I’ve been working in my little office at the marina—only steps from the boat I’m living on—for a few weeks. So far, the greatest struggle I’ve had is figuring out what to work on.

Being your own boss is unbelievably freeing.

There’s nobody standing over your shoulder watching your every move. There’s nobody telling you what to do, when to work & what to wear. There’s nobody deciding whether you’ll get a 3% raise or no raise at all.

But.

Being your own boss is unbelievably frightening.

There’s nobody standing over your shoulder guiding your every move. There’s nobody telling you what to do, prioritizing projects and telling you what not to waste your time on. There’s nobody prodding you along and encouraging you daily and depositing money in your bank account every two weeks.

It’s only you. Your dwindling savings account is your prod. Starting out, it’s tough knowing what say yes to and what to say no to and what to do next and what not to do next.

But the only thing that really matters is the do-ing. It’s easy to make 100 different lists about what you need to do and what you want to do and when you need to do it and then what you should do after that. It’s easy to become paralyzed worrying about outcomes you can’t predict or control.

But without the do-ing, the lists and the worrying are pointless.

Do something.


Bo is currently living in Orange Beach, Alabama trying to come up with ways to fund a sailing trip around the world. If you’d like to be a part of the adventure, consider sponsoring a mile.