Updated on 09.16.14

Thoughts on Working from Home – One Year Later

Trent Hamm

One year ago, I began my journey as a full-time writer working from home.

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.

What I’ve Learned After a 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.

Loading Disqus Comments ...
Loading Facebook Comments ...
  1. Megan says:

    I always enjoy reading about the “backside” of the Simple Dollar…all the behind the scenes effort that goes into creating this blog. I tend to romanticize what it would be like to work from home and apprciate you pulling back the curtain here.

  2. Dana says:

    Trent, thanks for sharing. I can relate to most of your issues. It is a very different challenge, when you’re the master of your time.

  3. Nick says:

    I am familiar with the phrase “tilting windmills”, from the classic Don Quixote, but I’m not entirely sure what it means to chase them. Most are a fairly permanent fixture in the landscape.



  4. kev says:

    I’d love to work from home, writing a blog. Except my blog writing experience usually goes; 1. Establish blog; 2. Get excited about blog; 3. Write first post; 4. Never post again; 5. Hope nobody ever finds that blog I abandoned when I was nursing unsavoury opinion about topic X.

    Speaking of unsavoury opinions, my posts always seem to get hung up in moderation for days and days on this site… I’ve been trying to make sure I don’t use any questionable words, and I generally don’t say anything TOO controversial… is it just me? My wife says I’m not terribly objectionable most of the time!

  5. kev says:

    @nick: The use of tilting in the phrase “Tilting at Windmills” refers to jousting or otherwise engaging in sporting horseback duels with windmills.

    Obviously, to tilt at windmills is to go on a fools errand, to waste your time and energy attacking non-existent enemies.

    Sorry if you don’t see this for a couple days, I’m on the moderation blacklist for reasons unknown.

  6. Stacey says:

    i can relate to the loneliness aspect – i work for myself (and until sept out of my house) but even though i am no longer in my home after renting an office, i still work alone – some days not talking to anyone buy my husband at lunch time and the children in the evenings. I also live in a very rural area (south dakota) and have to deal with the same cold winters in a place with no “outlet” (no mall, no walmart, no mcdonald’s, no theatre except the weekends and even then it’s just one movie, no YMCA or workout facility, nothing but the bars for “social” time…) glad to hear calling your folks keeps you charged – that doesn’t work so well for me! but if you come up with a column entirely devoted to “things to do in a small rural town to keep yourself sane” i will absolutely be bookmarking it!

  7. kev says:

    From people I know who do it well, part of the knack is keeping office space separate from home space, and also making sure you are dressed for work (even if that’s casual); basically, get up at a set time, shower, eat breakfast and then “go” to work, even if work is in the basement.

  8. I’m just curious, but is there a reason you’re staying in such a rural area of loneliness is a problem? Moving to a more urban (but not necessarily a city) area would probably help. Just being around people while getting work done in a cafe can really help with the feeling of isolation.

  9. Faith says:

    Perhaps some volunteer work 5-10 hours per week could help with the loneliness, especially something that is very people oriented so that you can meet new people and discuss different topics. Perhaps something that your family could also participate in so that you can interact with people AND get some great family time in. =)

  10. Susanne says:

    I can relate to much of this. My husband and I both work entirely from home, on the Internet. Funny – we have a ton of interaction with people on a daily basis through e-mail and discussion forums, but our face to face interaction with other human beings is severely limited. I am a pretty social person, so that can be hard for me. I’ve just had to make myself get out and try new, non-work-related things so that I can meet people.

    However, I also agree about the flexibility. We love taking time out of the day to go to the park or go grocery shopping or take a nap (it does happen every now and then!). We have a great deal of freedom with our time, and I am grateful for that.

  11. Nanc says:

    Your mediation/prayer sounds alot like what I do. My practice is based on the book Open Mind, Open Heart by Thomas Keating. I went to a workshop to get the basics and enjoy my time spent letting the world go by without me.


  12. Trent totally agree with Dana’s comments. Funny how most of us go through similar things. We just dont know it becuase not everyone SHARES what they are going through.
    Thank YOU for SHARING.

    Tim at Smile-Therapy.com

  13. Julana says:

    Thank you for posting this.
    We’re thinking about homeschooling next year, and some of these issues would come into play, in that case.

  14. Roger W says:

    Thanks for the wrap-up — it’s good to see others going through similar challenges. I started working from home part-time and enjoy having both options. As an overly analytical person, my challenge is getting used to what used to be a clear line between work and personal: Oh look that plant really needs watering. Am I “allowed” to water it? Of course, I tell myself, but can I now prune the dead leaves I found?

  15. Marianne says:

    As a SAHM, I can relate to so much of this!

  16. Frugal Dad says:

    Has it really been a year? Wow…time flies! I’m still plugging away on that first year and a half path you were on of trying to manage two careers. It really gets to be a time squeeze some days, but I’m making it work.

