I look around my house and am surrounded by boxes and boat gear and I think…how did we even get here???

No I am not having an existential crisis…yet. I’m taking a wee trip down memory lane to walk through how we arrived at this fairly unusual place. If you can stick it out to the end of the story I’ll be impressed…it’s long and in hindsight, a bit complicated.

(Of course there were a million other note-worth moments in the last 10 years - for at least half of it feel free to scroll through my Instagram feed. But the focus today is on what, at least right now, I see as some of the steps on the path that led us to moving aboard and sailing away)

March 2009

It all started almost exactly 10 years ago when Greg, baby Liam (15 months at the time) and I joined my parents, Greg’s parents, my brother (Kyle) and sister-in-law (Kristen), my brother-in-law (Andrew) and his new girlfriend at the time (now wife, Heidi) in an AMAZING house in St. Thomas, USVI. We rented the Cliff Haus (yes, fancy for “house on the cliff”…which it was, much to my Dad’s dismay giving his fear of…well…falling off a cliff).

Where was I?

Ok so here we all are in this beautiful house, on this beautiful island, watching my freakin’ beautiful baby take his first steps on the ceramic floor with the sound of the ocean waves in the background and Greg gets an idea…

At first it was just a thought in his head (unlike me every thought he has doesn’t automatically come out of his mouth). Earlier that day he saw a little dive-y bar and suggested we get the parents to watch the squirt and check it out. Kyle was waaaaay to “sleepy” from having a Rum Punch drinking competition with Andrew and he couldn’t join but Kristen came along for a bumpy ride down a random road to a little beach bar called Latitude 18.

Now Latitude 18 felt like the ultimate sailors bar; boats within view of the plastic chairs and folding tables in the sand and Cruzan Rum flowing along with the conch fritters and live music filling the air. We LOVED it. The three of us had some drinks, enjoyed the fritters and basked in the very laid back atmosphere. Well, at least Kristen and I did. Greg was scheming. Side note: as far as I understand, Latitude 18 has closed due to damage from Hurricane Irma…sadness.

April 2009

We arrive home after a lovely vacation and welcome spring by going for a walk in the neighbourhood with Rosie and Farley (our dogs at the time) . On said walk my husband basically turns to me and says “Let’s just sell it all and buy a boat and sail away”. Greg was working in Mississauga for an energy company, cranking out business processes so some rich people could make more money. He didn’t love it but it had some interesting challenges, he was VERY good at it (not shocking) and it was early-ish in his career. Me being super practical and not very romantic said something like this “Hahaha that’s crazy…hard no. However, if you really want to get back* into sailing, let’s consider having our own boat sometime. But not now”. Instead of sailing away, Greg decides to start an MBA.

We continue on with life.

*Context: Greg grew up sailing on his dad’s boat, but that is a story for another blog post.

Early 2010

We go to our first boat show…”just looking” we tell ourselves. We charter our first sailboat and take the “Live Aboard Cruising Standard” course…”for fun” we tell ourselves.

We continue on with life.

Fall 2010

We crack. We want our own boat. Enter Gong Show: the appropriately named J24 that became ours while I was expecting kid #2 (that’s Aden for those of you not keeping track yet). We have a few mishaps learning how to handle her (for example I break my hand while thinking I’m strong enough to prevent us from hitting another boat when Aden was 6-weeks and on board…good times) but overall we have a great time on this responsive little boat while nursing, changing diapers and taking lots of boat-naps!

We continue on with life.

Spring 2011

Greg left that energy company previously mentioned to be a part of a small solar start-up based in Santa Monica. My consulting company was doing very well and we had contracts and babies and staff and stuff.

We continue on with life.

Summer 2012

We try racing Gong Show and really prove that boat is well named. We may or may not have bumped into a competitor once on the course. It’s amazing what a bottle of rum will do to settle an irritated sailor.

We continue on with life.

*Below: Liam and Aden napping on Gong Show…Aden on the icky cabin sole, she would never say on her back!

Spring 2013

We have kid #3 now (that’s Grace, keep up people!) and decide that Gong Show is now too small for a family of 5. So we sell our J24 and see our sights on the future (which was looking bright).

Having sold Gong Show, Greg quickly misses sailing as a stress reliever so he finds a captain looking for some race crew in Oakville and crews on Heartbreaker, a competitive club racing S2 9.1. And has a blast. In fact he has so much fun he really wants me to join him and starts working that angle. Hard.

Around this time, for a fun distraction, we map out what a 3-year plan would look like to pack it in and sail away. How much money would we need? What ages would be best with the kids? How long would we go and where? On a blank piece of paper we sketch out 3 different 3-year scenarios (yes we are thorough planners) and just sort of leave it at that. I share that piece of paper with my dad. And to his credit at the time he did not say we were crazy or irresponsible; he said “That’s good honey, you and Greg can do whatever you guys want to do. You are both smart and capable and I trust you both to make good decisions for your family.” Grade A class act Dad!!

