What type of stubborn are you?

About the Video:
This video explores how persistence can turn into stubbornness — and how to tell the difference before it costs you what matters most. Through personal stories and hard-earned lessons, it reveals a simple framework for testing ideas, relationships, and change without losing yourself along the way.

Transcription:
There's a fine line between persistence and stupidity, and I've spent most of my life on both sides of that line without knowing which side I was on. I'm stubborn. Always have been now. Stubbornness built successful businesses. It got me through cancer treatment. It's kept me going when things got hard, but that same stubbornness, it also destroyed what mattered most.

Let me tell you about my biggest regret. I thought there was only one way to parent — be the strict parent. After all, I had rules at work that could never be broken. Why not at home? I remember one moment over 30 years ago, I was correcting my daughter about something. She told me to stop yelling. Instead of listening and stopping from her point of view, I doubled down. I showed her what I thought real yelling was — I screamed at the top of my voice. You know, I'm six five. My voice is big, my presence is intimidating. I terrorized my daughter that day, and 30 years later, she's still frightened of me and my temper. That's the cost of being stubborn in the wrong way — damaged relationships, broken trust, years of fear where there should have been safety.

So how do you tell the difference between good stubborn and bad stubborn? I finally learned a simple mantra: fail fast, fail cheap. Here's what it means. Most of us approach new things by going all in immediately. We invest heavily before we know if something even has legs. Then we're so committed we can't walk away because we've already invested too much.

Fail fast, fail cheap flips this. You test small, you invest just enough to learn whether something works. Let me give you a real example. Last year I tried skiing again after three years away. First day — complete disaster. I literally couldn't turn my skis. Old me would've kept trying the same approach, stubbornly insisting I just needed to work harder.

Instead, I asked Vermont Adaptive for help. What we discovered — I hadn't forgotten how to ski. I just didn't have the leg strength anymore. That was valuable information that cost me almost nothing to learn. Then I started a small experiment, building leg strength with my indoor bike and kettlebell swings. After getting myself into shape, I did try skiing again with stronger legs and more forgiving skis. 

It's a small test that will either work or not. Unfortunately, this one didn't work. Skiing is now in my rearview mirror — but it didn't cost me much time to figure this out. Now here's something: the same thing I did with my health. My foot ulcers have been a problem for three years. My podiatrist and I keep trying small experiments — different treatments, different shoes. Most have failed, but each failure teaches us something. 

Surgery might be in my future, but only after we've exhausted the smaller options first. Here's the key: get something to about 60% good enough to test. Then see if it has traction. Don't wait to be perfect. You know, that's how I built A Long, Strange Trip. I started with vulnerable posts on CaringBridge and one post on Substack. 

Then I tested the six topic areas. Each small experiment showed promise, so I kept building. But here's what I want you to know: I don't have all the answers. Fail fast, fail cheap works for me, but it can feel pretty harsh sometimes. There might be gentler ways to handle persistence I haven't discovered yet. 

That's why I'm doing this as a conversation, not a lecture. I wanna learn from you — how do you handle persistence in a gentler way? What have you learned about good stubborn versus bad stubborn? Let's figure this out together, 'cause I'm not the expert with all the answers. I'm just a fellow traveler who's learned some things the hard way, and I'm hoping we can learn from each other.

 So thanks a lot, and I hope to see you back here soon.