Welcome to our column that explores the one element that affects almost every career decision—Risk, with a capital “R.” 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 third installment, Brian reflects on how he and Jason were put on the spot to sell an idea they hadn't quite fleshed out.

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In early 2016, our five-year-old company was hitting all of the appropriate developmental milestones of a five-year old person: our vocabulary was growing, you could leave us alone with safety scissors, we were comfortable in public for short periods of time, and while our ability to do math was lagging a bit, we managed to make up for it in finger-painting techniques.

Our workshop was one of the first things we wanted to revisit with our newfound "maturity." We began to feel it wasn’t a proper reflection of the direction we were headed. So, for a few months, we stopped offering it entirely, and banged our heads relentlessly on the drawing board of possibility—which my co-founder, Jason, and I often mistook for each other’s foreheads.

We finally zeroed in on an idea for a workshop called “The Art of Risk-Taking.” The concept was built around an approach to help creatives, or entrepreneurs, or anyone really, become more comfortable with being uncomfortable. We believed that risk and uncertainty were key ingredients for us specifically, and for the design process more broadly. Without them, we felt that the best we could hope for (and therefore everyone else) were stale approaches, rehashed concepts, and meager improvements to someone else’s ideas.

Confident that the compass was finally pointing in the right direction, I wrote two choppy paragraphs about the workshop and updated the GFDA website accordingly. From there, we tabled further development in favor of the more immediate fires that demanded our attention.

Two very short weeks later, while on a working vacation in Louisville, I received an email from someone at a Fortune 100 company who stumbled upon those two paragraphs, and wanted to know more about our soon-to-be-wildly-successful-but-not-at-all-fleshed-out-much-less-built workshop on risk-taking.

Naturally, our website gave the entirely false illusion that we’d been offering this workshop for quite a while. Consequently the biggest pitch of my life didn’t happen with a suit and tie in a conference room with lots of planning and a fancy deck. It happened in a pair of gym shorts, over the phone, from the breakfast bar of my friend’s concrete kitchen countertop. I asked for more money than I had ever been paid, for a workshop that wasn’t finished, for an event happening in less than a month's time.

If you can believe it, the pitch was successful. It didn’t happen the way I would have ideally planned it—but then again, nothing ever goes according to plan, does it? Often the biggest and most important opportunities will manifest themselves at a moment's notice, and you’ll have no time to plan your strategy and approach. In the absence of planning all you’re left with is whatever life has prepared you for until that moment.

While the granular details hadn’t been worked out, Jason and I had previously invested such a tremendous amount of time around the idea, its goals and objectives, that I was well-equipped to act in the moment and decisively sell the idea.

Rolling the dice with zero experience is quite different than shooting from the hip informed by years of practice. One is reckless, while the other is a calculable risk. The difference is having the discipline to know the difference.