The Hardest Adjustment To Self Employment

I apologize in advance for spelling mistakes, because I am writing this on my iPad on the bullet train to Tokyo. Wonderful device, not so great for writing lengthy blog posts like my usual.

I am on the way to Tokyo because a high school friend is there this week. As soon as I heard, I told him to pick a day and I would be there. What day? Literally any day. My schedule is infinitely flexible.

That is what scares me the most about this job. Like most people, I have lived an entire lifetime conforming to schedules. They exist like the Greek gods: you didn’t ask for them but they are there, there is no negotiating with them, and prolonged association means you are likely to get your dignity violated by a bovine.

But schedules are structure, and structure helps. Be at school at nine AM. Seminar starts at 10:30, do not be late. Work starts at nine, Patrick, waltzing in at ten annoys people even if you are contractually permitted to do it and even if you will still be here at 2 AM. (Regardless of start time. If you thought the gods were rational, you have been reading the wrong mythology.)

At the very least, schedules put you and everyone else on the same page as to what you should be doing. Gainfully employed young men should be working at 2 PM on a Wednesday. I was having a late lunch and reading a novel at the coffee shop. The waitress asked me, confused, whether I was a student or not. Students have social license to do bugger all for a few years prior to working for a living. I told her I run a software company, and one of the perks is that I get to have lunch whenever. She was impressed, but asked how my customers and employees stand that.

That’s the the thing about schedules: once you have one everyone else needs to, too, preferably as close to yours as possible. My customers do not share my schedule: most use my software when I am asleep, and mail me with their urgent issues at 3 AM in the morning Japan time. I spend lots of effort decoupling their happiness from my personal availability. This does wonderful things for site uptime but it also means, perhaps regrettably, that there is generally no compulsion to work today.

My freelancers largely don’t share my schedule either. I just got the front page for Appointment Reminder redone after several months with placeholder graphics. The extraordinarily talented designer I worked with (Melvin Ram at Volcanic Web Design, a web design company) “met” with me for a total of perhaps twenty minutes, and we worked (him on having graphical inspiration, me on wrangling it into a functioning product) in temporal isolation for the rest of the project. This is the arrangement I almost always use for freelancing. It is wonderfully productive except in that it lets me off the hook for causing forward progress.

That is the other part about scheduling: with the debatable exception of my consulting work, I am terrible about setting and keeping multi week schedules for milestones. This never came up when I was employed, since I had managers to crack the whip and avoided doing anything multi week for my business, but it is now biting me with a vengeance. I wanted to have AR in beta six weeks ago. Between consulting, vacation, and BCC, I haven’t made almost any forward progress on engineering.

I know that to be true for AR because code isn’t getting written, but I always think it to be true for BCC. It turns out that I am smoking something: I ran a shell script to compare my productivity (commits, A/B tests, etc) prior and post quitting. I thought it would show me spinning my wheels. Turns out I am getting more done than ever. This is normally the point where I would paste a graph but, sorry, iPad. Suffice it to say I have run more A/B tests this summer than in the last year. (Interesting finding of today: Google Checkout really does increase conversion rates over having only Paypal as an option. I strongly suspected that, but now I know.)

Sales are up, too. Why doesn’t it feel this way? I think after a couple of decades of living by the clock I have become habituated to measuring my productivity that way. Insane and irrational, I know.

I am looking for ways to hack this: the discipline and social validation of having a schedule, without actually having to work at nine. I have been considering getting an office just to have mental separation between work and non work. (They give them away in this town if you work in tech. I could pay the rent with the savings in my iced cocoa budget.) Plus, if I have an office, I have an offsetting factor the next time I am accused of being unemployed. Sounds funny until it happens from a police officer who does not quite understand immigration statuses. (You know that controversial immigration policy in Arizona? Don’t ask me my opinions about it around sharp implements. Suffice it to say I can vividly imagine what getting stopped under it will feel like.)

Another way is, and you might laugh, a little iPad app called EpicWin which gives me fake RPG loot for making progress. Will it work? No clue, but one week in, I seem to be getting more of my “boring” chores accomplished. (I had considered building this into my business for a while, but resisted because I thought it would cause neglect of my nonbusiness priorities. It turns out that, if anything, I have the opposite problem now that I have infinite scheduling flexibility.)

And I just earned 100xp for this blog post.

