the lives of people around you – a change they’ll resist. I was lucky when I made my change that I had a lot of supportive people around me who knew I’d dreamed of spending more time with my kids and writing for a living for a long time, but this isn’t always true of everyone. What can you do? Listen to their concerns, but realize that many of the doubts expressed are actually their own doubts, not yours. Accompany those doubts with a well-thought-out business plan that analyzes those doubts and ensures that you’ll survive them.

Line Your Ducks in a Row
For Slim, this means getting appropriate support around you. A lawyer you trust. An accountant. Possibly a virtual assistant to help with the flood of emails and contacts you’ll get. You’ll face a lot of problems, and having support around you for the less important things lets you focus on the most important things – like how to overcome the problems that are set out in front of you.

When Is It Time to Leave?
Escape from Cubicle Nation winds down by asking the big question: when is it time to make the leap? Sure, there are logistical issues – do you have the money? Do you have the connections in place? Is the business plan ready to go? Have you already started (and is it successful)? But a big part of it comes from inside as well. It’s a major leap – are you mentally ready for it?

Is Escape from Cubicle Nation Worth Reading?
If you’re working in a typical job (employed by someone else) and have ever thought of going it alone or starting a small business, Escape from Cubicle Nation is an essential read. Slim goes through the factors worth considering in great detail, outlining the things that need to be considered and the things that need to be put in place.

My only complaint – and this is a minor one – is that the topics felt a little bit out of order. This is something I’ve been struggling with while writing my own book lately – are the topics really in the best order? I even sat down and tried to figure out how I would change it, but without blowing most of the chapters to bits and reconstructing them out of pieces, I don’t know what I would change. I think the problem is that Slim tackles so many ideas in the book – but is that really a problem?

Look at your own life. If this book matches the journey you’re on, it’s a must read.

It’s official: I’m ready to get out of here. I’m tired of working here and I have a lot of people lined up to hire me for home catering and cooking. I’m sure you did a bunch of planning before you made the leap. What exactly did you plan?

I know at least one other former coworker who is contemplating a similar move into a freelancing gig, though his plans are decidedly less clear at this point.

So what exactly did I do during that transition period? I started making a list of the things I did – then, soon, I realized that there were several things I wish I had done. Before I knew it, the email had ballooned into a guide that I thought might be useful to quite a few people.

Here are fifteen things I did (or wish I had done) during the months leading up to my transition to working for myself.

1. Learn to live on less.
One of the biggest challenges of freelancing/self-employment is the uneven pay. Gone are the steady paychecks of a typical job. Gone is the idea that you’ll make roughly the same amount next month as you will this month. During 2009, I have had months that earned only 25% as much as other months – and I anticipate a single month later in the year when several projects come to fruition in which I have by far the best month of the year.

If you allow your spending to match your income, you’re not going to be able to survive during the lean months. Instead, you need to adapt yourself to a consistent lower level of spending. Start looking now for fat to trim from your life. Every expenditure you have that’s not necessary for your basic living standards should come under very careful scrutiny.

Many people balk at this, but the truth is this: your first several months as an independent worker are going to be a real shock in a lot of ways. The last thing you need making this transition more difficult is a bunch of unnecessary expenditures. If things go well, you can always add some expenses back into your life – but you may find, surprisingly, that you’re quite happy without most of them.

2. Create a budget, both personal and business.
As I’ve written before, I’m not a believer in the “one-budget-fits-all” approach. Trying to make your budget or spending match an example provided by someone else is doomed for failure because that example doesn’t match your life.

I argue that the real value provided by a budget is that it reveals, loud and clear, how you actually spend your money and it can provide some clear pointers to where you need to make changes. Prepare a budget by just keeping careful track of what you spend for a month – make a giant list of every dime you spend, then organize all of that spending into categories that make sense to you. When you have that in place, look not only at the total amount you spend (you’re going to need an income level that on average exceeds that by at least a little), but also at the various categories – are there areas that you can cut?

A similar exercise for one’s business expenses is also useful, though it can be more difficult. Seek advice on the expenses that people typically have freelancing in your area of interest and use that for a basis.

3. Build up a big emergency fund.
If you’ve followed steps one and two and made serious cuts in your spending, you’ve now got a nice surplus of money coming in each month. Don’t be tempted to spend it. Instead, sock it all away into a savings account. In fact, do it automatically – instruct your bank to automatically transfer a healthy amount each week into a savings account on your behalf.

If you’ve done your budget, you have a good idea of what your monthly expenses actually are. I recommend having at least six months worth of living expenses in your emergency fund before making the leap. This will help you survive the lean months, particularly those early on in your freelancing experience.

4. Now make it bigger.
Quite often, people go light on the emergency fund before they make the leap. They have a bit of cash saved up, but they’ve convinced themselves that they’re ready – they have plenty of clients and opportunities lined up.

Don’t make that mistake.

The big problem is that freelancers and self-employed folks – especially early on – can have a tendency to count their chickens before they hatch. No deal, no matter how good it is, is a sure thing until contracts are signed and products are delivered. You might have ten potential clients that talk big about what they want to do, but when push comes to shove, all of them could vanish – and many of them will.

Be prepared for that. Don’t leave yourself in a desperate situation if a conversation doesn’t pan out. Cover your bases – and the best way to do that is with a healthy emergency fund. Build it now, build it later, keep it nice and fat.

5. Start reaching out to your audience and client base now.
There is no better time than right now to start digging for opportunities, even if your leap is far into the future. Get out there and start seeking out the people you want to know – and the people you want to sell to.

In a nutshell, this is market research – you need to find out if there are people that will buy what you do and figure out how to connect with them. Obviously, the internet and social media (like Twitter and Facebook) are good places to start, but they’re just a start. You should also go directly to where people who might be potential clients – or potential competition – congregate.

Start finding the people now. Join messageboards. Start Twittering. Start a blog. Pound the pavement in your local community. Dig through freelancing boards and other job boards. If you’re passionate about the field you’re leaping into – and you must be if you want freelancing to work – you have plenty already to talk about. Let the passion flow.

6. Eliminate as many regular bills as you can.
Back on the money side of the coin, start whacking your regular bills, particularly any related to entertainment. Ditch Netflix – if you want to watch a movie, use Redbox or a similar service. Ditch your cable bill entirely – use a digital converter box and Hulu to get your television fix. Sell your car – if you can use public transportation or ride a bike to work, do you really need one?

For the ones you can’t eliminate, trim. Make your living quarters as energy efficient as you can, with programmable thermostats and the like. Cut your cellular plan – do you really need that much data, those minutes, or that many text messages? If you decided to keep cable or satellite, whack some premium channels you don’t watch.

The more monthly bills you can eliminate or reduce, the more room you have to breathe when you make the transition.

