On Regret Minimization, Leaving Apple, and Playing Pinball

It’s been a month now since I left Apple to start a company. I’d been working on Time Machine (an interesting and challenging project) as a software engineer, with a fantastic group of people, and was in a situation that was really pretty great. So, why did I decide to leave and go do my own thing?

The answer is complicated and, in between bouts of programming, I’ve been trying to put it into words for a few weeks now without much success. However, there are a couple of quotes I picked up over the years that I think encapsulate my main reason for leaving and the main thing I want to do.

The first has to do with regret, and comes from Jeff Bezos, on leaving his stable, great job to start a startup:

So, it really was a decision that I had to make for myself, and the framework I found which made the decision incredibly easy was what I called — which only a nerd would call — a “regret minimization framework.” So, I wanted to project myself forward to age 80 and say, “Okay, now I’m looking back on my life. I want to have minimized the number of regrets I have.” I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried. I knew that that would haunt me every day, and so, when I thought about it that way it was an incredibly easy decision.

Jeff Bezos Interview, Academy of Achievement

I’ve been thinking about starting a company since high school, and maybe even a bit before that. Certainly by the time I hopped on the Internet for the first time, it had become one of my goals. Over the intervening years, I’ve had a few opportunities to start a company, but somehow have never just gone and done it. I’d always just kept thinking it was something I was going to do “someday”, but that, for the moment, there was something interesting to do at the place I currently was. Apple in particular is a pretty difficult place to leave, in that there are a huge number of interesting things to work on, a huge number of great people to learn from and work with, and is just really a very special place to be, especially over the past few years (Apple’s Silver Age).

However, I was increasingly feeling like the “someday” was going to need to become less abstract for me, or it would never happen. If it was hard for me to leave Apple to start a company in my 20s, with no wife, kids, or mortgage, it was only going to get harder from there on out. That knowledge, coupled with knowing that if I never actually started a company I’d regret it my entire life, was a strong impetus for me to gear up and give it a go.

Given that I’ve been thinking about starting a company for a long time, I’ve given what I enjoy doing and what I want to do with my time a lot of thought over the years, and found that what I really enjoy is playing pinball:

They didn’t have to name the bigger game. Everyone who had been on the team for a while knew what it was called. It didn’t involve stock options. Rasala and Alsing and many of the team had long since decided that they would never see more than token rewards of a material sort. The bigger game was “pinball.” West had coined the term; all the old hands used it. “You win one game, you get to play another. You win with this machine, you get to build the next.” Pinball was what counted. It was the tacit promise that lay behind signing up, at least for some. Holberger felt that way. “I said, ‘I will do this, I want to do it. I recognize from the beginning it’s gonna be a tough job. I’ll have to work hard, and if we do a good job, we get to do it again.'”

Soul of a New Machine, Tracy Kidder, p. 228

This quote comes from a book about the creation of a new computer by a small team at Data General. As the team eventually found out, Data General was a big company, and big companies don’t necessarily understand pinball. Success on a project likely means being kept on for continued maintenance of the project, not necessarily being drafted for the next big thing. Happily, however, some of them discovered later that the startup was a great way to play pinball.

Given that what I enjoy doing is building new things, I intend to do as much of that as possible. Essentially, my plan is to build a lot of small projects in succession, and see which ones take off. Certainly a big part of my inspiration in this approach comes from David Weekly, an acquaintance and Silicon Valley entrepreneur. David quit his job a few years ago, and dedicated his considerable talent and a huge amount of time to building a service that, ultimately, not many people used. Rather, the project that did take off for him was, literally, an overnight hack.

So, the lesson for me from all this is, as an individual entrepreneur, that my best bet for being able to play pinball is to build a lot of smaller, but still useful projects. Each project will either come at the right time and be the right idea, or it won’t be, but hopefully having more of them will ensure that the probability of eventual success will be higher. Or, at least, my probability of utter failure will be lower, and I’ll have a bunch of cool stuff to show for my time (and some “valuable operational experience”, as one of my friends describes failures).

So, that’s what I’m endeavoring to do, and so far I’m having a blast. I’ve eliminated a big potential regret from my life, and I’m getting to work on some new and interesting things. So, by those metrics, my little crash course in entrepreneurship is going very well. Anyway, enough rambling, I’ve got to get back to work!

6 Responses to “On Regret Minimization, Leaving Apple, and Playing Pinball”

  1. Josh Says:

    This entry is really inspiring to me, Andrew.

    At first I kind of wilted when I read, “If it was hard for me to leave Apple to start a company in my 20s, with no wife, kids, or mortgage, it was only going to get harder from there on out.” For me, those milestones are three checkmarks (since 2000, 2007, and two weeks ago respectively).

    But the Bezos quote and your way of calmly, logically approaching all this really brings it home for me. Steph and I have been talking lately about what we want out of life in a big-picture sense, and these thoughts are really valuable to have. I don’t know if I’ll build a startup or not, honestly, but it’s good to consider these things when I feel the fear of it after I get a good idea.

  2. Ben Says:

    Andrew: thanks for posting about your experience. I’ve recently considered a similar transition, and had to deal with a lot of doubt about the future that laid ahead for me away from my existing job. It’s extremely difficult to separate emotional and rational justifications for big life changes, and I’m inspired by your approach.

    The idea of small, simple projects does sound extremely appealing after living in a world of Big Software. I wish you lots of luck!

    Josh: I’d be curious to hear how having kids changed your plans for the future. I’ve found that I’m much more cautious about my plans than I used to be.

  3. Jens Alfke Says:

    Congratulations, Andrew, and welcome to the l33t 1nd13 club!

    Any hints about what sorts of projects you’re going to do? Web-based? Mac apps?

  4. Jamie Montgomerie Says:

    Nicely put, Andrew. Minimizing future regret is the way I try to live my life too. It’s what led me to Apple and California, and, although I think my underlying reasons are a slightly different, it’s what’s caused me to follow a very similar route to you now. As a philosophy, I think it’s a good one.

  5. Andrew Says:

    “Any hints about what sorts of projects you’re going to do? Web-based? Mac apps?”

    That would spoil the surprise. 😉

  6. kelly Says:

    very cool to read about your decision-making process…really admirable.

    i love pinball too. have you been to the pinball museum in vegas? it’s awesome, and has games from every era, all playable and at the original prices! i went with my dad (my pinball partner) and we stayed for like four hours…even though it kind of smelled in there.



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