Having It All and Still Asking: Is This It? with Josh Fineman

In this episode, we're joined by Josh Fineman . Josh had the career, the young family, the success but behind it all was exhaustion, self-doubt, and a relentless voice asking, “Is this it?”

In this honest and revealing conversation, Josh shares how growing up as the ‘good boy’ in a high-achieving North London household shaped his adult identity. He talks about the unspoken grief that filled the family home, the hidden cost of seeking approval, and the endless comparisons that wore him down.

What followed were years of chasing status, zigzagging through jobs, and numbing out until a crisis forced a reckoning. Therapy cracked the door open, but it was men’s work - raw, in-person, shoulder-to-shoulder - that truly began to transform his life.

Josh went on to create Mensch , a community where men come together to rediscover connection, purpose, and truth - with boots on the ground and fires lit -locally around the country.

We talk about masculinity, parenting, legacy, and why so many men who " have it all " still feel empty. Josh speaks candidly about fear of failure, starting something meaningful, and the power of local brotherhood.

If you’ve ever quietly wondered, “What happened to me?” or “Is this all there is?” then this episode is for you.