Welcome to our new column that explores the one element that almost every career decision is affected by—Risk with a capital “R.” Should we take the high-ranking job at that work-in-progress start-up, or stay in the predictable position at the stable corporation? Should we pitch that unconventional idea with loads of potential, or should we present something safe that we know will please our boss? Should we ask for a raise when we think we deserve it, but our company isn’t exactly profitable?

Since every choice we make carries a risk, Good F***ing Design Advice co-founder Brian Buirge is going to examine both sides of the equation behind the decisions that creative entrepreneurs have to make. And joining him in this column is GFDA co-founder Jason Bacher who will be designing the visuals that accompany each piece. (Fittingly, the duo lead a workshop in The Art of Risk-Taking.)

In this first installment, Brian reflects on the decision he made when two career opportunities unexpectedly opened up at the same time—a fantastic job offer normally reserved for someone with more work experience than he had, and acceptance into grad school at Kent State. After years of being a self-described "freewheeling-freelancer" Brian decides there is only one way forward.

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For nearly eight years, I've had the privilege of sharing the GFDA story with audiences around the globe. Save for a few bleary-eyed conversations at the bar, I’ve rarely taken the opportunity to discuss the experiences that landed me in the position to meet and befriend my co-founder Jason Bacher. So, it seemed opportune and appropriate to share a bit of my post-undergrad/pre-GFDA lessons in risk-taking to kick off this new column.

The first two years after I completed undergrad were a chaotic array of service jobs, false starts, bad freelance opportunities, and harsh lessons about business and life. During most of the first year I slept in hotel rooms, on floors (carpeted and uncarpeted), in chairs, on couches, next to friends, on tables, in attics and basements, and on the occasional mattress for good measure. Both my back and my personal relationships suffered as I struggled to pull together something that, if you squinted, looked like a career.

Along the way I managed the ethically-flexible position of temporary long-term, designing in-house at an ad agency in Cleveland. After a few months, I was finally able to afford my own apartment and traded in the compound job title of freeloading-freelancer for the much more streamlined and attractive, freelancer. I held that coveted position for two whole weeks before getting promoted to unemployed.

The economy of 2009 wasn’t a particularly stable one, and, as the budgets shrank and clients dried up, so did the work they had to offer me. Betrayed by fate, I manically skulked in my misfortune as I fervently searched for any kind of work in the field. I was burnt out, and things weren’t about to get any easier.

As though that weren't enough, my dad suffered a debilitating stroke about a week after I lost my job. My brooding turned into a constant state of fear and anxiety. My dad precariously recovered in the hospital over a period of weeks peppered with brief moments of relief that he survived in the first place—and was improving against the odds.

Through a bit of good fortune, I managed to land a part-time job teaching the intricacies of Adobe software at my recent alma mater Kent State. It was the ideal position I never knew I wanted. It paid my bills and, being part-time, it gave me the flexibility to travel back home to Pittsburgh during the week to support my family while my dad recovered.

Teaching was a new experience. Working with students helped to brighten my disposition, and even though life was stressful at the time, I knew where I was going to sleep every night.

I continued teaching into the spring semester, and, as my dad continued to regain his health, I spent less time at home and more time squatting in the graduate studio between teaching classes. While there, I interacted regularly with the design department's handful of grad students, in particular a sharp-witted and sharply-dressed Jason Bacher. We hit it off as we had both done our undergraduate at Kent State. We shared an unhealthy passion for good design, and we spent most of that semester finding ways to collaborate.

With things settling down in my life, and the economy picking up, I began to apply for jobs again. After the pandemonium of the previous year, I needed the stability of a normal job with regular hours and reliable pay. Health insurance and a bed frame to go with my mattress were also priorities.

In addition, and after some encouragement from the senior faculty, I applied to graduate school at Kent. While I enjoyed teaching, in my head, it was a back-up plan if I continued to fail at becoming gainfully employed.

Much to my surprise, I received both a fantastic job offer and an acceptance letter to graduate school a few days apart. Up until this point, my future seemed like it was going to be a miserable series of leaps from one place of desperation to the next.

My preference was weighted heavily in favor of taking the job and beginning my career. It was the kind of job that I thought I’d need a decade of experience before even having a shot at. On the other hand, I had graduate school. In retrospect, it was a great offer, but I was naive and didn’t look at it that way at the time. I couldn’t clearly see the benefits of going to graduate school. It looked like a mountain of work and zero security. A big part of me felt like I’d be staying in place, back in school again and not starting my life.

Something gnawed at me, though, as I contended with my hunger for security. I weighed my options and distinctly remember standing at the doorway surveying the grad studio listening to a voice in my head telling me, “If you don’t stay here you’re going to miss out on something important, and that guy you’ve been collaborating with over there has something to do with it.”

It wasn’t an easy decision, but I gave up that job and stayed in Kent. Becoming a student again would forever change the direction of my life. Six months later over early morning coffee, Jason and I laughed about an idea for a website called Good F***ing Design Advice.

The rest of that history is still being written (literally, we’ve got a book coming out next year!), but looking back on that time and those choices makes me think about how we often (incorrectly) weigh the costs and benefits of taking risks.

In my experience as an entrepreneur, designer, and workshop facilitator, it appears to me that we often gauge our capacity for risk-taking without taking both sides of the equation into consideration. We tend towards viewing risks as the actions we could conceivably take, and we forget about the risks inherent in the actions we don’t take.

There are an inexhaustible list of concerns associated with doing something like striking out on your own, or maybe smaller but nonetheless consequential things like taking risks on your next project or asking for a raise. Just starting to think about them might be enough to stop you dead in your tracks and go vacuum the rug. You need to balance the equation and consider the risks (and perhaps benefits) of not doing the thing.

In the coming series, we’ll take an honest, balanced look at risk as it applies to being a creative and an entrepreneur. Hopefully, after a few real-world examples have been laid out for you, you’ll be better equipped to contend with your own set of risks, personally, and professionally.