Shannon writes in with a great question:

I’m trying to figure out how exactly I should save for several goals that I have. Here are the things I want to save for:

1. A BlendTec blender – $300
2. A complete refinishing of the downstairs bathroom – $3,000
3. A vacation to Germany next summer – $5,000
4. A car replacement – $12,000
5. A house down payment – $25,000

How do I prioritize these things? How do I go about saving for different goals? Where do I put these different batches of money?

This is a great question, one that you spelled out incredibly clearly and one that most of us struggle with to some extent.

Let’s break down your question into multiple pieces.

How exactly do I save for multiple goals at once? The easiest way to do this is to choose a bank that facilitates this process quite easily. I can recommend two banks for this – ING Direct and SmartyPig. I’ve used both of these banks. They both have great customer service and they each have a set of tools to make saving for a lot of goals quite easy.

With ING Direct, you simply open an account there, which will give you a single savings account. Once you’ve done that, it’s quite easy to simply open additional savings accounts and give them each nicknames. Just create an account for each goal.

With SmartyPig, you actually create savings goals within your account. You can create as many as you’d like.

With both of these, you simply link your new account to your regular checking account and set up automatic transfers to fund each of the goals or specific savings accounts. Easy as pie!

But how much do I save for each goal? The key thing to remember with any and all savings goals is that you’re trying to come up with a certain dollar amount at a certain time. Shannon certainly knows what her dollar amounts are, but she’s mostly unclear as to the timeframe.

Let’s come up with some examples of deadlines that Shannon might decide on.

Shannon wants the blender before Christmas, so she has three months to save for the $300 blender.
She wants to refinish the downstairs bathroom next spring, so she has six months to save for the $3,000 renovation.
She wants to travel next summer, so she has nine months to save for the $5,000 trip.
She wants to replace her car in two years, so she has twenty four months to save for the $12,000 car replacement.
She wants to buy a house in four years, so she has forty eight months to save for the $25,000 house down payment.

So, how much does she have to save per month for each goal?

For the blender, she needs to save $100 per month ($300 divided by 3 months).
For the downstairs bathroom, she needs to save $500 per month.
For the trip next summer, she needs to save $555 per month.
For the car replacement, she needs to save $500 per month.
For the house down payment, she needs to save $521 per month.

Now, that seems pretty stiff, doesn’t it? That’s a total of about $2,200 per month to save. What if Shannon can only save $1,000 per month for her goals?

There are two ways to do this. One is to simply prioritize. Is there one goal (or more than one) that can be postponed for a while?

The other is to simply focus on the goals chronologically. In other words, she goes through that list and applies the full $1,000 toward each goal on the list, with the nearer-term goals at the top and the longer term goals at the bottom.

So, during the first month, she’d put $300 toward the first goal, completely fulfilling it. She’d then drop $700 toward the second goal. Over the next two months, the full $1,000 would go toward the second goal. In December, she’d put $300 toward the second goal, fulfilling it, then put $700 toward the trip goal. This will get her pretty close to fulfilling all five of the goals.

In other words, if all of the goals have a high priority, put all of your savings toward the one with the closest deadline. When it’s fulfilled, move on to the next goal.

Good luck, Shannon! You’re definitely on the right path.

A few weeks ago, I put out a call on Twitter and on Facebook for detailed posts that people would like to see. I got enough great responses that I’m going to fill the entire month of July – one post per day – addressing these ideas.

On Facebook, Joan wondered “What do you do when your financial goal seems out of reach?”

Goals that feel too out of reach are certainly a challenge. They can leave the goal-setter demoralized and feeling as though the goal will never really be accomplished, so why try at all.

I’ve fallen into this trap myself, often with fiction writing. I’ll have some great ideas for a fictional story, but when I sit down to write it, the story feels too big and the writing task just too immense to really tackle it at all. The sheer scope of it scares me away from even starting.

For others, goals such as eliminating all of their debt, starting a business, or having and raising a child can take on that particular flavor of out-of-reach hopelessness. I’ve found that there are seven techniques that really help me in dealing with my out-of-reach goals (and have helped me make some amazing progress on my fiction writing).

I’ll talk about these goals with the perspective of a recent goal-oriented experience of mine: working on my fantasy novel.