7. Write a business plan.
Don’t worry about being too formal when you do this. The purpose of a business plan is to make you think about all of the details of what you’re about to leap into. Have you really thought things through?

Areas to include: market analysis (is there actually a need or a market for what you’re doing), product or service development (what kind of service or product will you actually offer), marketing (how will you draw attention to what you’re doing), financial organization (the money), and risk factors (what problems might crop up and how you might handle them).

Spend some time on this. Include everything that comes to mind, and flesh out details on every point. Don’t sweat the formality – just focus on ideas. The more effort you put in here, the easier it will be to make this all work when things get rolling.

8. Now rewrite that business plan.
Quite often, most freelancers make only a minimal effort at a business plan, if they bother at all. Big mistake.

I suggest using a self-imposed deadline of sorts. Arrange to show your business plan to someone you trust on a certain date for their input. Putting that deadline in place will keep you focused on the project, as you’ll want to present something reasonable.

Then, when you deliver it, ask for feedback of all kinds – everything they can think of that might improve the plan. What you’re really asking for is advice on the work you intend to do. This is a double check to make sure you’ve thought everything through.

When you get the suggestions, use them to rewrite your plan. Then repeat, perhaps with another person who might read it and offer suggestions. A few such repetitions will go a long way towards creating a real plan that works – and making sure you’ve really thought this through.

A good business plan isn’t a boring thing to “waste” your time on. It’s a great way to make sure all of your bases are covered, and often the revision process is the most powerful part.

9. Find a mentor.
So who can you take that business plan to? A mentor, that’s who.

Seek out someone that knows what they’re talking about that isn’t a potential competitor of yours. Look for someone experienced at freelancing in a tangential field – not a direct competitor – and ask them for advice and help. Be specific in your questions and don’t take criticism personally – it’s offered with the goal of making you better, not cutting you down.

Recognize that the person is probably busy and contribute some value to the relationship yourself, by promoting their work or offering them something of value, too. For example, if you’re a nascent blogger and would like to attract a professional blogger as a mentor, spend some time simply promoting their best stuff. Write about it on your own blog and talk about their stuff on Twitter. Buy their book and write a review of it (if they have a book out there). Participate in their comments and in their other conversations online.

Actions like these are ways that you can make a mentoring relationship into a fair value exchange instead of just a “gimme gimme gimme” relationship.

I wrote a detailed guide on finding a mentor in the past that can be very useful reading.

10. Make it easy for people to see the good stuff you can do.
Create an online presence for yourself that makes it very easy for people to find your best work. Regardless of whether you’re doing online work or not, have a website with an easy-to-remember URL that contains links to examples of the best stuff you’ve created. Join social networking services (Facebook and LinkedIn) and make professional pages about yourself that clearly show off your best side.

If people hear about you, they’re going to Google you. You want to make it so that the first things they find are good, positive, impressive things – the types of things that will draw them in, not push them away. Never take the attitude that you can appear antisocial and that if they don’t like it, they can walk – that attitude will push many of your potential clients away because you’ll seem unreliable from the get-go. There is never a downside to appearing friendly and accessible.

11. Communicate, communicate, communicate.
The more you talk, the more likely people are to discover you. Share your thoughts and ideas and comments as much as you can, as widely as you can.

Start a blog. Join social media sites (Twitter and Facebook, for starters). But, most important, join in on conversations. Link to interesting people and ideas on your blog and offer your take. Follow interesting people on Twitter and respond to the things they say. Comment on interesting blogs (with a link back to your own of course) and make worthwhile comments.

Most important, stick generally in your area of expertise, but don’t be afraid to jump into topics that are at best tangentially related. The goal is to make people interested in what you’re doing, and the best way to do that is to always speak from your heart and from your mind. Be positive, put your voice out there, and good things will happen.

12. Build connections with local small business/entrepreneurship groups.
Even if your work is outside of your local community (online work, for example, or freelancing work for remote enterprises), it’s worthwhile to engage with local small businesses and entrepreneurs – after all, that’s exactly what you are. Such groups are almost always sources of good ideas and leads for areas where you might improve, and they’re also places where you can float new ideas and gauge them. Even better, leadership in such groups provides countless ways to reach out and connect to others in countless ways – conferences, meetings, and so forth.

Get involved in peer groups, both in your own physical community and in your professional community – and don’t be afraid to dive right in and participate, even before you’ve made the leap. The number of valuable connections you’ll make there will pay off time and time again.

13. Have a place where you can focus on work – and only work.
Many freelancers start off working at the desk in the corner of the living room – the same one that houses lots of personal material as well. What often happens, though, is that the personal material begins to interfere with the professional work and the lines begin to blur. You find yourself working when you should be engaged in personal activity, and doing personal things when you need to be working.

Find a location somewhere that you can devote solely to your work – no personal stuff. Ideally, it’s a place that you can isolate yourself from the things around you. For example, I have a room in our home that serves as an office. When I need to work, I go in there and close the door and I’m in “work” mode. When I leave that room, I’m no longer in “work” mode (unless I’m headed out to do some research).

Without that barrier, it would be incredibly easy for me to constantly take my eye off the ball – and if I did that, I would constantly find myself falling behind on my work.

14. Build your current bridges as strong as you can – and don’t burn them when you leave.
Many people, as they begin to transition mentally into freelancing, let their current work relationships slide, deciding that they don’t matter. Actually, quite the opposite is true – they matter more now than they did before.

Here’s why. The strong connections you have in your previous line of work will continue to serve you well after your transition. The connections may provide you with new clients and interesting angles to pursue. Plus, if freelancing doesn’t work out, you often have a strong foot in the door for returning to a position in your previous career path.

On the other hand, if you let those relationships burn out, you miss out on these opportunities – and that big safety net.

Spend your final months tying up loose ends, but make sure that the relationships you’ve built don’t fray, either.

15. Practice, practice, practice.
This is perhaps the most useful lesson of all. If you want to be a real standout in your area of expertise, keep practicing at it. Study it. Try new things, and work to get better at the things you already do. In short, practice every single day.

If you’re a writer, write (and share them, via a blog). If you’re a graphic designer, make designs and share them (via Flickr or other avenues). If you’re a musician, practice daily and share demos with the world. Doing this not only makes you better, but it shows that you’re a hard worker and helps you get a better grasp on what people like and what they don’t like.

As time goes on, you’ll get better and better at what you do – and you’ll have a long track record that shows how diligent you are at your work.

A Final Tip: Dig Into Freelancing/Self-Employment Resources and Communities
Here are five websites I visit all the time for advice and thoughts on being self-employed and accepting freelance work.

FreelanceSwitch
http://www.freelanceswitch.com/
FreelanceSwitch is my website of choice for thoughtful and insightful conversation on freelancing and self-employment issues. It’s a daily read for me.