So after that conversation with each other and later with my Dad, that piece of paper is put in a drawer and the intention is put out to the universe I guess…we didn’t dwell on it, but we didn’t forget it either. I can still picture the flow charts…I should find that damn piece of paper for old times sake!

We continue on with life.

Spring 2014

Greg and I obviously have an issue with things staying steady in life and he starts his own solar company with a colleague and some support from my consulting company. Big leap. Loads of stress. Loads of fear. Bit of fun. Things are interesting.

Something also really significant happens in our life. One of my very best friends, a warm, funny, kind and honestly open human being I met at university died of breast cancer at 34 with a young son and a dear husband. She was my first friend who shared my deep love of food and lame TV and taught me how to burp in public and not give a sh*t…I was one of the privileged few with her in her last hours and it left a mark on me that will remain forever. I loved her so much I could digress into a whole other thing here…how does this relate? Honestly losing Robyn made both Greg and I take a very very hard look at our lives and we made a promise to each other to find a way to step out and step away; to savour what was most important to us because truly, life is short, precious and precarious. I think this loss galvanized our resolve to implement that plan we put down somehow.

We continue on with life.

Summer 2014

‘Date night’ becomes ‘race night’ as I join Greg on Heartbreaker and swallow my distaste for learning new things in front of people to do my best and be useful in the pit. Fortunately my competitive nature and sailors mouth worked for me and we were good. Real good. We won every race we entered and had a collection of trophy’s at the end of that year. I really like winning.

We continue on with life.

*Below: Greg and I in our preferred post-race places on Heartbreak en route back to the club after a win

Spring 2015

Greg’s solar company is acquired by a massive renewable energy company and we buy our amazing Beneteau First 36.7, EXODUS. These two things are in the same sentence because they were closely related. We missed sailing our own boat and we wanted to indulge a tiny bit in the success and relief we both felt in the acquisition achievement. She was fast, she was fun, and she had 3 cabins so we could divide up the kids for boat naps during the day and have enough space to comfortably cruise for days on end as a family.

This boat was amazing for us. A joy to sail on Lake Ontario. And honestly it starts to feel like we could really do this for a long period of time. More than just day-sailing or a weekend cruise but could go somewhere…anywhere.

We continue on with life.

*Below: 1) EXODUS leaving Scarborough Bluffs 2) Passing by Toronto and 3) arriving at her new home in Oakville on a day with literally ZERO wind :P

Spring 2016

The massive renewable energy company that bought Greg’s company, whom Greg was working for goes bankrupt. Corporate America and all that jazz. So what now? Well due to the fact that Greg is good at his job, he managed to keep his original company and sell it again to another energy company (I know it seems crazy…it was then…still is). This amazing turn of events enabled us to set out a 2-year plan to actually do the whole “sail away thing” that he brought up back in 2009. We spend the next few years planning, and sailing, as much as we can including a few 2-week cruises down Lake Ontario to the 1000 Islands were we really wanted to just keep going and turn right ;)

We continue on with life.

*Below: 1) Sun rise after our night sail toward Kingston 2) our route upon arrival at our first stop 3) Aden and Greg navigating with the iPad 4) some weather we encountered outside of Coburg 5) beautiful day for the asymmetrical 6) boom tent, hammock, sweet anchorage and life is awesome!

Fall 2018

Still with me? Ok so now Greg is done his 2-year term that came along with the last acquisition and he is…retired? Ya, let’s call it that for now. Odds are there will be other things to do, jobs, projects, opportunities but as of Fall, 2018 he’s on a work-break. We sell EXODUS and welcome Matriarch into our family as the very first official big move to demonstrate to ourselves that we are actually for real, 100% doing it!

We continue on with life.

Present Day

So here we are, house mostly packed up, boat soon to be launched in Deale, MD and kids about to finish the school year for the last time in a long time…

As much as the last 10 years has been a crazy roller coaster ride it’s amazing to tell the tale and again acknowledge how fortunate we’ve been. I am so so so so so grateful for what brought us to this moment. In addition to the lucky dice rolls we’ve gotten (and we’ve gotten quite a few), the very scary moments, the late nights, stressful deal-making, hard work and proving of oneself over and over and over…all of it was worth it…and will continue to be. I don’t see us getting off the roller coaster ride anytime soon ;)

Some say luck is what happens when preparation meets opportunity…well, to me, this story is the epitome of that definition of luck. From when Greg first broached the subject on that dog-walk 10 years ago we started preparing ourselves for something we didn’t know was going to happen…in fact it was more than a long-shot. But then when the opportunity presented itself we were ready to jump and it didn’t even occur to us that we couldn’t do it!

Maybe that was the key? Dreaming of the crazy and then just being able to see it as possibility when the stars align? I mean…why not us? Why not now? I don’t know…I will leave the “how-to” type blog posts to Greg for now. This is just a tale of one family with some wild idea a long time ago and the damn good luck that presented an open door that we are walking through. Hope it doesn’t hit our asses on the way out :P

Much love

Megan