Why Being Sorry Is Better Than Being Safe

Just two short years ago my dream was to get paid to travel the world. Today I can say I’ve spent the past couple years doing just that.

The Intention

Call it the 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. Today, 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. Reflect on some of the decisions that brought me to where I am today and why I’m thrilled for what tomorrow will bring.

“It is in the moments of decision that your destiny is shaped.” – Tony Robbins

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.

Okay, I graduated from an expensive business school. The next step on the “American Dream” path was to get a job with a company I could be proud of…

Done. 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. 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 to 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 my 31st-floor view helped 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 and 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, it was clear how unappealing it looked. I considered giving up the American Dream to pursue the road less traveled.

The Crossroads

“Create luxury lifestyles in the present using the currency of the New Rich: time and mobility.”– Tim Ferriss

On one side I had the “safe” path —  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 “could 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 and unhealthy expressions of people who were 20-years into their roles, it was an easy decision.

The Road Less Traveled

“It seems to be a law of nature, inflexible and inexorable, that those who will not risk cannot win.” – John Paul Jones

I flipped the platitude of, “Better safe than sorry” on its head and ventured down the path that isn’t “safe.”

And perhaps even take the risk of being sorry.

Because of that decision I’ve been able to live one of the best years of my life. I’ve been traveling the world and meeting lifelong friends from all walks of life. All while working with some of the most inspiring people I could 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, then the regret of playing it safe my whole life.‍

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