Dog Catches Car: What Happens After You Achieve Your Life's Goal?
What happens when the chase is over and the dream is finally caught? In this episode, we sit down with Lionel Cartwright—whose career soared to the top of the country music charts—to explore the rarely discussed crossroads of success. After years of relentless pursuit, Lionel achieved all the milestones he’d imagined: record deals, number one hits, and recognition. Yet, in those quiet moments away from the spotlight, he was confronted with the unexpected question: Is this it?
We follow Lionel’s journey from cover band beginnings and publishing deals, to Nashville stardom and the unexpected tug to redesign his life. Along the way, we unpack the paradox of ambition, the need for alignment over applause, and the courage required to leave "success" behind for something more sustainable.
Together, we challenge leaders and creative pros to pause, reassess whether momentum is driving their choices, and listen for the subtle signs that realignment might be overdue.
Five Key Learnings from the Episode:
- Chasing the Dream Isn’t the Finish Line: Pursuing success provides meaning and adrenaline, but catching it brings new questions about fulfillment and sustainability.
- Beware of Momentum’s Seduction: Success often leads to expectations and obligations that can detach us from what truly sustains us.
- Alignment Beats Applause: True creative bravery lies in pursuing work that fits who we are, rather than playing roles imposed by past ambitions or industry pressures.
- Listen to Your Inner Voice: Quiet whispers of misalignment are worth investigating, no matter how much time or energy you’ve invested in the chase.
- Redirection Isn’t Failure: Leaving a high-profile path to redesign your work around life—rather than vice versa—is one of the bravest moves a creative professional can make.
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Listen to Todd's interview on Lionel's podcast Off The Charts: Spotify - Apple Podcasts
Todd Henry [00:00:00]:
Hey, everyone, this is Todd Henry. This interview is part of a two episode swap where I swapped interviews with my friend Lionel Cartwright. On his podcast called off the Charts, I told the story of how I spent years pursuing something career wise that I didn't get, but ended up in a place I never expected. And on this episode, Lionel's going to share the opposite story. How he spent years pursuing something he did get and then ended up being realizing maybe it wasn't what he wanted. So if you want to listen to my episode on Lionel's podcast, it's called off the Charts, and I'll link that up in the show notes. All right, here's the episode. Let's start today's episode with a familiar image.
Todd Henry [00:00:41]:
A car is going down the road. A dog sees the car. And what happens? It takes off running. It chases the car. But then something unexpected happens. The dog actually catches the car. Then comes the part that no one ever talks about. What does the dog do next? Because chasing is easy.
Todd Henry [00:01:02]:
Wanting is easy. Projection fills in all the blanks. The pursuit itself supplies. Meaning, adrenaline, identity. But when the thing that you've been chasing your whole life suddenly stops right in front of you, the story changes. This is the quiet paradox for many creative professionals. We spend years imagining what success will feel like. The recognition, the freedom, validation.
Todd Henry [00:01:24]:
We tell ourselves that once we get there, everything will settle into place. The pressure will lift, the doubts will fade. Life will finally align. And then something happens. We actually catch the car. The record deal, the hits, the platform, the promotion, the role that we've always wanted. The career that we describe with the words someday. And instead of relief, maybe something else shows up.
Todd Henry [00:01:51]:
It's weight. It's expectation. It's a sense that the life you've built may not actually be the life that you want to live inside of. That's the moment that this episode is all about. What happens when you catch the car? When the thing you thought you wanted arrives in full, undeniable form. And you're forced to reckon with a deeper question. Not is this successful? But is this sustainable for who I really am? Today's conversation is with Lionel Cartwright, a friend of mine. And it's a story about success.
Todd Henry [00:02:23]:
Yes. But more than that, it's about discernment. It's about listening closely when achievement reveals a mismatch. And it's about the courage that it takes to redesign your life after the dream stops running. This is Daily Creative. For 20 years, we've served up weekly tips for staying prolific, brilliant, and healthy. My name is Todd Henry. Welcome to the.
Lionel Cartwright [00:02:53]:
My family moved from southern West Virginia, Mason County, West Virginia, to the northern panhandle of West Virginia when I was nine years old.
Todd Henry [00:03:04]:
That's Lionel Cartwright. Lionel is a friend, but he's someone that I've known for a very, very long time. Not because we had a personal relationship, because I admired his music. In the early 1990s, Lionel was one of the biggest names in country music. He was taking Nashville by store, and.
Lionel Cartwright [00:03:23]:
The next Christmas, my brother got a four string baritone uke for Christmas. And on Christmas vacation I picked it up. It was laying there in this little baritone UK case with a Mel Bay cord book by it. And I saw you could make a cord with one finger. I don't want to get too mystical here, but when I started strumming that baritone uke, I like to say an app that was in me got fired up, it got installed, and I've never found a delete button for it since. And that was the very humble beginning of my music career.
