I’ve Been an Expat for Over 20 Years: Here’s What I Got Badly Wrong

After more than twenty years living abroad, I’ve spent a lot of time telling other people what they should do.

How to choose a country. How to manage your money. How to avoid the obvious traps. How to build a life that actually works once the holiday feeling disappears.

But there is another side to expat life that is probably more useful.

The things I got wrong.

I left the UK at 39. It wasn’t an impulsive decision. I’d done the research, understood the finances and thought carefully about the sort of life I wanted. Even so, some of the decisions I made cost me time, money and opportunities that I can’t get back.

That’s the uncomfortable bit about experience. You don’t get it by reading about other people’s mistakes. You get it by making a few of your own.

So this isn’t another polished list of expat advice. These are six things I wish I’d understood much earlier.

Key Takeaways

1. I Moved Too Fast

This is probably the most obvious mistake, particularly because I’ve spent years telling other people to do exactly the opposite.

When I left Britain, I committed to a location before properly testing what everyday life there would actually feel like. The research looked good. The decision seemed logical. But researching somewhere and living there are two very different things.

A holiday shows you the restaurants, beaches and good weather. Living somewhere shows you the traffic on an ordinary Tuesday morning, the quality of the local services, the bureaucracy, the neighbours and whether you actually enjoy your life once the novelty wears off.

I eventually found places that suited me much better, but it took longer than it needed to.

The lesson is simple. Rent first. Test properly. Then decide.

Don’t confuse excitement with certainty.

2. I Underestimated What I’d Miss

I wasn’t somebody who expected to miss Britain.

I’d made the decision to leave and was determined not to spend my life looking backwards. For years, I treated missing home as something I simply shouldn’t be doing.

That was a mistake.

What I eventually realised was that I didn’t necessarily miss Britain itself. I missed familiarity. Friends who had known me for decades. People who understood my references without an explanation. The social connections built over a lifetime.

You can make new friends abroad, of course. I’ve done exactly that. But deep relationships take time, and when you move countries more than once, you keep starting parts of that process again.

That doesn’t mean leaving was wrong. It means there was a cost I hadn’t properly included in the calculation.

And I think prospective expats should understand that before they leave.

You can love your new life and still miss parts of the old one. Those two things can exist at the same time.

3. I Got My Financial Planning Wrong

I was reasonably good with money. I wasn’t financially reckless. But I didn’t build the financial structure I should have built at the beginning.

I relied too heavily on capital in the early years instead of establishing a stronger income floor. I didn’t take currency risk seriously enough. I looked at healthcare as a current expense rather than something that could become considerably more expensive as I aged.

I also left estate planning until later.

That was particularly foolish. Once you have assets, income and personal interests spread across different countries, the financial picture becomes more complicated. Waiting until something goes wrong is an expensive way to discover that.

I eventually dealt with these issues, but later than I should have and with more disruption than necessary.

The naked truth is that your financial plan for living abroad needs to be designed for the life you expect to have at 70, not just the life you’re enjoying at 50.

That means thinking about income, currency, healthcare, taxation and what happens to your assets when you’re no longer around to deal with them.

4. I Confused Being Alone With Being Independent

I’ve always been reasonably comfortable in my own company.

That’s useful when you live abroad. You don’t need to be surrounded by people every minute of the day, and being comfortable alone gives you a degree of independence that I consider valuable.

But I eventually realised there is a difference between enjoying solitude and having enough genuine human connection.

You can be perfectly capable of living alone and still have too little meaningful contact with other people.

That distinction matters because the deficit tends to build quietly. Nothing dramatic happens. You simply become accustomed to a smaller and smaller social world.

I was slower than I should have been to recognise that independence doesn’t mean doing everything yourself.

A sustainable life abroad needs people. Friends. Community. People you can call when something goes wrong. People who know you well enough to notice when you’re not quite yourself.

That’s not weakness.

It’s sensible planning for the long term.

5. I Thought I Understood the Culture

Living in a country for years does teach you things. You learn how people communicate, how relationships work, what behaviour is considered normal and which of your own assumptions don’t travel particularly well.

The mistake I made was assuming that experience automatically meant understanding.

By my mid-forties, I’d already lived in several countries and was quite comfortable talking about cultural differences. I believed cultural intelligence was important, and I was right about that. What I had underestimated was how much I still had to learn.

Some of my assumptions were based on observation rather than genuine understanding. I sometimes interpreted situations through my own cultural framework and assumed I had worked out what was happening. On occasions, I gave advice with more confidence than my understanding justified.

