The Road Ahead

It’s a transitional moment for me, as I’m departing my school of 13 years, and potentially leaving the teaching profession forever. I don’t want to get too maudlin about it; I could break my foot next week and suddenly need quality health care and something to do other than walking. Life plays funny tricks on you sometimes.

At the same time, though, I’ve had pretty much the best teaching job I could ever hope for over the past decade, and it would be difficult to go back into a “regular” teaching position after that. So, in making the decision to depart, I had to be sure that I would be ok if this meant an end to my time in a classroom.

The reality is that I need a bigger challenge. I can’t really fail in the classroom anymore, and that makes it harder to keep growing. So, quite naturally, this leads me back to the trail in pursuit of some longer walks–some more significant physical challenges. It also redirects my focus more fully to writing, something I’ve always had to squeeze into the margins around teaching.

Here’s the initial plan for the next eighteen months:

1) Finish the ADT / Oregon Trail Walk

I’ve written about this in my previous post, including a compilation of posts from my previous, pandemic-disrupted attempts to walk across the USA (the red line above), from coast to coast. My walk resumes from Cincinnati on June 29, following the American Discovery Trail through Ohio, Indiana, Illinois, Iowa, and Nebraska, before branching onto the Oregon Trail for the remainder of the walk home through Wyoming, Idaho, and Oregon (the green line). If all goes absolutely smoothly, I’ll be back in Portland around mid-October, and dipping my toes in the Pacific a few days later

2) Writing and podcasting over the winter

From November through early February, my goal is to build a book out of the trans-USA experiences, so that will be my primary focus. Along with that, I have a book project related to the Camino Francés that has been kicking around the corners of my mind for the past handful of years, and I’m hoping to finally break ground on that. And in between, my goal is to churn out regular episodes of the Camino Podcast (episode 100 isn’t too far off now!), and maybe to finally get back to Sea to Shining Sea as well.

3) The Italy Mega-Walk (Spring and Fall 2025)

It has been too many years now since I was on the Via Francigena, and in the meantime other pilgrimage routes have been recovered/reimagined throughout Italy. I want to walk them all. Well, most of them, anyway. My plan is to max out my Schengen Visa in 2025 by spending three months in the spring walking north (after an initial southward dip around the heel), from Matera, the oldest city in Italy, to the Alps, and then spending another three months in the fall, moving southward from Genoa through Sicily. Along the way, I’ll follow the Cammino Materano, the Via Francigena Sud, the Cammino di San Benedetto, the Cammino di Assisi, the Cammino di Sant’Antonio, the Via Postumia, the Via della Costa, the Via Francigena proper, some freestyling through Naples and the Amalfi Coast, the Cammino Basiliano, and several branches of the Magna Via Francigena

4) Summer 2025 – Some Writing and… ?

I have to be back in the USA, or at least outside of the Schengen zone in the summer. My current thought is to grab some of that time to walk in England or Scotland (thank you, Brexit). Maybe I’ll take a chunk out of the California Mission Trail? And the rest of the summer, I’ll have more time for writing, hopefully to bring the USA and Camino Francés books to the finish line, and get the ball rolling on an Italy book. And some more podcasting, while I’m at it

5) Another winter (2025-26) spent writing and podcasting

The goal at this point would be to complete a book related to the six months of walking up and down Italy. And after that… who knows?

In support of all of this, I’ve decided to launch a Patreon. For those unfamiliar with the model, it’s a crowdsourced way to support people doing creative work. If you would like to support me over the next couple of years, this is a way to do it, with varying tiers available.

The reality is that there’s very little money in writing. We expect content to be available for free on the Internet, and more and more companies are trying to eliminate writers completely through AI-generated content. Even when books are published, the market is tiny. And even if I could, I’m certainly not looking to monetize the podcast; that has always been a fun thing I do for myself and the pilgrimage community.

Nonetheless, I would like to write and produce, and I’d like to be able to both for a while. My living expenses are covered; I’ve saved up for a while for this opportunity. But the more trickles of revenue that I can cultivate, the longer I can disable the fear triggers in my brain that will be shouting at me to be more responsible in the months ahead.

In the interest of full disclosure, most everything that I create will be available to everyone eventually, regardless of whether they support me through the Patreon or not. (I’m a terrible businessman.) It’s a rewarding thing to be read, and if I write something I want it to be out there for anyone, regardless of their means. But, the Patreon will offer first looks at some of the work along the way, along with some other bells and whistles. Think of it as the donativo model. If you have the means and inclination to support me as I take some big risks over the next couple of years, I will be grateful for it. And if you don’t, I’m still appreciative of you taking the time to read what I write, or listen to what I produce.