I quit my consulting job in New York City three months ago to pursue the cliche millennial dream of working for myself. Basic, I know.

I just didn’t feel right about living for the weekends and dreading Mondays during my early twenties the most important time of my life.

The previous year I lost several people very close to me, serving as a sobering reminder that we are all on a timeline. I decided to stop putting things off and go all in on pursuing my dream of working for myself.

I didn’t have much of a plan, and upon arriving to my destination of choice, Medellin, Colombia, It was time to start figuring things out fast.

I was fed up with the fluffy, BS advice you find online.

I decided to reach out to my role models. People who had already achieved the success I was after.

I asked each of these individuals to provide me with their very best piece of advice to their younger twenty something self.

I wasn’t expecting much, but within a few weeks, my inbox started filling up. Within a few weeks I had received responses from fifty, then sixty, then seventy individuals. Before I knew it I had spoken with more than 75+ best-selling authors, super bowl champions, CEOs worth millions, Olympic gold medalists and many more incredible individuals.

And the best part? The advice I had received really did change my life.

While there were many “secrets” or principles of success I learned in speaking with these individuals, in this post I’ll focus on one of the key principles: taking calculated risks. (Want to download all 75+ lifechanging insights I received from CEOs, millionaires, bestselling authors & more? Click here.)

Take Calculated Risks

Being a young twenty something, the chances you have any of the following are slim to none:

  1. A mortgage
  2. A babymama
  3. A wife/family to provide for

You have little to no baggage. Embrace that. Celebrate it. Take advantage of it.


  • Traveling
  • Pursuing your interests
  • Living abroad
  • Finding work that fulfills you

Here is what Steve Kamb had to tell his twenty something self:

If you don’t plan on trying to start your own company right away or going it alone, don’t chase the money with a corporate gig you don’t really like.

Go to work for a small company that you respect/admire and learn as much as you can from them – don’t worry about the job title or how much they pay you, just get your foot in the door and then bust your ass.

Sleep on friends couches if you have to, live as cheaply as possible, and learn about what type of work makes you feel fulfilled.

More money and a company car don’t matter when you aren’t enjoying yourself or making an impact – but it’s tough to go back to a different lifestyle once you start spending money on things you don’t need to try and get happy!

Experiences trump possessions every day of the week, so don’t be afraid to take risks.

Key takeaways:

      • Find work that fulfills you
      • Invest in experiences, possessions
      • Take risks

For those that don’t know Steve, he is a wildly successful blogger, author and entrepreneur who at one time was an avid travel hacker. His post, How to Travel the World for $418, has been read by millions and shared all over the internet. His journey took him to four continents and nine countries over the span of fourteen months. All while spending half the amount of money it would have cost to live in a major US city.

Now that is someone who took full advantage of his twenties and lack of baggage.

But what if I go broke?!

I just got a promotion! can’t just up and leave!

I have no idea what I’ll do!

I hear you, I hear you. All valid points.

However, fear and uncertainty are two of the most common dream killers that prevent people from taking action.

But, as we’ll discuss, taking action is a hallmark characteristic of top performers, plain and simple.

Top performers act before they are ready, because they understand that the perfect moment is a myth.

To combat this fear and uncertainty, it’s helpful to weigh the pro’s and con’s of your decision. It’s helpful to ask yourself two questions:

What is the best possible result?

What is the worst possible result?

Enter Sean Ogle’s advice to his twenty something self…


Your twenties will set the stage for the rest of your life. If you spend it all wearing a suit and tie and climbing the corporate ladder, there’s a good chance that’s what you’ll be doing until retirement.

Take calculated risks. I quit my job to move to Thailand when I was twenty-four. Worst case scenario? I run out of money, come back and get a new job. At that age (and even at thirty or later), you still have plenty of time to build up a career – and that global travel will only make your resume look better.

Best case? You live the rest of your life on your own terms.

Bottom line, your twenties are the time to take a chance on what you want to do. Your older self will thank you.

Key takeaways:

      • Your twenties most likely determine
      • Take calculated risks
      • Quit your job and move to _______ *

* optional

While I may have taken Sean’s advice to heart and quit my own job at twenty-four, I’m not suggesting you need to do the same. But what is important is that you use this critical time period of your life to make the decisions that are going to pay off in a big way down the road.

Don’t play it safe, you can do that later. Take calculated risks. @DifferentHunger (Click to Tweet!)

You can afford to fail. Remember, no babymama drama, no mortgage, no BAGGAGE…

As a young twenty something, you can afford to make mistakes.

As Sean mentions, the best case is that you live the rest of your life on your own terms.

Worst case? You go flat broke and have to start a Kickstarter to fund your way home (which would be a valuable learning experience in and of itself!).

The choice is yours. Coming from me, someone who waited 1.5 years to finally quit my job and set off on my own, I can say that the only thing I wish I would have done was quit sooner.

Similar to Sean’s advice is Jeremy Foster’s advice. Jeremy Foster is an award-winning travel blogger who runs TravelFreak and has been featured by The New York Times, USA Today, BuzzFeed, National Geographic and more.

Coming from someone who has gone bungee jumping naked in Queenstown, his advice is quite fitting…


Do all the stupid stuff you can while you’re in your twenties. You can’t get away with it (as easily) in your thirties.

Key takeaways:

      • Your twenties = the ideal time to take calculated risks
      • Do stupid things in your twenties*
      • Go bungee jumping naked*

* optional

The amount of your baggage will only accumulate and grow over time. Chances are that you will never be as free as you are right now.

Whether it’s quitting your job to pursue your dreams, traveling the world or bungee jumping naked, just do it.

Stop waiting.

Your older self will thank you.

Looking for some more inspiration?

Click here to find out what 75+ millionaires, CEOs, Olympians and more wish they could tell their twenty something self.

Matt Kohn is an adventurer, Crossfitter and web designer. He authors Different Hunger where he provides ambitious 20-somethings with practical insights and tools to improve their mindset, productivity and lifestyle. You can find him on YouTubeFacebookInstagram & Twitter.



Image courtesy of unsplash.com.