Making the Leap—Our Trip Begins

We leave on our trip tomorrow. It’s complicated leaving your “real” life for +4 months. Lots of things are getting checked off the list and added to the packing pile. Home-sitter? Check. Dogs? Check. Favorite underwear? Packed.

Preparation Panic


Sarah and I have been in a state of perpetual motion for the past several days—heads swimming. I actually caught Sarah yesterday cleaning the inside of our fireplaces. She told me that she can’t sit down and quiet her mind. It’s time to go! Everything will work out, according to Tegan Phillips,

I wish I had known how easy adventuring can be so I could have avoided the ‘preparation panic’ people often face before trips of any sort, where you somehow convince yourself that if you don’t have this particular tool or type of tent or type of saddle or type of clothing even then your adventure will be a disaster and you will probably die. As I discovered, whatever you are going to do, the chances are somebody has done it with much less than you and somehow survived.

What we are leaving behind

One of the really cool things about leaving is the realization of how many great friends and special things we have at home. We’ve had a few going away parties and personal conversations with dear friends and family. It makes me realize how much I take for granted here in Wisconsin. It’s human nature to not realize what you have until it’s not there. A great lesson from a trip that hasn’t even started.

Wilson!  A Parting Gift from Friends


Inspiration from the Experts

This is Webb Chiles.

webb chiles 49


He is 72 years old. He has lost sight in one eye. Oh, and by the way, he is also sailing around the world. By himself. On a lightweight boat that is only 24 feet long and 7.5 feet wide. If he makes it all the way around on his boat Gannet, it will be his 6th single-handed circumnavigation of the globe via sailboat. This is hard for me to fathom. Guts, determination, grit, discipline, courage. I could go on, but it’s hard to capture what this man is doing and has already done on the oceans.

Whatever you are interested in, there are experts out there doing it. This is one of the lessons I’ve learned being an entrepreneur. In each company I’ve helped to start, we went out very early and “engaged the thought leaders” in our market space. Today’s connected world makes this pretty easy to do.   And it reaps huge benefits. For a start-up, it helps to put you on the map.

I’ve tried to do the same thing for this trip, and I was thrilled to discover that Webb’s home base is right down the road in Chicago. And he was home over the holidays, leaving his boat in New Zealand. I took the opportunity to drive down and have lunch with him. It was pretty damn cool to sit down with someone who has spent more time alone on a sailboat on the ocean than probably anyone else alive.

Thanks Webb, for the inspiration. If and when things get dicey on our sailboat, I’m going to remind myself to calm down by thinking of Webb. It’s pretty hard to get worried about my very simple trip after considering what this man has done.

This is Scott and Brittany Meyers and Family


Scott and Brittany left their “real” lives a few years back, sailing off from Chicago as a newly married couple. In the past few years, they’ve sailed together from Chicago all the way down to Trinidad & Tobago and to lots of parts in between. They also had their first child and quickly added twin girls to the mix. When the twins were born, the Meyers moved in with family in Chicago. But they are just about to move back onto their sailboat in the British Virgins, with all three kids in tow.

Sarah and I had the good fortune of taking Scott and Brittany out for dinner (and drinks!) very early in our planning for our trip. Not only are they super cool and fun people, but they also helped us realize that we can do this trip. We can homeschool our kid on a boat. And we don’t have to be expert sailors. We will figure it out as we go along. As long as we sail conservatively, work hard and respect the ocean we will be just fine (I hope!).

The mass of men lead lives of quiet desperation.


I love finding people like the Scott and Brittany and Webb because they remind me that although taking risks in life is hard and scary, it is also well worth it. They’ve done different things obviously, but they are living proof that it’s possible to carve out the life that you want to live.


**Note: If you want to follow them, Brittany keeps a fantastic blog at and Webb keeps a “journal” at his wonderful site, that also includes an impressive collection of his books, photos, and other writing.

9 thoughts on “Making the Leap—Our Trip Begins

  1. Love you guys!! You are an awesome team and will thrive on this journey. Can’t wait to toast your success on the ‘other side’. Fair winds – the excitement I feel for you three is INSANE!!! GAH!!! You are DOING IT!!! WHOO HOO!

  2. Good luck with your travels! My husband and I started out our cruising years in Grenada in 1978. We thought we might travel for 5 years, and it turned into 14! So many adventures, and such a wonderful life, with a world full of memories. Happy days! Jean

  3. I’m not sure why it signed me as Oliver Baardsen – that was the name of the stuffed orangutan we had on board…. Maybe Oliver has taken over my computer. Anyway, we’re Jean and Ed Baardsen, and our boat was Tropic Moon, our home from 1978-1992. Ancient history, now – how the years do fly by! Once more, best of luck!

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