The Plan I Wrote Fifteen Years Ago

The Plan I Wrote Fifteen Years Ago

June 25, 2026 · 12 min · Episode 244

About this episode

Paul Fenner reflects on the inadequacies of long-term financial planning in light of personal family transitions over the past fifteen years.

Work with Paul: Schedule a 30-minute conversation What if the long-term financial plan I built five years ago is now describing a family I no longer have? That is the question I have been sitting with. December 9, 2010, is the day my triplets were born, and the day I founded TAMMA. Fifteen years in, I can tell you neither plan I wrote that day survived. And that was never the goal. In this episode, I share the number of short runs I did not account for in my own life, walk through a family that has been through five major transitions in five years, and unpack why senior professionals can be sophisticated about iterative planning at work and unsophisticated about it at home. The conflict is not capability; it's flexibility that is a maintenance burden, and most plans have nobody carrying it. The action step this week takes fifteen minutes. Name the last three transitions your family went through in the past five years. Then ask, for each one, what financial decisions in your current plan still assume you are the person you were before. That is the work. Connect with Paul If you're a working parent juggling a senior-level career and a growing family, and are tired of coordinating…

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