Skyelor Anderson Has No Plan B

There is one sentence Skyelor Anderson repeats when the conversation turns toward quitting.

There is no Plan B.

It sounds like a punchline when he says it. Anderson is funny enough to make almost anything sound like one. But underneath the joke is a reality that has followed him for years. Music is not something sitting beside another career option waiting to see which one works first. It is the thing.

Anderson has had plenty of opportunities to question that decision.

He has watched the cost of being independent pile up through studio time, demos, mixing, mastering, videos and every other expense listeners rarely see. He has experienced the moments where Nashville makes an artist question whether they are as good as they thought they were. He has watched people arrive in town convinced they are ready, only to leave when the city refuses to validate them as quickly as they expected.

He has thought about stopping himself.

Then he remembers the same thing every time.

“I don’t know what else I would do.”

For Skyelor Anderson, there is no Plan B because Plan A has already become his life. script

Memphis Born, Mississippi Raised

Anderson was born in Memphis, Tennessee, but he considers Southaven, Mississippi the place that truly shaped him.

Mississippi is where the early version of his musical life started forming. Nashville came later, particularly after Anderson appeared on The X Factor. He began making trips to Music City around 2013 and 2014, writing, performing and meeting people including Craig Campbell and Jerrod Niemann before eventually making Nashville home in 2019. script

The television experience itself was not something Anderson initially treated with enormous gravity. His mother was the person who pushed him to take the opportunity seriously.

He laughs now about how casually he viewed it at the time, but the experience became part of the education. His mother remained the person encouraging him to recognize that music could become something larger than a hobby.

“She’s like my biggest fan,” he says. script

The real shift came after the show.

Anderson remembers working construction back home and simultaneously playing shows at a local venue called Dan McGuinness. One night, the math became impossible to ignore. He could make more sitting on a barstool playing songs than he was making at the construction job.

There was suddenly evidence that the thing he enjoyed could also support him.

It did not mean the path would be easy.

It meant the path was possible. script

Soulful Country That Might Take You to Church

The easiest way Anderson knows to describe his music is soulful country.

Then he adds another phrase.

It might take you to church a little bit.

That second part matters.

Anderson is not interested in building a live show where every song sits in the same lane. He wants movement. Energy. Emotion. He wants enough unpredictability that even his band does not always know exactly where the next moment is going.

He calls a Skyelor Anderson show a musical journey.

The goal is to pull an audience away from whatever was happening before they walked into the room. For a little while, the bills, problems, bad day or whatever else is waiting outside can stay there.

“You kind of forget about your problems a little while,” he says. script

That idea of taking people somewhere goes beyond his live show.

When someone hears one of Anderson’s records, he wants the experience to feel almost spiritual. Not necessarily religious in the traditional sense, but connected to something deeper. Maybe the song takes the listener back to a specific day. Maybe it reminds them of someone. Maybe it reaches a part of their life they had not thought about in years.

“I hope it hits your soul.” script

That line may be the simplest description of what Anderson is chasing.

Building Skyelor From Pieces of Everybody Else

Anderson points first to Eric Church when talking about the artists who shaped him.

Church is more than a casual influence. Anderson calls him an idol.

But the list expands quickly.

Darius Rucker. Billy Currington. David Ruffin. Otis Redding. Smokey Robinson. The Temptations. Tim McGraw.

It is a mixture of country, soul and R&B that makes more sense once Anderson begins singing.

What connected him to many of those artists was not simply their voices. It was the way they told stories and built identities that felt specific to them. script

Anderson once saw a documentary about U2 and became fascinated by an idea he took from Bono’s creative process: an artist can borrow pieces of inspiration without becoming an imitation.

Take something from Elvis.

Take something from Bruce Springsteen.

Take something from the artists who make you feel something.

Then put the pieces together until they become yours.

That is essentially what Anderson believes he has done.

He has taken pieces from Church, Ruffin, Redding, Robinson, the Temptations, McGraw, Rucker and others and used them to construct something that sounds increasingly like Skyelor Anderson.

He is still working on it.

He expects he always will be.

“I love where I’m at now,” he says, while acknowledging that the craft is still being built. script

“Thank You for Your Service”

If Anderson had to introduce a new listener to one existing song first, he would choose “Thank You for Your Service.”

