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Beware of the tax traps if you're an expatriate about to leave the Island

Broadly speaking, in most countries, you will become tax resident in the country to which you move, from the day you move there (and possibly from before you land, which is why you need advice). The rules that the tax authorities apply in most countries are so obscure that you may owe up to a year’s extra tax, some of it on your Bermuda income, if you time your departure wrong.

Your behaviour in the year or two before you move may make it more sensible to take a month’s vacation before going home. Be sure to ask your tax advisor about it: most countries have tax rules that will do you no favours.

Generally, again, the country to which you move will require you to turn yourself in to the authorities soon after you arrive. The British, I know, require the completion of a form that asks you to identify and list every asset you own in the world. Not completing the form by the deadline (which is soon after you arrive) is usually a criminal offence — and always a dumb move.

If you’re wealthy, take advantage of the many legal opportunities you will have to limit your exposure to tax. If you’re broke, it won’t matter. If you have a little money, cheating with some of it will expose you to the risk of criminal penalties way out of line with the few extra dollars you might save by cheating.

Plus, cheats never prosper. If you try hiding money somewhere and fail to declare it, my guess is that you’d live to regret it. For one thing, you might get caught. Ex-spouses, former friends and associates, and jealous neighbours have a way of getting their own back. The US develops something like 40 percent of its tax cases based on information provided by the formerly near and dear. Everyone you know is aware that you’ve been in “tax-free” Bermuda, and many of them are secretly jealous, to a greater or lesser extent.

By not declaring some of your assets, you would permanently join the criminal fraternity, and for the rest of your life — barring an amnesty, this would be a decision that stuck with you that long — you would be looking over your shoulder to see who was coming at you. We’re talking jail and financial penalties that will force you to live in a cardboard box when you get out of jail. Don’t go there.

In most countries to which you might be moving or returning, you’re going to owe little or no tax on whatever you might have saved in Bermuda, and all applicable taxes on every penny you or your savings earn from the day you land in the country. This offers Brits, Americans and probably many others a sensational one-off opportunity to move all their savings out of tax for a lengthy period: they should buy a home in the country they’re going to live in. Don’t take my word for it; check that it applies to you. You’re going to need a roof anyway, so buy the most house you can afford to own and operate. Any of your capital sunk into it will remain essentially tax-free for as long as you own it, in many countries. Again, don’t assume this applies to the country you’re going to: ask your advisor.

The big question, central to two of the letters received, was whether there might be ways to take advantage of keeping one’s capital offshore when one went to live somewhere else.

Canadians, I believe, enjoy a five-year window of investment opportunity before the full weight of Canadian taxes bites them. For some sufficiently wealthy others, a trust set up before you leave Bermuda — again, this is just my opinion — may reduce your taxes in your new country.

Beating, rather than cheating, the taxman is always a good idea. Doing everything you legally can to minimise your tax bill is your right. If you want to make voluntary payments to the government in your new country, do it through another channel.

Listen to your tax professional; consider what you learn; and then act. Many of your options will expire the moment the airplane touches ground in your new country, so make sure you have it sorted out in advance. I know, I already said that twice. I wanted to make sure that everyone got it. You may have a once-in-a-lifetime opportunity, and I insist you cash it in.

Finally, some psychological comments. Fitting yourself into the unutterably inefficient tax structures of another country will be a depressing and demoralising experience after Bermuda’s less-intense taxation experience.

Your loved ones should be helped to understand the change you are going through (most will have not one jot of sympathy). You will go through dark periods when your money feels like a curse and life seems pointless. Do not be alarmed. Life is pointless for those who pay tax.