SHOW / EPISODE

24 Years Too Long

Season 3 | Episode 44
9m | Jun 9, 2026

We often treat time as if it automatically creates value. The longer a friendship lasts, the more pressure we feel to preserve it, even when it's become unhealthy.

In this episode, I reflect on the end of a 24-year friendship and the realization that history alone is not a good reason to remain invested in someone. What began as loyalty gradually became enabling. What looked like patience became a habit of overlooking reality.

The breaking point wasn't dramatic. It was a routine conversation that forced me to recognize a truth I'd been avoiding for years: the relationship existed largely because I kept making excuses for it.

I discuss the sunk cost fallacy in relationships, the challenge of navigating mutual friends after a separation, and why walking away from a long-term unhealthy dynamic can feel less like a loss and more like relief.

Having history with someone may be meaningful, but history is not a contract. Sometimes the healthiest decision is to stop investing in a relationship that no longer serves either person.

This week, consider where you're investing your time and ask yourself a simple question:

Is that investment actually paying off?

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Call Me Tony
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