About Patrick

Patrick is co-founded Starfighter, founded Appointment Reminder and Bingo Card Creator, and presently works at Stripe on Atlas. (Opinions on this blog are his own.) Want to read more stuff by him? You should probably try this blog's Greatest Hits, which has a few dozen of his best articles categorized and ready to read. Or you could mosey on over to Hacker News and look for patio11 -- he spends an unhealthy amount of time there.

19 Responses to “The Hardest Adjustment To Self Employment”

  1. Aaron August 25, 2010 at 11:39 pm #

    Hey Patrick,

    I’m living in Japan too, working on getting a business off the ground and doing consulting for clients in the states to pay the bills in the meantime. I completely know what you are talking about! Even though I was self-employed off and on before moving here, it’s different when your clients/customers are almost 12 hours around the clock from you. I feel like I’ve really been able to relax and am also much more efficient (as you noted). Great post!


  2. Sebastian Marshall August 26, 2010 at 12:03 am #

    Hey Patrick, Sebastian here, “Lionhearted” on Hacker News. I know what you mean – it can be brutal trying to set your own schedule. No one yells at you if you’re screwing off, you’ve got to be your own taskmaster and slavedriver, which isn’t always a healthy relationship with yourself.

    I wasn’t able to stay productive until I started tracking my time and having daily objectives – having a morning routine of take vitamins, stretch, exercise, decide my most key objective for the day, loosely plan the day – things like that, it helps a lot.

    I wrote up how my time tracking evolved here if you’re interested – “The Evolution of My Time/Habit/Life Tracking” –

  3. Marcin Komorek August 26, 2010 at 12:07 am #

    I consider the flexible schedule the best part of self-employment! This alone was worth quitting!

    • You don’t need to ask anyone if you can do that and go there at ….
    • You decide when to go on vacation.
    • You can enjoy the best weather in the summer and actually catch some daylight in winter time (I live in Poland) ;)
    • No “I hate Mondays!” (great Polish comedy BTW :).
    • No “Gosh! I’m 20min late, I’ll need to stay until 5:20pm”.
    • More time for non-profit hobbies (I turned my programming hobby into a profitable one).
    • You can still get the job done and have some guilt-free play by tracking your time. An hour here, an hour there…

    My 2-3 weeks/year vacations, which I used to take from my “day job” just expanded into 52 weeks/year.

    Well, there is still “My boss is such an …hole” from time to time, but that’s another story ;)

    All the best,

  4. Daniel Tenner August 26, 2010 at 1:34 am #

    Hi Patrick,

    Great article, and I totally agree (in fact, I wrote something similar here:

    I find that although counting hours per se doesn’t make sense, in order to be long-term productive with coding tasks you still need to protect chunks of time here or there. It takes about an hour to really get into a programming roll, and if I have interruptions every hour my productivity does in fact take a big hit. So what I do is I define some “working hours” for myself, and I resist doing anything else (like laundry, shopping, extended lunches, etc) in those times – unless I actually take the time off, of course, which is what I have done when a long-time friend was visiting from another continent.

    This is only necessary to protect those 3-4 hour chunks of time where all the great programming work gets done, but for me that’s still essential. You may find that setting yourself a few of these periods (they don’t have to be daily) each week helps you get the big pieces moving.

    Good luck! :-)


  5. Eric August 26, 2010 at 1:53 am #

    Hey Patrick,

    Staying motivated and productive is definitely one of the biggest challenges when you’re a solo. It helps to remember that you’re the only one driving the company forward, though. Working to decouple customer support response time from overall customer satisfaction by making the product work more seamlessly is a very worthy goal.

    Best of luck.

  6. Matthias August 26, 2010 at 3:11 am #

    How much of a difference did you see with providing google checkout as an option?
    I’d love to try google checkout, but it’s not available for vendors outside the US or the UK. How did you manage it from Japan?

  7. Phil August 26, 2010 at 3:54 am #

    I had some of the same issues a month or two into working on my own. I’ve recently gotten an office and it really does help. Something about being away from the distractions of home I suppose (coffee shops only worked a little better for me). Staying motivated, especially when you are successful is still elusive to me at times, honestly I think that’s why companies should grow. Once you have employees, etc… it’s easier to be motivated again.

  8. Arik August 26, 2010 at 5:18 am #

    Hi Patrick,

    I´m curiuos to know — is your increase in productivity proportional to the amount of time you work now? I mean, do you get the same amount of work done per hour as before?