The song came during 2020.

COVID had already placed enormous pressure on frontline workers and first responders when the Christmas Day bombing happened in downtown Nashville. A few days later, Anderson found himself alone in his garage around four or four-thirty in the morning, overwhelmed by everything he had watched unfold.

He remembers crying.

Then he started writing.

The idea became “Thank You for Your Service,” which Anderson later brought to Jason Cross and Michael Leatherman, who helped him finish the song.

It is one of the clearest examples of the way Anderson approaches songwriting. The subject is specific, but the emotion reaches beyond one event. For him, the song became a thank-you to first responders, frontline workers, military members and the people who continue showing up when everyone else gets to step away. script

But the music Anderson is making now is moving into another part of his life.

A Three-Song Journey Back Toward Faith

Anderson is preparing to release three songs that he views as connected pieces of the same season.

The first is “Church,” arriving September 25.

The second is “Peter.”

The third is “Just Checking In.”

Together, they reflect where Anderson finds himself personally as he approaches 32: getting older, raising a family, thinking more seriously about faith and reconsidering the relationship he has had with church throughout his life. script

Anderson is not an artist who feels pressured to release a new song every few weeks simply because the current industry cycle rewards constant output.

He sits on songs.

Sometimes for years.

He keeps a catalog and waits until a record feels connected to the moment he is actually living.

These three finally do.

“Church” began partly as a tribute to Eric Church. Anderson and Ryan Mundy had talked for more than a year about writing something that nodded toward the artist they both admired. When they finally sat down to do it, the process became exactly the sort of songwriting day Anderson loves: friends around a computer, a bottle of tequila in the room and everyone digging through Eric Church songs looking for references they could weave into something new.

Anderson says the finished song contains numerous lyrical nods that Church fans may recognize. script

But what began as a tribute now sits inside a much larger personal story.

Peter Was Written in Church

The idea for “Peter” arrived in a place that makes its subject difficult to separate from its origin.

Anderson was sitting in church.

His family had recently begun attending a church near their home, and one Sunday the pastor started talking about the biblical story of Peter. Anderson became fascinated by the imperfections in that story.

Peter denied Jesus.

Peter lost faith.

Anderson heard those ideas and recognized himself in them.

“I’m like that sometimes,” he remembers thinking.

Maybe everybody is.

He began writing the song during the service itself.

Later, Jamie Davis, a guitarist who works with Luke Combs, came into town and finally had an opportunity to write with Anderson after the two had discussed collaborating for years. Anderson showed him the idea sitting in his notes, and together they finished the song. script

The point was never to present himself as someone who had suddenly figured everything out.

Quite the opposite.

“Peter” works because Anderson identifies with imperfection.

“Just Checking In”

The third part of the story is perhaps the most conversational.

“Just Checking In” is essentially Anderson talking to God after being gone for a while.

He describes the feeling almost like calling someone you have not spoken to enough.

Hey. I’m just checking in. I’ve been running these white lines for a long time. Are we still cool?

The song was written years earlier with Cooper Greer, after both men began talking about feeling disconnected from church and wanting to find their way back.

The idea stayed with Anderson.

Now it fits.

The record was later produced with a musician Anderson identifies in the interview as Parker, someone who has also worked on the road with O.A.R. script

What makes the three-song sequence interesting is that Anderson did not necessarily write all three records at the same moment.

Life eventually caught up to the songs.

Now “Church,” “Peter” and “Just Checking In” collectively say something he could not have explained as clearly when some of them were originally written.

They describe the man he is becoming.

Time Waits for Nobody

Anderson is 31, approaching 32, and thinks about time differently than he used to.

He has lost friends.

Some of them were people he toured with, hung out with and expected to know longer than he did.

He has two children.

He has a wife.

He has seen enough life happen to understand that the assumption of unlimited time is exactly that: an assumption.

“Time waits for nobody.”

That realization is one reason the new songs matter so much to him.

Anderson describes himself as deeply emotional, even if the sunglasses, stage presence and blunt personality might lead someone to assume otherwise. He cries at movies. He cries at documentaries. He thinks deeply about the people he has lost and the family he still has.

At this stage, growth means trying to become closer to his faith, closer to his family and closer to the person he actually wants to be.

