541: Skills, Struggle, and Responsibility. With Jimmy May.

May 20, 2026

AI Summary

5 min read

The conversation with Jimmy May centers on operating principles for leadership, family responsibility, and structured support during major transitions. May draws from his SEAL career and post-retirement work to describe repeatable approaches for building capability in others while managing risk and resource constraints.

Teaching ownership through daily responsibilities

May applies consistent mechanisms when raising his youngest son. He assigns maintenance tasks with pay and titles, such as executive maintenance manager, to create clear accountability for results. When the boy wants later bedtimes on non-school nights, May asks him to propose the rule and timeline, then enforces it without repeated reminders. This reduces psychological reactance and increases compliance. Similar logic appears in rebuilding projects: May withholds a new bike so the child must restore an older one, creating investment through effort. The same pattern extends to work teams, where May prefers letting members build plans themselves so they value and defend the outcome.

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What you'll learn

1 (01:00) **Jimmy May background and military career** - Overview of his path from enlisted nuclear technician to SEAL platoon commander, troop commander, and BUD/S deputy.
2 (03:00) **Family life and second chance at parenting** - Discussion of prioritizing time with kids after heavy deployment tempo in the teams.
3 (08:30) **LinkedIn "Dad Drops" and practical parenting principles** - Series of posts sharing real-world lessons from raising his youngest son.
4 (09:19) **Build it yourself and do the maintenance yourself** - Teaching value through hands-on projects like rebuilding bikes and gear upkeep.
5 (12:13) **Respect for elders balanced with questioning authority** - Instilling manners without blind obedience.
6 (14:58) **Let them set their own rules** - Giving the child input on bedtime and other boundaries to reduce resistance.
7 (22:58) **Have excess capability before you need it** - Pre-positioning tools like snow chains and relationships ahead of crises.

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Show Notes

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Jimmy May returns to discuss life after the military, helping veterans transition, building stronger families, and teaching the next generation resilience and responsibility.

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