Articles, interviews and commentary.

James writes and comments on retirement, relocation and international living, with a particular focus on Southeast Asia.

Featured articles.

Cover of The Simon Letter, June 2026, the issue featuring this article

When the Plan Stops Working: The questions about retiring abroad that most people never think to ask

Most overseas retirement planning covers the exciting first chapter and very little of what comes after. This piece looks at the later years: health, dependency, bereavement and, if needed, an exit route. And why the best-prepared retirees are rarely the most optimistic.

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Could You Really Start a New Life in Southeast Asia on Your Own?

Many people imagine retiring abroad as something couples do together. But widowhood, divorce or a partner who would rather stay put can pose the question differently: could you really do it on your own? This piece weighs the psychological barriers against the underrated advantages of going solo, and argues for treating a move as a process. A trial stay, not a leap, where exploring the idea is not the same as committing to it.

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What If the Problem Isn’t Your Pension, But Where It Has to Work?

Most retirement planning treats the size of your pension as the problem to solve, and the country you'll spend it in as fixed. But what if the geography is the part that's actually negotiable? Using a UK benchmark for the cost of a comfortable retirement, this piece sets the like-for-like cost of that same life against three places in Malaysia, Thailand and the Philippines. It's not to chase somewhere cheaper, but to show the real question may be less about the size of your pension than where it has to work.

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How Do You Know Whether a Retirement Destination Really Fits You?

It's tempting to begin the search for somewhere to retire with a league table of countries, ranked by climate, cost and healthcare. But a place can score well on paper and still feel wrong to live in. This piece makes the case for starting instead with the life you actually want - the shape of an ordinary Tuesday, not the holiday highlights - and for renting before you commit, treating a trial stay as a rehearsal for real life rather than an extended holiday. The best destination isn't the most celebrated one; it's the one that fits.

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Why Some People Retire Abroad and Thrive While Others Come Home

Two people can retire to the same place, with similar finances, and have completely different experiences - one thrives, the other eventually decides to come home. It's tempting to put that down to luck, personality or simply choosing the "wrong" destination, but usually there's rather more going on. This piece looks at the less obvious things that shape whether retirement abroad works over the longer term: what someone expected the move to change, and the life and relationships they build once they get there. The same destination can be a wonderful fit for one person and completely wrong for another - and neither outcome necessarily means somebody made a bad decision.

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Five Southeast Asia Retirement Myths That Are Almost True

Some retirement myths are easy to dismiss. The dangerous ones are the ones that are almost true. This piece looks at five assumptions that come up again and again when people research retiring in Southeast Asia - on budget, healthcare, property, visa runs and leaning on family in a crisis - and asks what's genuinely reliable in each, and what just sounds safe enough to pass for it. None of them are baseless. That's exactly why they're worth examining before building a retirement plan around them.

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