There and Back Again - A Freelance Adventure

This may be a strange first post for a blog, but it's something that's been on my mind a lot, so I felt it was something worth writing about. I've started compiling a list of post ideas, with the hope that I can sustain a blog. In the past, I've had several false starts and have spent writing efforts elsewhere, but am hopeful that this time around, I'm in a good spot to keep posting.

Getting on with it…

I recently started a position as a full-time employee after about 2.5 years of work as a freelancer. Making the switch to freelancer and then back to full-time employment led to lots of introspection, at least for me.

Why become a freelancer?

Until early 2007, I had been employed by small companies and never had more than about a dozen or so coworkers. In 2007, the small company that I was working for was acquired by a 500 person company. This shift was a lot more drastic than I expected, even given the fact that our "group" was pretty self-contained and not completely integrated into the larger company. I've found that I prefer small companies and teams where everyone's contribution is extremely important to the success of the company. When a company gets large enough that some employees can "coast" through their career, I find it extremely frustrating. I got to a point where I had enough of the role I was in and I had some good freelance leads as well as some business of my own to build, so I took the leap to start freelancing.


In general, I enjoyed the work of freelancing. I had a good mix of work - Wordpress and Drupal customizations for the most part, with a longer-term Rails project in there as well - and most of the work was as a remote freelancer. Occasionally, I worked on-site at a client or with their team. I didn't run into any client non-payment issues or other things that tend to frustrate freelancers. For the most part, I believe that this was because I usually had previously existing relationships with the clients.

It was definitely an adjustment to realize that if I wasn't billing (for vacation or something), then I wasn't getting paid. However, having schedule flexibility and location flexibility was a good balance of this.

Why go back to full-time employment?

A lot of people talk about freelancing being a "feast or famine" sort of situation and as I looked at my freelancing history (and bank accounts), I was realizing that it was a bit more famine than feast for me. I had experienced happy clients and they were willing to pay my rates, so I attributed my famine times as just that - longer than ideal gaps between projects. The obvious cause being that I was not keeping my pipeline as active as it needed to be. I'm not remotely sales-oriented and find it even harder to sell myself, but it was more than that. I found it hard to make the context switch necessary to think about/find the next project when I was in the middle of completing the current project.

My last freelance project was as a contractor on a Rails app for a seed-stage startup. The work was steady and the other developer that I worked with was a great teammate and I learned a lot. Just as I was thinking that this long-term project thing could work, the startup ran out of runway (rather abruptly). I knew this possibility was always there, but thought I would have a bit more notice (or writing on the wall), so it was enough to get the panic going.

The search is on

I tweeted out the fact that my current gig was up and I was looking for something new. Fortunately, I got some solid leads pretty quickly. In my mind, the search for full-time employment started, but I was entertaining all options. Even though I love the startup environment - I tend to feed off the energy, passion, and optimism of company founders - I had grown wary and the "real world" of paying the bills was knocking on the door. Ideally, I wanted to find a smaller company, with a high-energy, smart team that I could learn a lot from. I wanted to continue my progress of diving deeper into the Ruby/Rails community as I was having a lot of fun with it.

Finding something

As anyone with just a few years of professional experience will tell you, personal connections make all the difference in a job search. Shortly after the search started, I started contracting with a company as a "trial" period for both parties to get to know each other. This transitioned into a full-time position. While the adjustment from contracting to full-time is strange, I don't regret any decision that I've made - it's not my style.

Settling into a full-time role has also provided some career development focus that I didn't necessarily have while freelancing. When freelancing, I was basically open to working on whatever came along (within reason). I have enough web development experience that jumping between technologies was not a huge deal. However, it's easy to spin your wheels trying to keep up with other tech when the platform of the next project was undetermined. In my full-time role, I know what I need to get up to speed on, and I have coworkers that can help overcome the little hurdles that can make learning curves more difficult.

There isn't really a moral to this post - I just wanted to get my thoughts out. Stay tuned for more posts and give me a swift kick in the ass if I'm not posting!

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