Choose Your Own Adventure

Thoughts on the freelance life.  

Hit start.  (Photograph taken by, and courtesy of,  Ryan McGuire  from his noble site,  Gratisography .)

Hit start. (Photograph taken by, and courtesy of, Ryan McGuire from his noble site, Gratisography.)


Designers. Art Directors. Creative Directors. Writers. Illustrators. Front-end Developers. UX Designers. Producers. Photo Retouchers. Animators. Production Artists. Carnies!

By all accounts, it’s happening more and more: People are leaving their full-time positions to pursue a more independent course as freelancers and entrepreneurs. Granted, sometimes it’s out of necessity (like when a company closes or relocates, which happened to me a couple years back). But it also seems to be becoming more appealing on its own terms.

For those fortunate to have the option, it can be a difficult choice to make. The security of a full-time gig with benefits and a clear path upward can be tough to trade in for the uncertainty of the independent contractor’s route. And like building a consulting practice or starting any business, for those who do make the jump, it may take some time to really get rolling — but that’s just issue number-one.

In an essay “A Love Letter to Freelancing” recently touted by Working Not Working (the creative freelancer’s Valhalla), the talented designer Claudio Guglieri covers some of the pros and cons of a freelance career, as he’s experienced it. And there are definitely pros and cons (he names some very significant ones).

As with everything in life, there are costs and benefits to every choice we make, all up and down that gloriously vexing decision-tree of life. But sometimes your choices will entail pros vs. still-pretty-damn-pro pros, or cons vs. perhaps-a-little-less-con-but-who-knows? cons. Though the tradeoffs will always be specific to any given situation and depend on an individual’s goals and value judgments, for those considering making the freelance leap, here some other general issues to consider.


Anywhere vs. Only There

It’s less true today that you’ll need to live where the work is. But technology hasn’t completely obviated the need for freelancers to be close to the action, and (rightly or wrongly) it certainly hasn’t erased employers’ preference for having their hired work close by and in sight, even when they’re contractors. It will be easier to find contract work if there’s a decent amount of agencies and businesses in a variety of industries where you live. If not, would you be willing to relocate? You might not have to, but it could make all the difference.


The Sweet Spot: Cash Plus Cachet

Yes, we all need to get paid. As a freelancer, as long as you have the available time to dedicate to a project or client, it’s usually smart to say yes to a project. Sometimes there might be a global brand or agency pursuing an ambitious (and therefore challenging, therefore likely fun) idea. But while it’s not uncommon for money and recognition to go together, sometimes it might be either/or. And conversely, sometimes even quite lucrative work will entail some unglamorous tedium.

Plus, no matter who you are doing creative work for, your process will largely be the same, and the goals for your clients will broadly be the same too. It’s never a good idea to let your ego lead you, but it’s a sad truth that people simply won’t care as much if they don’t recognize or relate to the business you collaborated with. Humans can be shallow that way.

Just remember that every project comes with an opportunity cost. For every gig you accept, those are hours you will not be able to devote to work you’d perhaps prefer, or to finding work you’d prefer, or to maybe being paid an even higher rate.

And when you do start getting gigs you enjoy from clients of a certain stature that pay a terrific rate, there are still other considerations to pile on top of this one.


Cogs vs. Sparks

Few people conceive of themselves as cogs in a machine, and few want to be treated as such. Alas, sometimes you might feel as though you’re being treated in just that way. No one listens to a cog; cogs have nothing to say. They just do their jobs, and only their jobs. The good news is that nobody’s really a cog. True, no person is indispensable, but it doesn’t follow that we are all interchangeable, mechanical, predictable, and devoid of spirit or agency.

We want the opportunity to be sparks, and to be recognized for our imaginations and contributions. Ideas can come from anywhere, so everybody’s voice should have a chance to be heard. Furthermore, the best working environments will not only respect people’s creative input, but also their processes. Experienced people know that the work that gets shown might be the 25th iteration of an idea that took pains to hone and deliberate through. Contributors should be given the opportunity to justify decisions made from hard-won experience, and to explain why they believe alternatives would not work as well.

On the flip side, it’s important to understand that because we’re human, all of us are likely wrong about many things multiple times a day. Everyone should have the respect to focus on ideas and not on their originators. This most assuredly goes both ways; when someone disagrees with your position or prefers another direction, don’t get defensive. Especially when you’re a freelancer, who by definition must be somewhat of an outsider. Always keep in mind that your client might just know their business better than you (though they should conversely value your outsider’s fresh perspective). Criticism is rarely ever personal, even when it feels like it. And if it is personal, it should be like water rolling off a duck’s back anyway. Just keep doing your best and remember that in life the only thing you can control is your own behavior, demeanor, and attitude.


Mercenary vs. Believer

While similar to the potential “cash vs. cachet” dichotomy, though not precisely overlapping, the Mercenary vs. Believer dilemma is common to everyone in the working world, not just freelancers. We all want a job that we care about. Dedicating 40/50/60+ hours a week to anything is easier and more rewarding — and therefore far more sensible — when you really believe in and like what you’re doing, and when you’re proud of the results.

This isn’t always possible, and no job will be 100% picnic. There will be times when we have to labor at something we find either uninspiring or even unpleasant. But if we do our best and try to grow and learn constantly, other opportunities will surely flow. Which leads to what is one of the more crucial considerations.


Plateauing vs. Learning

Stagnation is no fun when there is always something more to learn, different ideas or approaches to be exposed to, different skills to try to add to your repertoire or basic understanding. And there is always something more to learn. Get the points of view of people outside your discipline, who will often think differently from you and give you surprising insights. If you’re not learning new stuff, it’s likely in your best interest to move on before it gets too hard to do so.


How ’ s the weather out there, y ’all ?  (Another photograph taken by, and courtesy of,  Ryan McGuire  for his noble site,  Gratisography .)

Hows the weather out there, y’all(Another photograph taken by, and courtesy of, Ryan McGuire for his noble site, Gratisography.)

Security vs. Uncertainty?

Finding new work can effectively be a big second job for freelancers. Taking care of administrative tasks like time management, cost estimates, billing, taxes, and insurance sap time and energy. Sometimes bad situations will lead to the greatest opportunities ever. Other times opportunities dry up.

That’s why of all the above considerations, for most it will still come down to the main fault line: security vs. uncertainty.

Here’s the catch though. That security that full-timers might feel? It can be illusory. Maybe one reason that freelancing is on the rise is simply that loyalty to employees has waned. And it’s only natural that employees would react in kind. This is lamentable for those of us who value loyalty, but lamenting a fact does not make it less factual.


Own Your Own Upshot

On the album So Much Imagine by the Swedish musical duo Marching Band, there’s a brilliant song called “Young and Unafraid,” which has a lyric that always moves me: “So you ended up like this / ’cause you used your liberties…”

Ah yes, all those glorious, confounded liberties! Whether you’re a full-timer, a freelancer, or someone considering making a change, we are all ultimately in control of only one thing: our own actions, including how we react to all that is not within our control. Always do your best work. Act in the interests of your clients and employers. Show courtesy and respect to all, and sincere appreciation for all opportunities that come your way. Also keep in mind that if you’re lucky enough to have the luxury of going freelance should you so desire, it’s not like you’re forbidden by the ancient Contractors’ Guild from returning to permanent full-time work whenever you like.

But it’s 2016. Use your liberties, and put yourself first. Nobody else will.



Posted on April 6, 2016