Every family we've spoken to since we started travelling and especially since starting Roamsmith has their own version of "let's wait until". The excuses change but the pattern doesn't. And we call them excuses deliberately, because that's what they are. Valid-sounding reasons to avoid doing the scary thing.
The school year argument
"We can't pull the kids out mid-year." This is the most common one and it sounds responsible. But kids change schools all the time. They move towns, their parents divorce, circumstances shift. Schools are designed to handle new students at odd times. Your child will not be psychologically scarred by starting in February instead of September.
What actually happens when you wait for the school year to end is that you add six months to a year of delay, during which your motivation fades, your savings stay the same, and the dream gets pushed to "next September." Then next September comes and there's a new reason.
If your child is mid-primary/elementary, the school year doesn't matter nearly as much as you think. If they're in secondary, there's a stronger case for timing it with a natural break, but even then it's a preference, not a requirement.
The money argument
"We need to save a bit more." How much more? What's the number? When we ask families this, most can't answer. "A bit more" is not a financial plan, it's a way of avoiding a commitment.
What you actually need is clarity on three numbers: your monthly cost of living at the destination, the size of your financial buffer, and how long that buffer lasts without income. Once you have those, you either have enough or you don't. If you don't, set a specific savings target and a date. If you do, you're stalling.
We left Singapore with enough savings for about 1 year on the boat, assuming no income. That was tight and it stressed us out regularly. But it was a real number tied to a real plan, and it was enough to go.
The career argument
"I'll lose momentum if I leave now." Maybe. But momentum towards what? If you're building a career that you love and that's central to who you are, then timing matters and you should think carefully about it.
But most people I talk to aren't in that position. They're in decent jobs that pay well but don't excite them, and the career argument is really about security and identity rather than genuine professional ambition. They're afraid of what happens when the salary stops and the job title disappears.
That's a real fear. I felt it too. But it's different from a career argument. Be honest about which one you're actually making.
The family argument
"My parents would be devastated." "The kids are settled." "My partner isn't ready."
Family considerations are real and they deserve respect. But they also deserve honesty. Sometimes "my partner isn't ready" means "we haven't had the proper conversation because we're both avoiding it." And sometimes "my parents would be devastated" means "I'm using their feelings as a shield for my own uncertainty."
The honest version of the family argument is usually: "We haven't agreed on this yet and we need to." That's solvable. That's what our Decision Sessions are built for.
When is the right time?
There are genuinely bad times to move: during a medical crisis, a divorce, a bereavement. If your family is in acute stress, stabilise first.
But short of that, the right time is when you've done enough planning to feel 70% ready and you've committed to a date. Not 100% ready. Not "when the stars align." Seventy percent.
We left Singapore with two toddlers, no sailing experience, a boat we'd seen twice, and a plan that was about 60% solid. It worked out. Not because we were lucky, but because we adapted. And we adapted because we had no choice, because we'd committed to a date and booked non-refundable flights :)
If you've been talking about this for more than a year, the problem isn't timing. It's commitment. Pick a date. Work backwards from it. Tell people. Then do it.
And if you want someone to help you stop going in circles, that's what we do.
