Stop Waiting to Be Picked, Choose Yourself

by Dave Weatherall Dec 7, 2016

“Instead of wondering when your next vacation will be, maybe you should set up a life you don’t need escaping from.” -Seth Godin

I once wrote an article in a “young creatives” magazine about popular culture, money and its blinding effect on the search for happiness. I questioned why many Western millennials, like me, believe that money equals happiness.

Had our ideology been intoxicated by “MTV Cribs” and “Who Wants to be a Millionaire?” Did these television shows sell us hopeless dreams, telling us that money will solve all of our problems?

The magazine was published when I was 18 years old, working 50 + hours per week in a marketing agency. An era of my life devoted to drinking my way out of anxiety attacks and suppressing desires to nose-dive into Regent’s Canal on my walk to work at 8 AM.

4 years on, I have a different story to tell.

Since my humble beginnings, I have quit my job to travel the world. I founded a team of digital marketing nomads, whilst living and working from 7 different countries around the world. I also write a travel entrepreneurship blog that is slowly developing into a reliable revenue stream.

My favourite part of this story is, I’m only 22 years old. I don’t have a University degree, I quit my job without any savings (and I don’t have a trust fund for those of you who are wondering).

I am a “travel entrepreneur”, “digital nomad”, or any other buzzwords you can think of for working while travelling. I am exploring the world and enjoying the freedom of a perpetual working-holiday. I am free from the rat race and the empty promises of “good career progression and development opportunities”.

My advice to young people who hate their jobs:

Ask yourself, what makes you happy? And if the answer is different from whatever you are doing with your life, why is that?

I urge you not to spend the next 40 years investing your life into somebody else’s business in the hope of a secure future. In the better words of Jim Carrey whilst commenting on the life choices of his late father:

“You can fail at what you don’t want. So you might as well take a chance on doing what you love.”

It makes me sad when my millennial counterparts say “there are no opportunities for young people today”. We need to evolve from the archaic way of thinking that the only way to make money is to gain employment. The thought that it takes an external force to make your dreams come true. It’s 2016, you really can make money with just a laptop and a Wi-Fi connection!

Ask anyone in the 10,000+ strong community of startups who work remotely and digital nomads at Or the US Department of Labor who found there’s been a 50% increase in companies that have teams working remotely over the past 5 years! And FlexJobs who reported a 26 percent increase in the number of remote job listings in 2014, over 2013.

If you are waiting for something to happen, the chances are it never will. But when you actively seek and create opportunities for yourself, you can achieve almost anything. Stop waiting to be picked, choose yourself!

So, how do you make money while travelling?

I ask travel entrepreneurs and successful digital nomad teams this question every Sunday in my weekly interview series. I interview people of all ages, genders, and different backgrounds to provide a platform for encouraging travel and inspiration for those who want to redesign their lifestyle.

Of course, not all jobs require a Wi-Fi connection. You can teach English, become a surf or scuba diving instructor. You can work in hostels, volunteer, work exchange, guide tours, teach yoga, work on cruise ships, even house-sit!

There’s hundreds of opportunities and it will only continue to get easier as the Internet swallows up what’s left of reality. Take it from me; a 22-year-old without a University degree who founded a nomadic digital marketing team, travel & entrepreneurship blog, and hasn’t stopped to tie my shoelaces since.

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