Why Bozeman? The Shabby Sheek Origin Story…

It’s the buttcrack of dawn in late October, maybe mid-November. The sky is a blue grey, there's a cold fog low in the treeline, and it’s starting to smell like winter. Crisp and short air. It's genuinely silent. I’m sitting on my front porch with a blanket wrapped around my shoulders and a mug of hot coffee. I wish I had a hand-rolled cigarette but I gave those up years ago. Ugh. 

I look across the road at Peets Hill and the parking lot is empty. An odd car or two drives by, but nobody is out yet, except a family of deer slowly ambling down the path where the strollers and runners and dog walkers usually are. The momma deer looks up from grass-munching and straight at me. We lock eyes for a minute. She goes back to grazing and keeps sauntering down the path that in a few short hours will be busy with Bozemanites being all outdoorsy. 

For some odd reason I feel at peace. That’s not my normal channel. I breathe in deeply and express gratitude for this home I’ve built. This stability and comfort. I pat myself on the back for what I’ve sweated to build this home and life. I get up and go back inside, the screen door makes its familiar sound and the floor creaks its familiar creak under me and I just know: it's time for hot stew and tea and warm layers.

Bozeman taught me that true freedom needs stability underneath it. The mountains hold still so the rest of us don't have to.

I pulled into Bozeman with my family in the summer of 1996, back when Huffine Lane was still, believe it or not, a dirt road all the way to the mall. My family moved us here to do all the things: ski, hike, say howdy to your neighbor. Ya know, escape the big city and live outdoors. Sounds cliché but back then Bozeman wasn’t sold out even if old timers would already say before we arrived it was even more authentic. I think that’s always how places feel to those who spend enough time there to watch them eventually change…

Bozeman today still somehow feels like my childhood. I’ll drop some nostalgia now à la ‘ya had to be there’ but mean no offense. The laffy taffy puller at the old fashioned candy store. Trifecta Leaf & Bean - Poor Richards - Cactus Records on Main. Western Drug with its carpet and popcorn machine and tacky bumper stickers. The Blue Iguana (if you know you know). But Bozeman still and always has been a bubble — a very safe, very insulated bubble, for better and worse. And I was a freedom lover, an adventurer, someone who wanted to go far away and discover. So I left Bozeman one week after high school graduation and wandered around the world for a bit.

And by wandered I really do mean wandered. Yes I went to university, and yes I held a job or two or three. But looking back on my 20’s I see how, even then, in my core human essence, I crave the unknown. I crave experiences. Who doesn’t love to travel? Sure. But this was different. Everyone focuses their life compass naturally in certain directions. I see how my daughter at 14 has already been drawn towards books, literarure, stories, film, arts, fashion, design, (and also randomly, sharks and marine biology) since she was very small. For me it has always been, the world.

But life always seems to throw curveballs that, mayhaps, I needed in order to guide my general direction. And I found myself returning to Bozeman when my daughter was born, to be close to my mom. It was tough, as other single moms can relate. Where I was floating before, motherhood anchored me. It forced me to nest. Told me to build something of my own. I hadn’t given up on seeing the world. I longed to travel. But first I would need a real home.

I visted a basement apartment for rent next to Bogart Park. It reeked of cat pee. The walls were shredded with animal scratches, the upstairs neighbors were blasting techno, there was a rusty metal shed and the backyard fence was a bent-over sheet of what might've once been chicken wire. A total college-kid slum.

But I sat outside in my car afterwards and looked at Bogert park and I said: I have to live here. This location is unbeatable.

I moved in and started to clean. Cue “Eye of the Tiger montage showing the main character did a lot of work over a short period of time to conquer their demons”. The Shabby Sheek was born. It became our sanctuary, our foundation from which we could do the other things in life we needed to do. When you are nomadic, your focus is very often on the quick and external.

I bought the house in 2018 while still living downstairs, and — this is the part few people tell you about buying a fixer-upper — I did not renovate it in one triumphant swoop. First I ripped out the cat pee carpet of course, and then it was just one gallon of paint at a time, over ten years.

The house nobody else wanted

Built in 1947, the place came with a rusty metal shed out back, gray siding that had seen better decades, no real fence to speak of, and carpet upstairs that felt every one of its 80 years. It looked like nobody had touched it in a long time.

But I could see what it wanted to be.

My parents had been landlords too, so I borrowed their lease template and figured out the rest as I went — which included some genuinely bad tenants along the way, the kind who leave a mark. That's part of the job.

But there was one stretch of time that told me this house was more than a project. A run of tenants — upstairs, downstairs, all friends of friends — turned out to be musicians. Acoustic guitars, an electric piano dragged into the backyard. We started calling it the One Way Cafe, and for a while, our little scratched-up rental hosted its own backyard concert series. That's the moment I knew this place was special.

Why a blog, and why now

I'm writing this blog partly because I want to be selective about who stays at Shabby Sheek — I want renters who actually want this location, not just a location. At Shabby Sheek, you can live like a local — not cosplay one. There's a difference, and most visitors never get past the costume.

But mostly I'm writing it because I might I have something to say at this point in my life: about being a landlord and a single mom, home-basing in Montana while working remotely, educating a teenager across the world and back.

The thread running through everything I want to write here is balance: freedom and stability, community and solitude, working hard and playing hard, preparation and surrender, being local and going global. So expect a mix — local Bozeman tips (like our walk down the Gallagator Trail), international destination guides, our favorite local haunts, house updates and availability, and the occasional dispatch from wherever Shabby Sheek Abroad takes us next.

I hope you enjoy! And as always, this blog is powered by Shabby Sheek Rentals — see what's available in Bozeman.

Kendall's Bozeman roadmap A wavy road running left to right from 1996 arrival in Bozeman through to Shabby Sheek today, with six mile-marker stops and non-overlapping detail cards alternating above and below the road, styled in the Shabby Sheek brand colors and fonts. 1996 · First arrival From rainy Seattle, chasing ski season and four real seasons 2012 · Needing a home base Back as a single mom, wanting a place of her own, close to family 2015 · Finds the house Rough shape, cat pee smell, chicken wire — Bogart Park next door 2018 · Buys the house Bought it while still living downstairs while renovating 2015–2025 · A decade One gallon of paint at a time, plus the One Way Cafe concerts Today · Shabby Sheek A home base for renters, guests, and this blog from the porch Single mom win Building the Shabby Sheek Home Base