Elance
http://www.elance.com/
Elance is a clearinghouse of freelancing opportunities of all stripes. I like to keep an eye on freelancing opportunities in several areas.

Guru.com
http://www.guru.com/
Guru is a similar clearinghouse for freelancing opportunities.

Web Worker Daily
http://webworkerdaily.com/
If you do computer-based freelancing, this site is a must-read. Again, I read this one almost daily.

Freelance Folder
http://freelancefolder.com/
Freelance Folder offers a ton of widely varied and interesting advice on freelancing topics.

Good luck!

It’s no secret to long-time readers of The Simple Dollar that I loved Keith Ferrazzi’s first book Never Eat Alone. I thought it was a brilliant discussion of how to network ethically in the modern world by building real, valuable relationships with people centered on giving of yourself to others. Even though I’m an introvert, I’ve taken many of the principles in Never Eat Alone to heart in my own real-world experiences – and online as well.

While Never Eat Alone does a great job of outlining how to build relationships with a large group of people, it’s fairly self-evident that there’s a lot of value in building particularly strong relationships with a small group of people. These are people you trust and who trust you, wise and insightful and willing to spend significant time with you because you make each other better. Mentors, advisors, friends – all of those titles apply. Most people are lucky if they find a handful of such people in their lives.

Finding and cultivating this inner circle is what Who’s Got Your Back focuses on. How do you find these core people? What traits do you have that will click well with others, and how do you find the traits that will click well with you? How do you maintain relationships with them over the very long haul?

I’m a huge believer in the power of mentors, and I’ve discussed techniques for finding a good mentor in the past. Let’s dig in and see what Ferrazzi has to say on the subject.

One: Who’s Got Your Back
Ferrazzi argues that the need for an inner circle of mentors, advisors, and friends that you trust and respect is something that almost everyone in the modern world strives for – if that wasn’t true, why would things like “life coaching” be such a huge multi-billion dollar industry? Even more disturbing, according to a 2006 study in American Sociological Review, the average person has only two confidants, and 25% of people have none at all. In a ever more complex world, confidants and advisors are more important than ever before – yet people have fewer of them.

Ferrazzi then makes the case for how valuable “lifeline” relationships are, focusing on four ways that such relationships are critical:

1. To help us identify what success truly means for us, including our long-term career plans.
2. To help us figure out the most robust plan possible to get there, through short-term goals and strategies that would tie us in knots if we tried to go it alone.
3. To help us identify what we need to stop doing to move forward in our lives. I’m referring to the things we all do that hold us back from achieving the success we deserve.
4. To have people around us committed to ensuring that we sustain change so that we can transform our lives from good to great.

I know that in my own life, my chief “lifeline” relationship is with my wife, and I constantly talk to her about the things above. It helps more than you can ever know and often guides me towards difficult decisions that I might “chicken out” on if I did them alone.

Two: The Four Mind-Sets
Ferrazzi identifies four “mindsets” – more like traits, actually – that, when cultivated, provide the foundation for building such lasting “lifeline” relationships.

Generosity You have to be willing to give sincerely of yourself without expecting a thing in return. Generosity is the foundation of trust, and trust is what makes such relationships work.

Vulnerability You have to be willing to be vulnerable. Can you move outside your safety zone? Can you accept criticism from others?

Candor You have to be willing to be totally honest with others. If something’s on your mind, you shouldn’t hold it back. It might be valuable.

Accountability You have to be willing to follow through on the promises you make to others.

These four traits are vital for building lifeline relationships – ones where you can bounce ideas freely, receive criticism, and truly grow as a person as well as in your ideas and goals. Others that you build such relationships with must have such traits as well – without them, the relationship is not going to succeed over the long haul.

Three: Building Your Dream Team
So how exactly do you build this team? Ferrazzi identifies a nine step plan for finding these people, cultivating the relationships, and maximizing their value in your life.

Step One: Articulate Your Vision This means soul searching. What do you really want in life? What are your big goals and dreams? What are your interests and passions? What do you really value? For me, my values center around my family and my writing, so if I were looking for people for my own inner circle, I’d want someone that valued family and had some insight into creative careers.

Step Two: Find Your Lifeline Relationships Look throughout your life – your work, your extracurricular activities, your personal life – and identify people who match up at least somewhat with what you want in life. Get to know that person a little and find out if they actually exhibit those valuable traits. Are they committed? Do they have some know-how – knowledge of what they’re talking about? Do you get along well with them? Are they curious by nature? If you see a lot of these factors, you’ve got someone very promising.

Step Three: Practice the Art of the Long Slow Dinner Gradually get to know a potential lifeline quite well. Have a lot of meetings with them – lunches, dinners, coffee. Talk about anything and everything. Feel them out. If it’s right, you’ll know it – if it’s not, don’t be afraid to move on and try again.

Step Four: Broaden Your Goal-Setting Strategy The first real way to get your lifeline friends involved is to talk about the goals you have – and the goals they have. Offer candid input on their goals, and invite (and accept) their candid comments on your own goals. Develop new goals together – and talk about how you can get there.

Step Five: Create Your Personal Success Wheel The “personal success wheel” is a wordy way of describing the key areas in your life that you want to succeed in. Financial success, spirituality, giving back, physical wellness, intellectual stimulation, deep relationships, and professional growth are areas that Ferrazzi mentions that are common to most people. Ask yourself what you’re doing in each of those areas – and bounce your thoughts off of those people in your lifeline. Similarly, encourage them to do the same – think of their core areas, ask themselves what they’re doing in each, and bounce their thoughts off of you.

Step Six: Learn to Fight! In other words, you have to be able to (and be willing to) diasgree with people in your inner circle. More importantly, you have to be able to debate ideas without making it personal – Ferrazzi calls this “sparring.” The key is realizing right off the bat that you’re just comparing and analyzing ideas, not attacking each other, and you can both grow from this process.

Step Seven: Diagnose your Weaknesses Introspection is a key part of all of this. You have to be able to not only figure out your weaknesses (and Ferrazzi gives a lot of tips for this), but be able to reveal and discuss those weaknesses with others, along with strategies for overcoming that weakness (or turning that weakness into a strength).

Step Eight: Commit to Improvement Steps four through seven are going to give you constant ideas on how to improve your life (and, along the way, give the others in those relationships with you tons of ideas as well). In order to actually get something out of it, though, you have to be willing to commit to improving yourself. You need to take at least some of those ideas and actually implement them, making yourself better, or else you come off as very insincere. Doing is much more valuable than talking.

