Getting older is strange.

One day you’re the younger guy looking at older men thinking, I’m never going to be like that.

Then somewhere along the way, dinner at 5:30 sounds pretty good, restaurants are too loud, comfortable shoes make perfect sense, and being home before nine feels like a successful night.

In When Did We Become These Guys?, Brian takes a lighter look at the little signs that tell us we may have officially become “those guys” — and why that might not be such a bad thing after all.

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Failure has a way of getting personal fast.

One bad outcome can turn into self-doubt, replaying the mistake, blaming yourself, or carrying more than actually belongs to you.

In this conversation, Brian looks at what failure can teach us once there’s enough distance to see it more clearly — how to own your part without turning a mistake into your identity, how some lessons take years to show up, and what resilience actually looks like in real life. 

You don’t have to be grateful for every setback.

But you can decide it wasn’t for nothing.

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When you were younger, success probably looked pretty simple: get the job, make the money, move up, accomplish something — then go accomplish something else.

But somewhere along the way, the definition can start to change.

In this conversation, Brian looks at success through a different lens: what you’ve accomplished, the kind of person you’ve become, and the impact you’ve had on the people around you. 

Because titles change. Jobs end. Somebody else eventually gets your office.

What lasts is how you treated people, whether you kept your word, whether you showed up, and whether the people you love knew they mattered. 

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Sometimes being a better partner isn’t about having the answer. It’s about knowing when to listen.

In this conversation, Brian talks about the little things that make a relationship work—the things we often learn over time, usually after getting some of them wrong.

From listening instead of fixing to paying attention to the small things that matter, this is about becoming a better partner without pretending you have it all figured out.

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Some friendships don’t need constant contact. Months can go by, life gets busy, and somehow you pick up right where you left off.

In this conversation, Brian talks about the friendships that last — the guys you can call at 3AM, the friends who show up when it matters, and why those relationships become even more important as we get older.

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It started with a simple thought: somewhere along the way, a lot of us stopped having the kinds of conversations that really matter.

In the first conversation, Brian shares what led him to start Men of an Age and why he wanted to create a place for real stories, honest reflection, good conversation—and maybe a little whiskey.

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New conversations every Thursday.

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