He does not pretend that transformation is finished.

“I don’t think we ever figure that out,” he says about understanding who we are.

For Anderson, that uncertainty has stopped feeling like a failure.

The journey itself has become part of the point. script

Nashville Will Humble You Quickly

Anderson has watched Nashville chew through enough artists to stop romanticizing the process.

Everybody is talented here.

That is the first lesson.

An artist can be the best singer in their hometown, arrive convinced that everyone on Music Row has to hear what they are doing and discover quickly that nobody owes them attention.

Anderson remembers carrying some of that confidence himself when he first came to town.

He had songs.

Surely somebody had to listen.

Then Nashville taught him otherwise.

The city forced Anderson to grow quickly because, as he puts it, if you do not grow, Nashville can eat you up and spit you out. script

The lesson eventually became less about talent and more about everything surrounding it.

Who you know matters.

How you treat people matters.

Your attitude matters.

Humility matters.

You never know who is standing beside you.

And even when you secure a position, there is another musician behind you ready to take it the second you decide you do not want it anymore.

That reality can sound brutal.

Anderson sees it as useful.

It forces an artist to either become serious about the craft or get out of the way. script

The Rooms That Became Home

Among Nashville songwriter spaces, Anderson points to Uncut as one of the communities most connected to his story.

He says he has been involved since the beginning and credits the writers round with introducing him to people who would later become major names, including Morgan Wallen and ERNEST.

For Anderson, rooms like that are part of the hidden infrastructure of Nashville.

The song matters.

But so does being in the room where another relationship can begin. script

Then there is Chief’s.

That relationship is far more personal.

Eric Church has been Anderson’s biggest artistic influence for years, so being asked to become part of the venue carried significance beyond simply landing another Broadway gig.

Anderson says he was the first artist asked to open the bar, something he still describes as a blessing.

Today, when he and his band are in town, they regularly play Thursday, Friday and Saturday at Chief’s. Even when touring takes them away for weeks at a time, Anderson says the venue allows them to come back to their regular spot.

“It is just my spot,” he says. script

It is difficult to miss the symmetry.

The artist who once watched Eric Church and decided whatever that guy is doing, I want to do something like that my way eventually found a home performing inside Church’s own Nashville venue.

Energy First

A Skyelor Anderson show is not built around restraint.

The first thing he promises is energy.

Then he says it again.

Energy.

Anderson shouts out his longtime band members Bruce Campbell, Chris Dickerson and Andy Dixon, musicians who have spent enough years beside him that they understand how unpredictable he can be onstage.

The band has developed a language around that unpredictability.

They know the songs.

They know Anderson.

And they know the plan may change.

The goal is simple: good vibes and a good time. script

That improvisational instinct is part of the soulful side of Anderson’s music.

He is less interested in perfectly recreating a rehearsed performance than creating a moment that feels alive.

That is the musical journey he keeps talking about.

You should not leave exactly where you entered.

He Would Rather Tell You the Truth

Anderson knows he has a reputation.

He laughs about it.

Some people think he is an asshole.

His version is slightly different.

He thinks he is honest.

Anderson is the friend who will tell someone when a song is not working. He also expects the people closest to him to do the same when he misses the mark.

If he messes up at a show, drinks too much before performing, handles a situation badly or simply sounds terrible one night, he wants somebody in his circle willing to say it.

He would rather hear an uncomfortable truth than receive meaningless praise.

That attitude can be misunderstood, particularly in an industry where relationships matter and everyone has reasons to protect them.

But Anderson sees honesty as part of friendship.

“I want to make everybody better. I want people to make me better.”

He is comfortable with criticism because he believes criticism from the right person is useful. script

The sunglasses may make him look untouchable.

The person underneath them is significantly more emotional than the image suggests.

Songs as Therapy

When Anderson tries to explain what has shaped his music outside of music itself, he lands on one answer.

Life.

Getting older.

Death.

Family.

Demons.

Sacrifices.

The moments when everything feels great and the moments when everything feels impossible.

Most of Anderson’s catalog is not built around party songs.

His writing is often closer to therapy.

He takes something that happened to him, or something he watched happen to someone close to him, and turns it into a song because writing gives the experience somewhere to go.