    Funny, I don’t think I would miss much about work in the corporate world if I left it, but I’m sure after a few months I would share many of the same feelings you do. Hope you can find something to ease the loneliness – volunteering was a good suggestion. Maybe taking a break to head to a gym for a good workout with other people would be worth it for the social benefits, particularly if you had a friend you could meet for a noon workout (maybe around their lunch break).

  17. Avdi says:

    Have you considered coworking for the socialization aspect? I’ll be starting a job that allows me to work entirely from home soon, and I plan on joining a local coworking group maybe two days out of the month so I don’t go stir-crazy. Granted, a coworking membership might be an extra expense; but if it’s for mental health it could be a good investment.

  18. Roger says:

    Congratulations on one year of working on your own, Trent. Good to hear about some of the techniques you’ve been using to avoid getting around your loneliness as well as the other problems of self-employment.

  19. Pennie says:

    Yes, congrats to you Trent on your first anniversary of self-employment! DH and I worked from a home-based business for years, and the social isolation WAS a real-life issue. I began volunteering 5-6 hrs a week for the Red Cross, filling the void perfectly–I met so many nice people. The added plus? When I needed a little part-time work after my husband retired my 8 years of service (and the power of networking) led to a terrific job offer with them!

  20. Cyllya says:

    Thanks for sharing. I’m hoping to be self-employed and working from home soon, so it’s nice to have as much info as possible about the challeges I’ll be facing.

    But this isn’t the first time a personal finance blog has made me pity extroverts. I can count it among my blessings that I am an introvert.

  21. new fan says:

    I’ve been self-employed for 3 years and the loneliness is a huge factor, even though my work is very fulfilling. You really hit the nail on the head with that one and I’m already thinking about ways to fix that problem for myself. I’m somewhat of an introvert, but at least having others physically around makes an impact on my day.

    Google chat helps a bunch, having family and close friends on there, but it’s not the same as running into someone on the job and chatting it up.

    The good side is I’m extra excited to see my wife get home from her job everyday. :)

  22. Sally says:

    Is there a place with wifi where you can go and work a couple of hours a day? Hanging out a coffee shop, for example, may help you get to know the regulars. (Of course, the coffee costs money…)

  23. Dawn says:

    Thanks for sharing your experiences. I do have one question though – what did you do BEFORE making the leap to prepare for life after quitting? Did you first make sure you had a minimum level of savings to act as a buffer(if so, how did you know how much you would need)? Did you wait until you were making a minimum level of income from your writing before you decided to do it full time? Another writer I know of advised aspring writers to wait until their writing income is equal to what they make on their day job, for a period of two years, before quitting the job. I wonder if you had a similar rule for yourself? Your thoughts would be much appreciated and I apologise if this has been discussed elsewhere (couldn’t find the relevant posts).

  24. Great thoughts Trent! I would totally agree with your points. I’m self-employed and work from the house and there are a lot of days I schedule breakfast and lunch appointments with friends just to get out of the house and have some social interaction. But I love being able to be home with my wife and daughters during the day and build my schedule around what’s beneficial to me and our family.

  25. Battra92 says:

    Part of me would like to go into the working at home thing but I know exactly how it would be. I would basically become a more secluded and lazy individual. When I worked at a silver shop where I sat in an empty office for hours a day (my boss was terminally ill though he never fully let on how bad he was – or he didn’t know) with only the phone to keep me company I turned to sitting and watching Google Video / YouTube for hours and hours. If I worked from home I’d be glued to Huckleberry Hound reruns and be raiding the fridge.

    Or as Dilbert pondered, “Do I owe my employer eight productive hours or do I only need to match the two productive hours I would have in the office?” (then you factor in how much you’re saving the planet by not driving and it’s down to one hour. ;) )

  26. Melody says:

    I echo that I can completely relate to how you feel. I work at home running our family business, and my husband is either home or not. (he does the customer-side work) My 3-year-old is home with me most of the time, though, and that is becoming an ever-increasing challenge! I’m assuming, Trent, your kids are watched by someone – daycare or otherwise. Either that, or you have the opposite personality type I do! LOL She won’t leave me alone for anything.

  27. Jennifer says:

    Thank you for sharing your tips on how to stay focused and not to get obsessed on details. I live in PA and work in NYC. I commute 5-6 hours a day on the bus. (You do what you need to do to support your family!) I am trying to build my own business during my bus rides and in the evenings and your tips are helping me to keep me on track. (Oh and I have 2 children – a 3 year old with autism and a 1 year old). I love reading your inspirational articles so one day, I can be working at home too. I am saving this one to keep me motivated. Thanks Trent!

  28. Thanks for sharing.

    The secret to independence is self discipline and time management . . .

    I can relate to trying to take on too much– I often have to reign myself in . . .

  29. et says:

    Stacey – “things to do in a small rural town to keep yourself sane” starter list: if there’s no restaurant/meeting place (or just to save money), then start a regular “coffee klatch”, breakfast or lunch at home or trade off hosting among the members; start or join a book club; volunteer in schools, for church, meals on wheels, etc. (or start up a needed service program); start a community garden, poet’s society, artist group, etc.; check out online/virtual volunteer opportunities (the U.N. sponsors a worldwide effort & I’ve found others that proofread text-to-online books, etc.); craft blankets, premie outfits, hats, other items for groups that gift hospitalized or chronically ill people; read all those great books you never got around to; teach yourself a new musical instrument (there are good online guides for just about anything, if there’s no one local to teach you).

