South Island, New Zealand

Embracing Risk

Cameron Montague
Jul 10, 2017 · 6 min read

In the Spring of 2015 I faced my first major decision as an adult. I was deciding between two distinct career paths, either life as a clinician or a life in business, both of which required two years of graduate studies and a burdening tuition.

For me, continuing on my previous path towards working in healthcare as a clinician was the easy choice. Switching gears and focusing on business rather than science would require a complete shift in my mindset. Regardless of my multifactorial reasoning, it was an extremely difficult decision. Ultimately, I made the decision to pursue my MBA at Boston University — a perceived risk at the time.

Fast forward a year and a half, and I had just about wrapped up my business school experience. I had received two solid job offers and was in advanced talks with two other firms, which was truly a privilege. Many fellow students were still seeking jobs, never mind offers, so I was aware that I was in a great position. But even so, the period of time between when the offers were made and when my decision had to be given was excruciating. The waning moments before responding with my answer made me physically sick — literally sick. Something was off. It didn’t feel right.

Many trusted family members and friends told me the same two things: 1) if I were you, I’d take it, or 2) take it. But if this was so black and white, why was it so hard? Then it hit me.

It isn’t. If I’m feeling this awful about accepting a lucrative offer from a solid company, then it isn’t what I want.

Yet, what was it that I wanted to do? What did I want to be a part of? What was going to leave me truly excited about a position now, and also provide enough of a challenge (and opportunity) to keep me pushing forward? What would prepare me best for my long-term goals? Where did I want to be in two years? Five years? Ten?

I was working as a newly minted graduate when I first read Andy Dunn’s “The Risk Not Taken.” Although I highly recommend reading it for yourselves, in the blog, Dunn talks about risk from a relative perspective. It really resonated with me — so much that I reread it a few times a year so I don’t lose sight of the principles taken away from it.

In the post, Dunn writes, “The risk not taken is more dangerous than the risk taken.”

Think about that for a second. The risk not taken is more dangerous than the risk taken.

He references real risk — not having access to food, healthcare, etc., which is real and tangible. He also writes about octogenarians who often cite that their biggest regrets are not taking risks. Dunn provides his own reasoning: we find a way to justify the risk taken as learning.

More often than not, it’s easy to justify taking the safe job now to “get your feet wet and learn”, when in reality, the likelihood of taking a risk often decreases with age, and, the riskier job likely provides more opportunity for learning and growth.

Luckily, this past Spring I was working as a fellow for PULSE@MassChallenge, where I had the opportunity to work with early stage digital health startups. It was there that I realized I needed to be a part of something. I needed to build something. I needed to make an impact. I didn’t care as much about the oft-cited 90% failure rate of startups as I so much yearned for growth.

In hindsight, the realization made a lot of sense. For the past eight years, I’ve been working towards something (schooling), and to me, building something — whether it be a knowledge base, a skillset, a piece of art, or whatever it may be — is critical to my drive. Working at a startup would indubitably be a bet on myself. Of course, the success of a startup is highly dependent on the team, but I’d be betting that I could first identify an extraordinary team and product offering, get hired, perform, and ultimately help drive the growth and success of the company, and with no guarantee of meaningful success. I know I’m not the first person to do this, and I’m certainly not the last, but that doesn’t matter because that’s not the point.

The point is that it we often take the route that is safe and familiar. We take the route that is reliably reliable. The path of least resistance. It’s not a fault, but rather human nature. But sometimes our instincts need push-back. We owe it to ourselves (and the many others who have supported us throughout our lives) to continue to grow, learn, evolve, and otherwise push our inner boundaries. We owe it to ourselves to strive for our grandest aspirations and in doing so, discover our full potential. We owe it to ourselves to live our lives in however manner we wish. And most of all, we deserve to be happy.

“The risk is not in doing something that feels risky. The risk is in not doing something that feels risky.”

When making a decision about my future employment, I asked myself “where do I want to go,” and “how do I get there?”. Well, for me, it was Crayon. Crayon is a Boston-based software startup that provides market intelligence for marketing, product, and sales teams. I’ve been working here full time since the end of March, and suffice to say, I’m extremely happy with my decision.

Crayon is something I believe in — and thus the justification for taking on a risk. I don’t believe that businesses should only be focused on themselves internally, but rather should be focused on the entire ecosystem of their industry. Should businesses be strictly reactive? Of course not. But, much akin to my personal experiences, business decisions are never made in a vacuum. Instead, we widen our lense and survey the landscape before ultimately taking action.

Coincidentally, it was my own market intelligence that led me to find Crayon. Keeping tabs on investors and the startup scene, I came across a tweet that referenced Crayon and their recent seed funding. From there, I pounced.

It’s amazing what can be found on the world wide web. From a business perspective, firms optimize their digital footprint to reach mass audiences, which in the process of doing so, also leaves a crumb trail of insights into their strategy and secret sauce. Crayon combs the internet, unearths those crumb trails, analyzes and delivers that information so that businesses can act on those insights to ultimately drive smarter tactics and effective strategy.

It was the connection to my personal experiences and the implications for what Crayon could become that drew me to the company. The two outstanding founders and superb core team (all 16 of us! And growing!) was what sealed the deal. Ultimately, the risk in not joining Crayon seemed to be too large to stomach.

But what if I had taken the easy route and chosen to go the clinical path, and hadn’t taken a risk and attended business school? What if I had taken the easy route and accepted a safe job this winter? What if I hadn’t taken a series of risks along the way over the past eight years? Or, what if I hadn’t accepted risk and exposed myself to various other experiences?

Fortunately, we won’t know. Instead, I chose to take on and embrace each of these risks, and that has led me to a new adventure filled with opportunities for learning and growth. I took a chance to work for a startup that is armed with an incredibly knowledgeable and energetic team, and an impactful product offering. Crayon is still young and unfortunately doesn’t come with any guarantees, but that’s okay — because this is a path of developing a deeper understanding of my inner self. Sure, I’ll gain firsthand experience in building a great company, but more importantly, I’ll get a deeper understanding of what motivates me and why, because that is constantly evolving. Not in a negative way, but in the sense that as we learn and accomplish new things, our aspirations and understanding of life and ourselves evolves.

The best way to solve for that understanding? A little bit of risk.

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