Todd Henry [00:04:10]:
So you, obviously, you're a songwriter. I don't want to spoil the story here. When did you first discover that music could not only be something that you play, maybe with your Mel Bay chord book, but something that you could actually make? Do you remember your first song or a moment when the creative part of it started to resonate with you?
Lionel Cartwright [00:04:31]:
One of the phrases that I first heard you say, that rocked my world. Now, this is 10 years or so after I'd had hits on the radio, etc. But I share this line with so many people that cover bands don't change the world. So there was a large segment of my formative years as a musician where I was just a cover band, was a cover artist. You're learning. I'm learning. Songs by Elton John, Billy Joel, country songs, Merle Haggard and I. The jobs I got eventually.
Lionel Cartwright [00:05:06]:
Over the years, I worked on a radio show that was one of the old country music radio shows. I know you know about it, the WWVA Jamboree in Wheeling, West Virginia. And so I got hired to do this show for the Nashville Network. It was actually a sitcom called I 40 Paradise. And one day this couple, this married couple came through. I'm going to say they were in their late 60s, maybe early 70s. And as soon as I saw them, all these other people came and gone. I was like, yeah, that's great.
Lionel Cartwright [00:05:36]:
Yeah, that's great. But when Boudelo and Felice Bryant walked through those doors, being the album liner note nerd that I am, I knew full well who they Were who, by the way, wrote a lot of early rock and roll hits. They're iconic songs. Right. Bye Bye Love Wake Up Little Susie All I have to Do Is Dream. They wrote Rocky Top, for crying out loud.
Todd Henry [00:06:01]:
Yeah.
Lionel Cartwright [00:06:01]:
But it really changed me, and eventually I got to work with them on two musicals they were writing. I had never really worked with writers before, and I kept my songwriting hidden because I wasn't really confident about it. But that really inspired me to bring that out into the open and make that a part of what I was doing as a performer. Once I went there, I couldn't go back.
Todd Henry [00:06:27]:
Once Lionel began writing and sharing songs with others, he was offered a publishing deal. I mean, he's a great writer, which basically means that a company was now paying him to write songs, and they were trying to get other people to record those songs. They were called cuts, which means an artist would cut your song. And this is often the first step in many people's career in Nashville or in any place in the music industry. It's a sign that you're starting to make progress in the industry. So a publishing deal is a big deal.
Lionel Cartwright [00:06:57]:
That was one of my favorite experiences in the music business. It was just a small, little mom and pop thing. The Oak Ridge Boys actually owned the company. We never saw them, but they were the owners. But the people I was surrounded with. Todd. That was a little window in Nashville history of when singer songwriters were really making inroads into country music. And Steve Earle was there, Gail Davies was there, Harry Stinson was there, Gretchen Peters was there.
Lionel Cartwright [00:07:31]:
And it was so mom and pop. We would actually meet each other in the kitchen of this big, old beautiful house on the road there at the end of each day, and we would play each other's songs. We would tell them what we were writing. It was just the best. And especially my crossing paths with someone I respected so much, like Steve Earle, who, right after I got signed, had an album called Guitar Town come out that just rocked the country world. Yeah. But again, getting cuts. I got some cuts, as you say.
Lionel Cartwright [00:08:06]:
The publisher placed some really nice cuts for me. And it only reinforced the love of creation that songwriting is.
Todd Henry [00:08:18]:
And you were signed with MCA Records, you were working with Tony Brown, who, again, was, like, in the pantheon of, like, record label executives, producers, over time is one of the biggest names in Nashville history, probably in terms of just success and his ability to. To spot and create hits. And you were privileged to work with, again, like, mca. Everybody knows mca. Right. And so that had to be a huge thrill as well.
Lionel Cartwright [00:08:46]:
It really was. And then to not just get it on the radio, but to make the top of the charts was, I don't know, it was everything I thought I wanted to do, everything I dreamed of, this was like at that point, Todd, this is a 20 year old dream. I reached that point of getting on the radio and touring, having a tour bus. It was in, it was incredible.
Todd Henry [00:09:14]:
Lionel had in total seven top 20 hits, three of which went top five and one of which went to number one. And it stayed there for a long time.
Lionel Cartwright [00:09:24]:
I loved it. I loved being on the road, I loved every part of it. But as time progressed, we had our first baby, our first son. And I remember two incidents. One was the week my song Leap of Faith was number one on the Billboard country charts. This sounds, this is going to sound like I'm making this up, but this really happened. I was sitting on the porch swing on our first. On our, at our current house and I had Billboard magazine opened and I see my song there that I wrote, that I sung number one.
