The Only Way Out Is Through: There's No Map. Only Forward.
EPISODE 11 • Aug 12, 2026 • FAMILY DOUGH PODCAST • John Dewey
The Only Way Out Is Through: There’s No Map. Only Forward.
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If you grew up with money or inherited it, you already know it can mess with your head. I help you untangle your
identity from the family story. Face the shame that nobody talks about and live with real integrity without destroying
your relationships just to feel free. This isn’t about your portfolio. It’s about being who you truly are. Welcome home.
You’re listening to Family Dough. Hello and welcome back to Family Dough. This is John Dewey. The only way out is
through the Dark wood, the divine Comedy. And forgiving the man I was. If you haven’t noticed already, I love
movies. I love them enough that we built a theater in our house. My dear friend Dan pushed me to finally do it, the
thing I had always wanted. And that is a good lead into what I want to share with you today. Sometimes in the night
when I can’t sleep, I will go in and turn on a movie that I’ve seen several times, hoping to drift back to sleep because
I’m familiar with the script. Well, last night was not one of those nights. Last night was what I like to refer to as lesson
time. I call it lesson time because something had been brewing in me. I have been writing and reflecting quite deeply
lately, and whenever I’m in that state, I know there’s a doozy of a lesson coming my way. And my choice of movie is
never an accident when a lesson is on its way.
So which movie did I happen to choose? You are asking the bucket list. It is about two dying men, played by Jack
Nicholson and Morgan Freeman, who have nothing in common and become friends anyway through a long shared
hospital stay. Both of them fighting terminal cancer. Nicholson’s character, Edward, is a hyper agent. He built a
fortune building and running hospitals, and he has been catered to more and more as that fortune rose across his
career. By the time we meet him, the people around him do not tell him the truth because his hyper agency lets him
bend the world to feed his never ending needs and ambition. He has a habit of not calling people by their right
names, and he gets away with it because his agency lets him get away with nearly everything. And after all of that,
he still has not found the answers he is looking for. He is, to put it plainly, a cranky pants. The other man, Carter,
played by Morgan Freeman, is his opposite. Carter has the mind of a philosophy Professor and worked as a mechanic
his whole life. By this point, the two of them have just had a falling out. The time that I’m going to talk about. Carter
had pushed Edward too hard about mending his relationship with his daughter. Edward’s ego went into code Red
defense, and that was that. He left in a huff. And regular family Doe listeners know that I understand Edward’s pain
here, because I have a daughter who is distanced from me by her own choice.
Which brings me to the scene that stopped me cold near the end of the movie. Edward is back in his office now, in
remission, sitting in a meeting. But the meeting feels mundane to him now because he has finally begun to look

honestly into his own mirror. So instead of listening to the numbers and the strategy. He stops his employee mid-
sentence and asks him, out of nowhere, whether he has ever read The Divine Comedy. The poor man has no idea

what he is talking about. Edward says it again. Dante Alighieri’s Journey down into hell. He is not really asking about a
book. He is talking about himself, about the journey. He has just been through. The cancer, the trip around the world,
his wise, loving friend Carter. The whole thing that finally cracked him open, the Divine Comedy, the journey down
into hell. And then, as the movie ends, John Mayer’s song say, begins to play. Mayer is one of the most self-reflective
songwriters we have, and the whole song turns on a single question. It is the question that finally drove all of this
home for me. What truth are you withholding because you are afraid of the consequences? Let me repeat that. What
truth are you withholding because you are afraid of the consequences? I have heard the Dante line every single time
I have watched this movie through the years.

