
Career Coaching with John
A podcast about work, identity, and change.
Thoughtful conversations about the lives we build around work—and what happens when they stop fitting.
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This, My Friends, Is Purgatory — Episode 22
Career Coaching with John
Let’s rethink what we expect from work.
Work takes up too much of our lives to leave our assumptions about it unexamined.
Through stories, conversations, and coaching, we explore what we accept, what we want, and what we might change.
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Who are you when the career you've spent decades building is suddenly taken away?
For 30 years, Geoff Curtis worked in communications and public relations, building a successful career that became central to his identity. When his company was acquired and his future became uncertain, he found himself confronting a question he hadn't given much thought to: who was he without the job?
In this episode, Geoff joins me to discuss his book, Embracing Your Own Purgatory, and the uncomfortable, often disorienting experience of rebuilding a life after career loss.
We explore the relationship between work and identity, the temptation to keep ourselves busy rather than confront difficult questions, and what happens when the person we thought we were no longer quite fits.
Geoff doesn't offer a tidy story of reinvention. He's still figuring things out. And perhaps that's the point. We don't always know who we're becoming, and we don't necessarily have to.
Season One
Yoiur Guest: Geoff Curtis
What do you do when nothing is really wrong with your career—but you know something isn't right?
In this episode, I tell the story of “Jenny,” a client with a stable job, good income, flexibility and a life that, on paper, works. The problem is that she's bored. She's stopped learning. And when she tries to imagine something different, she doesn't know what she's looking for.
Strangely enough, that problem got me thinking about Ukraine.
Over the course of the war, Ukraine has been forced to build systems that allow ideas to be tested, challenged and improved at extraordinary speed. One of those systems is Brave1, an innovation ecosystem connecting soldiers, engineers, entrepreneurs, manufacturers and government around a continuous feedback loop:
Build. Test. Learn. Improve. Then do it again.
This isn't an episode about pretending that changing careers is comparable to fighting a war. It's about something much simpler: what happens when we stop waiting for the perfect answer and start building systems that help us learn?
Season One
We open the show with a reflection on Lady Gaga and Little Richard — two artists who built careers by refusing to be defined by a single identity.
Lady Gaga represents a more modern, deliberate version of identity: someone who crafted a persona that can move seamlessly between worlds — mainstream and fringe, polished and experimental.
Little Richard, on the other hand, represents something less tidy. A rock and roll pioneer, a religious preacher, a boundary-pushing performer — all at once. His identity wasn’t clean or consistent, and it didn’t always align neatly. But it worked.
Together, they raise a question that carries into the rest of the episode:
Do we need to simplify who we are to be understood… or can we succeed by expressing something more complex?
In this episode, John explores that question through a real conversation.
What starts as a discussion about influencers quickly becomes something deeper.
When John interviews content creator and client Emily Parr, he finds himself caught off guard by the difference between the person he knows… and the one who shows up on camera.
That moment raises a bigger question:
Are we supposed to simplify ourselves to be understood — or learn how to express something more complex?
Guest: Emily Parr
We open this episode with a side note on Raymond Chandler — a writer who reinvented himself when the world shifted beneath him. Out of job, out of structure, he disciplined himself to write and, in doing so, created Philip Marlowe — a character who could move through uncertainty with purpose.
That thread runs through this conversation.
In this episode, I sit down with Vince Charlo, a communications professional and educator who has watched his industry change rapidly. Immigration policy shifts impacted enrollment in Ontario colleges. Academic hours dried up. Digital media reshaped expectations. He retrained. He completed a master’s degree. He adapted.
And still, he feels behind.
Alongside guest coach Brian Epstein, we explore what happens when the structure that once defined you disappears. This isn’t just about job applications. It’s about identity, relevance, and momentum.
Guest: Vince Ciarlo
Guest: Brian Epstein
In Part 4 of the Your Path in Life series, John continues his coaching conversations with Luca — and runs head-first into something unexpected.
This episode isn’t about a breakthrough moment or a tidy realization. It’s about what happens when the framework doesn’t land the way you thought it would, and when the coach’s expectations start getting in the way.
