Conversations on the Road is a weekly podcast hosted by Jonathan Westley. Each episode is an honest look at the roads we walk: identity, love, family, grief, masculinity, and the quiet work of choosing peace. Some episodes are solo reflections. Some are conversations. All of them are real. Subscribe to The Jonathan Journals on Substack for the written stories behind every episode.
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I sat down with an old classmate from high school. We talk about where we've been, where we are today, and our plans for the future. An unexpected reconnection along the road.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
31 Aug 2026
Episode 13, Dim Lights on the Road...
No Fixed Address is a chapter of Conversations on the Road. In August 2026 I gave up my apartment, sold my car, and moved into a life of hotel rooms, airports, and wonder. These are the dispatches from that.
Week three of No Fixed Address. The US Open priced every hotel in Queens out of reach, so I got on a plane to Charlotte instead—which is when I started thinking about options as the word of the season. This one also has a dim hallway mirror I didn’t recognize myself in, what my meditation group had to say about avoidance and emotional safety, and what happened when I put out a post and a whole lot of people answered the call.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
24 Aug 2026
Episode 12, Postcards from the Road...
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17 Aug 2026
Episode 11, No Fixed Address: Act One
At fifty-four, I've unloaded everything attached to adulthood and set out on a journey I've been waiting on for thirty years.
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10 Aug 2026
Episode 10: No Fixed Address
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19 Jul 2026
A Therapist, A Trip, and A Journal
The story behind “Little Boy in the Driveway” —how I found my way back to writing, and back to myself.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
9 Jul 2026
The Letter
There's a family I've never written about. Growing up, I had four brothers—but only two I knew. The others were like ghosts: I knew they were there, I just couldn't see them. When my father passed, I finally held their names and addresses in my hands, and I did the bravest thing I could think of at the time — I wrote my brother Johnny a letter. And then I never sent it. It sat between the pages of a journal for years, until I lost it altogether. Johnny found me first, in 2011. We had about a year before he was gone. In this solo episode, recorded on a short drive, I finally read him the letter I should have sent — and send it out into the ether, hoping his soul catches the vibrations of my words
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
21 Jun 2026
Hurdles Be Damned
This is a Short Drive — a solo reflection under 30 minutes, thoughts you can take with you.
In this one I take you back to the first real hurdle of my adult life: leaving home at 18, Texas-bound, sure I had it all figured out — and finding myself four months later on a Greyhound bus riding home under the cloak of darkness. Looking back from this side of the road, I’ve come to understand that the bus was never the hurdle. The bus was just the receipt. The hurdle was me — my own unpreparedness.
This episode is about “the Texas question” I still ask myself before every new challenge: Am I as ready as I think I am, or am I about to find out that I’m not?
Show up ready — or don’t be surprised if you end up on the bus.
Hurdles be damned. Keep going.
Conversations on the Road — I’m Jonathan Westley, and I’ll see you on the next one.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
2 Jun 2026
Episode 6 1/2: Learning Life on the Curve
This mini episode is a side road to Episode 6, The Roads We Take Become Legacy. Recorded from a hotel room in London at 4:15 a.m., it’s a short reflection on what I learned while editing that episode—the tech fumbles, missed deadlines, stubbornness, and the reminder that most of us don’t learn on straight roads, we learn on curves. If Episode 6 left you wanting a little more, this is a look behind the scenes at the process and the life curve I’m on right now.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
31 May 2026
The Roads We Take Become the Legacy
What does legacy really mean?
In this episode of Conversations on the Road, I sit down with an old friend to talk about fatherhood, masculinity, identity, military life, and the paths we take when the lives we were taught to want no longer fit who we are.
Sometimes legacy isn’t what we leave behind.Sometimes it’s the road we choose to walk instead.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
8 May 2026
Trying to Fit Love Into a Space That Wasn’t Built For It.
This episode is about what I’ve learned, and what I wish I had known—about relationships, especially trying to navigate love in spaces that weren’t necessarily designed with us in mind.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
24 Apr 2026
Episode 4: Learning to Choose Peace
In this episode, I sit down with my friend Robert while in Dallas, Texas.
We talk about dating, relationships, and what it means to choose peace at this stage in life.
It’s an honest conversation about where we are, what we’ve learned, and what we’re no longer willing to carry
.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
16 Mar 2026
When Influence Sounds Like A Black Woman
In this solo episode, I reflect on my lived experience as a Black American and share some thoughts about how this country often reacts when Black women become visible and influential voices in public life, particularly in politics.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
3 Mar 2026
The Loneliness of Becoming
In this solo episode, I reflect on a decade of quiet loneliness, the kind that comes with shedding old versions of yourself and stepping into midlife.
This is a late-night conversation about visibility, protection, and what it means to begin taking up space again.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
21 Feb 2026
A Chat with Two Jonathans
A Chat with Two Jonathans
In the first episode of Conversations on the Road, I'm introducing the heart behind the show. This podcast is about reflection, growth, and the conversations we carry with us as we move through life.
To break the ice and begin this journey, my dear friend Jonathan Swisher joins me for an honest and easy conversation. We've known each other for years, and it felt right to start here....with familiarity, laughter, and real connection.
This is where the road begins.
This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit jonathanjournals.substack.com (https://jonathanjournals.substack.com?utm_medium=podcast&utm_campaign=CTA_1)
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