Freelancing in Retrospect

After a successful two years working for myself, I left the freelance world last December for a full-time job with this crew here.

The decision was surprisingly easy; having contracted with the company for awhile, I liked both the folks I’d be working with and the work itself. Plus, I relished the idea of being part of a team again. I really enjoy working collaboratively, and that was missing when I was on my own. I suppose I’m a social beast at heart, though I still work from home and use IM for most of my communication with my coworkers.

Looking back over those years on my own, I’m struck by a few things:

  1. If you have the chance to work for yourself at some point, you absolutely should. Two sizable freelance projects simultaneously knocked at my door, convincing me to take the leap. It was the best thing that could have happened. I was forced to build out  my skill set, learned a bit about business, and met a ton of people (including my current employer). It was freeing to know I could work for myself; my decisions became focused more on want to’s vs. have to’s (though of course there was a healthy dose of the latter).
  2. Working for myself was easier than I expected. I say that to underscore the reality that there’s a lower barrier to entry to self-employment than I initially thought, not that I’m a savvy entrepreneur. I’m sure it depends on the industry, and there’s plenty of web work out there. But I did little marketing beyond my online portfolio and business cards; every project or client I took on came through friends, clients and a trusted network of fellow freelancers (who also fall under the friends category). Anchoring project-based work with regular clients made things a bit more predictable and sustainable.
  3. Meeting other self-employed folks was huge. I got involved with IdeaXchange in Chicago, a fantastic group of writers, artists, designers and PR folks, most of whom worked for themselves. We met monthly to talk shop and share ideas, and it didn’t matter that we all worked in different industries (though I got mixed up with crew of local web design freelancers shortly thereafter, which was/is great for talking nerdery that no one else understands).
  4. The benefit of setting your schedule when self-employed is only partially true. There’s a glaring catch to this concept; time off actually costs you double, as you’re paying for travel expenses while not working, and thus not billing. I probably took a total of two weeks off per year, partly because I enjoyed the projects, but also because every hour was billable. My experience was definitely not cocktails at 2pm every Friday afternoon.

By and large I felt challenged and engaged by my work, and that’s fortunately still the case with my new role. Now if only the company would move to Indianapolis so I could fully enjoy the team lunch on Fridays…