Using a personal “needs” exercise, Luca identifies four core drivers:
- Make it happen
- Consistency
- Honesty
- Clarity
But instead of pointing outward toward an ideal work environment or future role, Luca turns the exercise inward — focusing almost entirely on personal accountability and standards he already holds himself to. That mismatch creates tension, hesitation, and discomfort — especially for John.
Guest: Luca Volentir
In Part Three of Your Path in Life, John continues his ongoing coaching conversation with UK-based podcaster Luca Volentir, turning the focus toward discomfort, intention, and where real value actually comes from—in work, creativity, and conversation.
The episode opens with a reflective side note on Yuri Gagarin, the first human in space, and the quiet tragedy of what happens when someone is celebrated, preserved, and prevented from evolving. From there, the conversation becomes deeply personal and practical: how expectations shape outcomes, why comfort can quietly stall growth, and how unspoken needs distort collaboration.
Together, John and Luca unpack what it means to move from interviewing to real conversation, and why the most meaningful insights rarely come from polished résumés or surface-level success stories—but from moments of friction, uncertainty, and self-challenge.
Guest: Luca Volentir
In this second part of the Your Path in Life series, we pick up the conversation with UK-based software developer and podcaster Luca Volentir, host of Path in Life.
We start with a detour into the alien abduction story behind Fire in the Sky — what happens when people invent a more comfortable reality instead of facing failure, fear, or unmet needs. From there, we dig into Luca’s own story: his podcast, his personal brand, and the tension between structure, success, and genuine emotional connection.
This episode is less about “how to podcast” and more about authenticity, self-image, and the stories we tell ourselves when our needs aren’t being met.
“How do you become the person who’s actually right for the content you’re trying to make?”
Guest: Luca Volentir
In this episode, John opens with a reflection on Voyager and Carl Sagan ’s Golden Record: a human message cast into the silent dark, launched with hope that someone, somewhere, might hear it. It’s a metaphor for how we all operate — in work, relationships, creativity, and connection. Whether it’s a job application, a first date, or a podcast, we’re all sending out signals, hoping someone out there understands who we are.
From there, John introduces a new collaboration with Luca Volentir, host of the Path in Life podcast. Both are creators trying to build something bigger than themselves, trying to figure out where their work is taking them. What starts as a simple idea becomes a multi-episode series of coaching, introspection, and shared ambition.
Guest: Luca Volentir
What happens when the story you’ve been telling yourself about your career no longer fits?
In this episode, John speaks with Laura Barbante, a marketing professional in Australia whose career path took her from government work to unemployment—and back again with a renewed sense of purpose. Together, they explore what it means to rebuild a professional identity, create authentic personal-brand content, and navigate an industry being transformed by AI.
John opens with a reflection on Taylor Swift—how she turned imperfection into identity and made vulnerability her brand. Later, he shares a story about a client struggling to see the link between the job she wants and the one she feels she has to take, and why the only way to build a brand is to simply start.
Because sometimes, suffering is okay—so long as you’re the one steering the ship.
Guest: Laura Barbante
What if confidence isn’t something you earn through titles, promotions, or endless hard work? What if the real shift comes from stepping into the right environment — the soil where you can actually grow?
In this episode, John explores the idea of place and purpose — from Josephine Baker finding her stage in Paris, to Jimi Hendrix breaking through in London, to Jackie Robinson building his strength in Montreal before entering the major leagues. Sometimes, confidence comes not from “toughening up” but from changing where, and how, we plant ourselves.
John is joined by Elaine Yuen, Intuitive Confidence Coach and creator of the Thrive Confidence Self-Mastery program. Elaine shares her philosophy of intuitive confidence and how breaking free of inherited patterns allows us to stop chasing validation and start thriving on our own terms
Guest: Elaine Yuen
Remember the Freedom 55 dream? Retire early, live free, enjoy the good life. In Thailand, Kasikornbank has reimagined that dream — except now the cut-off is 45, and it’s not about freedom, it’s about AI and spreadsheets. What looks like early retirement is really a story about cost-cutting, technology, and assumptions about age and value.
The Rest of Season One
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