Embed yourself deeply with people who have achieved what you wish to achieve
Make friends with them. Spend time with them. Read their books and their blogs. Listen to their audiobooks and radio shows. Know their experience of succeeding in this area as deeply as you can. This not only will help you to believe that it’s possible, but also give you an abundance of techniques for making it possible.

Over the years, I’ve read countless books on the art of novel writing and follow the blogs and Twitter feeds of many of my favorite fiction writers, including Neil Gaiman and George R. R. Martin. They provide a constant reminder that it is certainly possible to take the dreams and ideas and world you’ve conceived in your head and convert it to the printed page.

Shrink the goal down to a milestone that’s not quite so immense
Instead of focusing on paying off all of your debts, focus solely and exclusively on paying off whatever debt comes first in your debt snowball. If you’re focused on saving for a down payment, focus instead on the next thousand dollar milestone – $1,000, $2,000, etc. Using smaller milestones as your focus point makes it all seem that much more reachable.

For my writing, by focusing on a plot outline or a single chapter at a time, the entire project started to become more manageable. It moved me from simply thinking that the project was too big to really embark on to actually creating something, and simply by doing that, I put myself and the project in a better place.

Take baby steps every day
A goal is made up of thousands of little actions. You don’t get in shape without making the choice to exercise every day. You don’t improve your finances without choosing to minimize your spending every day. You don’t build a better career without doing your best at work each day.

For me, it was mostly a matter of committing to writing a small number of words each day (1,000 – but that’s a small number in the grand scheme of things for me). It didn’t have to be on the novel itself; that many words in character outlines and other materials are perfectly acceptable.

Reaffirm why you’re doing this
A goal without motivation is a hard one to achieve. There needs to be some sort of motivation, whether internal or external, to keep you moving toward your big goal. Without it, it’s easy to get distracted by immediate and short-term temptations. For my financial goals, I use my family as a motivator and I still usually keep a picture of my children wrapped around my credit card.

For my writing, I really get a lot of joy out of just getting into that “zone” where time seems to stand still. I try to get into that state as often as possible because I produce great material when I’m in that state and I feel great when I snap back to “reality.”

Be obsessed
It’s a lot easier to achieve a giant goal if you become obsessed (or nearly so) with it. If you’re enjoying the progress, there’s no reason not to allow it to fill up your spare time. Use your spare hours to cut your spending through frugality projects like air sealing your home. Use those spare hours to exercise or to prepare healthy meals. Use those spare hours to learn.

Whenever I find a spare hour, I usually try to either write or to read something that will inspire me to write. An open book and/or my Kindle are constant companions, as is a notebook of some kind.

Use reasonable metrics
Measuring your idea of success or failure against an incredibly long measuring stick is a recipe for failure. If the only way you can feel successful about your financial goal is if you achieve something that adds up to more than your annual income, you’re asking to fail. Instead, measure yourself by simpler things. Instead of focusing on the mountain of debt, focus instead on measuring how much less you spend than you bring in each month. By measuring this (and using previous months for comparison), you push yourself into actions that naturally move you toward the giant goal you want to achieve while also keeping things real.

My reasonable metric is word count for a month versus earlier months. I try very hard to exceed the word count of the previous month by just a few, which keeps pushing me to put my pen to paper (or my hands to the keyboard). I don’t worry about completing a novel or anything, as I know that if I keep up with the word count, I’ll get there eventually.

Remember that the only success that really matters is internal success
In the end, what really matters is that you’re internally happy with what you’re achieving or have achieved. If you don’t feel good about the way things are going, it’s going to be impossible to keep going. You have to have a deep positive sense both about the goal and about the steps you’re taking toward that goal.

I really, really enjoy writing and I really, really enjoy looking back at and re-reading what I’ve already written. That positive feeling is strong enough that it often pulls me along to continued future progress.

Mark sent me an email regarding my recent article, Some Thoughts on the Long Term, in which he asked the following question:

I still don’t see any compelling reason to worry about my future more than about five years down the road. I can think about where I’d like to be in ten years, but life shifts so rapidly that no matter what I think of it won’t happen. Why should I even think for a second about anything beyond five years or so?

It’s a good question and Mark does make a good point. I think there are a few pieces, though, that he’s missing.