  9. j_king August 26, 2010 at 6:40 am #

    I’ve been working from home for over a year now. I find scheduling leisure time to be the most difficult thing. I don’t have any other friends who work from home and so I find socializing to be difficult. After spending a whole day at the “office,” the last thing I want to do is sit around the “office” and try to relax. I want to go out and do other things… but everyone else I know just came home from a long day and just want to stay home and relax. It gets rather lonely.

    But I get a tonne of work done!

    The most challenging thing for me is the money. I’ve never been able to save up enough to start a business. Currently I’m in-between jobs right now and working on a project that may eventually employ me… but things are tight! I’m left wondering how other entrepreneurs have gotten through it (especially if they were the sole providers). Any thoughts on that?

  10. Robert Dempsey August 26, 2010 at 6:44 am #

    Hi Patrick,

    Self-management is one of the hardest things for any self-employed professional, as it’s something we’re not “trained” to do in school or conventional work places. In software development, self-management of people on teams is very important. There’s a method named Personal Kanban that works really well for me personally. I have certain appointments that are on my schedule, however after that it’s up for grabs. Using personal kanban helps to focus on the most important tasks, which can have due dates attached to them. Check out if you’re interested.

  11. Sebastian Marshall August 26, 2010 at 7:05 am #

    I’ve been thinking more about this. I wrote something up here –

    Title: Patrick – Is the problem that dislikable work feels more productive?

    “I’ve been thinking about this since I read it this morning. Could it be that work you dislike and are being mandated to do feels more productive? I did about six hours of great work today, but most of it was talking to people I enjoy talking to and learn a lot from and playing around in Google analytics. I felt like I got nothing done until I looked at my list at the end of the day – tons of good stuff checked off.

    One of the greatest things about working for yourself is that you can focus on what you want to do, and often that’s work-that-feels-like-play-but-also-pays-you. Isn’t that magnificent? Work that doesn’t feel like working that’s highly productive? Just, it’s easy not to feel productive afterwards, since it felt like playing all day… what do you think?”

  12. Andrew Warner August 26, 2010 at 8:10 am #

    People think it’s odd that I have an office and keep regular hours but I found that without a strong structure, I don’t get anything done.

    If I tell my friends that my schedule is flexible, they start to think they could pop in any time they want.

  13. Eli August 26, 2010 at 8:27 am #

    The iPad may be a handy device for you, but… consider writing your rough-draft with it, then finish the post with your graphs and analysis on another device, even if it takes another day to get to it. The conclusions are interesting, as is the context and discussion of the challenges, but the hard analysis is what really sets your posts apart. Don’t skimp on that just because the shiny new tool gets in the way.

  14. Russ Wallace August 26, 2010 at 9:55 am #

    This all makes perfect sense and gibes with my experience as well. I’m curious to check out that iPad app…

    Incidentally, I found this post through HN, which has another article that you might find interesting/helpful:

    Similar thoughts, with helpful advice and tips.

    Good luck!

  15. Jim Benson August 26, 2010 at 4:12 pm #

    Hi Patrick and everyone,

    There are two issues here in the post and the comments I see a lot. 1. Not being able to keep a schedule. and 2. Not being able to separate life and work when they happen in the same space.

    I hate to say it, but these are huge problems with human beings. We like definition – even when that definition hinders us. We think deadlines spur us to act – but they really spur us to drop the other 10 million things we’re doing to do what we were supposed to do in the first place. So we’d be better served limiting the amount we are doing – and finishing things before starting others – than we are by deadlines.

    The balance one is hard too. I was afraid that I would be playing Tiger Woods on the XBOX day and night if I worked at home. What’s happened instead is that I have to consciously stop working.

    I have also started treating my house like an office – which means I have business meetings here all the time now. I force the house to really be a home office. In turn, I’ve set up evenings out and set a goal to do that at least twice a week.

    Ultimately, you just need to be aware of what’s going on and make sure you are behaving appropriately. It’s an adjustment – but you’ll find yourself more effective in the long run.


  16. my life dream January 6, 2011 at 7:33 am #

    Hey Patrick,

    I love being A-schedule… Anti schedule. But it means I create my life on my own terms. I choose to work to a “CFT” schedule. Critical Focus Time which means I give core tasks certain time to get them done. This not only has increased my productivity but gets things moving and I get a tremendous sense of satisfaction from getting the important stuff done and out the way first.

    Best to you.

  17. Jon September 12, 2011 at 3:58 am #

    “They give them away in this town if you work in tech. I could pay the rent with the savings in my iced cocoa budget.”

    Mind sharing how to get those office spaces? I too live and work in Japan.


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