People warned us about visas, budgets, seasickness, and schooling. Nobody warned us about any of this.
1. You'll grieve a life you chose to leave
This sounds contradictory and it is. You can desperately want to go and simultaneously mourn what you're leaving behind.
In Singapore we had routines we loved. The hawker centre near our condo where our eldest ate chicken rice every Saturday. Emily's yoga class. Ben's Thursday night football. The friends we'd had since the kids were born.
We chose to leave all of it. Nobody forced us. And yet, about three months into our life on the road, we both went through a period of real sadness. Not regret, more like homesickness for a home we'd voluntarily dismantled. That was confusing and nobody had told us to expect it.
It passes. But if you're six weeks into your new life and you feel unexpectedly sad, that's not a sign you made the wrong choice. It's your brain catching up with what your body already did.
2. Some friendships won't survive the move
We had close friends in Singapore. People we saw every week. People whose kids played with our kids. People we assumed would be in our lives forever.
Some of them are. Most of them aren't.
It's not that anyone fell out. It's that proximity does a lot of heavy lifting in friendships, and when you remove it, you find out which relationships were based on genuine connection and which were based on convenience. The school gate friends, the neighbours, the couple you always saw at the same parties. Those relationships quietly dissolved within a year.
The ones that survived are deeper now than they were before. But there are fewer of them, and that was a loss we didn't anticipate.
If you're about to move, be realistic about this. Invest in the friendships that matter most before you go. And be prepared to build a new community from scratch wherever you land. That's a skill, and it takes energy, and nobody tells you how tiring it is.
3. Your identity will wobble
Ben went from "VP at an international tech company" to "that guy on the boat." Emily went from "business owner" to "homeschool mum who lives at sea."
In Singapore, people ask "what do you do?" within the first five minutes of meeting you. Your answer slots you into a hierarchy. When you remove that, you have to figure out who you are without the job title, the office, the salary.
That's liberating in theory. In practice, it's disorienting. Ben had a genuinely rough few months in year one where he didn't know how to answer the question "what do you do?" and felt embarrassed by his own uncertainty. Emily found the shift easier because she'd been thinking about it longer, but she still had moments where she wondered if she'd thrown away a career she'd worked nine years to build.
If your identity is tied to your job, which for most professionals it is, plan for this. It's not something you can think your way out of in advance. You just have to go through it. But knowing it's coming helps.
4. The guilt is real and comes from every direction
Guilt about taking the kids away from stability. Guilt about worrying your parents. Guilt about being privileged enough to even have this option. Guilt about leaving friends who were going through hard times.
The guilt doesn't go away entirely. You just learn to hold it alongside the conviction that you're making the right choice. Those two things can coexist. They did for us the entire time.
5. Coming back to "real life" is harder than leaving
This is the one that truly blindsided us. We sold the boat in August 2023 after nearly four years. We'd been looking forward to the change. We were excited about having space, water on tap, a kitchen with more than two burners, a school for the kids, supermarkets less than 3hrs away!
And then we landed and everything felt wrong. Supermarkets were overwhelming. Social norms felt rigid and strange. We'd been used to deciding each morning where to go, and suddenly our calendar was full of school runs and everything else that comes with that.
The kids adjusted faster than we did. Kids were thrilled about having their own room. They thrived on making school friends. But for Ben and me, the re-entry took six months of feeling out of place in a life we'd supposedly been building towards.
Nobody warns you about this because everyone assumes coming back to "real life" is the easy part. It isn't. If anything, it's the part that needs the most planning and the most support.
Why we're telling you this
Not to put you off. If you're planning a big family move, we think you should absolutely do it. But the emotional side of transition is the part most families are unprepared for, and it's the part that causes the most strain on relationships and wellbeing.
The logistics are solvable. Visas get processed, schools get found. The harder work is what's going on between you and your partner, between you and your kids, and inside your own head.
That's what we spend most of our coaching time on. We went through every single one of these things and came out the other side knowing what helped and what didn't.
If any of this resonates, come talk to us. No pressure. Just a conversation with someone who gets it.