Step Nine: Fake It Till You Make It – Then Make It Stick Ferrazzi’s big point here is that practice and repetition are vital. All of the steps above are ones that you should be constantly repeating. All of the ideas generated should constantly be worked on. They should just become a part of your life – and they easily can. Why? Because those “lifeline” friends will eventually become your closest friends – the foundation of your life.

Four: Make It Your Life
The final portion of Who’s Got Your Back picks up where the final point leaves off. The ideas in the book aren’t just a one time process, but elements of a successful life. Ferrazzi offers several worthwhile points to cap off those ideas – here are three.

A group of like-minded people is a great place to start. If you don’t know where to start, look for an already-existing group of like-minded people that share your interests. If you’re an entrepreneur, check out local small business associations. If you’re a parent, look for PTA meetings. Find people that share your passions and you’ll have a great group to start with.

Forming an actual group can be quite scary. Ferrazzi suggests several approaches, but the real foundation is the people. Your best bet to make a group work is to try to cultivate the relationships between people you have lifeline relationships with. If you can get, say, four people where every person has a one-on-one relationship of this kind, that group will be invaluable to all of you.

Suggestions are invaluable. If you have an out-of-the-blue idea that really fits a person you have a lifeline relationship with, write it down and treat it with the weight you would treat a great idea for yourself. If you’re doing this for each other, it’s like having two or three or four minds out there trying to come up with great ideas to push you farther.

Is Who’s Got Your Back Worth Reading?
To put it simply, I loved this book, too. The material in here applies well to virtually everyone, particularly people who are somewhat introverted who may need that extra push to build strong life relationships (I’d put myself in that group). What appeals to me, as with Never Eat Alone, is that everything is underlined with giving of yourself. Paying it forward is a strategy that has never, ever failed me in life.

This one is already on my re-read pile. I plan to let the contents of it sink in for a while, then give it another read-through in a few months.

My only criticism is similar to the criticism I had with Never Eat Alone, but it’s one that I understand. Ferrazzi has a tendency to name-drop in places. My interpretation of it is that Ferrazzi is actually much like myself – he’s an introvert who has to work on being an extrovert, and being able to drop those names makes it easier. I do a similar thing, to be quite honest – I tend to talk in big bursts when I don’t know someone well. I’ll be quiet for half an hour, then drop a two minute wall of words. It’s something that comes up as a result of my natural introversion – and it’s something I’m aware of and try to work on.

Put this on your Amazon wish list or your library list. This one’s really good.

Discover your passions and make a living from it.

It’s an idea I talk about quite often on The Simple Dollar – and it often gets pooh-poohed by people who believe strongly in work-life separation, that you should do a job that maximizes your income for your effort. My belief is that you can reach that same point and enjoy yourself along the way by following your passions.

Others argue that their passion isn’t possibly something they could earn an income from. For those, there’s Craft Inc. by Meg Mateo Ilasco.

The idea behind Craft Inc. is simple: you like making something, but you have very little understanding of how you can translate it into a business. Although the book focuses specifically on crafts (with a layout that reinforces that idea), it’s actually a great side business starter book no matter what you want to sell.

So what’s inside the covers? Let’s dig in and discover something interesting.

1 – Your Creative Mind
Many people have the spark of a great creative idea within them, but they bury it behind myths that aren’t really true. “I’m too old” is a myth. “I’m not an ‘arty’ type” is a myth. “I’m waiting for the right time” is a myth. “I need to do this full time before I start” is a myth. Don’t let myths hold you back.

The best way to get started is to simply do it. Spend some time every day practicing your craft. Keep track of interesting ideas. Find a place to work that makes you feel creative and energetic. Most of all, share your dreams with others – tell them what your wildest dreams are related to your craft.

2 – Your Business Mind
The first step in translating the craft you enjoy into a business that can make money is developing a business plan. Craft Inc. offers a great framework for doing this, identifying all of the key elements you need and discussing some in detail. More importantly, it outlines why you need to do this – more than anything, it’s a powerful way to get all of your ideas in order and make sure all of your bases are covered.

Do you need to file for trademarks? Maybe, depending on what you’re doing – and the book provides a brief guide. Do you need to file paperwork to start a company? If it’s just you and just a side business, probably not – a sole proprietorship will work at first. Where should the seed money come from? Your best bet is likely living frugal and saving up that initial investment yourself.

3 – Your Personal Style and Your Products
A boring product doesn’t sell. How can you be sure that whatever you’re making will leave a lasting and positive impression?

First, don’t try to please anyone – instead, focus on pleasing yourself. Create things that you like. Package them in a way that you like. If it’s not appealing to you, don’t do it – look for a different approach.

Attend trade shows and craft shows for ideas. That doesn’t mean you should copy the ideas you find, but having lots of input will help you figure out elements that work for you – and elements you should leave behind.

Keep a notepad with you at all times to jot down ideas and things that you observe that you like. Record those ideas as soon as they come to mind so you don’t have the chance to forget them.

Set clear goals. Figure out what exactly you’re working towards and what your next step is, then focus in on that next step. Don’t sweat the mountain before you – focus on getting the next step right.

If you need help with specific elements, ask for it. Ask people who are already doing these things (or similar things) how they handle that area. Don’t be afraid of the fact that you can’t do everything yourself.

4 – Production and Pricing Plans
Scaling up a hobby that you enjoy is tricky. Initially, you’ll try to price an item based on the work put in and raw materials invested in a single item, but often that price is too high to sell. So you have to lower it. Plus, you’ll start seeking supplies in bulk (reducing your cost per item) and rethinking everything about what you do.

The biggest step for most nascent businesses is to rethink the production of the items. You might have a great procedure down for making one quilt, for example, but there might be a much better strategy if you’re attempting to make twenty quilts.

In my own experience with The Simple Dollar and my other writing endeavors, I had to make the same transformation. It wasn’t simply enough to just write when I felt like it or to write one piece at a time. I had to organize ideas, schedule my writing, and plan ahead instead of just doing things as they came along. That change made my writing vastly more productive.

5 – Marketing and Publicity Strategies
Once you’ve got the manufacturing part in line, you have to start finding customers (and hopefully lots of them). Craft Inc. advises you to be your own publicist, especially at first. Start a website for your business (and spring for a good design and your own domain name). Start a blog and update it regularly, just writing off the cuff stuff – don’t worry about hard-selling the product.

One big key: take good photographs of your products. Try lots of things and take plenty of shots until you find ones that really make the product sparkle. The photograph of the product is often the first impression that people get – and a good first impression can often clinch the sale.

6 – Making Sales and Order Fulfillment
So, how do you actually make the sale? Craft Inc. makes the sensible recommendation that you should start in situations where others handle at least some of the mechanisms of salesmanship for you.

First, sell online. Sites like etsy are great places to start if you’re making handmade items. Another strong tactic is to try consignment – putting your items in a shop, but you retain ownership while the actual shop either gets a flat fee or a cut of each sale. The best way to get started on that is to simply start talking with appropriate shops.

