The Sequence: What to Handle After a Windfall, and in What Order

A companion piece argues that the risk in the first year after a windfall isn't bad investing: it's making an irreversible decision before you're in a state to make one well (The Dangerous Year Isn't the One You Think). The short version is the twelve-month rule: nothing big and permanent for roughly a year, while the money sits somewhere simple.

That naturally raises the next question: what do you do? Here's the order, in four stages, roughly in sequence, though real life blurs the edges a little.

1. Stabilise

Before anything else, get the money somewhere secure and boring, and get honest about what actually reaches you: because the headline sale price and your real number are rarely the same thing. Deal costs, deferred payments or earn-outs, tax on the proceeds, any warranty or clawback period that can still claw money back after close: know your real, final number before you make a single decision based on the number in the press release. Alongside that, rebuild your personal safety floor. You had a business income; you probably don't anymore, at least not the same one. Your own buffer matters more this month than it did last month, before a cent goes toward anything else.

2. Structure

This is the stage almost everyone underrates, because it's not exciting and it doesn't feel like progress. But how you hold the proceeds (what entities, what jurisdiction, what account structure, what's separated from what) is the foundation everything else gets built on. Get qualified tax and legal advice on the structure of the money itself, including anything genuinely time-sensitive (some elections and structuring windows close fast and don't reopen). Do this before you touch the next two stages, not after.

3. Decide slowly

The big, identity-shaped questions (what you do with your time, what fills the role the business used to fill, whether you start something new) deserve a real year of thought, not a weekend of enthusiasm. This is also where one specific piece of advice matters for founders especially: separate "new venture" money from "never risk this again" money, in writing, before you feel the pull to deploy either. You will feel the pull. The same instinct that built the business doesn't switch off at completion: it goes looking for somewhere to point itself, and "somewhere" is often a fast-funded new idea, a big purchase, or an investment made mostly to feel useful again. Deciding your risk budget on paper, while you're calm, protects the version of you that shows up bored and restless in month four.

4. Move, if at all

Only once structure is settled does "where should we live" become a sane question to ask. This is worth being direct about, because it's where the order goes wrong most often: residency is a trigger, not a lifestyle choice. Spend enough time somewhere, or establish the wrong kind of tie, and you can end up a tax resident of a place you never formally chose: sometimes of two places at once, which is the opposite of the goal. The destination question is real and worth taking seriously (there's a full framework for it in Where to Live After Selling Your Business, and on the residency-versus-passport question specifically in Second Passport vs. Tax Residency). But it comes fourth, not first.

The two mistakes that reorder everything

Almost every expensive outcome traces back to one of two ordering mistakes.

The first is moving before structuring: falling for a destination, or a tax number, before the underlying structure is settled, and only afterward discovering the sequencing mattered. Some of the best outcomes are only available if certain things happen before you relocate, not after. Get the order backwards and the door can close permanently.

The second is deciding where to live before deciding how to hold. These feel like the same decision. They aren't. How you hold the money shapes which residency options even make sense; picking a place first and reverse-engineering the structure afterward is how people end up boxed into worse options than they'd have had otherwise.

Here's the pattern, in miniature. One founder gets qualified advice on structure in month two, decides nothing about relocation until month ten, and ends up with real, well-understood choices when they're finally ready to choose. Another falls in love with a destination in month one, moves in month four to "get ahead of it," and spends the next eighteen months untangling a structure built around the wrong sequence. Same windfall, same intelligence, same good intentions. Different order. Very different year.

Frequently asked questions

What should you do first after selling a business or coming into money?

Stabilise before anything else: get the money somewhere secure and simple, confirm your real net number (after deal costs, deferred payments, tax, and any clawback period), and rebuild your personal safety floor. Only then move on to structuring how the money is held, and leave relocation and other big, permanent choices for later.

Why does structure come before deciding where to live?

How you hold your proceeds shapes which residency and relocation options even make sense. Choosing a place first and reverse-engineering the structure afterward is how people end up boxed into worse options than they'd otherwise have had. Some of the best outcomes are only available if certain things happen before you move, not after.

What are the two most common ordering mistakes after a windfall?

Moving before structuring (falling for a destination or a tax number before the underlying structure is settled) and deciding where to live before deciding how to hold the money. Both feel like single decisions but are really two, and getting the order backwards can close doors permanently.