freelancing lessons: part 1

I’ve been promising to share some of the lessons learned from my year of freelancing. Here’s one: you can’t put each of your fingers in a separate pie and expect to just eat the most delicious one.

When I started freelancing, my end goal was to do a startup, but I wasn’t keen on just dropping everything to run after somebody’s unproven (and unfunded) concept–and I certainly didn’t have a million-dollar idea of my own. So I figured, I’d do freelance consulting, working with any existing startup that would have me, building some client-facing skills and looking for a killer idea to hitch my wagon to.

In practice, what ended up happening was that my efforts were divided in 5 different directions at once: my main client was well beyond the “startup” phase and into the “sustainable” phase, but they were paying the bills, so I couldn’t ignore them. Some opportunities weren’t looking for a partner, some ceased operations, and some seemed like a good idea initially but ended up not being as appealing as I thought. My own project, doing iPhone development, soon fell by the wayside.

So, a few lessons out of this: first, if your goal is to be part of a startup, do your research up-front, then commit 150%. Early-stage ventures need someone who can be completely invested in just that venture, and any distraction may bring disaster. Second, you have to be incredibly self-disciplined to do solo freelancing work: if I were more focused, there’s no reason I couldn’t have been successful in running a number of completely unrelated projects, including my own development projects. Third, keep your exit in mind: my goal was not to end up with a sustainable freelance consultancy, but to be part of the founding team of a startup. Again, if you want to do a startup, do a startup.

Now, I don’t think that freelancing was time wasted–I’m taking some specific lessons from my consulting experiences that are going to be very valuable in any of the several directions I may go next. And, freelancing is a great way to explore skills and industries that you’re on the fence about, without making a long-term commitment. But you do need to be careful about your endgame.

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