Reboot: Leadership and the Art of Growing Up

About

Background summary — AI-generated; not source-grounded.

Reboot (2019) is the first book by Jerry Colonna, the venture-capitalist-turned-executive-coach who co-founded the coaching firm Reboot. Its argument is that better leadership begins with better self-knowledge: the patterns that sabotage founders and executives are usually “unsorted baggage” — unconscious habits carried from childhood — and the work of leadership is therefore the work of “growing up.” The book interleaves Colonna’s own story (a chaotic, insecure childhood; outward VC success shadowed by a depression so severe he became suicidal in his late 30s) with the coaching method he calls radical self-inquiry — asking the destabilising questions about one’s motives, history, and complicity that we are socialised to avoid. It draws openly on Buddhist framing (attachment and self-delusion as sources of suffering) and closes each chapter with question sets the reader can use. Colonna’s second book, Reunion: Leadership and the Longing to Belong (2023), extends the project toward belonging and ancestry.

In the wiki

• Jerry Colonna develops the book’s frameworks throughout Jerry Colonna on Radical Self-Inquiry, the Leadership Equation, and Why Teams Fail (Lenny’s Podcast, ~2025). He traces the signature question — “How have I been complicit in creating the conditions I say I don’t want?” — and the getaway-car gloss on complicity (accomplice, not perpetrator) to the book. See Radical Self-Inquiry.
• The Leadership Equation (practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resilience) is the book’s organising model, improvised at Naropa University.
• Two images from Reboot recur in the episode: the “pursuit of lemon drops” (his immigrant grandfather’s endless supply of lemon drops as a childhood emblem of safety and wealth — by his 30s he “had lemon drops but didn’t feel safe”), and the toppled oak tree (“here lies a good man”) that frames his meditation on legacy and elderhood.
• The book’s subtitle — the art of growing up — supplies Colonna’s claim that self-inquiry is a practice, “not a scientific moment where one day you wake up and you’re done.”