They were all fine jobs, and each paid more than the previous, but none were quite right for me at the time. I was probably a bit of an entitled twenty-something as well. So after saving up a little cash (and having been newly married), I became a full-time freelancer at age 25.

For the next ten years, the freelance life was good to me. I sometimes worked until 2AM on a Sunday. I sometimes slept until noon on a Thursday. I wore unfashionable shorts. I jumped across the country: a tiny Georgia village, a Midwest city loft, a crazy expensive NYC apartment. Over this time, we added three children to the mix.

But as much as I enjoyed freelancing for that decade, I soon found that there were more reasons for me to stop than to continue. Here are those reasons. I won't pretend that they apply to every freelancer, but they did to me...

Freedom was fast becoming more of an illusion.

This was the biggest draw to freelancing in the first place - freedom. The idea that I could schedule my work around the times that worked best for me was appealing. I loved working from my own environment that I found productive; while taking on as much or little work as I desired. But as my skills matured and I began taking on more sophisticated clients, I was needed at more hours of the day. Furthermore, as the digital landscape became more complex, more things had to be monitored. As a solo freelancer, it just became overwhelming..

My skillset and connections were stagnating.

Remember when the term “web designer” meant the “person who did anything with a website.” I was a web designer when I was coding C# forms, and I was a web designer when I was mapping out sitemaps. In the last decade, the industry has segmented into some very deep verticals, with positions in information architecture, database administration, interaction design, and the like. I began finding that my skills, while diverse, were only a few inches deep, and marketing that skillset was getting tough as a freelancer. Also, I wasn’t getting to work with others who were mastering the other facets of digital.

The most interesting projects seemed out of reach.

I enjoyed many interesting projects as freelancer, and was proud to see my work in various places (my favorite being a Flash-powered Times Square sign I made for the 2008 election). But the current digital landscape demands expertise at too many technologies to name, and most projects that were really interesting to me required a team. It was harder and harder for a freelancer to win a contract meant for a team (except as an external 1099 for that team).

Companies began integrating the aspects that made freelancing interesting.

Freelancing used to be the antithesis of “company work.” If you didn’t freelance, you might end up in a cubicle (think Office Space). But in the last decade, thanks in part to Silicon Valley and various startups, work environments in our space have changed to be more accommodating and thoughtful. My current “company” position allows me to work at home, take unlimited vacations, and enjoy many of the benefits once allowed only to freelancers.

I’m tremendously fortunate to have freelanced for a decade and support a family while doing so. I look on those days fondly, and am proud of my work and the things I learned during those years. So here’s to another ten years making digital things, this time with pants and co-workers.