Why I'd Rather be Sorry than Safe

The Intention

Call it law of attraction, dumb luck, or whatever you want to label it. 

One year ago I set the intention of being paid to travel the world and that’s exactly what I’ve been able to experience over the past year.

As I sit in my apartment in Costa Rica, after 10 months on the road, I’m taking time to reflect on some of the decisions that brought me to where I am today and why I’m thrilled for what tomorrow will bring.

Feeling Safe

One year ago I was following the typical “American Dream” life path.

I graduated from Fordham University business school, a prestigious private University with a fancy $200k diploma to show for it.

After graduating from an expensive business school, the next step on the “American Dream” path was to get a job with a prestigious company that I could be proud of...and maybe even flaunt at family gatherings and random strangers at the bar.

✅:  I locked down a job with Morgan Stanley, a Fortune 500 company that I was happy to name drop any chance I could.

My Wall Street job gave me the resources to live in the heart of New York City with my two best friends (hi Pat & Sam!). As a 21 year old, I lived on the 31st floor of a luxury high rise, bought whatever my heart desired, and lived the Manhattan lifestyle I always wanted.

Up until this point my life has been going very much according plan.

I felt satisfied.

I felt settled.

Ultimately, I felt SAFE.

Too Safe

Was this really what I wanted? At first, I thought so. On my time off, I had a blast with my friends and the view tried to convince me it was all worth it.

But deep down, I knew it wasn't.

I soon realized I didn't want push papers back and forth from 9-5 for the next 40 years in order to save up enough money to retire, travel the world and have the freedom to do what I want with my time.

I valued my time--my purpose--more than money or safety could compensate me for.

This is what Tim Ferriss calls the Deferred Life Plan.

When I saw the potential future that was in store by taking the “safe” path and saw how unappealing it looked, I considered giving up the American Dream to pursue the road less traveled.

The Crossroads

On one side I had the “safe” path:  to work for a multinational company for a sense of job security as one of its tens of thousands of dispensable employees.

On the other side I had the “might be sorry” path:  doing something that went against the conventional life plan, outside the scope of 'get a job, work for 30 years, and retire when the best years of your life are gone.'

After seeing the tired, unhealthy, and lifeless expressions on my managers who were 20 years into the role I had, it was an easy decision.

The Road Less Traveled

I took the decision to flip the platitude of, "Better safe than sorry" on its head and venture down the path that isn’t “safe.”

And perhaps even take the risk at being sorry.

Because of that decision I’ve been able to live one of the best years of my life. Traveling the world, meeting lifelong friends from all walks of life, and working with some of the most inspiring people I could ever ask for.

I don't expect everyone to have the same experience I had if they venture down the road less traveled.

But sometimes the “safe” path is the riskiest bet you can make. There's a tremendous amount of risk playing it safe all the time. The risk that your time and life will pass you by.

Take control of your decisions, actions, and life. Take a risk -- maybe you’ll be sorry, or maybe you’ll live a life of excitement and adventure.

Personally, I'll err on the side of the lessons I'll learn from possibly being sorry, than the regret of playing it safe my whole life.

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If you enjoyed this article check out my books on stressing less and escaping your comfort zone.