Unless you unexpectedly die at an unnaturally young age, you will grow old. It doesn’t matter where your path leads you. Eventually, you will grow old. Eventually, you won’t be able to keep up with the levels of productivity that you have right now. Eventually, you will be less employable.

Retirement is a long-term savings goal that makes a lot of sense to participate in for those reasons. It’s preparation for a situation that you know will happen down the road. Unlike many long-term goals, aging will happen and it’s worth your while to be prepared for it.

Most other worthwhile long term goals are centered around the accumulation of flexible skills and resources. Many people set goals in the five to ten year range in many areas: career advancement, business building, personal growth, a house down payment, and so on.

The vast majority of these goals have results that are incredibly flexible.

For example, if you’re saving for a down payment and your life path changes so that home ownership is no longer a goal you’re interested in, you still have a significant amount of financial resources saved up that you can apply toward whatever direction your life is now headed.

Another example: if you’ve set a long-term goal of heading the IT department at your company and you spend years building an appropriate resume and skill set, only to see your company fold up, you’ve still got a great resume and skill set to shop elsewhere and help your career.

I can go on and on with such examples. The core principle holds throughout all of them: a great long-term goal usually creates resources and skills that are still valuable even if the goal changes.

Many people are motivated by having goals of all terms. I find a big, ambitious long term goal to be really exciting and invigorating. The vision of doing something that leaves a major mark in my life and the lives of others keeps me wanting to move forward on that goal.

Short term goals motivate me as well, but in a different way. They often feel very reachable, as though it’s almost inevitable that I get there.

I can describe the difference as if you were a person standing on a hilltop in Seattle. There’s a street sign nearby and you could reach it quite quickly. It’s easy to see yourself walking half a block to get there.

On the other hand, you can see Mount Rainier off in the distance, about fifty miles away. Reaching it on foot is a long journey, but the idea of going there often seems exciting (particularly if you’re new to Seattle).

Long term goals are like Mount Rainier. They feel almost impossibly far away, but they look enormous and inviting in the distance. The idea of journeying there excites you and you can’t wait to get going.

Amy writes in:

I have no problem setting goals for myself. I follow the steps you suggest: make them realistic, make them numerical so I can keep track of them, write them down, and so on.

The problem is that when I come up with a plan to reach them, that plan completely falls apart within a week, every single time. I’ll have a four day run of working out at the gym, then a crisis will happen at work or my son will get sick and then I miss a day and once that chain is broken, I feel like such a failure that I don’t go back. I do the same thing with financial goals. I will do good for a while, then an emergency happens and I just give up.

What can I do? Help me achieve some goals here!

This happens to be a very common problem for motivated people who set strong goals for themselves. I usually find that when something like this happens to me, it’s a sign of one of three different basic problems, each of which has a different solution.

So let’s look at each one.

For examples throughout this post, I’m going to stick with the example Amy used of exercise goals, since it’s something many of us are familiar with. The same principles hold true for any sort of self-improvement goal, whether it’s financial or relationship-based or anything else.

Unrealistic or inflexible schedule
Your goal is to get into better shape. In order to do that, you decide that you’ll work out every day, perhaps using a system like P90X. For several days, you stick to it, but inevitably your life hands you some complexity that makes it impossible to work out for a day. Boom – you’ve fallen off your schedule and you feel like a failure.

The problem here isn’t your goal or your general idea for getting there. The problem is that your plan for getting there is so strict and tight that ordinary life will inevitably prevent you from getting there.

My suggestion is simple. Rather than saying “I will exercise every day” and feeling like a failure when you miss a day, say “I will exercise four times a week.” When you’ve set that goal, front load your week so that you have a good chance of knocking out those required four sessions right off the bat, then you can even shoot for exceeding that.

In short, give yourself a bit of room for flexibility. Assume that there are going to be times and days where things are going to keep you from executing your exact plan for that day. What kind of plan can you develop that takes that into account?

Poor measurements of success
As I’ve mentioned before, a good goal is one that offers a very clear way to describe success, often a numerical description, and completion of that goal often leads to the effect you want. “I want to lose weight” isn’t a good goal, for example, because it doesn’t describe what success is. Is it one pound? Is it a lot of pounds?

Of course, at the same time, “I want to lose 50 pounds” isn’t a good goal either, because pure weight loss is a rather poor metric for what you’re likely wanting to achieve.

