What would you do if you knew you wouldn’t fail?

What would you do if you were fearless?

You may have pondered these questions before, but have you really ever explored the edge?  Do you really know the answer to these questions?

Everyday at Under30CEO we give you advice on how to escape from the grips of society.  How to hone your decision making, leadership, marketing, and financial management, to successfully build your own venture, and give you the freedom and security you’ve been dreaming of.

It’s all bullsh*t.

What you really need is a lesson in assessing risk.

People have so many excuses.  They care what their friends think.  They care what their bank account says.  They care about their credit score.  And my personal favorite, they care about “the gap in their resume” when they went out and failed at starting a business or traveled the world.

But guess what?

None of this is real.

Your friends opinions are just words.  Your bank account is just a number that reinforces your limiting beliefs.  Your credit score is just another electronic number, certainly not backed by gold.  And, the gap in your resume… are you kidding me?

What about the gap in your life?

Is what you are doing today, true to your personal sense of integrity?  If you are like most of our generation– it probably isn’t, and you’ve probably vowed to change it…

Many of you are familiar with the story of the trip to Iceland that changed my life.  The moment when I said “life is too short to sit behind a computer”, and started a travel company.  (See the Under30Experiences travel story here)

I came home, after being totally blown away by a place on earth I never dreamed I’d visit, and sat down Jared my Co-founder and had a talk with him about integrity.

Every month close to a half a million people read Under30CEO, I told him, and we sit here and tell people to follow their dreams, take risk, and reach beyond their own personal boundaries and what they think is possible…

I needed to be true to myself.

Something inside me was calling me to travel.

I’ve dreamt of exploring the world since 3rd grade Social Studies class, hearing about famous adventurers navigating the high seas in search of trade routes.  I couldn’t let this opportunity pass me by.  

Especially not in my twenties.

After Iceland it was Costa Rica, and then across the border to Nicaragua, then across the world to Dubai, Indonesia and Bali…

I learned to surf, speak Spanish, practiced yoga among rice patties, discovered spirituality by way of Balinese Hinduism, and for the first time in my life saw true poverty, and realized what it felt like to make a difference through microfinance.

Go ahead, ask me about risk.

Most people’s risk breaks down into one of two categories: either financial or social.

First, for those of you taking home less than $75K in a major city like New York or San Francisco, you probably aren’t saving much anyway.  My roommate and I were paying over $3K/month to live in a fancy place in Manhattan and buying $12 cocktails downtown.

Trust me, living off 4-star villas for $50/night in Bali, or $1.50 Imperial Beers in Costa Rica, won’t put you in the hole like a weekend out in NYC.

Second, is social.  Guess what?  My best friend was heartbroken.  Dude, we’re probably going to be friends for the next 50 years.  My step-mom told me my family felt abandoned.  Um, remember the time I went to college and didn’t come home for months?  How is this any different?

Real Risk is Not Being True to Yourself

Through my travels I’ve seen sh*t in the world, that truly puts in perspective what people are afraid of when it comes to risk.

How about the Balinese woman who I rented the motorbike from for $5/day?  That morning she put a traditional Hindu offering on the bike, and told me how grateful she was for the bike allowing me to pick her children up from school (all 3 of them on the little moped).

It’s unbelievable how happy she is, I thought as I rode away and saw an entire family next door bathing in the stream on the side of the road.

And people in the Western world are worried about the financial risk of living out their dreams?!

I am no longer afraid of risk.

As an entrepreneur, I’m not afraid of sleeping on couches, because I’ve done it.  As a traveler, I’m not afraid to walk across the Nicaraguan border at night, because I’ve done it.

I’ve leaned into the fear, I’ve tip-toed the edge, and I’ve made all the mistakes.

Learn them at a young age and be forever fearless.

At the end of the day, let there be no gap in your life…

Matt Wilson is co-founder of Under30CEO and Adventurer in Residence at the travel company Under30Experiences.  Read his free e-book The Escape Manual, The secret to temporarily escaping your job, living a life that makes your friends jealous and making memories that last a lifetime.


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