Conversations with Thomas

A Gentle Note Before You Begin to Listen

This space holds truth—and sometimes, truth is tender.
The story I share here includes reflections on suicidal thoughts and lived experiences with mental health struggles. If this is a sensitive subject for you, please honor your heart as you read or listen. You have full permission to pause, skip, or return when it feels safe.
You are not alone.
Your well-being matters more than any story.
If you or someone you love is struggling, I encourage you to reach out to a trusted support, therapist, or crisis resource in your area. There is help. There is hope. And there is healing.
With deep respect for your journey —
Welcome. Please begin when you’re ready.

Start with How You Failed

In this episode of Conversations with Thomas, we flip the script on how we usually measure success. Thomas invites us to start by sharing our failures—the messy, mortifying, oh-shit moments we’d rather keep hidden. Because when we tell the truth about how we fell down, we give ourselves and others permission to get back up.

Drawing from his own life—like the day he almost ended it all at Bow Falls in Calgary—Thomas shares how failing to take his own life became his biggest triumph. That failure woke him up to the power of living, to the fierce desire to turn pain into purpose. And he reminds us: failure isn’t the end—it’s the forge that shapes us.

Alongside personal stories and scientific insights (like how the brain’s error-monitoring system actually helps us grow), Thomas weaves in humor and heart, showing us that failure is life’s way of recalculating the route.

He also shares how his own “coaching misfires” became the catalyst for authentic, human-centered connection—and extends an invitation to listeners to explore the gold in their own failures.

So, take a deep breath and join Thomas in this brave conversation. Because in the end, our failures aren’t proof we’re unworthy. They’re reminders we’re alive, we’re learning, and we’re loved.

Let your failure become the compass that points you to what matters most. 

What is Conversations with Thomas?

Conversations With Thomas is a podcast where humor, heart, and a touch of sass collide. Hosted by Thomas Kevin Dolan, each episode explores raw, real topics like self-compassion, healing, and the delightful mess of being human. As the seventh of ten kids, Thomas didn’t always have a voice—now he’s sharing it with you, and trust us, you’ll want to hear this.

Expect vulnerability, laughs, and thought-provoking questions that dive into subjects most people avoid (because, let's face it, some topics just need to be tackled). With a mix of wit and wisdom, Thomas takes you on a journey where you might cry, you might laugh, and you’ll definitely feel a little more connected to yourself and the world.

New episodes drop every 2nd and 4th Monday. Tune in for a dose of honesty, heart, and just the right amount of quirky.