What is it that you do want to achieve? Do you want to feel healthier? Do you want to look better? Do you want to live longer? Each of these has different things associated with it that you’d want to make happen, from diet to exercise.

Talk to people who understand these issues who can help you figure out what you should be aiming for with regards to success in those areas. These discussions should help you to have a much deeper understanding of what kinds of things you should actually be shooting for and provide you with some reasonable guidance for setting meaningful goals that will get you what you want.

Lack of external motivation
Another problem with many such goals is that they’re entirely internal. If you’re the only person involved with the goal, you’re the only person you let down if you fail to achieve the goal.

One way to break through this is to find a “buddy” who is working on the same (or a similar) goal as you are. This gives you someone to exchange tips and advice and motivation with as well as someone to actually participate in activities with. The key benefit, though, is that you’re no longer the only person involved with your goal. You’ve got another person who’s on the line with regards to your success. If you fail, you’re letting your buddy down, and that can be a huge motivator for people.

If you don’t have any sort of “buddy,” another method is to simply tell people about your goal and your plan to get there and ask them to keep you on your toes about it. When you know your close circle is going to be watching for your success, suddenly the motivation for your goal changes. Others are involved and the stakes are raised.

In the end, nothing can make you achieve a goal if you simply refuse to make progress towards it. However, just a few tweaks can turn something that feels insurmountable and pointless and not important to anyone else to something that feels reachable, vital, and valuable to people around you. That’s a drastic change in the nature of your goal and it can certainly make the difference between failure and success, whether you’re talking about financial goals, fitness goals, or any other type of personal goal.

I’m never going to play in the NBA.

That’s an unrealistic goal for me, and I knew it to be an unrealistic goal when I was ten years old on the playground. I wasn’t fast enough and didn’t have the natural reflexes of the other ten year olds on the court.

It was a painful thing for me to realize. I loved playing basketball. I still do. For me, basketball is a beautiful game.

The realization that I wasn’t NBA material didn’t mean I couldn’t be an effective basketball player. I had other skills that I could certainly utilize at the playground level. I was very solid and could plant my feet well, which meant that I could be a good defender, especially under the basket. I was willing to scrap for the ball. I was often more proud of a rebound or an assist than I was of a basket. I wasn’t fast and I couldn’t hit the broad side of a barn more than ten feet away from the basket, but I did have at least some skills I could utilize and work on.

It also didn’t mean I couldn’t enjoy playing basketball. I wasn’t going to be the next Michael Jordan. So what? That doesn’t mean playing basketball wasn’t – or isn’t – enjoyable. As I grew older, particularly during my later high school years and especially my first two years in college, I really enjoyed playing basketball. I knew what my areas of expertise were and I focused on maximizing those and being part of a team. It was a lot of fun and I had a set of experiences from those days that I’ll always remember.

It also didn’t mean that, if I committed to it, I couldn’t have spent my life around the game. Sure, I couldn’t actually play the game at a high level. However, I could coach. I could be an announcer. I could be a scout. I could be a basketball blogger. I could be involved in sports marketing. I could be involved in physical therapy. All of these were options that could have kept me close to basketball throughout my life. Each would have required me to add some additional skills to my repertoire beyond just the ability to play ball, of course, but that’s to be expected.

What’s the point of all of this?

First, some goals are too audacious. It is not realistic – nor has it ever been – for me to set playing in the NBA as a goal. It simply is not going to happen. It would simply be a path to failure for me to set being in the NBA as a goal.

Having said that, there is often some large element of even the most audacious of goals that you can achieve. It might not be realistic for someone to be President of the United States, for example, but it is certainly realistic for that person to aim to be mayor of the town in which they live or to be part of the White House press corps. It might not be realistic for someone to be an astronaut, but it is realistic for someone to become a NASA engineer.

If you find those initial but still fairly audacious goals easy, then aim higher. For example, if you decided that being President wasn’t going to happen, but you found yourself going from nothing to assistant Parks and Rec director to full Parks and Rec director to city council to mayor in a six year span, you might just have a gift for politics and might want to look higher. If you’re young and you decided to not shoot for the NBA but just be the best rebounder on your high school team and you set state records for rebounding during your sophomore year of high school, you might just want to aim higher.