Lionel Cartwright [00:10:07]:
It was just incredible that this was happening. And I felt this just. I don't know how to say this, this inner prompting. Ask a question. And it was a three word question. I'm telling you, I felt this, I felt that inner prompting say, is this it? To which I had a pretty strong reaction, yes, of course. Yes, this is it. Are you kidding me, Self? I've come all this way.
Lionel Cartwright [00:10:49]:
20 years of doing every kind of gig you can imagine, traveling in all kinds of vehicles. You know how it goes. There's. Oh yeah, sacrifice, wonderful sacrifice that I embraced totally. But to get to that point and to get to that peak and have something inside you say, is this really what you want to do with the rest of your life? That was one incident. The other incident, I remember I was playing a show out on the west coast of Canada. I can't remember the name of the festival, but I remember having a conversation with Billy Ray Cyrus that day in the tent. So there's 50,000 people out there, were going to do a show and the band was off the bus.
Lionel Cartwright [00:11:37]:
I was on the bus and I was on the phone talking to my wife and I heard our son Mason as an infant making noises in the background. And Nancy Griffith had an album out of ironically cover songs called Other Voices, Other Rooms.
Todd Henry [00:11:56]:
Phenomenal album.
Lionel Cartwright [00:11:57]:
Yes, it's phenomenal. And I also, to be fair, I saw that the stylistic nature of the industry was really changing. It was going very cowboy, very rodeo rock. All due respect to Garth, he's a Friend of mine. Good for you, Garth. Seriously. But I knew instinctively I'm not a fit for this. I just what I wanted to do musically, if I was honest and if I was not going to contort myself into being something that I was not, I knew that I wasn't a fit.
Lionel Cartwright [00:12:36]:
And also the role of father. Hearing that song, which Nancy Griffith covered, an old Harry Belafonte song called Turn around, and it's all about how quickly your kids grow up. Turn around and she's a young girl with babies of her own or something. I'm not doing it justice. It's an incredibly poignant song. And I sat on that bus and heard that song and also knew that I was not quite a fit. And I just had some tears on the bus that day thinking, wow, I between my porch swing moment and my back of the bus moment, I started thinking, I don't know, could it be that this dream that I've had since I was 11 years old maybe isn't for the rest of my life? So it was quite, quite a place to be in.
Todd Henry [00:13:41]:
There's a moment in every creative life that never shows up on the highlight reel. It's not the first hit. It's not the awards, it's not the sold out rooms, the radio countdowns. It's not the big promotion. It's not when everybody loves the project you've been working on for weeks. It's the quiet moment. It's the one that happens away from the stage lights, away from the attention, away from the contracts or the applause. For Lionel CARTWRIGHT, the early 1990s were loud.
Todd Henry [00:14:07]:
They were successful. They were relentless. Songs climbing charts, expectations climbing faster. Every win immediately followed by the next obligation, the next record, the next tour, the next version of himself that he was supposed to become. And somewhere in the middle of all of that momentum, a different question began to surface. Not can I do this? But do I want to keep doing it this way? Because success has gravity. Once it pulls you into orbit, it's hard to break free. The industry rewards consistency, not conviction.
Todd Henry [00:14:43]:
It applauds output, not alignment. And walking away, especially at the peak, looks irrational from the outside, but from the inside, it can feel a little bit inevitable. This is the part of the story that we rarely hear, the part where a creative person chooses sovereignty over status, where walking away is not failure. But it's a refusal to keep playing a role, a refusal to let momentum decide. Meaning Lionel didn't disappear because he ran out of talent. He certainly was at the peak of his career. He stepped away because he was listening to something quieter than the crowd, something more demanding than the charts. And that choice, the decision to stop, is often more revealing than everything that came before it because it forces the question that we all want to avoid.
Todd Henry [00:15:33]:
When the world keeps rewarding you, what does it take to say enough?
Lionel Cartwright [00:15:39]:
My first instinct was to fight it because it had been such a long journey. I guess I didn't trust that, that voice, that instinct.
Todd Henry [00:15:51]:
And others in his life didn't exactly go along at first either.
Lionel Cartwright [00:15:55]:
They did not like it. And I heard a talk. This has been 10 years ago or so by a writer that I know you and I both respect. Rodney Crowell.
Todd Henry [00:16:05]:
Yeah.
Lionel Cartwright [00:16:06]:
Who is one of the hall of Fame songwriters. We could list his songs and everybody would know at least one of them. But I heard him give a talk, and he had been through a similar process. And his. Where he got was he thought, I didn't feel like I. It was really me anymore. I felt like I was playing a role. But he said, and I resonated with him on this, that the machinery that gets built up around you as an artist, there's a booking agent, there's a manager, there's a label, there's a publisher.