The older I became, the more obvious the problem was.

You don’t reach some magical point where you have “figured out” a culture. The longer you live somewhere, the more complicated it becomes. You discover that the thing you thought was a simple cultural rule actually depends on family, class, age, region, personality and a dozen other factors.

That realisation has made me much more cautious about telling people what other cultures are “like”.

I can tell you what I’ve experienced. I can explain patterns I’ve noticed. But there is a big difference between saying that and believing you’ve got the whole country worked out.

Humility is a much better tool.

6. I Waited Too Long to Take My Health Seriously

This one bothers me more than the others because I knew better.

I left Britain at 39 in reasonable shape. I had energy, plenty of optimism and a new life ahead of me. For a while, that was enough to carry me along.

Then the standards gradually slipped.

I exercised less than I intended. My eating habits drifted. I drank more than I should have. Nothing happened suddenly enough to force me to deal with it, so each small deterioration became normal.

That is how these things often work.

There doesn’t have to be a dramatic crisis. You simply make slightly worse decisions for several years and eventually discover that the cumulative result is rather less attractive than the individual decisions seemed at the time.

It took circumstances in my fifties to force me to take an honest look at it. I quit smoking, stopped drinking, started training properly and fundamentally changed how I ate. The improvement in my energy, clarity and general wellbeing made something painfully obvious.

I’d wasted time.

Not my entire life. Not even close. But I had wasted years when I could have been building the physical foundation for the decades ahead.

That’s particularly relevant if you’re planning to live abroad into your seventies and eighties.

People spend an enormous amount of time thinking about the country they’ll live in during retirement. They research visas, property, healthcare, taxes, restaurants and beaches.

They don’t always spend enough time thinking about the body they’re going to take with them.

Your future health isn’t something that suddenly arrives when you turn 70. Much of it is being shaped years earlier by what you eat, how much you move, how well you sleep and the habits you decide are acceptable.

I eventually made the changes.

I just wish I’d made them ten years earlier.

What These Mistakes Have Taught Me

Looking back, none of these mistakes stopped me from building a life abroad that I’m very glad I chose.

But they did make the journey more expensive than it needed to be.

The interesting thing is that none of the lessons are particularly complicated. Slow down. Accept that leaving home has a cost. Build the financial structure properly. Make an effort to create genuine relationships.

The difficult part is actually doing those things when you’re 39, excited about a new life and convinced that you’ve already thought everything through.

I hadn’t.

And that’s probably the most useful thing I’ve learned from twenty years abroad.

Experience doesn’t mean you stop making mistakes. It means you get better at recognising them.

What I’d Tell Myself at 39

If I could sit down with the man who left Britain in 2005, I wouldn’t tell him not to go.

I’d still tell him to go.

But I’d tell him to slow down.

Don’t mistake the urgency of a new life for certainty about where that life should be built. Rent. Test different places. Find out what an ordinary week feels like before making major commitments.

I’d also tell him that missing people and familiar things isn’t evidence that you’ve made the wrong decision. It’s simply one of the costs of leaving. You can accept that cost without regretting the decision.

Financially, I’d start with a proper structure rather than sorting things out as problems appeared. Build an income floor. Think seriously about currency risk. Model future healthcare costs. Deal with estate planning early, particularly when your life and assets cross jurisdictions.

I’d make human connection a priority rather than something to deal with if loneliness eventually became a problem.

I’d also tell myself to be less certain about other cultures. Living somewhere for twenty years gives you experience. It doesn’t make you an expert on every person who lives there.

And finally, I’d tell myself to take health seriously much earlier.

The man you become at 70 is being influenced by the decisions you make at 40 and 50. You don’t get to postpone that investment indefinitely and then make up the lost ground later.

The Mistakes Were Worth More Than the Advice

Looking back over more than twenty years abroad, I don’t regret leaving Britain.

I’ve lived in Thailand, Malaysia and the Philippines. I’ve experienced different cultures, built new relationships and created a life that would have been difficult to imagine when I was sitting in Britain in my thirties.

But I also made mistakes.

Some cost money. Some cost time. Some were simply lessons I could have learned earlier if I’d been more willing to question myself.

That is probably the part of expat life that doesn’t make it into most guides.

People like to hear about the successful move, the cheap apartment, the better weather and the freedom. Those things can all be real.

So can the difficult bits.

The most useful question isn’t whether you’ve made mistakes. You will.

It’s whether you’re prepared to recognise them early enough to change direction.

That is what twenty years abroad has taught me.

Experience is useful. But only if you’re still willing to learn.