Doing Life Differently

53 | How We’re Redefining Success for Our Family


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What does success really mean? Is it about income, status, or something deeper?

In this episode, Michael and I sit down for a candid conversation about how our childhood shaped our views on success and how we’re intentionally redefining it for our own children.

We reflect on growing up in a small-town community, the hidden lessons we learned about money and work, and the challenges of raising kids in a world that often equates success with wealth and achievement.

We share three key ways we’re guiding our children in this area:

1. Focusing on Failure First – Helping our kids develop resilience and a healthy relationship with failure before they even define success.

2. Defining Success Holistically – Teaching them that success isn’t just about money or status but about relationships, impact, and purpose.

3. Highlighting Impact Over Income – Emphasizing service, generosity, and solving problems for others rather than chasing financial gain.

Whether you’re a parent or simply reflecting on your own definition of success, I hope this episode challenges you to think differently about what really matters!


Reflection Questions:

  • What was your definition of success growing up? How did your parents influence that?
  • Have you ever felt pressure to measure success by income or status? How has that shaped your decisions?
  • If you’re a parent, what messages about success do you think your children are absorbing from you?
  • How do you personally handle failure? Have you created space for yourself (or your kids) to fail without shame?


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Doing Life DifferentlyBy Katelyn James

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