This podcast is recorded in Honolulu, Hawaii on the unceded Aina of the Kanakamale,
the indigenous people of Hawaii. I live and work in the neighborhood of Kakako, and
I honor the deep stewardship of this land. Aloha, beautiful humans, and welcome back
to Conversations with Thomas. I'm your host, Thomas Kevin Dolan, pronoun he and him.
This podcast is a glimpse into my beautifully messy, sometimes profound, and most
times hilariously real journey. Sharing these messy truths brings me real joy,
and to be honest, a healthy dose of oh shit anxiety too. Today I want to,
I want to eke you into, I want to invite you into one of the most freeing,
powerful, and surprisingly delightful places to start any journey with how you fail.
You know, stories of success are fine and dandy, but stories of failure, oh, those
resonate in our bones. And as the saying goes, few reach the top,
but everyone's tripped on the way up the stairs. Let's be real.
Failure has a way of introducing us to parts of ourselves. We actually never knew
we would have met otherwise. Today I want to invite you to start with how you
failed because in that rubble, in that mess, oftentimes in that chaos,
we find the hidden gold. I'm not just talking about garden variety.
I forgot to return the library book failure. I'm talking about the big, messy,
"Oh my god, I might not get up again" kind of failure. I liken failure to taxes
and bad hair. It comes for everyone. Sooner or later, taxes and bad hair taste.
The only difference is how we relate to it when it does. Why do I They start with
how you failed.
Because stories of failure resonate more than stories of success. Think about it.
If you tell me you woke up one day and crushed it, no mistakes, no setbacks,
well, congratulations. But that's a little challenging for me to connect with. I can
connect with tripping over your own feet in a of you or you telling me you forgot
that the sweater that you put on, you actually put on inside out. Yes,
that last one was from personal experience. And I'm going to share one of my
biggest failures, the one I almost didn't live to tell this story. It's from my
book, Little Fag, A Journey of Self -acceptance and Healing. And honestly, thank God,
it was a failure. In the late 1970s, I bought a Smith and Wesson 357 Combat
Magnum. It was a handgun. Nickel plated, shiny as hope,
and heavy as despair. My older brother had died by suicide.
Another brother had tried, and I actually thought I was next in line. Twice I
considered using that gun. Once to protect my family.
That failure to end my life became my first step to truly living.
It was as if the universe said, "You're still here. Now go prove why." The failure
didn't just keep me alive. It lit a fire in me, a fierce desire to succeed,
to live a life of authenticity with meaning to create beauty out of brokenness. And
science backs this up. Researchers at the University of Calgary, University of
Calgary, researchers at the University of California, there we go, Berkeley, found
that our brains respond to failure like a GPS recalculating a route. The brain's
error monitoring system, specifically, it's called the anterior cingulate text.
It lights up like a Christmas tree when we screw up. And its purpose in doing that
is to help us adjust course and keep going. It's literally in our wiring.
Failure is how we grow. Another study from the Journal of Experimental Psychology
found that people learn more from observing others' failures than their successes.
Why? Because it's in the mistakes, the missed steps that we find the real greedy
wisdom. I have this thought. I'm off script here, and it's simply this. The failures
that my siblings, right? I'm the seventh of 10 children, so I looked up to a lot
of people who had come before me. A lot of the failures that they experienced, a
lot of the ways that they fell down, were these amazing moments of learning for me.
They were my teachers, and I'm so grateful to them. I've never thought about that
before, but the observation of their failures really contributed to the successes I
would create in my life. their missteps really helped me land on and find the real
gritty wisdom in my life. Thank you for allowing me to digress a little bit, but
that one I've actually never thought about before.
Let me pause for a second here. I want to add a mini promo because,
well, even podcasters like me have bills to pay. If you're loving these messy,
heartfelt conversations and want to work with me one -on -one, check out my coaching
practice at thomaskevindolen .com. I promise I'll show up as real as I do here minus
the podcast mic. Together I'll support you in turning your oh shit moments into oh
wow moments. Okay, back to the regularly scheduled programming, now with 25 % more
humor, and still zero gluten.
This brings to mind a favorite quote from Howard Thurman, a wise black mystic and
theologian he shared, "Don't ask what the world needs. Ask what makes you come
alive, and go do it. Because what the world needs is people who have come alive.
Failure is often the gateway to discovering what truly makes you come alive. Let me
give you a personal example. When I first launched my coaching business, I thought I
had to be perfectly polished.
My website was so carefully curated. My website was so carefully curated,
say that a couple of times in a row. It looked like it was running for mayor of
the moon. My first discovery call, during that first discovery call,
I was so busy trying to sell my services that I didn't remember to ask any real
questions about what the client actually needed. Talk about a face poem moment.
But that failure, that teacher, taught me everything I needed to know about showing
up real, not perfect. It happened for me, not to me. Here's the kicker. Failure is
feedback. It's life's way of saying, "Hey, you're a little off course.
Let's recalibrate." I like to think of it as GPS recalculating while you're driving.
You've heard it. Make a U -turn at the next corner. But Let's take a little bit of
