#29 - What Got You Here Won't Get You There

We explore why retirement is a true pivot point: identity shifts, new risks, and the move from one paycheck to many income streams. We share practical ways to plan with uncertainty, from guardrails to healthcare decisions, and how to retire to something with purpose.

• identity, structure and purpose beyond your job
• switching from saving to spending with multiple income sources
• taxes moving from reactive to proactive planning
• underspending bias and how to set guardrails
• sequence of returns risk and withdrawal design
• healthcare and long-term care trade-offs
• cognitive decline, decision-makers and family roles
• using the house: downsizing, reverse mortgage options
• flexibility, year-to-year reviews and practical next steps