We started talking about leaving Singapore in 2015. We didn't actually leave until May 2019. That's four years of planning.....
The planning that didn't matter
We spent entire weekends researching boats we couldn't yet afford. I built a spreadsheet comparing marina costs across the entire Mediterranean. We read every sailing blog on the internet, watched every YouTube channel, and bought books we never finished.
It felt productive. It wasn't. It was comfortable because it let us talk about the dream without actually risking anything.
What actually moved us
Three things changed everything, and none of them were spreadsheets.
We told people. Not casually, not hypothetically. We told our parents, our friends, our colleagues. "We're leaving Singapore in 2019." Once those words were out, backing down felt harder than pressing forward. Some people thought we were insane. That helped more than the encouragement did, weirdly. It made us want to prove it was possible.
We set a hard deadline. Not "sometime in 2019" but a specific date: June 1st. We booked flights to France for the boat handover before we'd even sold everything. Having non-refundable flights and a boat delivery date made everything else fall into line. Suddenly we were forced to deal with visas, shipping, school withdrawal, and a hundred other things we'd been putting off.
We accepted that we'd figure most of it out on the way. This was the hardest one for me. I'm the planner. I want every detail sorted before I commit. But you can't plan a four-year sailing trip with two kids under four from a desk in Singapore. The conditions change, the kids change, you change. At some point you have to accept that 70% prepared is enough and the other 30% you handle as it comes.
The stuff that actually needed planning
Not everything can be figured out later. A few things really did need to be sorted before we left, and I'm glad we did them properly.
Money was the big one. We needed to know how long we could sustain this without income. Not a rough idea, a real number. (If you want a first version of yours, our free cost of living calculator is quick.) We tracked our spending for six months, projected costs for life on a boat, and built a buffer for emergencies. It wasn't exciting work, but it was the thing that let us sleep at night when our savings were dropping faster than expected.
Health insurance was the second. Singapore's healthcare system is excellent and we took it for granted. Finding international cover that actually worked for a family on a boat, in countries that changed every few weeks, took real effort. We got it wrong the first time and had to switch providers six months in.
Then education. We didn't need a formal school plan yet, but Emily spent time researching homeschooling frameworks and connecting with other worldschooling families online. That network turned out to be one of the most useful things we had in year one.
What I'd tell you now
Pick a date. Tell people. Book something non-refundable. Sort out the money, the health cover, and the kids' situation. Leave the rest.
You will never feel ready. We stepped onto a 42-foot catamaran in La Rochelle with two toddlers and zero sailing experience. If we'd waited until we felt ready, we'd still be in Singapore.
The gap between planning and doing isn't information. It's nerve. And the only way to close it is to commit to a date and work backwards from there.
If you want help figuring out what actually needs planning and what you're using as a stalling tactic, that's literally what we do now. Book a free call and we'll help you sort it out.
