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.