How to Manage the Fear and Magic of Uncertainty

by / ⠀Career Advice Entrepreneurship / January 13, 2014

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In December 09, almost four years ago, I left my hometown of Sydney, Australia, a six-figure job, a girlfriend and a beautiful apartment to travel the world indefinitely on my own.

I didn’t know what I was going to do, where I was going to go or how long I was going for. All I had was enough savings to last me about six months, a backpack full of stuff and a one-way ticket to Bangkok, Thailand.

There were a few reasons I chose to do this including:

  • I was not getting any younger
  • I was longing new experiences
  • I wanted to get out of my comfort zone
  • I wanted to try to start a location independent business

Now, four years later I have traveled through sixty something cities in four continents, met thousands of amazing people,  climbed mountains, surfed beaches, boarded slopes, started businesses and partied in some of the most incredible locations on the planet. And the best part? It’s just the beginning…

The hardest part of this huge leap in my life, was getting over the fear of uncertainty. I had no idea what was going to happen… Was I going to get kidnapped? Have all my stuff stolen? End up in a foreign jail? Meet the love of my life? End up on a billionaires private island? Ruin my career? Make my career? I had no idea..

The possibilities both frightened and excited me.

Fortunately for me, the excitement outweighed the fear and I was able to overcome my fear of uncertainty. But for many this world this is not the case.

If I was not able to manage this fear, I would have missed out on the most amazing experiences of my life, so I want to share with you some tips I used to help me manage it.

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Realize it’s Possible

One of the big motivators for me was seeing that other people, just like me were doing amazing things. Traveling the world, starting businesses and building empires. Living amazing lives.

The book the 4 Hour Work Week and a number of “Digital Nomad” blogs were great motivators for me. Being able to  see through the eyes of others who were living the life I wanted, helped me say to myself “If they can do it, why can’t I”?

Identify What you Really Want

If your dream in life is to stay in a low stress job, live in the suburbs with your wife and play golf on the weekends, maybe you don’t need to overcome your fear of uncertainty.

But if there are things you want to experience and achieve in life above and beyond what you’re currently doing, you’re probably going to have to face at least one period of uncertainty to get there.

Now you know this, you know you have to deal with your fear.

For me, I really wanted to earn an income that gave me flexibility to work from anywhere. To get to there I knew I was going to have to take some risks and thus face some uncertainty.

Understand that it’s OK to fail

Failing will not kill you (unless you are actually attempting to do something that is deadly, in which case ignore this point).

If you want to travel perpetually and eventually run out of money and have to go home, you will be OK. If you want to get married and it doesn’t work out, you will be OK. If you want to start a business and it goes bust, you will be OK.

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Seriously, I know this topic has been talked about 1000 times but people still don’t get it. There are countless stories of people who have failed many times before succeeding. It will be fine, have faith in yourself and it will work out. The important part is taking the first step.

I never knew if I was going to succeed or fail (I still don’t) but I know that if I fail, I will be able to figure something out and I will be able to try again. All is not lost.

Have a Backup Plan

One of the major ways I managed my fear of uncertainty was to have a backup plan. I left my job as a Software Recruiter on a high note. I was a high performer with a strong track record. This meant it would be easy if I had to go back and get a job at some point.

I also took out a mortgage on an investment property before I left, this removed on the of the key motivators to having a ‘steady’ job – the ability to get a mortgage.

Having a backup plan might just be the crutch you need to take that important first step.

Whatever your plans in life, master your fear of uncertainty and watch as the world opens its doors.

Vinay Patankar is the CEO of Process Street, a productivity tool for process driven teams. Find him on Twitter or his Blog. Process Street is 100% free to use for small teams and freelancers. Create a free account here:

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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