  30. Courtney says:

    I find I have trouble focusing, too. Screen-sucking time is to the point where I close down all non-essential software when I’m “working”. I have also joined a couple of “mommy” groups just for some social contact.

  31. Time management seems to be my biggest hurdle right now. But I have created a time map for my day and that seems to be helping some.

    Good to see others also struggle with this, but also are finding solutions. Makes me feel both not alone and also like I will be able to succeed.

  32. Thanks for the insight, Trent. I’m way behind you, as I just started my blog, but I hope to be in your situation someday. I’m glad you touched on the negatives, this will help prepare me.

  33. Mona says:

    It’s so great that you journaled your experience in the beginning and can now reflect one year later.

    I worked from home, and home-schooled my children. And while I was too busy to even think about journalling it all, (most of my writing was in the form of lists and schedules) I received the most powerful insight and reflection just the other day: feedback from my one of my grown children.

    My concern, upon looking back was whether or not they got enough attention from me, since much of my time as home was spent working. I asked her if she felt it would have been better for me to choose a traditional career with them in daycare, rather that working from home and having them home with me.

    Her answer was an unequivocal NO. She remembered vividly the time spent in daycare… what she described as a continual “longing” and a “missing piece of the puzzle”. To her, even though I was busy alot of the time, I was still there if/when she needed me.

    And it was just the reason I made that decision all those years ago…

  34. Bill in Houston says:

    I have to ask, “How’s that working for you?” By that I mean, are you making enough to support yourself and your family? I’ve been a writer for 21 years, but I’ve always worked for one company or another (even as a self-employed contractor). I’ve never submitted an article or gone the e-tail route with a web site. I’m lucky in that my wife also works, but there’s always that chance that we could have a major income change. I hope things are going well. I enjoy your site and plan to buy your downloadables.

  35. Sharon says:

    Trent, for a change of pace, you might want to write in the field you worked as a researcher. Then you can go see your old colleagues and reconnect. Also, we need good science writers, and with your writing skills you would do well.

  36. IRG says:

    Econowhiner.com recently posted a great article on the loneliness of those who work alone/at home.

  37. About 6 ago I did working from home for about a year. My biggest concern was loneliness and gaining weight.

  38. How do you stay focused working from home?
    I’m working from home for a few days, and I find it really hard focusing on my work like I would if I were at the office. How do people do this for a living and actually accomplish anything? Way too many distractions!

  39. sharon says:

    Wow! Thank you so much for sharing and to your reders. I just made 1 year working from home for a company and have lots of e-mail and phone contact but don’t ‘know’ any of those folks. To combat the lack of social interactions, I make lunch dates with my friends and former colleagues.

    Being out of the ‘mainstream’ created major doubts if I’d made the right choice but it seems to be working out thus far, at least financially.

    Thanks for sharing your experience and having this forum where others can share their experiences. It’s nice knowing one is not alone.

  40. Alison Law says:

    Congratulations on one year! I celebrated my first year of working from home in February, and it’s been such an education. I’ve learned many of the same lessons and experienced the same revelations that you’ve shared here.

    Timing is everything – had the economy taken such huge tumbles in late 2007 instead of late 2008, I probably would have remained in a job that was not right for me out of fear. Instead, thanks to the support of my friends and family, I took the leap.

    I started spending more consciously and putting the right financial fundamentals in place way ahead of the curve – before many others were forced to cut costs because of lost jobs, furloughs or other symptoms of the economic malaise. I tell people that our (my husband and I) biggest accomplishment is that our savings is the same amount it was a year ago, even after my husband was laid off from his job and we were without health care benefits and a steady paycheck for six months.

    When you take the steps necessary to disentangle yourself from your the ill-informed belief that money is everything and stop measuring your self-worth by your annual salary, then you have the ability to take control of your life and your career. Thanks for your insights here.

    P.S. All of the comments and subscriptions here should make you realize that you are not alone. :)

  41. Congrats on being your own boss for a year! I’m at the half way mark with my little art and design business. I’d say the hardest parts for me are the loneliness, time management and distractions. Distractions and time management are especially tough because my living room doubles as my studio so it’s very hard to separate work from life. My next apartment will definitely have a separate office space!

    I like the way you laid out your problems and solutions. The meditation sessions are a great idea! I think that most people forget that at the core of being in control of your business you need to be in control of yourself.

  42. RateNerd says:

    I can completely relate to your situation. I am going on my third year of self employment – one of the best things I have adopted is my “A.D.D. Break” from around 11 AM – 2PM each day. I work out, go walk the dog, ride my bike, etc and it recharges me. I could never do that when I had a big corporate job. Congrats!

Leave a Reply

Your email address will not be published. Required fields are marked *