But tonight, with that question hanging in the air behind it, it stopped me hard. I got the chills because I realized
sitting there in 2026, that I have actually made that journey down into hell and back out the other side. And the man
on the couch tonight is not the same man who first heard those words in a theater in 2007. I want to tell you about
that, because I think there is something in it for anyone who has ever been truly lost and I mean really lost. The kind
where you cannot find the door. Here’s the thing about The Divine Comedy. In 2007, I knew about it. I could have told
you it was Dante, that it was a journey through hell and purgatory and heaven, and that it was one of the great
books. But it was just knowledge to me, something I knew and I could spit out to people trying to convince them that
I was smart, because deep down inside, my own wound was my younger self who still believed he was not good
enough. It was a thing educated people referenced at dinner. I had no idea what it actually meant. Now I do now. It is
not an idea. It is the map of my own life. It is where I found the most important answers I have ever found. And the
almost funny part is that the answers were not new. I used to think that they were 700 years old because that is
when Dante wrote them down.
But they are far older than that. The Greeks had a word for this journey long before Dante. Katabasis the descent
down into the underworld and back. The answers were never the problem. I just was not ready to understand them
yet. You cannot understand the map of hell until you have walked it. Here is something I have to say about how I was
raised and about that movie. Everything in my world pointed at Edward, the Nicholson character. He was the one you
were supposed to become. He had the money, so he got the attention. And the lesson never set out loud, but taught
all the same. Was that the goal was to be him, the man with the means, the man who could buy the room. But watch
what actually happens in the story. It is Carter, the mechanic with no money, who brings the idea of the bucket list,
and when Edward sees it, he does not say, I can do this. He says we. He says we because, yes, he knew he had the
means to make it happen, but he also knew somewhere inside of himself that he could never have done a minute of
it alone. He needed Carter. He needed Carter’s wisdom, his dedication to actually living, his understanding of what a
life is, even for Edward’s money, bought the plane and the plane carried them to the far corners of the world.
But the plane was never the point. The plane was the whimsy. The real insight, the thing that changed. Both men
came out of the two of them together. One brought financial resources, the other brought wisdom, resources, and
only together did either one of them get off the ground. I was born on the money side of that, and I will tell you the
truth that nobody expects to hear. I was always hungry for the other kind, the wisdom resources. That is what I was
actually chasing my entire life. Yes, it was nice, of course, to have access to the financial ones and I am not going to
pretend otherwise, but I carried so much guilt and so much shame wrapped around that money that I could not enjoy
it. I could not sit still inside it. The very thing everyone is taught to want, I had. And it felt like a weight inside of a gift,
and I could not think my way out from under that weight. I had to go through hell first. Dante opens the whole poem
with one of the truest sentences ever written. He says, midway upon the journey of our life. I found myself within a
forest dark. For the straight way was lost midway. Not at the beginning. When everyone expects to be confused in
the middle when you are supposed to have it figured out by now. That was me in 2006. I was in the middle of my life
and the straight way was gone.
I had just ended my attempt to finish my doctorate in clinical psychology. Years of work and I walked away from it
and I carried it like a verdict. Proof that I could not finish. My father was sick. My father was dying of terminal cancer.
And the truth I could not say out loud was that I had made my father into my safe harbor. My whole sense of solid
ground. And as the harbor disappeared. I found there was nothing underneath me. I was lost. I was bound. I did not
know which direction was out. And here’s a part. I have never said this plainly. When you are that lost, you will grab
on to anyone who seems to know where they are going. At that time, the person closest to me was my wife. Then she
had a way of dealing with pain. Her way was to distance, to pull back from people, to go cold and to cut off. And
because I had no map of my own, I followed hers. I distanced too. I pulled away from people who loved me. I was in
the house, but I was not present for my children. I was trying to make sense of my own family, my own wake, and I
could not. So I quietly borrowed somebody else’s way of being in the world and called it mine. That is the thing I most
want to name for you. I was not listening to my own center.

