progress – Surprised By Joy

“You never fail until you stop trying.” – Albert Einstein

I suspect that my podcast guests rarely listen back to the episodes that they record with me. After all, they lived it once, why listen to it again? (Anyone that has podcasted with me or Vicki, feel free to jump in and contradict me on this!)

And, speaking for myself, there’s a smidge of fear when watching myself that I’ll discover something terribly wrong that I said or spinach in my teeth that I can’t undo.

But there’s a huge upside in listening back to what we’ve recorded in that it helps to see ourselves from another angle.

I recently was a guest on the What Do You Know To Be True? podcast with the incredible host, Roger Kastner. What Do You Know To Be True? features conversations at the intersection of leadership, neuroscience, belonging, and personal growth—inviting guests to explore the truths that shape how they lead and live.

Roger is a master at getting his guests to reveal their superpower. Watching back the episode I did with him, I was blown away by how skillful Roger is at digging into the heart of what I know to be true. [It also reminds me that I like to talk with my hands and tell a lot of climbing stories!]

In my case, my superpower is trying. In this conversation, Roger and I talk about:

How my electrical engineering background helped me develop my superpower
Why trying is different than persistence
How mountain climbing helped shape and shift my ability to try
What my system is for creating order when trying
How trying helps keep us from being stuck
How documenting what we’ve tried helps us to pass on the learning to others

Here’s the podcast episode on What Do You Know to Be True?

Other ways to watch this episode:

Apple podcasts and Spotify: How To Overcome the Fear of Failure & Feeling Stuck | Wynne Leon
YouTube: How to Overcome the Fear of Failure & Feeling Stuck | Wynne Leon on

Links for this episode:

What Do You Know To Be True? website

What Do You Know to Be True? on YouTube

Roger Kastner on LinkedIn

“You can never really live anyone else’s life, not even your child’s. The influence you exert is through your own life and what you’ve become yourself.” – Eleanor Roosevelt

Back when I was interviewing my dad about his faith, I came across a passage in psychiatrist and author Dr. Scott Peck’s book Further Along the Road Less Traveled that described four stages of faith. He described an experience of what can happen generationally when kids grow up in stable, religious homes:

What happens to a child raised in such a stable, loving home and treated with dignity and importance? That child will absorb his parents’ religious principles – be they Christian, Buddhist, Muslim, or Jewish – like mother’s milk. By the time the child reaches adolescence, these principles will have become virtually engraved on his heart or ”internalized,” to use the psychiatric term. But once this happens, they will no longer need to depend upon an institution for their governance. It is at this time, which in healthy human development is usually at adolescence, that they start saying, “Who needs these silly myths and superstitions and this fuddy-duddy old institution?” They will then begin – often to their parents’ utterly unnecessary horror and chagrin – to fall away from the church, having become doubters or agnostics or atheists. At this point they have begun to convert to Stage Three, which I call “skeptic/individual.”
Further Along the Road Less Traveled by Scott Peck

I’ve heard this progression described in other contexts as well. From social psychologist Jonathan Haidt who described kids who grow up as beneficiaries of capitalist wealth demanding more socially and environmentally responsible policies as they come of age.

And from therapist Jacob Ham who talks about first generation survivors of war being primarily focused on physical and financial security with little capacity to talk about their emotions. It isn’t until the next generation comes along that they start to unpack emotional intelligence.

How life changes between generations is the topic of my latest post on Wise & Shine: Enough is Enough.

Tag: progress

Generationally Speaking