The next step usually revolves around craft fairs, which is a great platform once your business is taking off. Craft fairs help you make connections with shop owners, directly sell to customers, and network with others doing similar things.

7 – Ups, Downs, and Next Steps
Craft Inc. closes with an “odds and ends” chapter, covering several topics in brief. How does one deal with knockoffs? How does one deal with burnout? When is it time to quit? How should you be reviewing your business? When is it time to expand, particularly when you need to outgrow the spare space in your home?

I was particularly intrigued by the discussion on burnout. The big key for avoiding burnout is to focus on the areas that made the hobby interesting in the first place. That may mean delegating some of the activities – quite often, burnout is a sign that you either need an employee to handle the drudgery or you need to rethink the whole business plan (change prices, find new suppliers, etc.).

Is Craft Inc. Worth Reading?
If you’ve ever had a hobby and thought about whether or not you could turn it into a business, Craft Inc. is a wonderful handbook to help you get started on that path. It offers a ton of great advice on transitioning something that’s just a hobby you’re passionate about into a side business – or even more. I’m a big believer in following this path, guiding your passions into a channel through which you can earn a living.

Having said that, I think you need to bring some significant passion in the door to make the ideas in this book work. If you don’t have a hobby you’re passionate about, Craft Inc. won’t help you get there – instead, it helps you translate a passion into a side business.

Craft Inc. is a very worthwhile read if you’re interested in following that path, even if your passion isn’t directly related to crafting. Most of the advice in this book applies well to any passion that you might want to translate into a business.

Transferrable skills are often left by the wayside in competitive college majors. In order for a computer science major to get a leg up in the post-graduation workplace, for example, it’s often preferable to jam in another programming or algorithms class than it is to insert another public speaking class. Even if the program does require classes on transferrable skills, those classes are often looked down upon as “blow off” classes – ones that have to be finished in order to get down to the real classes within the major.

I believe this is a mistake. As change in this world accelerates, people are spending less and less of their life strapped to one particular career. They have the freedom to choose other avenues – starting a new career, starting their own businesses, and so on. In that environment, transferrable skills become more and more valuable. In fact, a well-polished transferrable skill makes for brilliant resume fodder no matter what your job – communication skills and leadership experience are a plus for almost any post-college job you might apply for.

Obviously, course loads often aren’t very flexible in a college environment, so my recommendation would be for college students to seek out other sources for picking up and mastering transferrable skills – extracurricular activities, internships, and other sources. Beyond college, transferrable skills are useful for everyone to work on at any stage in one’s career

Here are six significant areas of transferrable skill well worth working on, both to improve yourself and to prepare for your future.

Leadership Can you actually lead a team? Can you herd a group of people towards a greater purpose? Are you self-motivated enough to do this? Can you set goals and actually achieve them? Can you plan large projects and push them forward?

How can I get it? Join a community or student organization and take charge of a large project. Later, run for a leadership position within that group. The best way to learn leadership skills is to learn them in the laboratory of life, and organizations provide the perfect opportunity.

Administrative skills Are you able to prioritize the tasks in front of you? Can you analyze information and then describe it in layman’s terms for others to understand? Can you interpret rules and use them effectively?

How can I get it? Get involved in the planning of as many large projects as you can. Project planning teaches you many of the administrative skills you’ll need in life. If there is a large project, volunteer to help with the planning – if there’s already a planner in place, learn everything you can from that planner.

Information management Can you actually research a topic? Can you take a pile of research and use it to answer worthwhile questions? Can you communicate those facts to others? Can you manage a budget and handle financial records? Can you use a wide variety of computer programs?

How can I get it? If there are opportunities to present anywhere around you, take them, even if you aren’t familiar with the topic. Of particular use are topic areas where you’ll have to do some research in order to get the presentation right. Another great avenue is to volunteer to be the secretary or (particularly) the treasurer for a group. Such activities will require you to carefully manage a large amount of information on behalf of a large group.

Creativity Can you come up with interesting ideas of all kinds? Are you good at coming up with marketing ideas? Are you good at formulating the next step in a process? Are you good at creating visually appealing layouts?

How can I get it? Create some websites for groups – and learn how to do it along the way. Whenever there’s an opportunity for brainstorming, get involved and throw out ideas. Creativity is something that is best learned by practice – so practice it.

Interpersonal communications Are you willing to speak in public? Can you communicate your ideas well in writing? Can you lead a conversation? When you communicate with others, do they understand your ideas?

How can I get it? Participate in conversations and meetings instead of just sitting there. Volunteer for any and all public speaking opportunities that come your way. Volunteer for difficult and arduous tasks of documentation – that’s the best way possible to practice writing to communicate information.

Personal development Can you use the experiences in your life as a source for growth and personal change? Do you have a personal moral code that you actually follow? Can you effectively and honestly evaluate the strengths and weaknesses of others (both people and things)? Can you deal with stress?

How can I get it? Don’t shy away from challenges – step up to big projects. Keep a journal and use it to explore what you really think about things, particularly the people around you.

Every moment you spend learning the above skills is a valuable moment. You’ll find yourself returning to these skills time and time again throughout your life – and they’ll provide a surprisingly strong backbone for your career and personal success.

Rich Like Them by Ryan D’Agostino follows in the tradition of The Millionaire Next Door and The Difference: it interviews a large group of millionaires in order to figure out what traits they have in common.

Rich Like Them takes this tactic and runs in a slightly different direction with it. The author, Ryan D’Agostino, identified the fifty richest zip codes in the United States and went to forty nine of them. He quite literally went door to door, knocking on the doors of people in these communities, and asking them if they’d be willing to discuss how they “made it.” Surprisingly, he got a roughly 10% success rate, even including the droves of people that weren’t home or avoided the interview.

The result of these interviews is Rich Like Them – a collection of the advice that D’Agostino collected on this journey. In fact, he codifies all of this advice into five general areas.

One: Open Your Eyes
We’re all almost drowning in opportunities. The problem is that many of us simply don’t see them. We’re either too focused on the specific little thing at hand or simply aren’t keeping our mind open when we’re “off the clock.” Every person you meet and every situation you’re in is an opportunity not only to improve yourself, but to connect to others and open the door to money-making possibilities.

What steps can you take? Build relationships with people – and, even better, try to connect those relationships to each other, because bringing people together in a useful way is one of the best things you can do. Listen to what people are actually saying and doing – and try as hard as you can to keep your own conclusions out of the mix.

Two: Luck Doesn’t Exist
Luck is mostly about preparation. If you have the ability to record great ideas and to take immediate advantage of opportunities that come your way, you’ll seem much more lucky than the guy who never writes anything down and doesn’t have a hefty savings account.

