Why Selling the Wrong Asset First Is One of the Most Expensive Expat Mistakes
- Thomas Sleep
- 38 minutes ago
- 10 min read
Most expats do not sell assets because they are trying to be clever. They sell because they want to create liquidity, simplify their finances, reduce stress, or bring order to something that has been sitting in the background for too long. It usually feels like a sensible move, especially for someone who is organised, pragmatic, and used to taking decisive action.
That is exactly why this mistake is so common.
Selling the wrong asset first rarely feels like a mistake in the moment. It feels tidy. Responsible. Often overdue. You have cash in the account, the portfolio looks cleaner, and you can finally stop thinking about whatever you just sold. There is a sense of relief that comes from making a decision and moving on.
But for expats, the order of asset sales is not just an admin decision. It is a structural decision. Once you sell something, you not only change what you own. You change what you can do next. You change how future income can be shaped. You change how future tax outcomes might land. You change the flexibility you have when your life changes again, and for expats, life nearly always does.
If you want a simple way to think about it, here it is. A bad investment decision can sometimes be repaired with time and discipline. Selling the wrong asset first often cannot. Once it is gone, the option it represented is gone too.
Why does this expensive expat mistake hide inside sensible behaviour?
When people decide to sell, they usually ask practical questions. What can I sell easily? What feels non-essential? What would I rather not hold anymore? Which holding is annoying to monitor, or simply no longer feels aligned with my identity?
Those questions are normal. They are also incomplete.
They focus on convenience, emotion, and present-day preference. They rarely consider how each asset functions within a broader plan. They do not always account for the fact that some assets are far more useful later than they are today, not because of their returns, but because of the flexibility they provide when residency, tax rules, and life stage shift.
This is why capable people still fall into this trap. The decision is not irrational. It is just missing a layer.
If you have ever told yourself that you are selling something simply to “clean things up”, it is worth pausing. Cleaning things up can be a brilliant move. It can also be the moment you quietly give away optionality that would have mattered far more later than it does today.
Why selling the wrong asset first is especially costly for expats
In one-country financial lives, selling decisions can be inefficient. In international finance, selling decisions can be permanently costly.
The reason is not that expats are worse with money. The reason is that expats operate across systems that do not behave consistently. Residency changes how assets are taxed. Different countries treat income and gains differently. Currency exposure interacts with lifestyle and future spending. What looks like a harmless sale today can become a costly loss of flexibility later, particularly if you move, repatriate, retire earlier than expected, or simply change your income needs.
This is also why many expats misread the true risk. They assume the risk is in the market or in the investment itself. They underestimate the risk of reshaping their future choices.
The uncomfortable truth is that selling the wrong asset first is often not a “mistake” you notice through a statement. It is a mistake you notice through a feeling, months or years later, when you are trying to plan income, and the options in front of you all seem slightly worse than they should.
The hierarchy most people never map
Every portfolio has a hierarchy, whether it has been designed intentionally or not.
Some assets are best preserved because they offer future flexibility. Some assets are best used later because they allow income to be shaped more efficiently. Some assets should be drawn first because they create less disruption to future planning. Others should be left alone precisely because they give you more control during the years when control matters most.
When this hierarchy is not mapped, people default to what feels obvious. They sell what feels least important, or least emotionally attached, or most annoying, or most “non-core”.
That logic is easy to defend. It just is not always correct.
If you want a test that reveals whether you are thinking in the right direction, ask yourself this. Am I selling this because it is truly the right asset to sell first, or because it is the easiest to part with?
Those are not the same thing. And, if you don't know, we need to speak.
The moment of realisation that comes too late
There is a moment I see people arrive at, and it is rarely dramatic.
It often comes during a transition, a likely move, a change in residency, a shift from accumulation to thinking about income, or the first proper conversation about retirement. They look at what remains in their portfolio and realise that the asset they sold years ago would have been the perfect tool for their current situation.
The frustration is not that they sold it. It is that they sold it first.
They begin to see that what they still hold is less flexible. Their income choices are more constrained. The tax outcomes are harder to manage. The “simple sale” they made in order to tidy things up has made the future harder to tidy.
That moment usually lands as a quiet sentence. “I thought this would give me more flexibility.”
This is why the order matters so much. Not because people are careless, but because the consequences often arrive after the decision.
A quote that explains the human side of this mistake
“The investor’s chief problem, and even his worst enemy, is likely to be himself.” — Benjamin Graham
This is not about intelligence. It is about human wiring.
Selling something produces relief. It reduces uncertainty. It gives a sense of progress. It removes mental load. For busy professionals, that feeling is powerful, especially when life already has enough complexity.
But relief is not always progress. Sometimes, relief is the feeling you get when you remove the very flexibility that future you would have valued most.
Convenience can quietly sabotage future planning
One of the most common drivers of poor asset-sale sequencing is convenience disguised as prudence.
People sell what is easiest to sell. They sell what feels peripheral. They sell what they no longer want to think about. They sell what seems replaceable.
The problem is that convenience is not the same as suitability.
The asset that feels replaceable today might be the one that provides the most control later. The holding that feels irrelevant now might be the one that becomes valuable when income needs change. The thing that feels like clutter today might be the thing that would have protected flexibility during a future transition.
If you are selling for convenience, you may still be making the correct decision. But you should not assume you are. For expats, convenience is often the enemy of long-term control.
When income planning exposes the error
The cost of selling decisions tends to show up most clearly when income becomes the goal.
During the accumulation phase, people can tolerate inefficiency without noticing it. They are earning, saving, investing, and focused on growth. Small tax leaks or lost options do not always feel meaningful.
