Almost Fearless

After Seven Years, Travel Has Finally Changed Me

Drew here. If you follow this blog, you may have picked up on a running theme, that I am not a natural when it comes to travel. The main thing I have going for me is that I am willing to try, that I am just curious enough to want to know what happens next, that I trust my adventurous, brilliant wife to not lead us to our imminent doom.

For years, I have lived outside of my comfort zone. I like the challenge of it, I think there’s a part of me that enjoys suffering, just a little. When I told people I was taking Greyhound buses from one place to another, some of them 24 hour trips, I made out like I was putting on a brave face – the truth is, I get a kick out of that particular sort of misery, as long as it’s done solo. No need to subject my kids to that sort of torture.


But real change takes time, it takes effort. Self-help books can make you feel good, like progress can be made with a positive frame of mind and a willingness to follow a program. What they rarely tell you is that many people are more like rocks than they are like water. They can be formed into something new, but the effort it takes to change into that new thing requires a monumental effort, or a great deal of time. Not many people are patient enough to get there.

I’m not patient enough to get there either. I haven’t exerted some monumental effort to change, I just trusted my wife, and I sort of like to suffer. Add time to that, and somewhere along this film tour, something clicked.




Los Angeles was sort of a mess. I had a great time with my old college roommate, then got sick. Then got him sick. And his four year old boy. I changed the venue for the screening but forgot to change it on the website, which led to a few people not going to the right place. I learned about this just as the movie was starting, and sat through that screening, essentially having a panic attack over how I had screwed up. I’ve always had a sort of irrational fear of Los Angeles, and my experience there didn’t help ease that fear.



As much as I wanted to curl up into a ball and turn invisible, the tour had to continue. The trip to Denver took me through Utah, which was lacking in cell signal, but made up for it by looking like I was on another planet. Denver was an amazing city. I stayed with friends, but also couch surfed for the first time (I recommend it) and also stayed in the grimiest hostel I have ever witnessed, and I have stayed in a LOT of hostels.





Something cracked in Denver. I ran into a lot of people. Different types of personalities, made new friends. Somewhere along the way, I had encountered enough personalities, pivoted over and over throughout the tour, bouncing from place to place.

Anxiety burned away, cynicism gone, judgement vanished. I had grown flexible in small increments over the last several years, but a massive shift occurred in Denver. All throughout the tour, during question and answer sessions that followed a screening, I kept coming back to the same theme.

“We’re all just trying our best here.”

It came up because I felt a need to remind people that even though The Wireless Generation shows people traveling and working online, the message isn’t This Is The Way To Live. It’s just *a* way people live. There are lots of right ways for someone to live their lives, and if someone is content, happy with how they live, then that’s the whole point of everything, right?

It also came up when I had to explain why Christine and I didn’t have any plans to come back to the US to raise our kids, that it was frustrating to feel like in the US, it doesn’t matter how you raise your children, because there will always be a large group of people there to tell you you are doing it wrong.

You’re too free range, your kids will die.

You’re a helicopter parent, your kids won’t be ready for the real world.

I feel like I’ve seen enough at this point to recognize parent shaming as a useless way to make yourself feel better about the way you parent. I’m over it.

“We’re all just trying our best here.”

Somewhere in Denver, I had said the phrase enough I decided, maybe I should apply it to everyone. When I did that, everything got easier.

I posted a ride-share on craigslist to see if anyone was going from Denver to Austin. I had never done anything like that before, the idea of spending 14 hours in a car with a perfect stranger was daunting. Two days later I made a new friend.






In Austin I spent time with an old friend and my new friend listening to Bluegrass music. At the screening I reunited with more friends and met a whole new batch of awesome people to talk with. The Denver screening had been a boozy fun time in a beer cannery, but Austin’s screening may have been the most satisfying one yet, and in a fully packed theater. The empty seat you see above was my seat.


When I posted the above photo to Facebook, many people assumed a person sleeping on me would be irritating. How could it not be? But I had watched him over the course of three hours sleepily try his best not to lean on me.

He literally was trying his best. It was a short flight. In my mind, I cut the kid some slack. A year ago, I may not have.


Processed with VSCOcam with b1 preset



The Boston screening is next week, and I have been spending the time in between screenings visiting my parents for the first time in years, which is like having someone showing me a map of my brain that fills in all the paths that lead from one decision to another, highlighting hurdles and pitfalls that I know exist in my thinking but can’t easily identify until it’s too late. All of the things that I find irritating about my parents, the things that drive me the most crazy, all of that exists within me. Of course all of the good things are all there as well, and I struggle with this. Seeing my parents again reminds me of all the good things I see in them that I want to foster in myself, and the things that I want to avoid. I am grateful for the road map.

Mostly though, this trip has taught me to give myself, and my parents, a break.

Because we’re all just trying our best here.

Christine Gilbert

I’ve been dragging my husband around the world since 2008 always with the promise that, “Yes, Drew there will definitely be hammocks there.”