A review by emilyinherhead
To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret by Jedidiah Jenkins

adventurous reflective slow-paced

3.0

Having read and loved two of Jedidiah Jenkins’ later books, Like Streams to the Ocean and Mother, Nature, I was excited to go back and check out his debut. This one covers a bike trip he took in 2013-2014, when he had just turned thirty and was trying to Figure His Shit Out.™

It was solidly okay! He and I are just a few years apart in age, so I think if I had read this in my early thirties when it came out, it might have been a little more relevant and relatable. At this point in time, though, it feels pretty dated. We’re along for the ride as he sorts through his Christian upbringing trying to figure out his spirituality, as he thinks about patriarchy and encounters ideas of white privilege for the first time—all topics that, in the year of our lord 2025, seem… obvious? Or at the very least, no longer groundbreaking. And having experienced his more recent writing first, I definitely read this earlier work as a step backward.

Still, dude can write. Here are a few of the passages and turns of phrase that really grabbed me:

I have learned this for certain: If discontent is your disease, travel is medicine. (1)

There is a weird paradox in trying to live a meaningful life, one that you will talk about and tell about. There is the present experience of the living, but also the separate eye, watching from above, already seeing the living from the outside. (56)

I didn’t know what I was holding on to. I had wrapped my life in the fear of messing up. Of disappointing God, which really meant disappointing my mom and friends. I was finding that so much of my life had been about avoiding the feeling of being in trouble. (211)

I looked, and my eyes were happy. (292)

And the scenery Jenkins describes along his journey is beautiful! This book made me long for a return to Chile, where I studied abroad in 2008.

I’m not sorry I read this one, but if you’re new to Jedidiah Jenkins, I might recommend skipping ahead and starting with Like Streams to the Ocean.