Crazy Guy on a Bike

"What am I doing?", New England edition

This morning I rode my bicycle down Route 9 in Massachusetts (the Boston Turnpike), along a skinny shoulder that kept disappearing and reappearing.

I’m cycling from my friend’s place in Worcester to an alternative school in Boston, as part of a big loop through New England. The route is frequently lovely, with protected paths, rail trails, and quiet neighborhood streets. And just as frequently, it reminds me of who this world is made for.

I’m back in the United States after 2.5 years abroad. I’m attempting to exist and travel across this continent, without a car, for six months—a relatively insane decision.

What am I doing?

Boston Turnpike in Worcester

I’ve just published a book that glorifies the proverbial “crazy guy on a bike,”¹ arguing for the importance of glorious weirdos, gonzo adventurers, and downwardly mobile privileged people—to kids, families, and society writ large.

Here I am, trying to live by example.

Do I really believe this? Or did I write the book to justify my pre-existing habits, neuroses, and deficiencies?

Why do we make decisions like these? Am I really deciding, or am I fabricating rational explanations for emotional choices made long ago?

What am I doing?

cycling through a nature reserve in Western Massachusetts

The first wave of book promotion is done: guest posts published, complimentary copies shipped, podcasts scheduled, reviews arriving, and Western state speaking engagements booked (at a bike store, deli, bookstore, library, and brewery). I’ve even enjoyed some surprising success on social media.

Yet I don’t want to become one of those authors, entrepreneurs, or creatives who “promotes” obsessively, to the exclusion of doing the things worth promoting in the first place.

shameless promotion

I’m hesitant to document this bike trip. I wince when I set up a tripod and microphone. I’ve given up on short-form video, abandoned the dumpster fire which is TikTok, and hold deep reservations about helping Meta sell any more deodorant and chicken sandwich ads.

I want to do—write, cycle, speak, and slap “Dirtbag Rich” stickers everywhere—and also share what I do with the wider world. (That’s why we’re here, right?) But striking the right balance feels like walking a tightrope… or like cycling down a skinny, evanescent shoulder on a state highway.

Newark Airport Amtrak Station

So, what am I doing?

The same as you—just trying to stay upright, keep pushing pedals, do what I know, and delude myself a little bit less, with each passing year.

❤️ Blake

(If you’re in Boston, Providence, or New Haven, do say hello.)

Connecticut

1. I borrowed the phrase “crazy guy on a bike” from Neil Gunton’s delightfully old-school blogging platform of the same name.