When income planning begins, everything changes. Income planning reveals whether your remaining assets allow you to shape withdrawals, manage tax outcomes, and preserve flexibility over time. It reveals whether your portfolio is robust or merely successful on paper.
This is why selling the wrong asset first can become such an expensive mistake. The sale may have felt neutral during accumulation. During drawdown or pre-drawdown planning, it becomes obvious that it was not neutral at all.
If you are nearing a stage where income matters, or you suspect that it will matter sooner than you once thought, sales decisions deserve far more scrutiny than most people give them.
Why is this rarely about returns?
People often assume that the “wrong asset to sell” is the one with the best future performance.
Sometimes that is true. Often it is not.
The more common issue is the loss of returns. It is lost control.
The cost shows up as higher taxes over time, reduced ability to shape income, fewer levers to pull when circumstances change, and more forced compromises because the remaining assets no longer cooperate as they should.
This is why two people can have similar net worths and very different financial experiences. One can move countries and restructure calmly. The other can feel boxed in, even with more money, because the wrong assets were sold first, and the remaining structure offers fewer good options.
False urgency and the temptation to “just do something”
Expats experience a particular type of urgency that can lead to poor sales decisions.
It is the urgency of complexity. The sense that there is too much to manage, too many accounts, too many jurisdictions, and too many unknowns. Selling something can feel like the quickest way to regain control.
Sometimes it is.
Other times, it is simply the quickest way to lock in a future problem.
If you are feeling pressure to sell because you want to simplify, pause and ask what is really driving it. Is this a deliberate step in a plan, or is it a desire to reduce mental load? If it is the second, the decision might still be right, but it deserves a second look.
Timing risk does not only show up in when people act. It shows up in why they act. If the driver is pressure rather than strategy, the chances of selling the wrong asset first rise sharply.
Why is it hard to see clearly from your perspective?
Even financially astute people struggle with this, because assets are not just numbers. They carry history. They carry identity. They carry stories about why they were bought in the first place.
This makes it difficult to view them purely as tools. Some holdings feel like “wins”. Some feel like “mistakes”. Some feel like baggage. Some feel like comfort.
From the inside, it is easy to sell the one that feels emotionally clean to let go of, rather than the one that is structurally best to let go of first.
This is why outside perspective matters most before a sale, not after.
The goal is not to stop you from selling. The goal is to make sure the sale strengthens the rest of your plan rather than quietly weakening it.
Why do people speak to me before selling, not after?
Most people do not come to me asking, “Can you help me sell an asset?”
They come because they correctly sense that selling is not just a transaction. It is a permanent change to their future options. They want to know which assets can be sold without damaging future flexibility, and which assets should be protected because they will matter later, often in ways that are not obvious today.
They also want to know whether the urgency they feel is real or false. Whether the desire to simplify is strategic or emotional. Whether they are selling because it is the right move or the easiest move.
That clarity is only available before the sale takes place.
If you are considering a sale and part of you feels uneasy, that unease is worth listening to. It is often your intuition recognising irreversibility.
A final thought
Selling assets is not inherently risky. Selling them in the wrong order is.
The most expensive expat mistakes are rarely dramatic. They are quiet, sensible decisions that feel right at the time and only reveal their cost much later, when life changes, and flexibility becomes more valuable than simplicity.
If you are about to sell something, the most important question is rarely, “Is this a good asset?”
It is, “Is this the right asset to sell first?”
Once it is sold, there is no second chance to ask that question meaningfully.
About Thomas Sleep and Skybound Wealth
Living internationally changes everything about how money works.
Income can rise quickly. Tax can fall away. Assets build across countries, currencies, and legal systems. On the surface, life often looks successful. Underneath, complexity accumulates quietly, and small decisions made in isolation begin to shape outcomes years in advance.
Thomas Sleep is a UK-qualified Financial Adviser at Skybound Wealth, specialising in cross-border financial planning for expatriates and internationally mobile families. Based in Dubai, he advises professionals, senior executives, and business owners across the Middle East, the UK, Europe, and offshore jurisdictions.
With over sixteen years of experience living and working abroad, Thomas helps clients bring clarity to complex financial lives. His work spans investment strategy, tax efficiency, retirement planning, and long-term wealth protection, aligning these areas into a single, forward-looking plan that adapts as circumstances and locations change.
Thomas is UK-qualified and regulated and holds the CISI Level 4 Financial Planning &
Advice Diploma. Through Skybound Wealth, he provides regulated advice within a firm known for its strong governance, international regulatory coverage, and client-first approach. His advice is measured, analytical, and outcome-driven, helping clients understand not only what decisions to make today but also how those decisions affect flexibility, tax exposure, and security over the decades that follow.
As both an adviser and an expat himself, Thomas understands where problems typically emerge. Wealth grows faster than planning. Assets are built in silos. Tax considerations evolve quietly until they can no longer be ignored. By the time these issues surface, options are often narrower and more expensive to implement.
Much of Thomas’s work focuses on identifying these risks early and addressing them deliberately. Through Skybound Wealth, he helps clients build resilient portfolios that travel with them, reduce future tax friction, and ensure their wealth supports their family and lifestyle long after their working years end.
This advice is for people who want clarity, control, and confidence that their financial life will continue to work as circumstances change, not just when everything feels stable.
Book a Discovery Meeting
An initial conversation with Thomas Sleep at Skybound Wealth is a structured discussion, not a sales call.
It is designed to clarify your current position, identify risks and inefficiencies that may not yet be apparent, and outline practical next steps to materially improve your long-term financial position.
This conversation is most valuable for individuals with high incomes, international assets, or future relocation plans who want confidence that their finances are aligned, resilient, and built for what lies ahead.
Book a 45-minute call to decide whether working together is the right fit.
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