Friday Five: ‘Denali, Alaska’ author Tyler Dempsey

‘Each essay is a tiny vessel exploring the mosaic of my experience…’

Don’t let the title of Tyler Dempsey’s latest book, Denali, Alaska, fool you. That may sound like the name of a travelogue or guidebook, but this collection of essays, now out from Trident, is as expansive as the state he called home for more than a decade.

A black and white image of a man sitting on a couch with two dogs, one on his lap and another behind him, looking relaxed in a cozy indoor setting. On the right side, there is a book cover titled 'Denali, Alaska' by Tyler Dempsey, featuring a scenic mountain landscape.
Left, Tyler Dempsey with his two dogs (husky Ally and Labrador mix Wilt). Right, the cover of his new essay collection, Denali, Alaska, now available from Trident.

Yes, there are plenty of first-person accounts of Tyler’s adventures in the wilds of The Last Frontier, including a stint as a backpacking guide for a Belgian film crew to the site of a famously doomed American adventurer (the subject of the book’s penultimate essay). But each of these essays, like the author himself, covers a lot of territory, from life in Alaska (“the size of two Texases,” Tyler reminds us) to banana farms in Hawaii, hitchhiking in Montana, leaving his native Oklahoma, and hanging out in the Bay Area of California, “trimming friends’ marijuana for supplemental income.” From these and other geographical jumping-off points, Tyler takes us on a journey about family, love, sex, physics, Native American rock writings, ultramarathoning into the hottest places of the U.S., close encounters with bears, and many and sundry internet rabbit holes that have piqued his curiosity over the years.

What makes each of these fifteen essays so interesting and enjoyable is the way Tyler deftly connects seemingly unrelated ideas and weave them into a cohesive fabric. His nonlinear, hopscotch lateral thinking style shines through in every essay. As he writes in “Stop Making Sense,” he is “plagued by ideas.” His mind is like “a drunk toddler grabbing flash cards. … Though I may not understand it when I begin, something is connecting the disparate strands.”

The result, as he puts it in the interview below, is a set of essays, each of which “is a tiny vessel exploring the mosaic of my experience, sticking to one thing for a few seconds before moving away to see what jumps up from the goo next.”

An adventurous soul who has endured some of the most extreme climates and conditions in North America, Tyler is also the product of a single-parent household and some of the common and not-so-common realities such a life brings, and he and his wife are new parents. He’s also Blake Shelton’s stepbrother, a tidbit some writers (like myself) might latch on to as fodder for an essay all its own. But that factoid barely merits a mention in Denali, Alaska. Tyler simply has too many other interesting things to say.

Denali, Alaska is Tyler’s fifth book and first essay collection. Many of the pieces were previously published in popular alt-lit magazines over the past few years. You can find all his books on his website, as well as some of his essays and other writings. Until this year, he also hosted a podcast called “Another Fucking Writing Podcast” (archived on his website) and for six years published an annual roundup of his favorite short stories.

Tyler now lives in a small town in Northern Arizona with his family.

Read on to learn more about Denali, Alaska, why Tyler stepped away from his podcast, why he prefers to write nonfiction, and more.

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Something I’ve been itching to tell you

My responses to 10 questions from The Itch Lit

Last week, The Itch Lit published a 10-question interview with me about memory, inherited beliefs, storytelling, and what I’ve learned from writing nonfiction, among other things. You can read it here.

The Itch Lit is relatively new to the online literary scene. On its about page, the editors describe it as “an online literary magazine devoted to the stories, poems, and essays that won’t leave us alone. We believe the best writing follows readers home, tugs at their sleeves, and demands another look.”

I’m grateful to The Itch Lit for publishing my creative nonfiction piece “Killing Machine” last June. This up-and-coming magazine is publishing some captivating writing. Check it out.

Friday Five: Some thoughts on ‘Writers on Writing’

What some of the best in the craft say about voice and rhythm, getting started, similes and metaphors, and the need for writers to “admit that nothing in this world makes sense.”

It was a cool winter’s day and I was on a minor dusting spree when I discovered tucked away in a far corner of my bookcase a paperback called Writers on Writing: A Bread Loaf Anthology. Published in 1991 by Middlebury College Press and edited by a couple of Middlebury English professors, Robert Pack and Jay Parini (neither of whom I’d heard of), the list of authors displayed on the cover piqued my interest. There, presented on a slant, a graphic treatment no doubt trendy in the late ’80s and early ’90s, was an all-star cast of writers I recognized–Stanley Elkin, Richard Ford, John Irvin, Erica Jong, Joyce Carol Oates, Tim O’Brien–along with many names I didn’t. Holding the book in my non-dusting hand, I studied the cover and concluded I must have purchased it at some long ago library book sale, then tucked it away for safekeeping. (I’m always a sucker for books about the writing craft, and buy any I find, especially if they’re cheap.)

I set aside the dust rag and began reading. Dusting would have to wait.

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Three months in

A status report on writing during the first quarter of 2026

From a writing standpoint, 2026 has been a good year so far. As of today (March 31), I’ve had seven pieces published in seven different places. The latest pieces, published Monday and today, are “Scenes from a Chinese Restaurant,” a bit of flash fiction published in luckycreature‘s #MuckyMondays, and “How to Fish,” a short story in Cowboy Jamboree‘s latest issue, a tribute to the late great grit lit writer Lucia Berlin.

Looking ahead, I have acceptances for six more pieces, most of which will be published in April.

So far this year, I’ve submitted to 50 journals. I’ve received rejections from 30 of them, putting me on track to again this year join the 100-rejection club.

Here is everything I’ve had published during the first three months of 2026:

New flash non-fiction: ‘Livin’ la Vida Pocha’

Some thoughts about cultural identity and assimilation into the Great American Melting Pot

For years, I’ve had a fascination with my Mexican-American heritage and how little I am connected to it–how there is little more to that heritage now than the surname, Careaga. Some thirty years ago, when I first learned there was a term for people like me, pocho, or pocha in the feminine (see more about the terms below), I started writing short pieces, mostly non-fiction or maybe autofiction, about coming to terms with this lost identity and claiming this pocho identity. “Livin’ la Vida Pocha,” published in Issue 4 of the outstanding literary magazine In Short: A Journal of Flash Nonfiction, is the first of these pieces I’ve had published. I’m working on others, so stay tuned.

My attempt with this piece is to express my mixed feelings about my cultural identity and assimilation into the Great American Melting Pot in a direct, deeply personal style. I hope you like it. Many thanks to In Short founder and editor-in-chief Steph Liberatore for her support of this piece and for her edits, which improved the piece greatly.

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