What steps can you take? Write down ideas as soon as they come to you. Have an “opportunity fund” in the bank in cash form that you can use when something great comes along. Surround yourself with people who are doing useful and interesting things.

Three: The Economics of Obsession
Find something you’re passionate about and throw yourself in head first. Become obsessed with what you’re doing. Read everything you can get your hands on. Meet everyone even remotely related to your passion. Try it all. Practice, practice, practice.

What steps can you take? Figure out what you’re truly passionate about, then when you find it, make it central to your life. Surround yourself with people and activities that reinforce that passion. Become so obsessed, in fact, that others sometimes find it almost scary.

Four: The Myth of Risk
Risk is real, but most people use risk as an excuse not to try things. Instead, you should build a safety net for yourself and take that leap sometimes. A risk that others aren’t willing to take is often the source of an incredible opportunity for someone who is passionate and is prepared.

What steps can you take? Make your own life as financially secure as you can. Dig into opportunities and figure out their real risks. Realize that if something is truly in your wheelhouse, you’re likely to face less risk than someone less impassioned.

Five: Humility
Above all, no matter what happens, be humble. Humility takes you far in life – you can mess up and you will. The way you treat others often winds up matching the way they treat you, especially at that key moment when you really need their help.

What steps can you take? Treat everyone well. Don’t complain about the behavior of others – instead, set your own example. Be humble about your accomplishments instead of bragging about them.

The Best Part: Little Points of Wisdom
The part of this book that really stuck with me was the short principles and quotes inserted throughout the book every few pages. I collected these pieces together, simply because I thought they were so incredibly worthwhile:

Don’t forget your goal – even when you’re on vacation
Where others see death, imagine life
When you hear someone say “If only I could…,” you’re hearing an opportunity
Connect the people you meet
Even when you find the sure thing, save some money for a rainy day
Once you connect the dots, follow through
Choose your purpose, and don’t let anyone tell you you’re wrong
Remember: with time comes free money
Watch your pennies, no matter how many you have
Keep your cool – it’s a big part of persevering
Don’t deviate from your planned path to get a quick gain
Perseverance doesn’t take forever
Once you find your calling, persevering is easy
Remember that you can’t do a business transaction with yourself
Prepare to get lucky
Find a driver other than money – it’s usually more lucrative than money alone
Do one thing and do it well
Obsess over whatever job you have
Take your mind off the money – you’ll earn more
Don’t plan a career – plan a life
Obsession makes you work harder
If you look forward to going to work, that’s a good sign
Discover love through immersion
Turn fear into passion
Never stop being a student
Calculate every risk – even the one you live in
Look for your window to go solo
You want autonomy? Let it motivate you
Be cocky when it counts
Don’t worry about what other people think
Reduce risk by believing in yourself
When you fail miserably, rejoice
If you hate your career, um, change it
Sometimes the biggest risk is doing nothing
Never let pride get in the way of profit
Be humble even if you’re as rich as Brooke Astor
Understand your limitations
Don’t be a slave to Plan A – it’ll prevent you from seeing plan B
Don’t be afraid to make less than your spouse
Never feel as if you’re too successful to sweat
Remember that you are not, nor will you ever be, a god or goddess

Good stuff, all around. Somewhere in there is a piece of advice that is probably a life changer for you.

Is Rich Like Them Worth Reading?
Rich Like Them is a spectacular handbook for someone who is a self-starter with an entrepreneurial bent. If you’ve got a strong desire to build your own success, the advice in this book can provide a great foundation.

If that doesn’t sound like you, Rich Like Them doesn’t have as much to offer. Unlike The Millionaire Next Door and The Difference, the focus here is strongly on entrepreneurial behaviors – taking advantage of the opportunities around you.

So, here’s the deal: if you have an entrepreneurial nature, Rich Like Them is an excellent read; if not, I highly recommend giving The Millionaire Next Door and The Difference a read.

Since then, lots of readers have written to me, asking for ideas on how to start a simple side business. What follows is a list of 50 of those ideas that I’ve collected over the last year or so. Each of these ideas is very simple to start, and most can be done as a sole proprietorship at first (meaning you don’t have to file any legal documents to get started, though you will want to do that if it starts to take off). Most of these can be done at home in your spare time in your spare space, too.

Ready? See if there are any ideas below that fit you well. If you find an idea, seek out a guide on how to get started in that area.

Antique refurbishment This is a perfect side business for people who love antiquing. Take worn-out antiques home with you, invest the time and care needed to transform those old items into something amazing, then resell them at a profit.

Auto detailing Have a meticulous eye for detail and love to get things gleaming clean? Auto detailing is probably a perfect side business for you. In essence, your job is to make cars sparkle inside and out – and many people are quite happy to pay well for this service.

Babysitting Got lots of evenings free? Like kids? Babysitting may be a great side business for you. Keep an eye on multiple children on Friday and Saturday nights and you can earn some solid income.

Bed and breakfast Have some extra space in your home? Turn that extra bedroom into a “bed and breakfast” room. This works particularly well if you have a somewhat older home or live near an area that attracts regular travelers and tourists.

Blogging If you enjoy writing, find a topic you’re passionate about and start a blog on the topic. All you need is a computer, some time, and some energy to consistently write.

Cake decorating Enjoy baking and have a bit of an artistic touch? Learn how to decorate cakes and make them for special events. One of my mother’s old friends does this and makes quite a bit of money on the side.

Candle making Candle making is a great little craft to learn. You can often easily sell the candles at local shops and also through websites like Etsy.com.

Candy making Homemade candies are easier to make than you think and quite popular. Package them in nice little boxes and sell them through a local gift shop.

Card making This is another artistic “crafty” angle you can follow. Make greeting/birthday cards from scratch using your own photographs, some blank cards, and a healthy dose of artistic flair. Again, you san sell items like these through a local gift shop or at sites like etsy.com.

Catering If you love to cook, take the “Blondie” route and start a home catering business. Catering is a business that’s perfectly designed to reward those who plan well and can often fit perfectly into weekends, lining up wonderfully opposite a normal workweek.

Childcare service Many states allow people to start up in-home daycares with minimal licensing and paperwork. If you love children and have plenty of time and space at home, this is a perfect business to get into.

Cleaning services for businesses Many businesses and civic institutions have a need for individuals who will provide cleaning services at a low cost outside of business hours. This is a great side business for those who can put in a few hours late at night or on weekends.

Collectible trading If there’s a particular type of collectible that you know a great deal about, you can often make good money as a collectible trader, utilizing tools like eBay and opportunities to find those collectibles in the community. I had some success with this myself with both trading cards and video games in the past.

Computer troubleshooting I had some success with this in the past, though I’ve largely moved away from it now. If you have a knack for fixing computers, this is a good place to start.

