In this deeply insightful and refreshingly honest conversation, I sit down with retirement coach and former financial services executive Toni Petrillo, founder of Retire with Intention. We explore the emotional complexities and personal transformations that often define life after full-time work, diving into the hidden challenges retirees face, particularly around identity, relationships, and what Toni calls the “messy middle.” From evolving partnership dynamics to redefining self-worth and navigating the in-between, this episode offers both practical wisdom and warm reassurance for anyone feeling unsettled in retirement.

What You’ll Learn

• Why a solid financial plan isn’t enough, and what you need instead

• The concept of “retiring with intention” and how to do it well

• How relationship dynamics shift after work ends (and how to prepare)

• The danger of rushing through retirement's “messy middle”

• Tools and exercises to rediscover identity, purpose, and self

• Why curiosity and honest self-reflection are underrated retirement superpowers

• The real reason so many retirees feel lost, even when everything looks great on paper

Key Topics

• Toni’s journey from financial executive to retirement coach

• Letting go of your business card and your professional identity

• The new relationship rules for life post-career

• Setting boundaries with adult children and grandchildren

• Rebuilding your relationship with yourself in retirement

• Understanding and embracing the “messy middle” of post-work life

• Designing a retirement based on your individual AND shared vision

• The power of pausing, experimenting, and reflecting

• The underestimated emotional labour of retiring

• Why permission, especially to feel, pause, and evolve, is everything

Resources & Mentions

• Retire with Intention — Toni Petrillo’s coaching practice

• Harvard Online Course: Managing Happiness (mentioned by Toni)

• Statistics on Grey Divorce in the UK 

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