I had a heart. I had a direction. I was in there the whole time trying to get a word in, but I had turned the volume
down on it and turned the volume way up on everyone else. And the man living off of a borrowed map will always
end up somewhere he never meant to go. There is one more thing that movie keeps showing, and it is the trap I fell
into. Hardest of all, Edward Nicholson’s character is a man who is certain. He is certain he is right. He is certain he
has life figured out, certain his money has bought him the truth. And all of that certainty has left him completely
alone. The story quietly makes the point that the people who are most sure they are clutching the magic ring. The
one true answer usually have no idea that they are not holding it at all. I was no different in 2007. I was so certain of
what I believed. Certain my father was my safe harbor, certain that the way to handle pain was to go cold and pull
away because that was the map I had borrowed. Certain, certain, certain. And the truth. The thing I can only see now
is that I had no idea the ring I was gripping so tightly was not the ring at all. So here is what I would tell my younger
self and what I will tell you the moment you are most sure you have found the answer is exactly the moment to hold
it a little more loosely.
The things that finally saved me did not come from what I was certain of. They came from staying open long enough
to be surprised. There is no way around it. What Dante understood and what I did not understand until I lived it, is
that you cannot go around hell. There is no detour. The geography will not allow it. The only way out is down. All the
way to the bottom and then through. I went to the bottom. My drinking climbed in those years. Because I did not
believe I could survive the grief any other way. I numbed it. I ran. I have said it before that I was exhausted from
running. This is the running I meant I ran for years, but here is what the poem promises and what turned out to be
true for me. The bottom is not the end of the story. In the poem, the only way out of hell is to climb down past the
very center of it, past the worst of it, and keep going until the ground itself turns over and you begin to rise. You have
to pass straight through the middle of the thing you are most afraid of. There is no other door. There never was.
Turning the volume back up. So how did I start to climb? I started to listen. Not to the experts, not to my ex.
Not to what my family expected or what the system I was born into wanted out of me. I started slowly and very, very
clumsily to listen to the thing in the center of my chest that had been trying to talk to me the entire time. My heart.
My own direction. It is the simplest thing and it is the hardest thing. Follow your heart. Sounds like a line on a
greeting card, right up until you have spent 40 years not doing it. For me, it meant trusting that the way I speak to
people, heartfelt in a voice that is mine and nobody else’s was not a flaw to be corrected. It was the gift. It was the
compass. Every good thing in my life now grew out of finally turning that volume back up and turning everyone else’s
down. Forgiving the man in the woods. And now we come to the part I think matters most. Forgiveness of myself. I
could take everything I just told you. The abandoned degree, the distancing, the drinking, the years. I was not truly
present for my kids or for my ex. And I could use all of it as a weapon against myself. I know how to do that. I have a
special set of skills which most of us are experts at. We carry a critical voice that would happily replay our worst
years on a loop and call it honesty. I’m not going to do that anymore. Not because I’m letting myself off the hook.
Because I have learned that the critical voice does not make you better. It just keeps you in the woods. The voice
that actually gets you out is the other one, the warm one, the one that can look at the lost man I was, and say, of
course you got lost. Your father was dying. You had no map. And here’s the big painful truth. I never had a map. My
father had never given me one, even though I convinced myself that he had. And that is okay. I was doing the best I
could with the tools I had. Now let us keep walking. That is not weakness. It is the only thing that has ever worked.
When I look back at 2007 now, I do not see a failure. I see a man in the dark wood who simply had not learned yet
that there was a way through. I forgive him. The truth is, I am grateful to him because he kept walking even when he
could not see a single step ahead to see again the stars. Dante ends his journey through hell with one line and it is
the most beautiful last line I know. After all of it, all the descent, all the horror, he writes. And thence we came forth
to see again the stars. The stars were there the whole time. He just could not see them from inside hell. He had to
come all the way through before he could look up.
It is 2026. I came through and I can look up now. The confidence I carry today is not the confidence of a man who
won at his career, because I didn’t or finally finished the degree, which I didn’t, or built the monument to my
accomplishments outside of myself. It is something quieter and much harder to take away from a person. It is the
confidence of a man who went all the way down, walked through the middle of the worst of it, and came out the
other side and saw the stars again. I know in my body that there is a. Through. Nobody can argue me out of it
because I did not read it in a book. I lived it. The book just told me 700 years later what I had been through. Why am I
telling you this? Well, let me say plainly why I am sitting here saying all of this out loud. Why am I bothering to make
any of this at all? It is not because I arrived. I want to be very clear about that. I have not arrived. I do not have the
answer wrapped up with a bow. What I have is a lot more clarity about who I am in the world than I have ever had.
And it took years to get. And it took searching in every direction you can imagine. The answers came from
everywhere, from books, from friends, from failure, from people who had no idea at the time that they were helping
me out at all.

