Why Taking a Giant Risk Might Be the Safest Thing You Can Do

Let’s rewind about four months. It’s February, and I’m on a tiny Colombian island in the middle of the Caribbean. It’s 85 in the shade.

I’ve got a fat grin plastered on my face. Even better, I can feel the sun on my bare skin. I also realize that I can no longer remember what a Boston subway train filled with musty, wet, snow-covered commuters smells like.


My grin grows even wider. No road salt is going to ruin my flip flops here.

Though I’ve just quit my comfy university job just a month ago in exchange for an unpaid fellowship in Bogotá, I’m feeling pretty good. It’s really amazing how the Caribbean sun can magically erase any doubts you may have had about quitting your job in snowy New England.

There is a lot of uncertainty about the future — where I’d go from here, or when I might start, oh I don’t know…earning an income again?! But with my ass planted securely in the sand and the taste of cold beer on my lips, I just try to enjoy the present moment — which, in San Andrés, isn’t terribly difficult. As my brother often says, all of that is Future Rebecca’s problem.

The following morning, I’m groggily awoken around 5am to my phone vibrating.

I try very hard to stick to a policy of not checking my phone during the precious hours that I should be sleeping, but this morning, something inspires me to roll over and glance at the screen.

It’s a message from an old friend, also involved at the university where I used to work.

“Hey, did you hear what happened to your old department?”

I feel a shot of adrenaline run through my body. I left my old job with some sadness — I was very close with my former boss and teammates. They taught me what it is to trust in your team and your manager, and have them trust you back. A sense of foreboding tingled through my stomach. What the hell had happened to them?

I wouldn’t usually answer a message at this time, but I’m definitely awake now. Going back to sleep is no longer an option.

My friend responds back right away.

My stomach drops to the floor.

The news?

My entire department had been eliminated, and my entire team fired.

I immediately think of my coworkers — some with families, kids — suddenly jobless, and my heart sinks even further.

The sadness and shock last for a few days, but over the coming weeks, they become less jolting, and I begin to think.

I had left my comfy salary (pretty good for a liberal arts major straight out of school), my good benefits (they’d paid for an expensive orthopedic surgery on my arm), and my own office (I could control my own heat!) in exchange for an unpaid six-month fellowship at a startup in a giant South American city that I’d never even been to, during which I’d be living off of my own limited savings.

It sure sounds like ditching a very safe option for a very risky one.

But what would have happened if I had stayed with the “safe” option?

As it turns out, just one month after when I had quit, I would have been unemployed anyway — stuck in the brutal Boston winter, with no income, no career plans, and probably mildly depressed.

Instead, I was equally salary-less — but I was in the gorgeous country of Colombia, about to embark on a new adventure, new challenges, and new learnings that would propel me towards the career I actually wanted in social entrepreneurship.

Talk about having your mind blown. I felt my entire understanding of this new journey — leaving the “safe” to take a chance on the “risky” — do a complete 180.

I had thought that if I stuck with the comfy salary, I could count on it. I knew that if I stayed there, I could continue saving, stay in a familiar city with my friends, and keep hanging out in my comfort zone.

But there’s nothing very comfortable about being called into a last minute meeting on a Friday afternoon and being told you don’t have a job on Monday.

I realized that the choice I had made was actually much less risky. I was already investing in my own career and taking on new challenges that would bring me to a new professional and personal level, rather than sitting and waiting in a job that I already knew I didn’t want to do forever — and apparently wasn’t even going to last.

It’s often said that nothing is guaranteed in this life, but we usually hear this in reference to something negative — death, breakups, bad luck. But what if we allowed this phrase to liberate us?

Sometimes we stick with the status quo out of fear: fear of change, fear of failure, fear that by taking a risk you’ll end up worse than before. The status quo, though often mediocre, is the only thing we know. It seems familiar, static, certain. We know the day in and day out; we’ve seen both how good it can get and how bad it can get; and we are okay with it. It’s comfortable.

But what if we allowed ourselves to understand that even the status quo — as reliable as it seems — is no more guaranteed than the next option? And what if we turned fear of change into the freedom to do what our hearts yearn for?

I had followed my gut and my passion even when it felt a bit like jumping off a cliff.

As it turns out, my other “safe” option would have ended with me getting pushed off a cliff.

So which was the risky option after all?

I only have a handful of years on this earth, and I plan on living the hell out of them. If you need me, you can find me carving my own path, following my passions and most importantly my gut. And I’ll be taking risks to get there — comfort zone and corner office be damned.

I may have jumped off a cliff, but I sure as hell hit the ground running, and I’m eagerly on the lookout for my next big leap.

guasca view

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