a deeper dive. Failure also tests our relationships with ourselves and with the
people who hold us. When we admit, when I admit my failures out loud,
when you admit your failures out loud, when we can say, here's where I messed up,
and here's what I learned.
It invites others to drop their own masks. It's like you're cracking open a window
letting in some fresh air.
I've had the most profound conversations when people, when that person and I have
both shared our failures first. Imagine instead of meeting somebody,
if you are somebody who's seeking relationship and instead the first couple of
quotes, "Hi, obviously, what's your name? Where are you from? What do you do? What
if you shared this question? Hi, my name is Thomas. Thank you. Hello,
Mario. It's nice to meet you. I'm wondering if you're willing to share with me a
short story, maybe not your worst, but what's the story of how you failed in life?
And maybe before you do that, I could do that with you. Imagine that as an opening
line to meeting somebody
because it, like I said before, might be the story that helps somebody unlock some
courage for them to actually really allow you to see who they are. Think about the
last time you heard someone share a raw real story. You probably thought, "Oh, thank
God, I thought it was the only one." So here's a practice to find the gold in
your failure, I think five steps in it. The first is to name it.
Think of a time you failed, big or small, inviting your nut to shy away, and put
a name to that.
And then, because this is a memory, right,
Where in your body do you feel that memory? It might be a tight chest,
it might be actually a warm flutter in your belly.
And then having named what it is, knowing where it resides in your body,
begin a really gentle dialogue with it. Close your eyes and ask it,
"What's your purpose?
What wisdom do you hold so you've named the failure you could feel it in your body
You're gonna ask it. What's your what's your purpose? What wisdom do you hold
and then you've got an opportunity
To rewrite the story
if this failure was actually a guide. What is it pointing you towards?
And here's the fifth, the fifth step where you're going to, I'm going to invite you
to call on the bravest part of you is to share this, to share the name of the
story that was a failure, bigger, small for you, to let somebody know that you
actually felt a tingling in your stomach and my anxiety might be fear, Right, you
asked it what its purpose was. You asked it what wisdom it held. And then you're
going to share, you're going to tell a trusted friend, perhaps your partner. Or if
that doesn't work for you, maybe you can journal.
The key is with someone safe or someplace safe, where you can give that failure a
voice.
Every time that I do this, it's extraordinary what I learned about myself. And when
I choose to share this with somebody, it's extraordinary the response. You might be
surprised what emerges when you put words to it. Because failure in my life,
it isn't a stop sign. It's a signpost. It points me to where the real work is.
"It asks me, and perhaps it's going to ask you, will you keep going even though
it's hard?" And that's where the alchemy is, right? That's where lead gets turned
into gold.
And speaking of alchemy, here's a wonderful example of what it is that I've just
chatted about that actually was used by, of course, Nelson Mandela, whose journey
from a young anti -apartheid revolutionary to a global symbol of resilience and
leadership. It's a powerful story of learning from failure. Mandela spent 27 years in
prison for his activism against apartheid. During that time,
he often reflected on his mistakes and early what called NIST calculations.
He said, "Do not judge me by my success. Judge me by how many times I fell down
and got back up again." Let's be honest. Sometimes our failures are freaking
hilarious. Like the time I tried to make vegan pancakes that could double as talkie
-pucks.
Humor is the balm that makes failure easy to hold. So laugh about it,
because if you can laugh, you can learn. So my friend,
here's your invitation. Start with how you failed. Let it be the compass that points
you to what matters. Failure is a part of the deal. As Maya Angelou said,
"You may encounter many defeats, but you must not be defeated." So let's honor our
failures. Let's see them as a litmus test. Let's see them not as proof we're
unworthy, but as the forge that shaped us. Imagine using and bringing to light a
failure that you suddenly realize is the forge for who it is that you become,
that it didn't happen to you, that it happened for you, and you're willing to
actually kind of mine it for the lesson. That would be extraordinary.
Allow that failure to be a forge that shape you.
May you walk today with the courage to share your failures and the curiosity to
find gold in them because there is I guarantee you there was gold. I used to think
the gold was in the dark.
The gold is actually in the failure. I look at them as often as I possibly can
and as readily as how it is that I screwed up yesterday, literally,
with the compassion and empathy for how it is that I'm gonna screw up tomorrow.
It's this cosmic joke. It's this setup for me to know that the fall is only an
opportunity for me to rise. Am I willing to do that? Are you willing to do that?
I'll say yes. I'm gonna project on you and say that you're gonna say yes as well.
research to make your therapist proud. But let's be clear, it's not a replacement
for professional care. If you're facing big mental health stuff, please talk to a
licensed therapist or healthcare provider. They're the real MVPs. This show has
brought to life with heart, a clearly a microphone, and the tech wizardry of my
amazing husband and co -executive producer, Adam Ma, who makes sure I don't
Accidentally record in slow motion. Yep. I have been there. I have done that until
next time take a breath Unclench that jaw of yours and remember and remember You're
not a mess. You may feel like one. You're actually a masterpiece in motion