Table of Contents

  1. Stickies
    1. More Sailing
    2. Buy a Boat
    3. Find Dream Job
  2. What does boat life mean to us?
    1. The Pros
    2. The Cons
  3. Time to go to the spreadsheet!
  4. I’m on a boat
Andrew & Denise motoring through Corinth Canal, Oct 2017
Andrew & Denise motoring through Corinth Canal, Oct 2017

In today’s story, we follow-up our whiteboard discussion and describe how we went about deciding to turn our life upside down to go sailing around the world. During a pivotal Sunday morning session in October, 2019, we chose to combine the following post-it notes to begin our discussion…


More sailing
Buy a boat
Paid to do what you love doing

More Sailing

Before we met, Andrew and I both spent a bit of time sailing. When he was living in British Columbia, he owned a catamaran (her name was Periwinkle), which he took out all the time on his own around Boundary Bay.

I had taken a variety of ASA courses, joined a sailing club which got me out on a 36’ Catalina twice a month for a few years, chartered yachts from time to time, raced in the summer Wednesday sunset regattas out of Marina Del Rey, did a moonlight sail in San Francisco (caught in the fog with strong currents was a memorable experience), and crewed a 10-day trip island hopping in the British Virgin Islands.


After we met, we continued to do a little bit of sailing together and even went to Greece on a sailing trip from Corfu to Athens via Corinth Canal. But because life took us in different directions since then, we thought why not see how we can re-incorporate that love of sailing back into our lives.

Buy a Boat

What better way to incorporate sailing than by buying a boat? It seems rather than pay to charter boats for sailing vacations, signing up for offshore expeditions, or join sailing clubs much like the one I had experienced at CSC, we wanted a far more meaningful experience than being weekend sailors. We went through an 8-step process to define our needs. 

Once you begin to let go of the notion of living in a house and consider moving aboard a sailboat, the economics flip. Sailing no longer becomes an incremental expense. Sailing becomes the primary living expense, and rent/mortgages, transportation costs, and other big ticket items go to zero.

Find Dream Job

The other big idea to tackle was how do you go about finding a job and get paid to do what you love doing.


Now I realize in the spectrum of Maslow’s Hierarchy of Needs, this is akin to a level 5… self-actualization needs.

Collectively, it seemed in varying degrees we weren’t struggling with levels 1 through 3; there may still be work to do in level 4; and certainly we wanted to see how we can put the idea of becoming the best person you can be in whatever way you can define it.

So that was it. In some respects, having chosen a few things to focus on suddenly made things actionable.


What does boat life mean to us?

Under a topic of “Boat Living,” we began to map out what that would look like to us. These included: 

  • expanding our sailing certification/knowledge/experience,
  • learning boat maintenance,
  • determining how long we would want to do it,
  • then making a transition by downsizing all our belongings,
  • maybe doing a trial run, 
  • buy a boat,
  • move aboard.

We then assessed the pros and cons.


The Pros

At the top of the list of Pros for a life of sailing around the world:

  • No commute!
  • More Travel!
  • More time together!
  • Reduced possessions!

I’ll underscore this last point, because there is something about the What’s in your backpack speech that resonates with me. Imagine how much lighter it feels to move around having shed all this… this stuff. Now that it’s empty, you can then selectively curate experiences rather than possessions. We explore this topic further in 30-weeks to minimalism.

For me, I start to envision a mash-up of activities I love such as sailing to a remote island with rocky cliffs, dropping anchor, dinghy to shore, and rock climb/deep water solo existing routes or maybe even establishing new routes.

Chris Sharma climbs without ropes a.k.a. deep water solo. Photo by Wallpaper Safari
Chris Sharma climbs without ropes a.k.a. deep water solo. Photo by Wallpaper Safari

How cool is that?

Other activities assumed while sailing would include music, seeing new places, hiking, even snowboarding if we were to sail to high latitude destinations, learning boat systems, doing more handy work, knitting, photography, reading, and of course cooking.

Morning Haze is an aluminium-hulled Bestevaer 55ST built specifically for high latitudes cruising. Photo by Benedict Gross
Morning Haze is an aluminium-hulled Bestevaer 55ST built specifically for high latitudes cruising. Photo by Benedict Gross

Imagine being able to pursue your current passions and to be doing them whenever the f&ck I please. Before my imagination runs amok, there are of course some downsides to this new lifestyle.


The Cons

For us, the cons would include not having a reliable source of income and potentially reduced social life. If I were to pick the first thing to tackle, it would be the money.

Time to go to the spreadsheet!

We began to do some research across bank accounts, 401Ks, etc. and once you add up all the bits and pieces into a spreadsheet… I was gobsmacked.

It’s a funny thing that at the start of my career, I set up all the automatic withdrawals, selected a few broad index growth funds and ka-ching! Just like that, I got the empty backpack feeling. I was now looking at the world through a different lens, one that saw many opportunities for adventure. All of a sudden, our lives in Southern California driving to and from work seemed so little.

A life of sailing the high seas seemed like a very real and very sustainable possibility for the rest of our lives…

I’m on a boat

For the past couple of years, The Lonely Island channel has been featured in our car and each time “I’m on a boat” comes on, I crank it up! 

If you would like to delve deeper into our adventure as it unfolds, please consider joining the Serenade Wind Crew. Our sister site provides more information on what it means to be part of the crew, unlock the pirate’s booty, and receive other exclusive access and benefits.The first 50 members have a gift waiting.