Encore Anxiety and Future Directions

in which I discuss paid offers, my thoughts on monetization, and getting back to life after the tour.

I recently reached a new milestone: I’ve been off the road for over a month.

I really had a hard time writing this. Or write anything, in my first month back from the trail.

Before I typed about 70,000 words on my phone this summer, I thought it was easier to type from a screen with a keyboard and the ability to type as fast as you think and move large chunks of text. Now that I’m back to keyboards, I think it might be the other way around. But it’s not about the tools, it’s about the approach.

The thing about writing from a path is that there is so little external information, so little external stimulation, that I can carry out a thought without distractions. In fact, I can hear myself thinking. And now that I’m back, it’s much easier to make a really long list of all the things I could do instead of writing (especially all the to-dos that have piled up since I went for a walk). All seemingly «productive» things, but mostly to keep me busy enough to avoid doing actual work.

I went to a meditation center for a week, ran errands, planned a family vacation for the holidays (we’re going to visit my grandma in Shanghai and ski in Japan!), met up with a lot of friends, talked to literary agents about writing a book, deep cleaned my equipment, talked to friends of friends who have been in the creator business longer than me, did a ton of media and interviews (the ones that have been published so far are: one Outside Life Podcasta Outdoor/Backpacking Magazine Articlea piece in the guardianand a short clip for CBC also known as Canadian NPR).

All the good things, but all the distractions. All entries to prevent me from having to notice the lack of results.

As with any other creative activity, when writing it feels safer not to finish the work. It’s safer to not even start it, because then you’ll never know if it ends up being bad. And upon returning from the trail, I felt so much pressure to create, and especially to create something *good*, because I had an audience that repeatedly told me they missed me. Like I was responsible for cultivating a personal relationship with a hundred thousand people on Instagram and TikTok, when I really wanted relief from having to be «on» every day. I don’t know if that pressure really came from them or from within me.

In my normal life, I’ve never been someone who is always on social media, so the idea of ​​creating content and then additional premium exclusive content seemed very daunting to me. I didn’t post a carousel of every trip I took or upload photos from the day to Instagram stories. So posting every day was a huge effort to mine and excavate my emotional life in order to document my walk.

Well, now I’m back.

My friend and two of her children greet me upon my arrival at their house.

I write this as the third gusts of the season are falling here in Vermont, on traditionally Abenaki land. There will be enough snow in northern Vermont to open ski resorts this weekend. We are about to leave autumn and will soon land properly in winter.

When I returned from the trail, I wanted to give my brain a break from the constant processing it was doing, where each day had to be selected and summarized into a succinct set of life lessons. I wanted the freedom to live my life privately, without a daily creative deadline or constant movement north. At the same time, I was grappling with a concept I recently read about: repeat anxiety: a self-inflicted fear that nothing you do will ever be as good again. Nothing I walk will ever have as much meaning again.

I know that’s not true, but the fear is there.

My friends’ cat, Marnie, watching the documentary on extreme bird watching READY

The fall of such a monumental experience is always hard. I’ve been through that before. I am someone who fights to simply beand going from an experience that required a lot of me, every day, to a life without that kind of structure and rigor, is a really disorienting process.

When it was just me and I posted something every day, it didn’t have to be perfect. You just had to do it and publish it, and performance didn’t matter. Having to film everything and metabolize my day into something coherently processed was a forced function, a daily creative output that was really generative for me. Opening a space forced me to introduce myself.

For many weeks I struggled with this responsibility that I felt I should continue to share. Now the general arc has disappeared. Now it’s just my life. I’m not trying to turn my life into The Truman Show.

The more I thought about what he wanted to say, the more it overwhelmed me. When we were in the middle of autumn, I ran into a friend and expressed this sentiment to her. I loved what she said: «your summer was all growth and now it’s time to harvest.» I love that. We tune our bodies to the seasons. We flow with the rhythm of the earth.

Certificates of Completion and Patches from the CDT Coalition and the GDT Association

What I asked myself, however, is: does reaping what I have sown mean it’s time to monetize? Should I start trying to get paid for the work I do? Because it’s work, this emotional excavation. Does that cheapen my work by turning it into a transaction, or does it reveal its true value? I don’t want to make noise for money. I didn’t want to arbitrarily pay for a portion of my work and charge a premium for producing it. I would feel exhausted and my work would lose its authenticity.

Admittedly, and I think not without reason, I was afraid to turn my back on a stable corporate salary and instead invite myself into a life where I make a living as an artist, writer, and creator. (You could say that when I left my job to go hiking, I already made that decision, but a return to stability was always an option.)

However, like all fears, as soon as you start to overcome a fear, it becomes clear how irrational it is. Billie Eilish is an artist and billionaire. There is no reason to think that asking for financial support to make this creative work sustainable is inherently cheap.

I recently recorded an episode of Backpacker Radio with The Trek in Golden, Colorado (coming out mid-December!) and they gave me this fun hat. Sorry too, I just noticed all the cat hair on my sweater, wow!

So to be very clear: Signing up as a paid member of my Substack community is not a fee for service, but rather an investment in unlocking the commons for everyone. (For those of you reading this on The Trek, I’ll continue to post hiking-related content here, but I’ll return to my Substack roots now that I’m out of the way. For a description of the benefits of paid sponsors, read the Substack version of this post.) By supporting me financially, you are making it possible for me to produce authentic and creative results, in a sustainable way. You are giving me a creative position and offering me a way to engage more deeply with you, the people who make this possible.

I recognize the names of people who have donated over and over again while I was on my walk, but there is only so much I can do to thank those people on Venmo. With your sponsorship here, you offer me permission and I offer you a promise: to continue creating.

Lastly, please be patient while I implement this. This is all super new to me and I’m still exploring how to do it. It will continue to evolve. As always, thank you for being here. We look forward to creating with your support 🙂

xx

stitching

A Different Kind of Birdwatching in New York City

*P.S. Much of my thinking about a sponsorship program is inspired by Craig Modand I’m sure it will continue to evolve.

This website contains affiliate links, which means The Trek may receive a percentage of any products or services you purchase using the links in the articles or advertisements. The buyer pays the same price they would otherwise pay, and their purchase helps support The Trek’s ongoing goal of bringing you quality backpacking information and advice. Thank you for your support!

For more information, visit the About page of this site.