Most people frame this decision as "should I move to Cayman?" The more useful framing is the reverse: what does staying exactly where you are actually cost you, every single year, compared to the alternative? Staying is the default, but it isn't free — it's a decision with a real number attached, and most people never actually run it.
If You're in the United States
Federal tax on high earned or investment income runs well into the 30–37% marginal range before you even get to state tax. If you're in a high-tax state — California, New York, and similar — add another 9–13%. Moving to Cayman doesn't touch federal tax, since the US taxes citizens on worldwide income regardless of residence, but it can eliminate state income tax entirely once you properly establish non-residency, and can open structuring options (Cayman entities, the Foreign Earned Income Exclusion) that meaningfully change the picture. See our full tax guide for the mechanics.
If You're in Canada
Canada taxes residents on worldwide income at combined federal/provincial rates that often exceed 50% at the top end. Unlike the US, Canada taxes based on residency, not citizenship — which means genuinely severing your residential ties can take you out of the Canadian tax system entirely. The catch is the departure tax: the CRA treats most of your property as sold at fair market value the day you leave, which can trigger a real capital gains bill on exit if it isn't planned for in advance.
If You're in the United Kingdom
The UK's top income tax rate is 45%, plus National Insurance, plus a shrinking non-dom regime that no longer shelters foreign income and gains the way it used to. The Statutory Residence Test determines whether you're still considered UK tax resident based on days spent and ongoing ties — and UK inheritance tax is shifting toward a residence-based test too, meaning long-term residents can stay in scope even after they've left.
What Staying Actually Costs, Compounded
A single year's tax difference looks like a big number. Ten years of that same difference, left to compound if reinvested rather than taxed away annually, is a fundamentally different number — often the difference between a comfortable retirement and a genuinely wealthy one. That's the number worth actually calculating for your situation rather than eyeballing.
Run your own numbers with our free tax savings calculator — it now shows both the annual figure and the 10-year compounded picture, so you're comparing the real decision, not just one year of it.
What Moving Doesn't Cost You
People often assume relocating means starting over. In practice, for most remote-capable founders and investors, it means keeping your clients, your business, and your lifestyle — just based somewhere that isn't actively taxing away a third or more of what you build every year. The operational cost of the move itself (company restructuring, residency filing, moving logistics) is almost always small relative to a single year of the tax gap it closes.
The "should I move" question is really a "what is staying costing me" question wearing a different hat. Worth actually running the number before deciding either way.