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The Checkpoint Podcast: Questions
The Checkpoint Podcast: Questions episodes
- Episode 0 - The Beginning
Episode 0 – The Beginning
Welcome to the pilot episode of The Checkpoint.
In this first episode, I share why I started this podcast, the journey that's led me here, and the questions I've been wrestling with as I approach the next stage of life. From running an IT business for nearly two decades to searching for more meaningful work, this is the story behind The Checkpoint and the community I'm hoping to build.
If you've ever found yourself asking, "What's next?"—whether it's your career, purpose, relationships or life in general—this podcast is for you.
43 min
About The Checkpoint Podcast: Questions
From the publisher's feed
Somewhere around your late 40s or 50s, the questions change.
Not "what's next on the to-do list?" but "what's next, period?"
Who am I now that the kids need me less? What happens…
when work stops being the whole story? Is this actually it — or is there another level to play?
The Checkpoint Podcast: Questions is where Dex Eugenio sits with the questions that show up in midlife — career changes, identity, relationships, health, money, purpose — the stuff nobody really prepares you for. Some episodes are Dex thinking out loud and some are real conversations with people mid-reinvention. But all of them start with one question.
This isn't about having it all figured out. It's about admitting you don't, and staying curious about what's next anyway.
If you've built a genuinely good life and still catch yourself thinking "is this it?" Welcome, you're not the only one still figuring it out.
New episodes regularly. Every question is a checkpoint. Every checkpoint is a chance to keep playing.