What no one tells you about leaving the beaten path

My college roommate, Will, and I had a tradition. On the last night of each semester we pushed our beds together and fessed up to all the stuff that we hid from one another during the semester (And yes, I’m aware that’s weird.)

Generally it was stuff like, “I used your hair product for 3 weeks ” or, “I made out with a girl on your bed.”

But this time, I had a real confession. A fear.  He knew that I had plans to drop out of college and travel the world starting in January. What he didn’t know was that I was terrified that I was going to go too far off of the beaten path.

I told Will, “I’m afraid that my life experience will be so different from other people’s that I wont be able to relate to most other people any more. I’m afraid that chasing my dream will be isolating.”

Will thought about it for a moment and said, “Yeah, that’s entirely possible. I think you should do it anyways.”

And I did. I dropped out of college and started travelling the world.

Since that moment, I’ve experienced a lot of things that I feel wildly fortunate for that required leaving the beaten path. I’ve:

  • Travelled to 30+ countries
  • Started two profitable businesses
  • Addressed audiences of over 1,000 people and gotten standing ovations
  • Collaborated with senior government officials, best selling authors, Fortune 500 executives, and the top 1% of my generation

But also, there were insane lows and challenges I could have never predicted. I:

We are often told that we should blaze our own trail, but nobody ever tells us what it’s actually like when you’re out there on your own. In my experience it’s a blend of amazing, agonizing, and downright weird.

The amazing parts of leaving the beaten path

More than anything else, finding the courage to do what’s true to you is an amazing experience…

It unlocks your true potential. Society has set out a clear path for us: get an education, get a job that pays the bills, find a partner, settle down.

This path is well worn, but it doesn’t lead anywhere desirable, it leads to soul crushing mediocrity:

And for my readers who are not in the US, most other developed countries have similarly scary statistics about health, leisure time, and job satisfaction.

The “straight and narrow” will not allow you to access your full potential. Truthfully, the only thing that all world changers have in common is that they’ve blazed their own paths.

Only when you find the courage to leave the beaten path will you create the opportunity to live your life to the fullest.

You get to make the rules. If you follow the beaten path your life will look pretty much like everyone else’s. You’ll have a 9-5 where you slave away making someone else’s dreams come true.

When you leave the beaten path, you no longer have to report to other people’s expectations. Instead, you can begin shaping the contours of your life and making your own rules.

You become more fully alive. Whenever I walk around the city during rush hour, I’m shocked by the expression on peoples’ faces. Their eyes lack light and excitement. They seem plagued by a quiet acceptance of dissatisfaction with their lives.

When you reject the status quo and take life by the reigns, you start to come fully alive. It’s what you were meant to do anyways. The fire and vivacity comes back to you. Your experience of life is more intense than the averages person’s. You start to realize that even the shitty days have a certain beauty to them because at least you’re feeling something true and human. At least you’re living.

You experience life more richly. Leaving the beaten path allows you to create opportunities that just don’t exist for other people. If you’d like to, you can see the Great Wall of China, DJ at a club in Amsterdam, ride on an elephant in Thailand, take iowaska with a shaman, and a million other great things that normal people will never get to do.

The agonizing parts of leaving the beaten path

But leaving the beaten path is not without it’s own unique challenges…

It’s way harder than it seems. Let me state it bluntly because no one ever mentions this: leaving the beaten path is amazingly hard work.

It’s easy to go with the flow and have a normal life. It’s what everyone else is doing.

It’s much more difficult to find the courage needed to swim against the current and create something amazing.

But something interesting happens if you stick with it for long enough. You start to find your lane and life speeds up.

It’s kind of like building a water wheel to change the direction of the current. It’s going to take a lot of work to build the wheel, and even more work to get it spinning, but eventually, if you stick with it, it will redirect the river just a bit. Then more. Then more and more and more and it will eventually become effortless.

It’s terrifying. Two separate trips. One to Asia, and one to Africa. My brother was driving me to the airport and in both instances he asked, “Are you nervous?”

Before that moment, life had been a blur of visas and planning and packing and saying goodbye and all that stuff. I hadn’t really taken the time to check in with myself.

Both times when he asked me, “Are you nervous” I realized, “Holy shit yes, I’m terrified.” On both occasions I considered scrapping the trip then and there, en route to the airport.

But of course, I didn’t. And I’m glad I didn’t. The best things that have happened in my life often started off as the most terrifying.

The allure of the well-worn path is that you know where it leads. Leaving the beaten path is one of the scariest thing you can do, because it forces you to give up the stability and predictability that most people crave.

