The Myth of the “Free”-lancer

Today, I planned on working. I planned on having a full day to focus on finishing up some projects. In fact, I planned on using most of this week for that purpose, though obviously Christmas was excluded—that day is always reserved for family!

So today I sat down at the coffee shop, flipped open my laptop, and fired off a few emails. I fixed a bug that was holding up a project’s completion. I started syncing a remote site to local, then hopped on Twitter to pass the time. Then I noticed a tweet from Ryan Sullivan from WP Site Care:

I’ve noticed a decent amount of posts lately that laud the seemingly infinite benefits of freelancing. Who wouldn’t enjoy making their own schedule? Who doesn’t want to define the limits of their income? No more putting in “time-off” requests three weeks ahead of time to make it to your future child’s ultrasound—just shut down your station, and go!

These are the benefits I’ve had (and questioned) for the past year and a half. 2014 marked the first full year I’ve worked for myself. Previously, I’ve flipped burgers, sold Kias, and been an Atlas-like employee at a (now dissolved) WordPress agency.

This last position was the one responsible for my lust for the “free” in freelancer. I was tired of company bureaucracy, politics, bosses, project managers, hectic deadlines, sales people who didn’t understand what they were selling; the list goes on. In short, I was burnt out. To me, freelancing seemed to be the answer—albeit a frightening one. I was not unaware of the added responsibility and possibility of failure that comes with self-employment. To me, though, the benefits far outweighed the risks. I felt I had the chops to solely manage the process I’d seen go so wrong. I didn’t need a sales person to sell, especially when they usually over-(or under-)sell. I didn’t need a project manager when I could use an App For That™.

I’ve been talking about all of this in the past tense, so I know you must expect what comes next: I’m ready for a change. Some might call it a regression, though I’d have to disagree. Quite simply, the boots I’ve put on are a bit too big. I have some growing up to do, and I’ve been too stupid, too afraid, or too prideful to admit it.

As I sat down today to work, I realized just what I was doing: working the day after Christmas. I also worked the Eve of, until around 6:00 PM. It hit me today, what I had traded for this. I asked for the “freedom” of managing my schedule. But this means I’m wholly responsible for my income. In my current state as a freelancer, a day lost = income lost—no if, ands, or buts about it. I have greatly enjoyed the ability to drop work at a moment’s notice, but I’ve been fooling myself. All I’ve done is shift my work to later nights, to more weekends, and the day before and after Christmas.

That is the first reason I’m ready for a change—to be able to turn work off. Not at a moment’s notice or on a whim, not when I just don’t feel like it, but at a predictable time, on predictable days. When I transitioned to freelancing, I thought I was trading rigid constraints for flexibility; I feel that I’ve really traded reliable structure for wild unpredictability.

Besides what I hope to gain in predictability, there are a few other key things that have convinced me to give up the reigns:

– Experience with a team will make me a better employee and a better person. I feel like I have a decent handle on working in a team, but in general I have never had a good experience working with a team larger than 2 on web projects. I need to see a project handled *correctly* from start to finish. I need to learn how to fill one role and rely on everyone else’s capacity to fill theirs.

– Job stability will give me the time—more importantly the passion—to ship stuff I’ve been waiting to ship. Obviously I’m not gaining more hours than are in a day. But when my income is a direct result of the time I put into client work every day, side projects without guaranteed (or immediate) return quickly fall to the wayside. Not only this, spending all day finding work and working burns me out. I don’t have any passion for working on side projects because my day saps me dry.

The last reason is a little more selfless than the rest:

– I don’t know much about business. Sure, I took some finance and business classes at college in pursuit of a BSBA in CIS (whew!). But I’ve realized that at this time, wearing the hats of project manager, sales person, and developer may be doing a disservice to my clients. Trying to learn how to run a business as I go is not only unfair to my clients, it greatly adds to the stress of my day. Of course, I’m not saying that one has to know everything before freelancing. I am saying that it’s not as easy as it is advertised, and those that urge you to jump into it without first evaluating your ability are giving foolish advice. I’m also not saying that one cannot successfully bear multiple roles; some are able to do this, and distributing those roles to your own team can alleviate those pressures and responsibilities to a degree.


Part of this post is an announcement (and thank you for reading this far, I’m almost done!): I’ve been selected for an apprenticeship at Upstatement. I leave in a few days (the 30th), and start on the 5th of January. I’m very excited about the opportunity, but I’ve been very quiet about it. I think I now know why: I’ve sat on this blog post since the moment I received the news of selection, because the apprenticeship comes with the possibility of an offer of employment.

When I first heard this, I thought, “No way! I’ll never be an employee again.” However, as I started thinking more about it I realized that I’ve never experienced long-term enjoyment at a workplace (thankfully I’ve relatively only just begun!).  Since spending more time in the WordPress community, I’ve become aware of the many generous, good companies in existence here. Places and people who want to foster their employees’ happiness as much as their business’ income. There are places that my talents can be used as they are and honed to be something better, without having to don all the hats I’ve been wearing.

So, I’ve decided to whether or not an opportunity awaits me at Upstatement when my apprenticeship comes to an end, I will soon be entering the market and looking for opportunities as an employee.

All of my thoughts boil down to this: I want to work somewhere I can best be used and shaped. If that eventually leads me back to where I started (freelancing) then so be it; that time is not now, but it may be a part of my future.

“Lots of seasons in life too.” I’ve seen only a couple. I believe it’s time for a new one.