Consignment buyer Consignment shops and consignment auctions are often loaded with good deals if you know how to identify them – quite often, you can turn these good deals around and make a nice profit elsewhere. Get started by visiting some consignment shops and critically evaluating the prices on the items there.

Cookie making Much like candy making, homemade cookies can be a great seller. Bake the cookies, package them well, and resell them through a local gift shop. Often, you can find people in your social network who will buy batches from you for special occasions.

Dinner preparer I recently met a woman who earned quite a bit of money as a very part-time chef. Once a week, she would go to someone’s house and prepare a homemade meal for their family, then do all the dishes and cleanup work. This gives the family plenty of together time, while earning the lady some cash in the pocket. If you love to cook, this can be a great opportunity, but you may have to put a lot of work into searching for clients.

Event coordinator Events like family reunions and large parties are often full of busywork that many people simply don’t want to tackle. That can be the perfect place for you to step in and take charge of the planning and coordination.

Event DJing Are you an audiophile? If you have a great sound system and a large selection of music, you’ve already got what you need to hire yourself out as a DJ for various events and receptions. This is a great way to fill an afternoon and evening while also earning some cash in the process.

Exercise teacher Many gymnasiums will trade membership and often a bit more for a person willing and able to teach an exercise class. If you’re in good shape, this is a great opportunity to earn some extra money, plus it can often lead to additional income with one-on-one teaching opportunities.

Furniture making If you’re adept at woodworking and have just a bit of basic equipment, it’s easy to get into business making deck furniture. It only requires a few items – a saw, a drill, a sander – and some creativity and passion for working with wood.

Garage sale management One person I know holds a garage sale at their house almost every weekend during the summer. As a result, that person has a lot of regular customers who stop by almost every weekend to see what’s on sale. That person then goes to neighbors and friends and offers to sell their stuff at that yard sale for them, splitting the proceeds. People are usually happy to do this, since they don’t have to go to all of the work of running a yard sale, but still get rid of unwanted items and earn a bit of money, too.

Gardening services I’ve actually had requests from others for people willing to do this, so the demand is out there. To put it simply, some people are willing to pay others to get a vegetable or flower garden started for them in their yard so they can have access to ultra-fresh produce without all the legwork.

Handy man services Skilled at basic home repair? Let people know that they can call you for little repair jobs, like basic plumbing and other things. You’d be amazed at the simple things people are willing to pay others to help them with.

Housecleaning Many people simply don’t enjoy cleaning their homes and are willing to pay a reasonable price to have someone do the work for them. This is a great way to earn extra money in a flexible way, particularly if you have time off during the workweek.

Interior decorating Fascinated by interior design? Have a huge collection of interior design materials around? Many people are quite happy to hire individuals to help them decorate their home – I know, for one, that I have no eye for this type of thing.

Jewelry making If you have a good eye for detail work and a lot of patience, homemade jewelry can be quite profitable. As with other items on this list, there are many opportunities to sell such items through local gift shops or at sites like etsy.

Knitting / crocheting / quilting Skilled at creating blankets and sweaters? There’s a huge market for these types of items – even better, you can usually make them in your spare time whenever you have it. As always, local shops and places like etsy are great places to go to sell such items.

Landscaping services Willing to mow lawns and trim bushes and trees? Many people are quite happy to pay for such services. Not only is this a great side business for a fit adult, it’s also a great way for a teenager to get a small business started.

Meal-to-go preparations Remember my earlier post about breakfast burritos? Making meals in advance is a great way to save money for yourself – but you can often prepare these for others as well and sell them for a markup. Prepare eight casseroles, for example, then sell six of them to cover your costs, and you’ve got two free dinners for your family (and maybe a bit more). You can grow this by taking orders from others and finding out what they like.

Online media consultant Like participating on messageboards, Facebook, Twitter, and so on? Become an online media consultant and help people promote things. Start small – help local businesses get a presence on Facebook and set them up with Twitter. From there, you can grow to whatever works for you.

Personal shopping Many very busy people and elderly people are willing to pay a fee for people to do their shopping for them. Simply retrieve a shopping list from them, return with the receipt, and accept payment for the purchased items (plus a little fee). You can often do this in conjunction with your own shopping trip if you’re well-organized (take two carts!).

Pet grooming Many people loathe bathing their pets and trimming their hair – I know I do. Pet groomers perform these tasks for a small fee – a perfect job for a person who loves dogs and cats.

Pet sitting When people go on trips, they’re often concerned as to what will happen with their pets. That’s where you step in – offer yourself as a safe place to leave their pets, or be willing to go to their home to take care of their pets.

Pet walking Many busy people leave their pets home all day, but realize that those pets really could use a vigorous walk (and an opportunity to relieve themselves) during the day. Pet walking is a great opportunity for exercise, fresh air, and some pocket money if you have free time during each day.

Pet yard waste cleanup For many people in suburban areas, cleaning up pet yard waste is a real hassle – it’s disgusting, for one. Instead of cleaning it up themselves, they might hire someone to do it regularly, two to three times a week. There are several such services in our area, actually.

Produce selling Like to grow vegetables? Focus in on one vegetable and sell the excess to grocery stores and at farmers’ markets. My father does this with tomatoes and earns some solid extra money during the summer months. You can do really well, though, if you can grow things inside during the winter – February fresh tomatoes can sell quite well.

Proofreading Have strong English skills and exceptional grammar? You may have opportunities to work as a proofreader from home. Advertising for this can be difficult – seek out those who might actually be able to use your services and advertise directly to them.

Public speaking If you’re the type of person who can get the attention of a room easily, public speaking might be for you. Take advantage of every public speaking opportunity you can and you’ll be surprised at the opportunities that make themselves available for you.

Scrapbook making Many people dream of having beautiful scrapbooks. They collect all the materials they want in the scrapbooks but never follow through on the actual creation. You can step in here – take their ideas and materials and assemble a scrapbook for them.

Senior citizen assistance Many elderly people need assistance with a wide variety of simple household tasks – cleaning, laundry, and so forth. Many children of elderly people are quite willing to hire someone to help out their parents.

Sewing and alterations My wife is quite handy with a sewing machine and often hems and modifies our children’s clothes. She could easily take this a step further and offer her services to others, doing basic garment repair and modification for a small price on lazy evenings.

Soap making Making amazing homemade soaps isn’t as hard as you might think – it just takes time and patience. Again, items like these can easily be sold via local gift shops and through websites like etsy.

Teaching music If you know how to play an instrument (particularly the piano or the guitar) and have patience, you’ve got what you need to teach others how to play. Offer lessons in that instrument to others – this can also be an excellent thing to barter with, too.