One way to achieve this is to set goals not based on achievement, but based on performance. Let’s say you dream of a political career but are just getting started with a chance to be an assistant parks and recreation director, look at that position and ask yourself what kinds of things you can do in that position to hit a home run in that position while also setting yourself up for higher steps. Make a plan to succeed in just that regard. Set specific short term goals that will define your success and build the relationships you need to climb from there.

Similarly, let’s say you decided you wanted to be a basketball announcer. As I mentioned before, I have a friend who goes home in the evenings, turns the television on mute, and practices announcing the games he sees on television. It turns out that he records these sessions and then listens to them, noting what he’s doing wrong along the way. He’ll watch games while listening to his recorded coverage of them, and he’ll also listen to the straight audio in the truck.

His big goal might be to be announcing games on TNT and hanging out with Charles Barkley, but his short term goal is the priority. His goal, every single day, is to record a play-by-play of a basketball game, listen to another play-by-play, and critique it. Beyond that, he’s making connections in sports broadcasting at every level, using Twitter and personal interactions to meet people who are actually in the business, particularly production folks.

Those are goals that are based entirely on the process of achieving his big goal. Even if his big goal doesn’t come true exactly as he envisioned it, I don’t think anyone would argue that he’s not creating a very compelling path for himself in sports broadcasting.

It gets better. His medium-term goal is any paid job broadcasting basketball games. Anything. It can be for a local radio station broadcasting high school games. It can be voiceovers for a website. Whatever it takes. Again, he has a plan for that goal that’s loaded down with the things he can do today.

If you’re reading this, you probably don’t have the skill set needed to be president or the skill set needed to be a Major League Baseball all-star or the skill set needed to be CEO of a Fortune 100 company. That’s okay. There’s still nothing keeping you from having a life filled with doing the things you love. Focus instead on who you are, what skills you can build, and what you can do.

You might just find a better path than you expect.

Over the last few days, I’ve been thinking a great deal about the goals I’ve set for 2011. For a quick reminder, here they are:

Goal #1: Get fit, which basically meant meeting a few fitness metrics

Goal #2: Play music, which meant being able to successfully play four pieces on the piano

Goal #3: Read 100 unread books, which meant largely clearing out my to-be-read list

I’ve had the most success so far with the third goal, far and away. It is the reason for that success – and the failure on the other goals – that left me thinking. Why that goal?

This morning, it hit me, out of the blue. When I put the revelation in context with the other goals I’ve previously accomplished and failed with in my life, it makes complete sense.

I succeed at goals where the goal itself is a process toward some further end. I fail when the goal is merely that further end.

Let me break it down and explain what I mean.

With the third goal, reading 100 unread books, the real thing I hope to accomplish is to become more well-read. The reading list I put up there is diverse, and by reading all of that stuff and absorbing it to the best of my ability, I’ll likely become a more well-rounded person.

However, becoming well-read is not the goal I set for myself. The goal I set for myself directly sets down the process for becoming well-read. Simply by accomplishing the goal of reading 100 books, I will have naturally become more well-read in the process.

Thus, I’m left with a goal that explains what I need to do right on the surface. Read. Read what? These 100 books I have listed here. I can go right down that list, knocking off book after book. There’s no question or deliberation about what to do. I just simply follow that goal.

The other two goals have failed because they don’t make it clear what I need to do. They both sound noble on the surface – get into shape and learn to play the piano – but they don’t immediately translate into some sort of action.

A successful goal, at least from my perspective, is one where it’s immediately clear from the goal itself what needs to be done and by doing what’s suggested, you’re pushing forward strongly on some value in your life.

So, let’s recast those two goals a bit, shall we?

The first goal is to get into shape. Being in shape is the outgrowth of following a routine exercise regimen. After talking to a trainer, we set up something of a plan for exercising every other day (with a day in between for rest) that hits cardio each time and a certain muscle group every four sessions.

If I were to actually do those sessions, being in shape would be a natural outgrowth. So, my goal should actually be go to the gym every other day. If I actually just accomplish that very simple thing, then the personal change I want – being in better shape – is a natural result.

The second goal is to play four pieces on the piano. Again, being able to play these pieces is the outgrowth of practicing them. Simply put, all I really need to do to be able to play these pieces is to simply practice each day.

