Why I’m Not Working on My Startup (Yet)

I’m not sure if it’s nature or nurture, but either way, the savvy gambler will bet that I’m going to run my own company at some point. I grew up in an entrepreneurial house. I share a Y-chromosome with a guy who built up a company and made it work with the (un)usual combination of moxie and dedication and wit that makes any business work. And, he did so with two small children. No small feat.

I’ve always planned on starting my own company. I’ve been a fan of Paul Graham’s writing ever since I discovered it. I live in Silicon Valley, and the startup vibe is in the air. I work as a web developer, and I’m good at what I do. I am very interested in the business of software, and have a lot of ideas about how things could be done in new and better ways. It’s not so much “if”, but “how” and “when”.

I’ve worked at Yahoo for 2.5 years now, already about 6 months longer than I’d initially expected to. Compared with working at a small company, it has many advantages. I’ve had the opportunity to be a part of several different projects, and Yahoo can afford to pay quite a bit more than my former employer ever could. I’ve been able to talk to and work with some of the most gifted hackers I could ever hope for. When I got the job, it was really a dream come true, and I’m still proud to be one of the cogs in this engine. It’s been even more satisfying than I’d thought it would be.

But there are drawbacks as well. In a company of Yahoo’s size, bureaucracy creeps in. Decisions are sometimes made very far from the code, and even further from the users. Despite Jerry’s and Ari’s best intentions—and sternest directives—when they talk about Open Initiatives, the “not invented here” syndrome can cause big problems. I don’t think I coined the term, but I’ve taken to referring to the malaise as the “purple cloud”, a stifling and noxious gas that obscures reason and reduces visibility. No doubt about it: that part of the job sucks.

On an almost daily basis, I’m tempted to quit and strike out on my own. Yahoo is an unusually good employer. But despite the perks, as long as I work at Yahoo, I don’t work for Isaac. I might love the company, love what we’re doing, love the opportunities it affords, but there is a definite lack of control and lack of ownership that leaves me unsatisfied sometimes. Being a manager wouldn’t solve the problem; it would make it much much worse. At least as a hacker, I fully own the code I write. If I can’t be on the top, I’d rather be as close to the code as possible. (Best would be both at once, of course.)

So Why Not Leave?

I’ve been reading a lot of articles recently with titles like Why you should quit your job and start a company and Why you should keep your day job and work on your startup at night. I know my hacking rhythm pretty well by this point.

What I’ve gathered from these resources and my own introspection is:

  1. It’s incredibly hard to focus on a startup and also have a separate full-time job.
  2. It’s even harder to focus on a startup and not pay rent or eat.
  3. If I spend less than 50 hours a week working, I’ll go crazy.
  4. If I spend more than 30 hours a week working on something I don’t love, I’ll go crazy.
  5. If I’m working on something I love, and I’m not working on it all the time, I’ll go crazy.

Going crazy is not an option. This isn’t the fun crazy with mania and interesting delusions; more like the super-depressed, hate-my-life, stop-communicating-with-other-humans kind of crazy. I’ve been there before. Life’s too short for that.

The “8+2″ workday wouldn’t work for me. I’ve tried it. I hated it, with a burning passion. I’ve always had side projects, but they remain on the side (like this blog.) I go through phases of being very interested and working hard on them, and completely ignore them at other times. If I had to focus on them enough to turn them into something that users would pay money for, it would have to turn into a full-time gig. My ventures into paying side-projects were tremendous failures for that reason.

Even more importantly, I can’t work just 8 hours a day. Either you ride the biorhythm, with its highs and lows, and capitalize on every bit of go-time that your brain gives you, or you crank out boring hours for your handful of dimes. “Healthy work-life balance” is for bank tellers. An artist doesn’t stop being an artist when he goes home.

I love what I do at Yahoo, and I care enough about what we create that I want to focus all my energy on creating value for users. It’s good practice. But as long as I work at this job, I won’t have enough left over at the end of the day to seriously invest in anything else. Some people can find a middle ground there; I’ve learned that I can’t, and I’m ok with that.

