Dreaming with Discipline - 3 of 7 - Cast Off

by EMILY ORTON

This is week 3 of 7 in a series counting down to the launch of our new book, Seven at Sea.

First family overnight sailing experience, Florida Keys

First family overnight sailing experience, Florida Keys

First Family Overnight Sail

Our family had the big idea to live on a sailboat for a year before the oldest of our five kids left for college. We took several sailing classes and joined a club where we could sail a few times each month on a twenty-foot boat with no motor. None of our kids had ever spent a single night on a boat. It would be prudent to test that out if we wanted to live aboard as a family.

One long winter break, we drove from New York City to a boat rental in the Florida Keys. Erik was at the helm. I and the two oldest girls each held fenders outside the hull to make sure we didn’t bump any other boats as we pulled away from the dock. Erik eased us forward and then…chunk. We stopped. The girls and I could easily see that we hadn’t hit anything so Erik proceeded to troubleshoot. He quickly found the problem—we were still tied to the dock.

Are You Tied to the Dock?

There are a lot of ways to be metaphorically “tied to the dock.” Maybe it’s a hurried oversight like ours in Florida. Or maybe it’s a fear.

There is a good chance living aboard a sailboat is not your dream. Whatever your aspiration, we want to encourage you to cast off. Here are three techniques that have been helpful to us.

Life is Not a Dress Rehearsal

“Welcome to your life.” I say this to our kids almost every day as we gather for school. We are preparing for the future, but right now is also real life. It’s not just future moments that matter. Right now matters. It’s not eighteen years at home and four years of college before “life” begins. What you are doing right now matters now and it will also affect later. It is the main event at the same time as it is preparation for future events.

This mindset begs the question, What are you waiting for?

Erik has been rock climbing since he was fourteen. He’s been dreaming about climbing El Cap in Yosemite since he was fourteen. If you’ve seen the movie Free Solo, that’s the slab of granite I’m talking about.

One day, our daughter SJ asked where this legendary Yosemite was located on the planet. Erik showed her a map pointing it out in eastern central California.

“You mean that place I’ve been hearing about my whole life is in the United States of America?”

When she put it that way, Erik felt a little silly for not having taken care of this unfinished business sooner. It pushed him past his fear, beyond reading about preparing, to actually doing it. Within the next 2 years, he trained, lost 40 lbs. and climbed El Cap with ropes and protective gear (unlike like Free Solo).

Base camp support team, El Cap Meadow in Yosemite National Park

Base camp support team, El Cap Meadow in Yosemite National Park

Throw Your Hat Over the Fence

Erik learned this phrase from his mother and taught it to me. How do you get over the fence? You throw your hat over it. Then you have to figure out a way over the fence because you have to get your hat back. It’s committing to something before you’re ready, believing that your public commitment will inspire you to be ready when the time comes.

Chatting with a friend over dinner one evening, he dared me to write an article for the New York Times. I accepted. I learned about the publication’s parameters and acceptance process. I listened to a podcast interviewing one of their editors and I wrote my article. I rewrote, rewrote, rewrote and finally submitted letting my friend know I’d put it out there. The NYT didn’t publish it. But the national magazine Your Teen and local magazine NY Metro Parent did. It’s in the print version for our friends around town.

Throwing your hat over the fence doesn’t always lead to the consequence of your choosing. It does generally draw you closer to your goal than staring at the fence.

With help from our friends at  Smith Publicity

With help from our friends at Smith Publicity

Better Done Than Perfect

Back to the Florida sailing story--despite our false start, we cast off that dock. And we lived on a sailboat for most of 2014. That year, we met some savvy sailors in St. Martin on s/v Silverheels III. They told us, “A lot of people never get off the dock.” Years after buying a boat, some people were still preparing to sail. They were always adding boat bling or thinking of one more thing that would make it ‘perfect’ when they finally set sail. It's important to prepare, but maybe they liked dreaming more than fulfilling the dream.

We were clumsy rookies who didn’t even know the right oil to fuel mixture for a two-stroke outboard motor because we’d never used one before. We got off the dock. Now, we do know. In all our failings, we were encouraged by the fact that we were actually out there learning from experience instead of waiting until we knew everything to get started.

St Martin 2014

St Martin 2014

Waiting for perfection can be paralyzing. Doing is liberating. It’s an iterative journey. You will grow as you go. Cast off.

What are you waiting for?


Week 1 – Choose Your Own Island

Week 2 – Chart Your Course

Let’s Talk

We’ll talk about Navigating Out of the Harbor next Saturday.  In the meantime, please join us on Tuesday, February 5th at 1pm (ET) for a FB Live discussion about this post.  If you can’t make it at that time, you can watch the recorded discussion on the Fezywig Facebook page.  

Also, we’re excited to announce that the ebook/Kindle version of Seven at Sea is now available to order.  So for those of you who live on the go or who just hate paper, here’s your big chance, Seven at Sea, the digital book.

Get Digital

Prices may vary

Prices may vary