Jump to Content

Take the Trip

“You should come, too!”

It’s easy to brush an invite off as an empty courtesy, or to decline for any number of arguably legitimate reasons. It feels safe to turn down an invitation.

But what are we missing out on by being safe?

Wanna Hang Out in the Forest with a Bunch of Sweaty Nerds?

A couple weeks ago, I found myself in Nashville, TN as part of a trip to Kentucky and Tennessee that I’d planned with my friend Nate. While we were there, Nate called his friend Steve Kamb, the creator of Nerd Fitness, and we all met up for dinner.

At one point during the conversation, Steve started talking about Camp Nerd Fitness — a weekend out in a remote area of Georgia with a bunch of healthy-minded nerds.

He wrapped up his description of the event with, “You should come!”

This was September 5. Camp Nerd Fitness started September 18. As far as notice goes, it doesn’t get much shorter than that.

Nate already had travel planned, so he couldn’t make it. But I had no plans at all.

My immediate impulse was to decline. Two weeks isn’t enough time. I’m traveling right now; it would be insane to take another trip so soon. I have too much going on at work.

Just Take the Trip

One of the best pieces of advice I’ve ever received was from Craig Weller; we were discussing travel and happiness one evening, and he told me, “Just take the trip.”

The way Craig sees things, if there’s an opportunity to do something, and that opportunity doesn’t create actual problems,1 he will absolutely take the trip. No questions asked.

As a result, Craig has been all over the world in circumstances ranging from a comfortable family-style getaway in Italy to living with a monkey in a tent in Africa. His stories are incredible, and none of them would have happened if “too busy” was an excuse.

What’s Really at Stake, Here?

Thinking a little harder about Steve’s offer, I realized I wasn’t risking anything if I chose to go.

I had plenty of airline miles; I could book the plane ticket without spending any money. I was mostly caught up on projects, and two weeks is a good amount of time to crank on things and get a bit ahead to cover the day and a half I’d miss for the camp. Steve seemed like a really smart guy — someone who could bring a lot to the table both as a friend and as a business contact.2

My first reaction was to think of everything that might go wrong if I took the trip; what I needed to consider was all of the opportunities I’d miss by staying home.

You’ll Only Regret the Trips You Don’t Take

It can be tempting to let fear hold you back, but — when I really think about it — I only regret the trips I don’t take.

I had a chance to see George Carlin in 2007, but I decided I was too busy to go. “I’ll wait until his next tour,” I said. Now I’ll never get the chance3 to see one of the greatest comedians of all time, all because I couldn’t take a break to go see a show.

I can’t recall a single trip I’ve taken that I actually regret. I can think of things I wouldn’t do again, but the experience and lessons I took away from the “bad” trips were worth taking the trip.

Are You In?

A day or so after we got home from Kentucky, Nate connected Steve and I via email, and Steve sent the question:

Are you in?

I still had reservations, but I couldn’t think of any real excuses. I took the trip.

Camp Nerd Fitness
Credit: Will Byington

I spent the last weekend playing ultimate frisbee, reliving my mid-20s in an informal powerlifting competition,4 and not understanding all the comic book, anime, and video game references that were being made.

Because I decided to take the trip, I met a whole new group of people I never knew existed, made some new friends, learned some new tricks,5 and had a really unique experience.

And — perhaps more importantly — because I took this trip, nothing went wrong in my life personally or professionally.

Are You Ready to Take the Trip?

What trips have you taken, even when you felt nervous?

What trips have you turned down for artificial reasons?

Of the two, which do you feel better about?

What To Do Next

If you're like me, the idea of traveling permanently while making a living probably seems like a dream — but you don't think you can pull it off.

I felt that way right up until I actually boarded a flight to leave the United States back in 2014 — and now I can't believe I didn't start living this life sooner.

The secret to a life on your terms — work where and when you want, living anywhere in the world — is remote work. And there's good news: it's easier than ever before to join the ranks of location-independent workers around the world.

I want to help you. The best remote workers all have a set of non-technical skills, and I’ve put together a free 6-point checklist to help you master them — and ultimately master your time and ability to work anywhere in the world.

Click here to get the free checklist now.

Jason Lengstorf in Tokyo

Escape the Office: Get My 6-Step Checklist and Learn:

  • How to create a location-independent income source (or how to make your current job remote-friendly).
  • The additional skills remote workers need to master if they intend to remain remote workers.
  • A remote worker’s most valuable tool for balancing work and play. Because what good is having the freedom to live anywhere if you can’t go explore?

  1. The “actual” is paramount, here. “Too busy” is not an actual problem. “Too short of notice” is not an actual problem. They’re inconveniences. An actual problem is something like, “I’m in my friend’s wedding that weekend,” or, “My parents are in town that day.”
  2. Steve, have your people call my people. We’ll do lunch. I’ll fax you the details.
  3. George Carlin passed away in June of 2008.
  4. And then, as I hobbled around on my aching joints, remembered why I stopped training like a powerlifter.
  5. Parkour! Handstands!

About the Author: Jason Lengstorf

I’m living Post-Hustle.

I don’t believe in extremes. You don’t have to make a choice between a successful career and a fulfilling life outside of work. I’m living proof that you can have both: I work 40 hours a week while traveling the world — all while saving money and feeling happier than ever.

Learn More
Jason Lengstorf in Tokyo