The toothpaste squeezer.

It’s what I remember most about meeting “Papa Koaloha” in Hawaii five years ago.

Papa KoAloha

Papa KoAloha in his ukulele workshop in Hawaii. (image from

At the time he was the head of a family business that was building – and still does – some of the most sought after ukuleles in the world. The company celebrated it’s 15th anniversary this year.

But before he had found success in this unlikely business he’d followed many dreams: Some to success, some not. The failures didn’t bother him.

One of the things he shared with Ish and I as we visited with him was that he had once created a tiny device that could squeeze the last bits of toothpaste out of the tube. He reached into a drawer and gave one to each of us that day and I remember the smiles we shared when later, in our hotel room, we successfully put it to the test. I also remember the smile on Papa’s face as he told us about developing the idea.

The toothpaste squeezer had not made him a millionaire, but it still made him happy.

When I’m traveling, I’m always looking for other Papa Koalohas.

I met one half of a couple in Anguilla a few years ago that fit the bill too.  Bob and Melinda Blanchard

Bob Blanchard

Bob Blanchard and his wife Mel followed their dreams to Anguilla

left their home in Vermont because they wanted to live on an island in the Caribbean. Eventually they started a restaurant on the beach, befriended locals and made a new home for themselves. But before they could reap the rewards they had to  risk failure.

The closest I’ve come in my life to taking that sort of risk was when I started freelancing full time in 2007. The decision to freelance full-time instead of diving back into a legal career was scary but not nearly as scary as spending another 30 years doing something I didn’t want to do.

I still remember the fear involved in leaping without a net. It’s what I’ve been feeling lately as we make list after list in preparation for our year-long trip around the world. Traveling with my family for a full year will be the biggest risk we’ve taken in a long time.

Stories like those of Papa Koaloha and the Blanchards serve as reminders that while there is always a risk of falling, if you don’t jump you can’t fly.