If I set my goal to be the straightforward practice the piano for thirty minutes each day instead of the less clear and more lofty one I have in place, then actually playing the pieces I want to play will be the natural result of the steps.

I can even improve the third one. If the change I want to affect in myself is to be more well-read, reading that list of books will accomplish that. However, it still doesn’t point toward a simple action. How about spend an hour each day reading something challenging? I exceed that most days, but this gives the right idea. It pushes me constantly toward the change I want to bring about in my own life.

All of us have big changes we want to make in our lives. Success in making that happen comes often from the little steps along the way. Focus on those little steps for a while without worrying about the big goal. Spend your time just dribbling the ball instead of wanting to be the next Allen Iverson. Spend two hours on your side business each day instead of talking big about building a major enterprise.

Do the little steps right and your destination will sneak up on you.

Whenever I consider whether or not I should be doing something, I ask myself a very simple question.

Is this moving me towards my goals?

The outcome of that question casts a strong light on the activity at hand. Sometimes, it’s a positive light and it encourages me to move forward. At other times, it’s a negative light, and it makes me back off a bit.

It’s a very simple and very effective litmus test for everything that I do. Let’s break it down a little bit.

First, you’ve got to have goals
For this question to work, you need to have goals for the future. Almost always, I have a bunch of goals going on at once. Some of them are very short term, to be accomplished within a week. Others approach a lifelong journey.

Here’s a snapshot of a few of my goals, just to show you what I mean.

By March 16, I want to have the house prepared for a nearly weeklong visit from my sister-in-law and her soon-to-be spouse.

By the end of June, I want to have about three weeks of articles banked for The Simple Dollar so that I don’t have to worry about content production when I visit Seattle for the aforementioned wedding (and give myself a little bit of breathing room on either side).

By the end of 2011, I want to have “Project X” completed. What is Project X? I’ll tell you about it in the future, but it’s intended to be a fully passive revenue stream.

By the end of 2013, I want to have our home’s mortgage completely paid off.

Four goals. Four different timeframes. Four different sets of influences on me.

So, when I’m looking at what I’m going to do right now, I keep those goals in mind.

An example: I was out running errands earlier. I was near the local gaming shop, so I stopped in. There was a game there that I knew that Sarah and I would enjoy playing. Should I buy it?

Well, Sarah and I play a lot of games together – it’s one way we spend time together in the evenings (a positive towards the goal of being a good husband). On the flip side, we have several games on our shelves already that we’re itching to play (negative toward being more diligent about using stuff we already have), plus the game would cost $40 (negative toward every spending goal). I could also definitely afford to go home and research the game a bit more and perhaps buy it online at a later time, saving some cash.

So I move on, knowing that such a choice is not really taking away anything I might enjoy, but also knowing that it is yet another step towards goals that I have.

Does a bad answer always mean no?
Now, it would be easy to perceive this as being a reason to never indulge in anything that doesn’t take me toward a goal. Abandon fun, all ye who enter here? Not so much.

Yes, if something is a negative towards every goal that I have, I won’t choose to do it. Drug use? It’s not going to happen, because it’s a negative towards many of my goals (savings goals, being a good parent, etc.) and a positive towards none of them.

On the other hand, when a friend calls me up and invites Sarah and I over to do something fun, I’m almost always going to say yes. Sure, that time spent might be a negative towards some of my goals – I certainly could spend my time getting prepped for my sister-in-law’s visit or working on “Project X” – but it’s also a positive towards other goals, such as building key friendships and enjoying non-idle leisure (my friends don’t just sit there watching whatever’s on television).

Sometimes, I’ll even go ahead with things that are contradictory to more goals than are benefited by the choice. For example, I might decide to buy a new boardgame out of my personal spending allowance for the month. Yes, I could save that money for another goal and yes, there probably are games on my shelf that could be played instead.

But I recognize that such a choice really is a rare splurge. It is not something I do every day – or every week. Occasionally doing such a thing not only maximizes the fun of doing something so frivolous, it also reminds me that doing this every day would not be nearly as fun.

Doing something like that is a fun occasional splurge, but it’s not nearly as fulfilling over the long term as making consistent choices that take me towards my goals.

The big win
Of course, the best options are ones that simultaneously bring me deep enjoyment and move me towards a number of goals.

