Hey there. I made you a mixtape. But first, I want to talk about why we’re programmed to keep trying even when we know it’s long past time to stop.

Don’t Forget to Celebrate the Endings

Four years ago this month, Kerrie and I rode the Filthy Fifty, a 50-mile gravel race through the backroads of Lanesboro, Minnesota. Lanesboro is the kind of place people travel to so they can fly fish in relative solitude amongst the Amish farmland. It’s beautiful — so beautiful, in fact, that for a split second you might (briefly!) forget that the race you’re racing is actually the biking equivalent of a living hell — 50 miles, wind, 4000+ feet of elevation gain. Some people are built for this kind of thing. Some people long for — even ache for — this kind of challenge, and I tip my sweaty bike beanie to those people.

The ache was a bit different for us. It was the hardest ride we’ve ever done — harder than the century, harder than any of the days of RAGBRAI or any other tour we’ve been on. But as we finished, exhausted and filthy (!) and sore in joints we didn’t previously know about, we also felt this wave of accomplishment. We pushed through and persisted, and while we finished in second to last place, we still felt really really proud.

So, this year, four years later and four years older, we decided to do it again. We kind of assumed it was going to be hard, but we decided to do it again, as if we’d forgotten the entire ordeal.

And maybe we had! I’ve read a myth that when someone goes through childbirth, there are certain parts of the process that are selectively wiped from memory — a kind of childbirth amnesia that helps forget the pain of giving birth. The assumption here is that no one would want to go through it a second time, so a kind of forgetting helps humans persevere.

Medically proven or not, amnesia in this sense is an act of persistence. Nature’s only plan for us is to pass on our genes, and anything it can do to prolong our innate dedication to this act — to literally persist — is fair game. But persistence is a flawed idea. Persistence depends on being blankly dedicated to progression at the expense of our own mental health. Persistence wants only to move forward, despite our lives being jagged lines of back and forth, of love and loss. We felt this crucial flaw as the Filthy Fifty date got closer and closer. We stalled in booking a camping spot, and we didn’t bother to train much, and we kind of resigned ourselves to the idea that we were once again going to be miserable.

In the face of persistence, we couldn’t quite bring ourselves to let go.

A few years ago, I signed a contract to write a book on design communication for a respected publisher, and I was incredibly proud, both of the topic and of being selected in the first place. But when that respected publisher went out of business shortly after, I had a choice to make: keep writing, or let it go.

Nearly everyone said I should keep writing, but I couldn’t do it. I didn’t have that kind of heart for it. I’d already self-promoted a book and I couldn’t bear to do it again. It happened again earlier this week, with something as simple as a sore throat. Our 17YO came down, hoarse and ragged, sleep-deprived, and headed out the door with the kind of eyes that said “I would ask to stay home, but my dad is weird about school attendance sometimes.” And I was. I expected he’d feel better, that he’d persevere, and it took a call from Kerrie to convince me to let go. To let him stay home.

These situations put us in an uncomfortable place, because we have to face our own definition of what we’re “supposed” to do. We are taught, early on, that being strong — that pushing through — is a valuable skill, and while I still totally believe this, I’m frustrated that we have to learn the other side of this for ourselves: how to stop pushing. How to understand when we can let things go. When to choose the easier ride. When to go back upstairs and go back to bed.

When to leave a job that’s helped foster your entire professional image.

At the end of this coming week, I will leave my job at Blend Interactive. I have been a part of Blend for 16 years — my 19YO and 17YO kids don’t really remember a time when I didn’t work at Blend. Blend has supported my writing, my speaking, and my family. They have let me build something that I’ve always been proud of, and they gave me the space to build a team that has helped me look really really good for a really really long time.

They are still an incredible place. It’s hard to leave an incredible place, and it’s even harder when you know the result will be felt. For 16 years, there have been a few constants at Blend, and I was one of them. So when my mind would wander a bit — when I’d look at the industry and wonder how I’d continue to fit in — I persevered.

The agency world is a weird one right now. It’s changing, quickly — blah blah AI, economy, technology blah blah — and, just as quickly, it’s becoming something I don’t recognize. I had a hundred reasons to stay in the client services space, but I was starting to find a hundred more reasons that I should leave — that the life of an agency director was rapidly passing me by.

Mostly, I’m getting older. My kids are both nearly out of the house, and the constant shifting from project to project, from hat to hat, from client to client to client … it’s wearing me out. I started to doubt my impact and my honesty in what I was saying day-to-day, and I felt it was time to start reassessing the next phase of my career. (That next phase is nonprofit web work, apparently — in a week and a half I start my new job with the national American Red Cross digital team.) I had to overcome the fear of what I’d be leaving behind, and the fear of what would happen in the wake of my leaving. But, more than anything, I had to overcome my fear of giving up. Of no longer persisting. I had to stop trying to push through it, really, hoping I’d suddenly find my place again.

Life celebrates beginnings: births and weddings, first steps and first days of school and first jobs. Even the things we complete are celebrated as beginnings — graduations focus on next steps, retirements focus on a new stage of life. But we hide from endings. We’re afraid to talk about break-ups and divorces and deaths, because these things are complicated. They go against the grain of what our lives are supposed to be — happy, together, living. New beginnings become a public act, while endings are done privately.

We marvel at the strength and courage it takes to begin new things, while completely ignoring the strength and courage it takes to let them go. To admit that things would be better, if not for this; understanding that endings aren’t always failures, and even if they are — who cares. Endings are necessary. Saying “I’m done” is crucial.

Two days before we rode the Filthy Fifty, we changed our registration. We opted to ride the 25-mile route. Instead of the hardest ride I’ve ever been on, it was merely the second-hardest ride I’ve ever been on, but we rolled in while there were still people on the streets and we celebrated the ride and then went on with our day. That night, we watched a wonderful little bluegrass band while surrounded by 50 of Lanesboro’s finest NPR subscribers and went to bed not as sore as we could have been but just as fulfilled.

I don’t know what it will look like now that I’ve switched jobs. I don’t know if it will be too easy, or too hard; too frantic, or too boring. But sometimes you can’t plan for uncertainty at the expense of your current state. I feel good that I pushed back against my own assumptions, and I feel good that I’m able to take on something new. I also feel good that I can celebrate this ending in a way that doesn’t feel like giving up. Looking forward, persisting in a new way.

This Month’s Mixtape

October 2026: Don’t Forget to Celebrate the Endings

Listen on Spotify. Listen on Apple Music.

• “A-House” — Everyone Asked About You
• “Good Enough” — Mudhoney
• “Hours Were the Birds” — Adrianne Lenker
• ”Breeze!” — Kali Uchis
• “DENIAL IS A RIVER” — Doechii
• “expectations” — Olivia Rodrigo (w/ Chappell Roan)
• “From One Primadonna to Another” — 90 Day Men
• “Over the Edge’” — Wipers
• “Come On” — Acetone
• ”Itzsoweezee (Hot)” — De La Soul (w/ Yankee B.)
• “FLOWERS” — Tierra Whack
• “Give Up” — FKA twigs
• “Darklands” — The Jesus and Mary Chain
• “Race for the Prize” — The Flaming Lips
• “I Threw a Brick Through a Window” — U2
• “High Flyin’ Bird” — Richie Havens

This post is saved for posterity at Corey Vilhauer Dot Com. Every typo is probably because I ate too much Halloween candy.