Lionel Cartwright [00:16:36]:
In oftentimes, they don't like it. And I get it. I'm not throwing shade on them. They've invested time, they've invested energy. As one person said, you're my horse. I wanted my horse to win. But I had one day a conversation with Cindy, my wife, in our kitchen, and she has been incredibly supportive. Never a gotcha moment at all.
Lionel Cartwright [00:17:05]:
But she did say to me, very kindly, one day in the kitchen, she said, something's got to happen.
Todd Henry [00:17:13]:
Now there's a sentence that changes the temperature of a room. Something's gotta happen. It wasn't an ultimatum. It was an observation, a recognition that the life that they were living no longer fit the people they were becoming. And so, for the first time in a long while, Lionel didn't argue with the truth of it. Instead of pushing harder, he paused. He called a friend, someone who knew a different way, someone who had worked in film tv, where music lived in service of story, not necessarily in the spotlight. What would it look like to make music without having to perform a version of yourself every night? So this friend, the TV network, set him up with an opportunity to score a show.
Todd Henry [00:17:52]:
And scoring television shows opened a door he didn't even know he'd been looking for. Here, music mattered deeply, but kind of anonymously, he was able to work in his home studio. It was Emotion over ego, craft over celebrity. Long hours with sound and silence shaping feeling rather than feeding momentum. And something kind of unexpected happened. The music didn't shrink. It expanded. This wasn't quitting music.
Todd Henry [00:18:20]:
It was reclaiming it. Because sometimes the breakthrough isn't finding a new dream. It's letting go of the one you thought you were supposed to want. And Lionel has some advice for those of us who might also feel a little bit like our work has become a role that we are playing rather than a mission that we are pursuing.
Lionel Cartwright [00:18:38]:
My first word of advice would be pay attention. If you're sensing even a little whisper inside of you that might be suggesting this isn't the best fit for who you really are. And that's key to me. What is your wiring? What does your software look like inside? And I wouldn't let the number of years you have chased something with all the intensity and all the desire that you've brought to it. I wouldn't let that shout down the quieter voice that might be suggesting it's time for a change. It's time for that. A lot of times, what looks like a detour is actually your main route. I would first just say really pay attention to that.
Lionel Cartwright [00:19:39]:
Give it some serious due.
Todd Henry [00:19:43]:
As you think about Lionel's story, here's the question I want to leave you with today. Where in your life has momentum started making the decisions for you? So many creative pros, so many leaders, confuse capability with calling. Just because you can succeed at something doesn't mean that you are meant to keep sacrificing for it indefinitely. One of the most dangerous traps is succeeding your way into a life you never actually chose. Lionel didn't abandon his creativity. He redirected it. He paid attention to the signals. He listened to the people who knew him best.
Todd Henry [00:20:17]:
And he had the courage to redesign his work around the life he wanted, not the life he thought he was supposed to want. This is the work for all of us to regularly step back and ask, not just is this working, but is this worth the cost? It's demanding of me right now because, again, the goal is not applause, it's alignment. And the bravest creative decisions often happen far away from the spotlight. Lionel has a brand new podcast. It's called off the Charts. You can check it out. I was on a recent episode. You can hear my entire story of my history in music and more in his podcast.
Todd Henry [00:20:57]:
Again, it's off the charts. It's available wherever you listen to podcasts. Okay, thanks so much for listening. If you'd like full interviews with Lionel and all of our guests. You can get them absolutely free@dailycreativeplus.com just go there, enter your name and email. We'll send you a private feed to download all of our interviews and bonus content. My name is Todd Henry. You can learn more about me, my speaking events, my books, and more@todhenry.com until next time.
Todd Henry [00:21:26]:
May you be brave, focused and brilliant. We'll see you then.
Artist, Musician
Lionel Cartwright is a West Virginia native whose unconventional creative path has taken him from country radio hits to television composing and beyond. As part of country music's early 90s class, he scored chart-toppers including "Give Me His Last Chance," "I Watched It All On My Radio," and "Leap of Faith," followed by years of national and international touring alongside country's biggest stars.
When country music's direction shifted in the late 90s, so did Lionel. He pivoted to television composing, landing hundreds of placements across various TV shows while building a home studio that allowed him to balance creative work with being present as a father and husband.
"My path has been very unconventional, but it's been a good fit for me," says Lionel. "I've been fortunate to do work I love while being totally invested as a dad and husband. I'm grateful for a life that is both relationally rich and creatively flourishing."
Today, Lionel hosts the podcast and YouTube series Off The Charts, which reexamines creative success beyond fame and money. He encourages others to find their unique creative voice through whatever outlet fits their wiring—whether songwriting, gardening, starting a business, community service, or any of thousands of other creative endeavors. "I believe all humans are creative," Lionel maintains, "and finding a healthy expression for your unique creative outlet is key to experiencing a meaningful, satisfying life."