It’s isolating. Leaving the beaten path can be a deeply lonely experience because your life will no longer look like the lives of the people around you.

When I first dropped out of school to travel, I used to get emails from friends back in college talking about the great parties they went to and the gossip in the group. It was hard to read those emails and know that they were all back there having fun without me.

But there is something magic that happens with a few of your relationships. Your really good relationships get deeper, and occasionally you meet people who you click with instantly. These are the people who have also gone off the beaten path, these are your friends who are also honestly expressing themselves and living their lives to the best of their ability.

Leaving the beaten path makes it harder to relate to the average Joe and Jane, but it also enables you to quickly connect with other amazing people who will see parts of themselves reflected in you.

The weird parts of leaving the beaten path

And finally, I would be remiss if I didn’t mention that a few weird things happen when you leave the beaten path too…

Your life looks different than everyone else’s. A few months ago I wrote to a close friend from high school, Kyle. Every single guy in our group of friends from back then is married now except for he and I.

I asked him, “What’s up with that? Where did we go wrong?”

Kyle has also gone way off the beaten path. Though he’s a brilliant engineer he’s spent most of his adult life working as a ski bum and house painter. He’s also lived in Hawaii, driven across the country several times, travelled internationally, and started a small business.

When I asked Kyle what was wrong with us, he laughed and said, “Dude, you can’t expect your life to look like other people’s if you’re living differently than they are. You’re fine.”

Well said mon ami.

People find you polarizing. I remember when I started telling people that I was going to drop out of college to travel the world. Without fail they would have one of two reactions:

1) They would tell me that’s the most idiotic thing ever and that I was messing up my life.


2) They would be wildly encouraging, enthusiastic, and happy for me.

I’ve had similar experiences every single time I’ve made bold decisions. Some people get excited and encouraging, others freak out and become discouraging.

I have a theory as to why this happens: we all have the ability to be true to ourselves and to chase our deepest desires, but few of us do.

When you start to do so yourself, some people will feel threatened. Your decision to take control of your life makes other people realize that they are in control of their lives too. Instead of taking responsibility for that difficult reality, they’d rather bring you back down to Earth by discouraging you than be reminded of their own latent personal power.

On the flip side, people who are encouraging, I think they get it. Something inside of them responds to something inside of you. In a little way they share the experience with you. These are the people you want.

So, should you leave the beaten path?


Quite simply, yes. Go blaze your own trail. Find one that feels true to you and follow it for a while. See what happens.

If you leave the beaten path and decide it’s not for you, you can always find a new path, or just get back on track with everyone else.

When I mentioned to Will that I was concerned that chasing my dreams would be isolating and that it would make it harder to relate to most people, it turned out to be a valid concern.

And every now and then I’ll have a sky rocketing success or a soul crushing failure that I struggle to share with people because they can’t relate to me.

But those are just the things on the fringes, the sort of tax that we pay for having an unusual level of beauty, awesomeness, and serendipity in our lives.

When Will said that he thought I should do it anyways, he was spot on. Leaving the beaten path is scary, but it is amazingly worth it.


Photo credit: “…drops” by Carlo Sherer

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12 COMMENTS ON THIS POST To “What no one tells you about leaving the beaten path”

  1. Tom Pollak September 3, 2014 at 7:23 am

    Thanks for your honest, scary and inspiring post!
    And keep at it 🙂

    • Jason September 3, 2014 at 2:28 pm

      My pleasure, Tom!

  2. Michael Johnpoll September 3, 2014 at 8:39 pm

    It’s funny that I find myself in a weird way relating. I mean… I’m at the directionless part of my life between graduating college and doing something with my life that doesn’t involve video games, liquor and my dad’s couch. I guess it’s just nice to be able to draw from someone’s experiences and try to figure out this “life” thing a little better.

    Oh, random thought: you gave a pretty cool presentation at Stetson University earlier this year and I had been hiding in the back taking notes with a tangerine on my head. Sorry~ serious life altering comment followed by a silly one. Makes for a little fun.

    • Jason September 3, 2014 at 8:54 pm

      Michael – dude, I remember you! I’ve had thousands of people do that orange thing and you’re literally the only one to keep it on his head the entire time. Bravo!

      For what it’s worth those times of latency (for me at 22 it was Jack Daniels, Guitar Hero, and my parent’s basement) can be valuable – even necessary. Try to keep a bit of silence and space in your life each day so that inspiration and serendipity have the chance to strike. And when inspiration does strike and you start to feel the pull of direction, go at it full force. Good luck my friend!

