Brian’s Story

Brian Di Bartolomeo tells his life pivot story from start to finish. On the outside it looked like success: an EVP title, a team of 120, a real-estate portfolio, an early retirement plan already in motion. Underneath, he was giving away a little more of himself every year and calling it fine.

Then it all arrived at once. The company sold to private equity. His mother died. A month later, his marriage ended. On one work call the disrespect crossed a line, and he hung up and said out loud, “I’m done.” He skipped a party weekend in London for a retreat in Big Sur, and spent the next eighteen months between here and there: knowing something had to change, not knowing what. He came out the other side with one word: less.

In this episode

• The house fire that cleaned the slate when he was young, and how the wanting crept back
• Why “gripping” is the feeling to watch for, and the signs he now sees a decade before the break
• The question from his coach that took months to answer (who am I?), and the Thanksgiving moment of clarity about his marriage
• Letting go of perceived certainty and what other people will think
• Learning to say no, non-negotiables, and why what you’re pivoting from becomes your boundary
• Brian’s advice for anyone on the edge of a pivot: listen to yourself, be vulnerable, let go

Chapters

• 00:00 Who is Brian today
• 03:11 The word: less
• 04:41 Life before the pivot
• 07:24 Gripping
• 08:56 The house fire
• 13:45 When everything arrived at once
• 18:50 The call, and choosing a retreat over London
• 27:13 Eighteen months between here and there
• 32:43 Retreats, contemplation, and asking for what you need
• 34:09 Who am I?
• 37:24 The Thanksgiving moment
• 40:40 “I’m going to be okay”
• 42:52 Perceived certainty and what people will think
• 44:40 Saying no, and the harder work of rebuilding
• 47:47 How Brian has changed
• 53:04 What keeps him on the path
• 54:26 What you pivot from becomes your boundary
• 55:12 Non-negotiables
• 58:54 Success vs. happiness
• 1:01:02 Advice for someone on the edge of a pivot