A period of writing where the pressure is off is a great example of this. I thoroughly enjoy writing when I’m not under some sort of time crunch, plus such writing almost always carries me towards lots of personal goals.

Planting the garden is another great example. It’s often a goal in and of itself, but beyond that, it’s a very frugal activity that gets me outside and gets some exercise (using the hoe, etc.). I enjoy every second of it, too.

Going to thrift stores with my wife often hits several things at once, as I’ll sometimes find things we’re looking for at a huge discount, plus I’m bonding with my wife without spending much money at all.

Playing with my kids, reading a challenging book, preparing dinner at home – these all fall under that umbrella.

When those things happen, when I hit a bunch of goals and do something deeply enjoyable, then I truly feel like my life is headed in the right direction.

I want to run for mayor of a large city.

I want to publish a series of fantasy novels that appear in every bookstore in the country.

I want to pay off the $300,000 in debt that I owe.

I want to start a restaurant chain.

I want to visit 100 countries by the time I’m 40.

I’m a fan of overly audacious goals. Setting a huge goal for yourself can shock you into action and sometimes make you go beyond what you believe you’re capable of.

In 2002 and 2003, I worked on a software development project that was far, far over my head. During the course of that project, the technical advisor (the one helping me figure out the actual specs of the software) essentially quit, leaving me to not only write all the code, but also design the interface of it based on what the customers would want.

Waiting around for additional hires was not an option. I either had to move forward or the project went under and I would be looking for another job.

Add on top of that the fact that I was writing all of this in a language that I was largely unfamiliar with (as I was under the impression I would have plenty of room to learn on the job).

When I realized the scope of what I had to do, it was almost overwhelming.

Not only did a two man team manage to pull it off (myself and a database expert), the project is still in existence (albeit in very modified form) to this day, using largely the same code I wrote in 2002 and 2003.

How did this happen? There were three real factors involved here, in my opinion.

First, a big part of this project was the personal challenge. I wanted to show myself that I could do this and, in the end, I was really the person that I was accountable to. If I failed without really trying, that sense of failure would hang over me for a long time. If I failed with a sincere effort – or better yet, succeeded – that would stick with me as well.

Second, a spectacular failure was worth far more than no action at all. I realized pretty quickly that if I gave this project my all, I would still get something out of it even if it failed. I would learn a great deal of domain knowledge. I would learn some significant skills. I would have an entry on my resume and a good story to tell. I would also learn some lessons from failure.

Finally, I had supportive people in my corner. The people up the food chain from my project were pretty supportive of what we were working on. They wanted us to succeed. They cheered us on when we needed it. They took care of peripheral things that would have just distracted us. They gave us carte blanche to use our own judgment, but were willing to provide input when we asked.

To be sure, not every big, audacious goal works. Any enormous goal you set for yourself needs to have a few key elements.

It must not seriously damage your life if you fail. No goal is worth risking the key things you need to have in your life. No goal is worth sacrificing your childrens’ needs or the well being of your marriage or your closest friendships or your career. If the worst case scenario of a goal is apocalyptic, it is never worth it. If you’re setting a big goal, spend some time teasing out the worst case scenario and make sure that you can roll through it. Often, this means that you need some advance planning before you leap into your big goal.

Ideally, you gain some degree of benefit if you only partially succeed – or even if you largely fail. For example, if you want to travel to 100 countries by the time you’re 40, but you only make it to 80 of them, you’ve still succeeded big time and you have a huge warehouse full of stories and memories for the rest of your life. If you want to pay off $300,000 in debt in seven years but only get rid of $240,000 of it – you got rid of $240,000 in debt. That’s not a bad thing.

It must be met with the support of key people. If you’re married, this always includes your spouse. It can also involve your coworkers, other family members, and close friends. The people you rely on most need to be in your corner when you approach something audacious.

The real fire has to come from within you. You’ve got to want it so bad you can taste it. If you don’t have the fire to make something happen, it won’t happen. Think of those moments in your life when you’ve most wanted something. That’s what this goal needs to feel like within you, because without that fire, you won’t go beyond what you think you’re capable of to reach that goal.

Set a big goal for yourself, something you’ve always wanted for your life. Throw yourself into it. You might be surprised at what you find along the way and on the other side.