  3. Mark Taylor September 4, 2014 at 1:38 pm

    Hey Jason,
    Awesome, candid post. I agree that when we don’t have the societal standard of a ‘secure job’, it can make us feel more alive. There’s never an operator’s manual for leaving the beaten path, but that’s why eccentric individuals like yourself and Kyle exist; each find their own.
    Do you think that part of the reason you were able to break from the beaten path was because your passion for travel took such deep root in your being? I’d like to think all humans would passionately pursue a dream/lifestyle once they figure out what it is they want. Have you ever spoken to any of your similar-aged married friends with regrets about what they wanted to do?

    Thanks, keep ’em coming,

    • Jason September 5, 2014 at 1:57 pm


      Thanks for the kind words man. In my lower moments, I long for an operator’s manual to life and the road less taken. 🙂

      Personally, if I have broken free I think it’s for a combination of reasons. 1) My parents were and remain very supportive of my bro an I chasing our dreams, which always helps. 2) Growing up and even in my first year of college, I felt like I was always reading and hearing about the world, instead of actually experiencing it. That feeling of wanting to see and be a part of the world inspired me to drop out and travel. 3) If I’m being honest, some of the times when I leapt off the beaten path were the result of pain and being frustrated with my current situation and feeling the need to make a change.

      And I completely agree – I think when/if people get clarity on what it is they want, they’ll blaze their own path too. The trick is finding that clarity which takes a good bit of silence and introspection.

      Finally, most of my close friends who are married seem fairly happy. Their marriages are categorically good and I don’t think they’d change a thing but almost all of them have made big sacrifices (I can think of at least two who stopped chasing their life dreams) in exchange for stability.

      Thanks Mark!

  4. Katie Post September 9, 2014 at 9:12 pm

    Hey Jason,

    Thanks so much for sharing your thoughts about branching out. I’m currently studying abroad in Spain, and have had many of those weird and agonizing moments in the five days that I’ve been here. Like you, I’m not the person who coul turn around and go home without some major regrets, so of course I’ll stay. But at the same time, I find the experience to be quite challenging–mentally and socially.

    Anyway, seeing the articulation of someone else’s very honest and conscientious feelings has helped me to find some inner peace, at least for tonight–which is all I can do anything about right now. Really appreciate your post, thanks for being a leader in finding your own way in life, and in helping others manage their own struggles in finding the path unique to them.


    • Jason September 10, 2014 at 5:22 pm

      Katie – thanks so much for the kind words, you’ve totally made my day. 🙂

      And yeah, one thing that I don’t think people talk about very often is that study abroads are actually really friggin hard, especially in the beginning. You change… everything for a while and that takes some serious adjustment. New people, new places, new language and culture, new habits – it’s a lot, actually for any one person to take in.

      Hang in their Katie, if your experience is anything like mine you’ll find leaving the beaten path WELL worth the investment.

  5. Camila May 21, 2015 at 11:52 pm

    Wow, this post is everything I wanted to find. You literally wrote everything I think and expressed it perfectly. Is it okay if I emailed you my personal experience and a few questions related to this? Or it that email in the contact information only for business? Thank you for writing this amazing post.

    • Jason May 22, 2015 at 12:05 am

      Hi Camila. Thanks so much for the kind words. Yeah, I kind of wish I knew a lot of that stuff before I left the beaten path. I’m glad that I did, I just wish I knew what I was getting into. And yes, of course, you’re welcome to email me. Jason@ignitedleadership.com. I look forward to hearing from you.

  6. Alec Harper January 7, 2016 at 11:30 pm

    Will you always be a spectator in the crowd? … or, will you finally get up and quietly leave out the back door and put great distance from the noise and distraction? What gives your soul nourishment? Is it a solo hike to a high-alpine lake? Spending another night in your old VW hippy bus in Southern France as you meander the countryside? What in your life made you feel truly alive?

    Our culture rewards those who conform and fit in. Naturally… But must we? And, is it really a ‘reward’?

    So much breathtaking living happens on paths less beaten. Maybe an impromptu conversation in a cafe in Khatmandu with a chap from New Zealand just back from riding mules in Bhutan, playing rock and roll in la plaza major in the heart of Madrid, or meeting fellow mountaineers atop a remote volcano in Ecuador.

    Dare to dare. Wait not for a crisis to jot down some ideas in your journal.

    Live to work or … work to live. Broke free from the madness of the big city and retired early, we did.

    And the bucket list grows and I wonder… is that the road less trammeled calling to us?

    Cheers, Alec 🙂

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