On doing what you love, loving what you do, and not burning out along the way

There’s been a lot of talk over the past few days about Michael Arrington’s blog post concerning the long hours and dedication it takes to work for a startup.

I’ll keep my general criticism of Arrington to a minimum here, but to sum it up as I understand it: he founded a popular tech blog, stirred up controversy by investing in some of the companies he covered, sold said tech blog to Huffington Post, fought with Arianna Huffington something something CrunchPad/JooJoo something something Aol. Now he’s a VC, to more perfectly promote himself, which is what this all seems to be about anyway. (In short, I’m not a fan, and had solidified my opinion long before this week’s events.)

His blog post, berating overworked startup employees for being whiny crybabies (because they need things like sleep and a life apart from their jobs), while also somehow implying that Zynga is creating something of lasting value to the world, quoted extensively from a 1994 online diary (blogs didn’t exist back then) of former Netscape programmer Jamie Zawinski. Zawinski was, to put it mildly, not happy that Arrington used his words in the service of Arrington’s VC agenda. In the wake of Zawinski’s retort, there’s been a swelling of further outrage on Twitter and by bloggers like Amy Hoy and Rachel Andrew, among just a few links I’ve clicked in the past 48 hours.

All of this is increasingly resonating with my own experience. I’ve never worked for a Silicon Valley startup, but I’ve had a couple of startup-like experiences in my 15-year career as a web professional. I’ve never actually been driven to the point of sleeping under my desk and not leaving the office for days at a time, but the opportunity was there for me, if I had wanted to take it. Instead, I walked away, every time.

First, in 2000, just before the first tech bubble burst, I was brought in to be the “HTML guru” on the first e-commerce venture of a certain big box retailer. It was no startup, but it was being run like one. The .com team took over a (very) large conference room, turned off all of the overhead lights, and built a cubicle maze lit by floor lamps and dotted with potted trees. Aeron chairs and (promises of) vast fortunes in stock options for all! After a few months I started to see through the façade. The likelihood of a separate .com stock spinoff (the thing that was really going to make us all rich) evaporated, and our inspirational, visionary VP resigned the Friday before the site launched. It wasn’t long before I was gone, too.

Then, in 2008, I went to work for a (more-or-less) real startup. It was a “fun” work environment where we were entitled to all of the free breakfast cereals, ramen noodles, and caffeinated sodas we could consume. There was an XBOX 360 with Rock Band (which was still cool at the time) in the breakroom. We could hang out, bring dogs to work every day, ride around the office on scooters, all of that. We were encouraged to think of ourselves as “co-presidents” (actual shares in company ownership notwithstanding). We were also expected to log 36 billable hours a week. Maybe that’s no big deal when you’re fresh out of college, have no external commitments, and can be adequately enticed to stay at work until 11 PM with the promise of free ordered-in burritos. But I was 34, with two preschool-aged kids at home. And having to log 36 billable hours when you’re only in the office for 40 (and have to reserve enough energy to chase two kids around when you get home) can prove just as stressful as working 60 hours a week when you’re sleeping under your desk. (Or so it seemed at the time. I don’t care to try to prove it.) I only lasted at that job for 3 months.

As it happened, just as I was beginning that job I was also subconsciously assembling the pieces of what I really wanted to do, which was to go out on my own as a freelance web developer and consultant. I had acquired the necessary technical skills over a (then) 12-year career working for the two aforementioned companies as well as four others. I had built up a large enough network of contacts that I could tap into to drum up business (if you’ll permit such a ghastly mixed metaphor). All I needed was the confidence to take the leap and do it.

My goal was not to get rich (at least, not directly). It was not to revolutionize the industry. It was just to do what I do well, on my own terms. To please and delight my clients with top-quality work. To do what I love, and love what I do. And let it grow from there.

Three years later, I’m still here. I’m not rich. I haven’t started a revolution. But I’m making a stable living, and I’m meeting my target of 25 to 30 billable hours a week. I have a growing list of satisfied clients, and I’ve built something pretty cool along the way. This business is working, and I’m working on my own terms.

I don’t say all of this to gloat. I am proud of what I’ve achieved (and that I’ve done it without an “angel investor”). But there are a lot of people who’ve achieved a lot more in the Internet than I have, and probably more than I ever will. Still, there’s room for me, and there’s room for more, too. You just need to have the confidence to take the risk. But when you do it, do it for yourself.

You can’t specialize in everything

It’s been one of those weeks that a freelancer dreads. Lots of fires to put out. You’re trying to swim upstream (as always) but instead you’re treading water in a rapids. Without a team of coworkers to depend on, when a problem arises, there’s no one to pass the buck to, or at least to, uh, share it with.

The problems haven’t really been that bad. Just a few bugs to squash, a few scripts to optimize, a few clients to reassure. But when you feel like you have to be the expert at whatever you do, this kind of week can be a source of anxiety.

It doesn’t help when your main lifeline to the tech world is the expert blogs you follow. Read a few articles on A List Apart and you’ll feel both inspired and a little despondent. There are so many incredibly talented, creative people out there doing amazing things. So why am I banging my head against the wall trying to figure out why all of my form fields suddenly disappeared in IE6? (Turns out it was the position: relative on the #main element, easily fixed by overriding it with position: static in the IE6-specific CSS file I wish I didn’t have to create.)

The point is, as a freelancer, at least one who aspires to be good, if not great, at what you do, you are your own harshest critic and worst enemy. There’s no way any of my clients would ever beat me up the way I beat up myself. I don’t think I’ve ever even had one detectably angry with me. But I am constantly getting frustrated with myself for not being on top of every single technology I put my hands on, and I’m inclined to treat every bug as a personal failure.

The sad fact is, it’s impossible. You can’t specialize in everything. It’s right there in the word. Specialize. As a freelancer, you have to pick a few things to focus on as your greatest strengths, while becoming as well-rounded as you can. But there’s always someone out there who knows more about CSS3 or HTML5 or PHP or jQuery or Whatchamacallit than you do. The great thing about being a freelancer in the age of the Internet, especially if you work on the Internet, is that a lot of those superstar über-geniuses are willing to share that knowledge with you for free. All you have to do is search for it.

The biggest danger in following the superstars of your chosen field, though, is idol worship. You get to know so many facets of their work and their personalities (especially if you follow them on Twitter), that you may be tempted to think you know them personally. You might even have a brief exchange with them about baseball. But that doesn’t mean you know them or know what their lives are really like.

We all make sacrifices to live the lives we choose. It’s inherent in the finite nature of human existence. Chances are, I’ll never be a web development “rock star,” because I’ve made choices that took me on another path. I wanted to be able to work on my terms, and fit my career in as one aspect of my life. I’m not logging the kind of hours I’d need to in order to get rich doing work for hire, or building the next great social networking site. But I have time to spend with my kids and SLP (though probably still not as much as would be ideal). I can make music. I can try to set the world record on my Asteroids cocktail table. (OK, that’ll never happen, but it’s 2 feet from my desk in my home office, if I ever decide to get serious.) I can take an afternoon off to take my son to see Toy Story 3 or head down to Target Field for a Twins game or write on my coffee blog or get some fish tacos at Sea Salt.

Or, I can spend half the morning beating myself up because I’m not Jeffrey Zeldman. But, who is? (OK, he is. But that’s it.)

The point is, I’m me. I’m damn good at what I do, but I can’t do everything. And that’s OK.