I Would’ve, Could’ve, Should’ve Been A Cowboy
Sorry to be away for so long.
This email is less about country music and more about me, the guy telling you about country music. I’ve included links to my recent country reviews and TikToks below, as well as my country playlist. More yeehaw is coming. Thank you for being patient.
When I was 14, I convinced a room of adults to allocate $5,000 from our village’s annual entertainment budget to let me—barely a teenager—reopen a local music venue (with the help of a nice older couple).
This November, I turn 36.
At no point in the twenty-two years in between have I not considered myself a ‘music professional’ in one way or another.
I’ve probably been lying to myself on more than once occasion—like my short stint managing a Hot Topic—but that act of self deception kept me going. “Fake it if you make it,” if you will.
In 2022, I took my greatest leaps yet: I walked away from a job I had for nearly a decade, and I abandoned the comfort of rock coverage to pursue my passion for country music.
Telling myself to do it was one thing.
Doing it was another.
Living with it…that’s a special kind of beast.
I haven’t felt more like an imposter in my life than I have the last six months. My brain is constant cycle of hope, doubt, and impatience. That is, whenever I’m not avoiding the questions that keep me up:
- Is this going to work out?
- Was every choice the right one?
- Who am I becoming, and what will it take to get there?
- Even if I know those answers, am I mature enough to do it?
- How do I establish new routines for old skill sets?
- How do I learn new skills without losing my talent in other areas?
- Will anyone take me seriously?
These thoughts were always here and always will be, but they are so loud recently.
Then I figured it out.
(To be honest, my wife, Laura, explained it to me in a way I understand while in the middle of my third or fourth spiral of the month.)
I currently feel how I felt at 14 when I first received that grant.
The same way I felt at 20 when I started my first music blog.
It’s how I felt at 26 when I left a full-time job to work remote with a small startup I connected with over Twitter.
The panic and joy and fear and hope that I felt when my now wife agreed to move to Michigan and take a chance at building a life with me knowing damn well I had a lot of growing up to accomplish—it's all here, and I feel it constantly.
What I feel is the excitement and terror of new beginnings. It’s the first few pedals on a two-wheel bike.
I may be older now, but the feeling is the same, if not amplified. Unlike the previous versions of myself, I have more to lose and a greater appreciation for loss.
But this IS the journey. The next grand adventure doesn’t happen in the offices of a massive corporation or from behind the Helpdesk of a startup you have to explain every time you say its name—it’s right here and now. Each day is a new opportunity. Each post a new chance for connection and identity.
The places I want to be and the acceptance I seek are things you earn along the way. Nothing comes free or easy if it's worth having. Some people may be born with a silver spoon and keys to endless doors of opportunities, but that has never been my life, and I can't expect that to change now. The idea that I have done "enough" to justify the blind acceptace I seek speaks more to my ego than anything else, and it only reveals the need to mature.
Tomorrow I may forget this sunny outlook. Tomorrow I might wake up and apply to half a dozen jobs I qualify for regardless of my interest in the position because some little voice is telling me to fold and quote/unquote “grow up.”
Steven Pressfield calls this phenomena “resistance,” and says every person faces it everyday. If that applies to you—consider this a reminder that you are capable of more than you realize. Keep going.
Here’s the country content you’ve been looking for…
I’ve been attending a ton of country concerts as of late. You can find recent live reviews of Lainey Wilson, Parker McCollum, Danielle Bradbery, and Spencer Crandall.
Back in January, my friend Eric Michael Taylor released a song for anyone caught in a “situationaship”—a word my millennial self didn’t know before he used it—and I couldn’t help covering it for Substream.
Linking all of my TikTok content would be next to impossible, but my first video to cross one-million views is definitely worth watching.
Personally, I love this video on Keith Whitley:
@countryminuteNow that #MorganWallen has introduced a new generation to his name its time we celebrate #countrymusic icon and Kentucky native #KeithWhitley. Considered a king of neotraditional #classiccountry, its hard to find anyone who hates Whitley’s music. Whats your favorite song? #countrymusicfans #countrymusictiktok #countrymusiclover #classiccountrymusic #countrylegends
Tiktok failed to load.
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LAST BUT NOT LEAST
My friend Nick Martin recently started a newsletter about his life and times in music. Nick is one of my oldest friends in the industry and arguably among the most successful. Give him a subscription when time allows.
