Up until I turned 40 I was always told the same thing. “Wait your turn. You’re too young. Too inexperienced. Not ready yet.”
So, I decided to stop waiting.
I started a small outdoor sailing program in the San Juan Islands. Just me, a beautiful wooden boat, and a belief that young people needed to discover what they were capable of. Outward Bound heard about it. They came to me. Eventually they bought the whole program and made me the director.
Turns out waiting your turn is overrated.
After leaving Outward Bound I started an online music company, helping international artists get their music heard by a North American audience. I built a catalogue of world music unlike anything else that existed. National Geographic heard about it. They came to me. Offered to buy the business and make me their music guy.
Two acquisitions in my 40’s. Not bad for someone who was told to wait his turn.
But then I turned 50. And suddenly the internet happened. The new heroes of business were 20-somethings running companies filled with people under 30. Anyone my age was a dinosaur and couldn’t possibly understand the digital age.
I started an online marketing agency anyway. Uphill battle doesn’t begin to cover it.
Here’s what I know now that I didn’t know then. The thing they said would disqualify me, my age, my experience, my analog roots, turned out to be the whole point.
Because in a world full of performative, algorithm-chasing content, what people actually trust is someone who has lived something real.
And I have.
My whole career, from Outward Bound youth on a sailboat to expert business owners on camera, has been about one thing: Helping people expand what they think is possible for themselves.
That work never got old. And neither did I.