Leaning into Risk

“If you could go back in time and share one piece of advice with your 28 year old self, what would you tell them?”

In December, I made the decision to leave my employer in pursuit of a new challenge. Before leaving, I sat down (virtually) with some of my peers, mentors, and executives for one final hurrah where I could garner life and career advice — trust me, it was a hoot. I was genuinely curious to hear what these individuals, all of whom I highly respected, had to say — with my time travel question taking centre stage.

While there was diversity in the responses I received, the common underlying theme across all my discussions was clear: take more risks.

Views from 12,500 ft

Speaking of risks, a few months ago, I crossed a huge item off of my bucket list and went skydiving. Let me get this out of the way right now and say that skydiving is easily one of the most exhilarating, pensive, and euphoric experiences you will ever have. Contrary to what people might think, it’s actually not that scary; although, your loved ones might feel a strong sense of trepidation.

The whole thing has a sense of anticipation around it. You arrive at the location, check in, run through practice poses, meet your instructor, and harness up. Each subsequent activity ratchets up your excitement until it’s finally time for you to step onto the plane and fully commit.

In truth, there is one moment that’s terrifying. A moment where your mind starts to spiral out of control, triggering a cascade of doubt around what you’re about to do. That moment comes when the door you initially used to enter the plane flings open at 12,500 feet.

Even though you’ve rationalized the experience to this point, the fear you feel having to slowly scoot towards the door and allow your legs to freely dangle above the clouds is paralyzing. Every instinct in your body tells you not to move; and overcoming this very moment is the hardest part of skydiving. Fortunately, the instructors are there to support you. They move fast and don’t let you get inside your head for too long. You teeter on the edge of the door for a few seconds, then rock back for one, rock back for two, and on three, you let go.

Once you drop, the first five seconds are of course, a frantic scream for dear life; after which calmness settles in for you to enjoy a view like no other. Pure elation.

The Pivotal Moment

Reflecting back, it’s jarring how a few seconds of fear, right at the pivotal moment, may very well have sabotaged my experience and robbed me of a lifelong memory. Skydiving might be a bit of an extreme example because in all fairness, you probably should be a little scared. But, how often do you find yourself coming to the cusp of a decision — going for a run, taking a new job, asking someone out — only to back out at the last moment?

The parallels of this, apropos the advice I received from my colleagues is plain as day. When taking a “risk”, the fear of failure shouldn’t vastly outweigh the hopes of success. Unfortunately, this is often not the case. I can think of a few examples in my own life, far less death defying than skydiving, where I was willing to abandon my plan at the last second. Though, I wouldn’t say this constitutes the majority of my flakiness. Once I make a decision, I tend to follow through.

My inclination is to back out of a decision long before execution is in sight. During the early stages of discovery, just as I start flirting with an idea, my brain immediately starts poking holes and convinces me not to act. In some cases, this tendency is a good thing. For example, it’s probably wise to immediately convince yourself out of alligator wrestling. For others, such as actively networking during a pandemic, the behaviour is detrimental.

Perhaps our critical nature is an unintended consequence of academia or the society in which we live, where our intelligence is conveyed by how well we can lambaste the ideas of others. We’re just hard wired to find flaws, even in ourselves. 

Circuitry aside, the worst case scenarios that seed the greatest doubt for me aren’t usually rationale; they’re social. In other words, the thought of losing my job, lack of skills or time are generally not the major detractors. It’s always the perceived opinion of others that hamstrings me.

What will others think of this idea?

What if they don’t like it?

What will people say if I fail?

We live in a world where our failures can be amplified and criticism is easier to deliver than ever before. As a result, we unfortunately assign a disproportionate amount of weighting to the approval of others in our decision making calculus — or at least, I do.

Playing the Long Game

I’m not going to pretend like I have the answer to overcoming the fear of failure and societal pressures that we all likely face. Decision making is a vast and complex field that may provide hints as to how we can take more risks and live a happier life. However, one thing that has worked for me is to zoom out and consider things with a broader perspective by looking years into the future. Yes, the same simulator that causes you to spaz out in the face of risk, can also be used to talk to your 50, 75, or even 100 year old self.

Let’s consider my situation of starting a new job. Against the backdrop of our current economic climate alone, most would consider relinquishing existing trust, relationships, and a steady pay cheque in favour of a bold new adventure to be risky. Not to mention the fact that I will be pivoting industries and onboarding as a fully remote employee, in a highly cross functional role, in a different time zone than my team — compelling reasons to reconsider a transition.

While there were positives that countered the concerns, I found solace in the fact that I still have approximately 37 more years left in my career. What’s the worst thing that could happen, really? If I were to get axed during my probationary period, that would only represent 0.67% of the remaining time in my career. Money and security will come, but the opportunity to learn new skills, discover new relationships, and develop new levels of resiliency, well, I’d say that’s well worth the 0.67%. 


Every situation is going to be unique. Of course, there will be instances where it makes more sense to err on the side of conservatism. However, there will also be scenarios that  will open up new doors, enable us to grow, and derive a sense of fulfillment if we have the courage to act in the face of fear. Don’t let a few seconds of doubt rooted in either your own or others’ perceived criticism hold you back. Play the long game, be bold, and try new things.

It’s an odd formula, but at the nexus of composure in the face of fear, sprinkled with a hint of commitment to the experience and a sense of belief lies a profound catharsis.

Key Takeaway: Don’t let a little fear in the face of a risky decision prevent you from growing. Consider things with a longer time horizon and commit.


2 thoughts on “Leaning into Risk

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