“A lot of them are just real shit about Skyelor Anderson life.”

It is one reason his catalog can move from patriotism to heartbreak to faith without feeling like completely different artists are making the records.

The genre may be country.

The connecting tissue is autobiography. script

Success Looks Different at 31

There was a version of Anderson who measured success primarily through the biggest milestones.

Stadiums.

Number-one songs.

Writing for major artists.

He still wants all of them.

But the definition has expanded.

Anderson says he has not worked what he considers a conventional job since he was 16 years old.

He has made his living through music.

He has not missed meals.

He has paid his bills.

His family is taken care of.

They have a home.

When he wants a steak, he jokes, he can eat a steak.

“That’s fucking success to me.”

The statement is not resignation.

Anderson still wants bigger rooms. He still wants to improve as a songwriter. He still wants a number-one hit.

He has simply learned that success can exist before the stadium arrives. script

There is something powerful about realizing that the dream has already worked in ways you were too busy chasing the next milestone to notice.

Eric Church and Red Rocks

That does not mean Anderson has stopped dreaming big.

Ask him for the dream collaboration and there is no hesitation.

Eric Church.

The story has already moved farther than younger Skyelor could have imagined.

Anderson says he eventually had an opportunity to open for Church, something he could not publicly promote at the time because of an agreement surrounding the performance.

Now that he can talk about it, he describes it exactly as expected.

A dream come true.

But opening the show is not the end goal.

Anderson wants to sit down and write with Church.

He says he already has songs he would like to show him. He is waiting for the right moment. script

Then there is the stage.

Red Rocks.

That one does not require much explanation.

It is on the list.

Slow Down

If Anderson could return to the beginning and give his younger self advice, he would tell him something almost opposite to the energy he brings onstage.

Slow down.

Take it seriously.

When he first entered music, Anderson did not know whether it would actually become his life. He had never spent childhood imagining himself as a singer-songwriter. Then he saw Eric Church perform and something in him changed.

He picked up a guitar.

Opportunities began happening.

Anderson found himself opening shows for artists including Jamey Johnson and Jon Pardi, yet part of him still assumed the whole thing could disappear.

Maybe it was just a phase.

Maybe this would not last forever.

Except it did.

Years later, he wishes he had understood earlier that some of those moments deserved more attention.

“Slow it down and just enjoy the journey.” script

It is advice that only makes sense after living long enough to realize how quickly the journey moves.

A Letter Sent to Chief’s

Anderson has received plenty of messages from listeners, but one recent interaction stood out because of the effort behind it.

A package showed up for him at Chief’s.

Nobody knew what it was.

Anderson was nervous enough that he waited two days before opening it.

Inside was a handwritten letter from someone who had seen him perform. The fan included questions, asked for a photo and explained what Anderson’s music and performance had meant to them.

What stayed with him was not simply the compliment.

It was the time.

Someone had physically written a letter, packaged it, addressed it to the venue and mailed it because the performance had mattered enough to make the effort.

For an artist who talks so much about wanting music to reach someone spiritually and emotionally, the package became proof that sometimes it does. script

Underestimated

Anderson struggled for a moment when asked to choose one word for his next chapter.

There were several less printable options.

Then he found it.

Underestimated.

It carries a little defiance.

Not anger exactly.

More like the energy of somebody who has heard “not right now” enough times to wonder what the same people will say later.

Anderson has already spent years proving that he can survive in this business.

Now he wants to find out how far the work can actually go. script

“Church” begins the next phase September 25.

“Peter” continues it.

“Just Checking In” completes a conversation Anderson has been having with himself for years.

The songs are about faith, but they are also about age, imperfection, family and the strange process of becoming someone new without pretending the old version never existed.

They arrive from an artist who has spent more than a decade learning what Nashville can give you and what it can take away.

An artist who learned that talent is common here, but endurance is not.

An artist who measures success differently now because he finally understands that providing for his family through music is not something he has to wait for a number-one song to appreciate.

And an artist who still wants the collaboration, the bigger rooms, Red Rocks and everything else.

There is no backup career waiting in the wings.

There never really was.

For Skyelor Anderson, there is still only Plan A.

And it is finally starting to sound like the life he is actually living.

Music City Musicians, Issue 016: Skyelor Anderson.

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