Toy making From simple things like sock monkeys to more elaborate things like handcrafted chess sets, many people are willing to pay good money for handcrafted toys that you can easily make at home in your spare time. Again, gift shops are the place to go with items like these.

Tutoring Did you major in a particular topic in college? Do you have patience with children? You likely have what you need to tutor kids in particular subjects. Seek out parents and let them know that you tutor in a particular subject and provide materials for them to share and phone calls will often trickle in.

Video preparation services Many people like to have videos made for special events, such as weddings, or for gifts. This may mean actually taking the video yourself at a special event, or it may mean simply assembling materials and creating a video from those items. Either way, with a well-equipped PC, some taste, and some patience, you can make quite sophisticated video productions at home.

Virtual assistant Many ultra-busy professionals appreciate having someone who can check and answer their email, organize task lists for them, update their calendars, and so on, with minimal interaction. The best part is that you can provide this service from home with a good internet connection.

Web site design Many small businesses in your community could use a very basic web presence to tell others about their business. Quite often, these businesses don’t have a large budget for such things. That’s where you come in – get a bunch of clients from the local community by beating the pavement, create sites for them, and maintain them for a small fee. Get enough businesses and you have a nice side business of your own that doesn’t require a ton of maintenance time.

Wedding planner If you’re one of those people who can’t help but flip through bridal magazines and think about various wedding arrangements in your daydreams, wedding planning might be the perfect thing for you. A great way to get started is to develop a website on the topic, get to know people online, and offer your services throughout the community.

I’m betting the readers have many, many more ideas along these same lines.

Prior to making that leap, I worked full time in a research lab with a small, rather tight-knit group of people and I spent my spare time (when I could find it) working on The Simple Dollar. After a year and a half of essentially managing two careers, I began to realize that it was creating a great deal of wear and tear on my family and on my relationships, so I made a difficult choice – and took a leap of faith on the writing.

I did a status report at the four month mark regarding how the transition was going. Among the highlights:

The huge amount of time that I didn’t have before has opened the door to countless projects
I feel genuinely fulfilled by my work
I miss my old job – at least the socialization aspects of it
I get stir crazy and often have to leave to go do something
Time management is a completely different challenge than before
My biggest frustration is the interruptions
The new money management stresses me out sometimes

That’s actually a great description of the situation as I saw it four months after changing my career. At this point, though, different things have moved to the forefront and other things have moved to the back burner. Here are the big things I’ve noticed after a full year of working from home.

My biggest challenge is often loneliness
This might seem like a strange complaint, but it’s true: the biggest frustration I regularly face is simple loneliness. I miss the ability to simply stroll across the hall and talk to people throughout the day. I miss social interaction, in short. This was made somewhat worse by a very rough Iowa winter, coupled by the fact that I live in a rather rural area, meaning there isn’t a local place I can visit for that interaction.

What’s the solution? One of the best tactics I’ve found is actually just calling people regularly. I call my parents quite often during the afternoon, mostly to hear what they’re up to and recharge my social batteries. Not only do such calls help keep the social circle going, it enables me to get past any loneliness I may be feeling, gives me a sounding board for ideas, and also helps me keep in touch with the concerns of others.

My biggest benefit is time flexibility
The single biggest benefit of working from home is the time flexibility. I can easily address any task that I need to focus on, whether it’s personal or work-related, as it comes up, provided I’ve built up enough of a “buffer” with my work tasks. Aside from a solid three hour block of time each day that I devote to my family (5 PM to 8 PM, roughly), my weekdays are basically filled with whatever task (in any aspect of my life) seems most urgent at the moment.

There are some big caveats here, though. First, I have to maintain a work buffer – that means I usually have quite a few articles already completed and ready to go before you read them. Second, I have to have a good sense of what’s a priority and what isn’t. Both of these attributes take a great deal of time to develop and maintain in order to gain flexibility. Things don’t become flexible just because you’re self-employed – you have to be able to make the situation flexible.

Meditation and prayer have grown in importance for me
When I was at my previous job, I rarely felt like I had time for things like meditation or prayer. They seemed like good ideas, but there was always something else to do. When I switched careers, I made it a goal to get more in touch with my spiritual side – and it’s the best thing I’ve done in terms of my personal growth.

Each day, I spend a bit of time in what I would describe as a mix of meditation and prayer. Most days, I do it twice – once early in the day and once in the late afternoon. These sessions are simple – I usually just attempt to relax myself, empty my mind of cluttered thoughts (I actually jot down everything I think I’ll need to deal with later), then sit still for a long while, clearing my mind of everything. Whatever comes, comes. Doing this twice a day has done wonders in terms of my clarity of thinking in all aspects of my life.

If I ever return to a “nine to five” career, I will take this aspect of my experience with me.

It’s easy to get overly introspective
It is very easy for me to start chasing windmills. I’ll get obsessed with some little detail of some project I’m working on or on some strange idea in my head or some little aspect of my health, and it will draw all of my focus if I’m not careful.

For me, good task management helps. I’ve become devoted to the use of task management tools to keep me going with my work. Whenever I finish a task, I try to move quickly to a new one. If I find a task is becoming overwhelmingly detailed, I stop, make an effort to break it down into smaller pieces, then work on those pieces. I also make an effort to eliminate distractions, and I’ve come to pride myself on days where I stick to my “to-do” list and accomplish as many items as I can on it. Without that kind of guidance, I’d get obsessed with all kinds of wasteful things.

Finding the right balance of not taking on too much is still a challenge
Sometimes, I feel like I can accomplish far more than I’m doing. Other days, I’m hit with a gigantic case of writer’s block and I can’t seem to accomplish anything. Given that I choose what I work on and what to commit to, I can put myself in great danger if I commit to too many things – but I’m also driven enough to want to commit to plenty of projects. There’s a balance there – and it’s still a tricky one.

My solution revolves around doing as much work up front as I can. If I’m going to start a series on The Simple Dollar, I usually have the whole series framed and quite a few of the articles already written. If I’m shopping a freelance article, that article is either done or close to it. My second book is already extensively outlined and half-written, but I still haven’t signed a contract for it.

Doing things this way gives me the maximum amount of freedom to work with my own personal ebb and flow. I can work hard when things are flowing well and not be panicked if I get a big dose of writer’s block.

Careful bookkeeping is essential
When you work for an employer, keeping track of taxes and other expenses is done for you – you just collect your paycheck and do your taxes at the end of the year. Once you’re working for yourself, you have to keep careful track not only of any income, but also of any spending that you do during the year that’s related to your work.

Take the time to develop a filing system that you understand. Mine tends towards the simple – I mostly just focus on making sure I have every receipt and invoice in a constant place. I also maintain a careful calendar of all financial due dates – quarterly tax dates, for example. Without it, things would get problematic very quickly.