John Allen on Country Music, First Singles & Dreaming Bigger
Every artist who eventually plays a stadium starts somewhere smaller.
A corner of a bar.
A restaurant.
A local festival.
A small stage where half the people in the room may have no idea who’s about to start singing.
For John Allen, those stages aren’t something to rush through.
They’re where the story begins.
When John joined me on The Travel Wins Podcast, we weren’t talking with a country star looking back on decades of success.
We were talking with a young artist who’s just getting started.
John recently graduated from Oklahoma State University, released his first original singles in 2026 and made the decision to pursue music as a full-time career.
He’s playing smaller venues around Oklahoma, traveling to Nashville to record and learning what it actually takes to transform a love for country music into a profession.
And somewhere in the distance is a much bigger stage.
Boone Pickens Stadium.
John’s alma mater.
Oklahoma State.
Tens of thousands of people.
That’s the dream.
But right now, he’s focused on earning his way there one song and one audience at a time.
From Oklahoma State to Country Music
John Allen’s path into professional music isn’t exactly conventional.
The Chickasha, Oklahoma native attended Oklahoma State University, where he earned a master’s degree in accounting.
That’s a pretty solid career path.
Accounting offers structure.
Music offers considerably fewer guarantees.
But sometimes the safe path isn’t necessarily the path you’re supposed to take.
John had been interested in music throughout his life, and after college he reached a point where he had to decide whether music would remain something he enjoyed—or become something he was willing to seriously pursue.
He chose music.
Starting at the Beginning
There’s something I really enjoy about interviewing people at this stage of their careers.
Success hasn’t been edited into a highlight reel yet.
The story is still happening.
John is experiencing many of the firsts that established musicians may barely remember.
The first original song.
The first professional recording session.
The first release on streaming platforms.
The first time someone you don’t know requests your song.
The first crowd that actually came because they wanted to hear you.
Those moments matter.
And John is living them right now.
Writing “Regret”
John’s first released original song was “Regret.”
The story behind it is exactly the kind of beginning you’d expect from a country songwriter.
Heartbreak.
John has said that after getting his heart broken, the song seemed to arrive almost unexpectedly. It became the first real song he had written and helped establish the direction he wanted to pursue musically.
Sometimes that’s how songwriting works.
You don’t necessarily decide you’re going to write something meaningful.
Life gives you something you need to say.
You pick up the guitar.
And suddenly there’s a song.
Hearing Your Music Come Alive
John followed “Regret” with his second single, “Dying Days,” released March 27, 2026.
But one of his most memorable experiences so far wasn’t simply releasing the songs.
It was hearing them professionally recorded.
John has described his first studio experience as one of the standout moments of his young career—the experience of hearing professional musicians and engineers transform lyrics and ideas into a finished recording.
That’s a milestone.
For years, a song may exist only in your head or with an acoustic guitar.
Then suddenly it sounds like a record.
Nashville Changes the Perspective
John has already had opportunities to travel to Nashville to record, bringing another important dimension to his development as an artist. Local reporting earlier this year noted that he had been invited to record in Nashville twice and planned additional releases throughout 2026.
For a young country singer from Oklahoma, Nashville can be both inspiring and humbling.
- Everywhere you look, somebody can sing.
- Somebody can play guitar.
- Somebody has written a great song.
- Somebody is chasing the same dream.
- That can either intimidate you or motivate you.
- Sometimes it does both.
The Importance of Small Clubs
Right now, John’s career is being built in much smaller rooms.
And that’s exactly where it should be.
He’s been performing around Oklahoma, including the Bricktown area of Oklahoma City and venues throughout the state. In August, for example, he performed a three-hour set at The Lodge on Main in Broken Arrow.
Those gigs are where performers learn lessons no classroom can teach.
- How do you read a room?
- What happens when people aren’t paying attention?
- Which song gets people to look up from their conversations?
- When do you tell a story?
- When do you stop talking and play?
- How do you recover from a mistake?
- How do you turn someone who has never heard your name into someone who follows you before leaving?
Small rooms teach big lessons.
Country and Red Dirt Roots
John performs within the country and Red Dirt tradition, a natural fit for an Oklahoma artist.
That gives him an opportunity to develop his own sound while being surrounded by a region with a strong musical identity.
Oklahoma has produced generations of influential country artists and songwriters.
But John isn’t trying to start at the finish line.
He’s figuring out who John Allen is as an artist.
That takes time.
The Dream: Boone Pickens Stadium
Then there’s the big dream.
Someday, John would love to return to Oklahoma State not simply as a graduate—but as the guy onstage.
Imagine the journey.
From playing intimate clubs around Oklahoma…
To releasing those first songs…
To Nashville recording sessions…
To building an audience…
To eventually walking onto a stage inside Boone Pickens Stadium at the school where you spent such an important part of your life.
That’s the kind of goal that sounds enormous.
It should.
Dreams aren’t particularly useful if they don’t make you a little uncomfortable.
Everybody Starts Somewhere
It’s easy to look at major artists performing arenas and forget they once played to 30 people.
They once loaded their own equipment.
They once introduced themselves to rooms where nobody knew who they were.
They once released a first song.
They once wondered whether anyone would listen.
That’s why John’s story is worth following now.
We’re seeing the beginning.
If he eventually reaches that stadium stage, there will be plenty of opportunities to talk about what success looks like.
Right now, we get to talk about what starting looks like.
The Business of Becoming an Artist
John also brings an interesting educational background into the music industry.
He has a master’s degree in accounting.
That might seem completely unrelated to singing country songs, but I wouldn’t underestimate its value.
An independent musician is essentially running a small business.
Revenue
Expenses
Travel
Equipment
Studio costs
Marketing
Merchandise
Contracts
Streaming income
Taxes
The creative side may attract someone to music.
Understanding the business side can help keep them there.
Why John Allen Fits The Travel Wins
John’s story represents another side of what The Travel Wins Podcast is about.
Sometimes I interview people who have already reached extraordinary heights.
Other times, I want to talk with someone who’s just boarding the plane.
John is at the beginning.
He’s traveling to perform.
He’s traveling to record.
He’s meeting new people.
He’s learning new rooms.
He’s figuring out which opportunities matter.
And he’s discovering what kind of artist he wants to become.
That’s a journey worth documenting.
Don’t Wait Until the Stadium to Celebrate the Win
There’s also a lesson here that applies far beyond music.
We often postpone recognizing progress until we’ve reached the biggest goal.
That’s a mistake.
The first song is a win.
The first recording session is a win.
The first person who knows your lyrics is a win.
The first Nashville trip is a win.
The first packed small club is a win.
You don’t have to wait for the stadium.
That’s something I’ve learned through years of conversations on The Travel Wins.
Better is better.
Progress matters.
Watch My John Allen Interview on The Travel Wins Podcast
If you enjoy discovering country artists before everybody knows their names, I think you’ll enjoy this conversation.
John Allen is just getting started.
We talk about graduating from Oklahoma State, choosing to pursue music, releasing his first original singles, recording in Nashville, playing smaller clubs and learning the business one performance at a time.
And, of course, we talk about the dream.
Someday:
Boone Pickens Stadium.
Will it happen?
That’s the exciting part.
Nobody knows yet.
But every stadium career starts on a smaller stage.
And John Allen has already stepped onto his.
Connect with John on his social media pages:
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The Travel Wins intro song by Allison Johnson and Steve Stevens
