On Rejection: Kevin Alexander

Welcome to the On Rejection interview series! Every other week, I’m inviting people from every walk of life to talk about their experiences with rejection and how they got over it.

This week, we’re joined by Kevin Alexander, who writes the wonderful On Repeat, a Substack all about music and amazing playlists. I’m so excited to have him join us because I have found a lot of wonderful new music through him. Enjoy!

I'm a native Oregonian, currently in the upper Midwest with my wife and 2 teenage sons. In real life, I've spent my career in commercial aviation, mainly on the operations side. When the pandemic hit, I decided I'd go back to school as a sort of "solidarity" gesture to my kids, both of whom were learning online. I chose "Writing for Social Media" for 2 reasons A) I am a very online person, and B)  I thought it'd be easy. What I didn't realize is that it would reignite a long-dormant love of writing. That led to writing on Medium, on Substack, and even collaborating on a book that was published last year. If I'm not at the airport or writing, odds are pretty good that I'm at a soccer field. 

Kevin, tell us about a time you experienced rejection.
As writers, we experience it quite often; unsuccessful pitches to editors, stories on platforms like Medium didn't that didn't go viral like you'd hoped, etc. I'm certainly not immune to that. Lately, what has stung more than is seeing those "unsubscribed" emails pop up in my inbox. Maybe it's the way Substack is built—people have subscribed to hear from you specifically—but it always seems personal, even when I know it's not. Heck, even when I tell people it's not. 

How do you get over it?
I get over it by remembering that my work isn't for everyone and that it shouldn't be. If I'm writing for everyone, then I'm writing for no one. Isn't that the slogan we all tell ourselves? Newsletter fatigue is real, and if someone doesn't enjoy seeing my work land in their inbox, then it's okay for them to hit the exit.

If you could go back and tell yourself anything right before or after that experience, what would you say?
Hindsight is 20/20, isn't it? I wish I knew now what I knew then; or rather, I wish I was better at remembering it. Even today, it's a work in progress.

Are there any songs or albums about getting over rejection that you can recommend? 
Anything by The Replacements. It's hard to stay sad/angry/whatever when listening to them. They've carried me through breakups, and at least one firing. And there is no problem listening to New Order can't cure. 

What are you working on now?
My latest project is a Substack called On Repeat. I used to be that kid that made mixtapes for everyone; now I help you build better playlists. 3x a week I send out a song. Might be an old favorite or a new discovery. I also include some sort of link (interview, biography, etc.) for anyone that wants to go a little deeper. Paid supporters get extra content in the form of playlists, record reviews, and deeper dives on artists, and the industry as a whole. My tagline is "Give me 2 weeks and I'll give you a new favorite song!" 

My goal is to deliver on that promise. A lot. 

I'm also working on a book about my family's life during the pandemic. I made a playlist every week for a year, and those serve as a throughline as I talk about how my family went from "normal" --> fully locked down-->  that weird ersatz normal--> reemergence. A look back at life as it happened; everything from carrying a  letter from my employer certifying that I was "essential" in case I got pulled over, to my son having to navigate HS soccer during COVID. It was weird for all of us, but the music made it just a little more manageable. 

Follow Kevin on Twitter and Instagram.