I also really hate worrying about bills. One joy of working for Yahoo is that I get paid enough that I don’t know exactly how much a cup of coffee costs. In poorer times in my life, I was acutely aware of every nickel increase in the cost of a pack of cigarettes. That sucks. Living economically is just good sense; deciding whether your last $10 should be spent on gas or dinner seriously gets in the way of enjoying life.

Having My Cake…

Here’s my plan: keep working at Yahoo for the next 2-3 years or so. Pare down my expenses as much as possible during that time, and sock away as much money as I can. When I have enough saved to live for at least a year without a job, I’ll quit my job and work on whatever idea seems the most promising at that time.

You see, the idea is the cheapest part. Ideas are so plentiful once you learn how to cultivate them, they may as well be falling from the sky. And my ideas have tended to be at least good enough, even if they’re not exactly earth-shattering. In the last year, I’ve seen two startups execute on ideas I’d had, and they seem to be having some success, which I find extremely comforting. I’m not trying to claim that I could have had the same success, but clearly, “finding an idea” isn’t a limiting factor.

So, assuming that my idea will be there when I’m ready to work on it, I’m saving up to buy myself a year off to work on it, whatever it ends up being. I’ve considered getting a part-time job when the date rolls around, just to bring in enough of a baseline income to pay a few bills without sapping my creativity too much. In a way, it’s a bit like creating an angel investor, one who believes in me 100% and is 100% committed to my success like no one else ever could be.

I realize that this plan is a bit risky. The risk is laziness. A dream without execution has a funny way of staying a dream forever. But I’ve made plans like this in the past, and have managed to be ready when the time came to act. That’s how I got to California, after all.

The real challenge is that I’m really not sure exactly what a year costs. I can sit down and crunch numbers, but everything seems way off. I don’t have nearly enough hard data about my lifestyle, and even less about what it could be. Depending on how I spin my estimates, the range ends up being about ±50% or so, which is useless.

I know that I can live cheaper than I am, but I’m not sure which things ought to be cut, and which things are worth the cost. Maybe coffee is worth $1.46, but not $1.55, when balanced against the PITA of brewing it myself and the joy I get from drinking it, multiplied by the number of cups of coffee I buy. I’m not sure. I do know that, while nicotine is a pleasure I deeply enjoy, there’s really no way to justify the physical and financial cost, and withdrawal will be a serious distraction. So, I’ve been wearing a patch—and breathing easier—since June 1, 2008.

A wise man once said, Never optimize before you profile. Then he said it again and again, because no one seems to listen. When it comes to optimization, our intuitions and guesswork are almost always wrong, and only hard data can be trusted. For the last few months, I’ve been tracking my expenses using mint.com and trying to just “act naturally”. Over the next 6 months, I hope to collect enough information about my habits to make wise adjustments.

The 6 months after that will be spent living-as-if, and trying to strike a workable balance. Considering that I make more than double the national household average, and don’t have any kids, I should be able to save enough within 2 years to be able to coast for at least a year, if I just make a concerted effort to stop pissing away so much of it, even at SFBay prices.

Advice Welcome

This sort of plan flies in the face of the white-knuckle hardcore hacker work ethic that seems so prevalent in the startup culture of Silicon Valley. In a way, this is just a rationalization for wimping out. Why put it off until my 30s when I could take that leap of faith now? The way I see it, if a bus is coming along later, why run?

It strikes me as foolish and irresponsible to throw away the opportunity that Yahoo gives me just because I have a distaste for being an employee. (The fact that I have a non-trivial pile of stocks vesting at the end of next year speaks to the wisdom of procrastination, as well.)

I don’t suspect that Foo Hack really draws in the financial planner crowd, but if anyone has any suggestions or experience that might help in the temporary-retirement project, I’d love to hear it. Is this crazy? Am I going about this all wrong? Have you ever done anything like this?