That is the whole point. I did not climb out of those woods alone. Nobody does. I had so many people reach a hand
back for me along the way and I could not have made it without a single one of them. So now it is my turn. That is
really all this is. I feel an obligation to reach a hand back because somebody reached one back for me. And you never
know when your moment is coming. You never know when the one thing that finally turns the ground over for you is
going to arrive, or who is going to be carrying it when it does. So I want to be one of the people standing on the path
contributing back. Just in case, today is your day. If you are anywhere on the path. So if you are in the dark wood
tonight, midway through your life with the straightway lost, I am not going to hand you a map. The one thing I
learned is that a borrowed map is what got me lost in the first place. But I am not only talking to the people at the
very bottom. If you are anywhere on the path at the beginning, in the muddy middle. Almost out. This is for you.
Keep going. Keep searching. Do not give up because that is the part that matters most of all.
I searched down a hundred directions. At least that led nowhere before I found a few that led somewhere, and I had
no way of knowing in advance which would be which. You will not either. That is not a reason to stop. It is the reason
to keep moving, because your moment could be the next direction you try. And if you are not on the path at all, if
you are not searching and you have no interest in searching right now, that is all right too. I am not here to drag
anyone anywhere. They do not want to go. I am just leaving the light on for the ones who are looking for it. What I
will give you is the only true thing I know. The only way out is through. And it is okay because there is a through. I am
standing here as proof of it. Go down. If down is where you have to go, listen to the center of your own chest. Even if
it is a whisper under everyone else’s noise. Forgive the lost version of yourself. He was doing his best. And keep
walking. You will see the stars again. They have been there the whole time, waiting for you to come up enough to
look. Have a great day everyone! Remember, this isn’t about perfection. It’s about awareness, choice, and forward
movement. So before you go, ask yourself, are we making progress? I’ll see you next time on family dough.

In Today's Episode, we discuss:

Sometimes the biggest turning points in our lives don’t come from finding a new answer—they come from finally understanding an old one. In this episode, I reflect on a late-night rewatch of The Bucket List, Dante’s The Divine Comedy, and the unexpected question that stopped me in my tracks: What truth are you withholding because you’re afraid of the consequences? That question became the starting point for a conversation about grief, identity, inherited beliefs, and why some lessons can only be understood after you’ve lived them.

I share my own journey through a season where I felt completely lost—walking away from my doctorate, losing my father, struggling with alcohol, borrowing other people’s ways of navigating life, and eventually learning that there was no shortcut around the pain. We explore why certainty can become its own trap, what it means to stop living from a borrowed map, how self-forgiveness becomes part of healing, and why I believe the only way out of our darkest seasons is through them. If you’re in the middle of your own “dark wood,” my hope is not to hand you a map, but to remind you that there is a path forward—and that one day you’ll see the stars again. 

 

Topics We Cover in This Episode: 

  • Why one scene from The Bucket List completely changed the way I understood my own story
  • The question I couldn’t stop thinking about—and why it’s worth asking yourself
  • What Dante’s journey through The Divine Comedy reveals about navigating life’s hardest seasons
  • How living from a “borrowed map” can quietly pull you away from your own values
  • The surprising difference between financial resources and wisdom resources
  • Why certainty can sometimes keep us stuck more than uncertainty does
  • What self-forgiveness actually looks like after years of regret and self-criticism

 

Join me for a conversation about grief, identity, certainty, and what it actually takes to find your way back to yourself. If you’ve ever wondered whether the struggle you’re in has a purpose, I think you’ll find something worth sitting with in this episode.

Resources Mentioned:

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