Thinking of selling your business? Here’s why it pays to know your number first

Most business owners spend years building something valuable. But how do you know that the value you’re building will deliver what you want?

Over the years we’ve worked with many business owners to develop their plans, and we begin by helping them to work out what is their ‘number’. As your business becomes more successful (and more demanding!) it’s a calculation that becomes more and more important. Doing this work can be invaluable in developing a business strategy that ultimately delivers the life you want. But in our experience, whilst most business owners have some form of plan for their business, their own personal plan takes a back seat.

The gap between business value and your personal number

A good accountant or corporate finance adviser can tell you what your business might be worth on the open market. That’s a business question, and it has a business answer.

But there’s a separate question, and it’s a personal one: how much do you actually need, after tax, after fees, after the sale completes, to fund the life you want next? We call this your number. Some business owners have never sat down and worked it out. Others have a rough figure in their head that hasn’t been tested against reality for years.

The two figures — what the business might fetch, and what you actually need — are rarely the same. Sometimes the gap is reassuring. Sometimes it’s uncomfortable. Either way, it’s better to know before you’re mid-negotiation than to find out afterwards. And the earlier you start this process, the better idea you’ll have of what needs to be done in your business to achieve that great outcome you’ve often thought about.

Why timing catches people out

The instinct is to think about financial planning once a sale is close, or once there’s a buyer at the table. By then, many of the useful options have narrowed. Tax planning that needs years to be effective can’t be compressed into months. Decisions about how proceeds are structured, or when completion happens relative to a tax year, work best when there’s room to plan ahead rather than react.

Speaking with a financial planner early doesn’t commit you to anything. But it does mean that you’ll gain real insight into how your personal and business finances can be planned together to put you in a much stronger position when it comes to a sale. It means that when the right opportunity or offer does come along, you already know whether it meets your number, and you’re not doing that maths for the first time under pressure.

What knowing your number actually gives you

Clarity changes the negotiation. Owners who know their number tend to negotiate from a calmer position, because they’re not guessing whether an offer is “enough.” They can say yes with confidence, or say no without second-guessing themselves.

It also reframes the sale itself. A business sale isn’t really the end point — it’s the start of a new phase, whether that’s retirement, a new venture, or simply more time for the things that got squeezed out over the years of building the business. Knowing your number early means that next phase has been thought through, rather than left until the proceeds land in the bank and the questions start.

Where a financial planner fits in

This isn’t about replacing your accountant, your solicitor, or your corporate finance adviser — each plays their own part in a sale. A financial planner sits alongside them, focused specifically on what the proceeds need to do for you and your family once the deal is done, and working backwards from that to check the numbers add up well before a term sheet is on the table. That’s why we regularly work with other professionals to be able to give you the complete picture, not just a one-sided business analysis. Our clients have found this approach invaluable as they continue to build and plan for their future success.

For business owners who haven’t thought about this yet, the starting point isn’t complicated. It’s a conversation about what life after the business looks like, and what that life costs to fund. Everything else follows from there.

If you’re a few years out from a sale, or even just starting to think about what “eventually” might look like, that conversation is worth having sooner rather than later. You can contact us to get started any time via our website.


Frequently asked questions

When should I start financial planning before selling my business?

Ideally two to three years before a sale, though even earlier is better if you can manage it. Some tax planning and structuring options need time to be effective, so starting early gives you more choices rather than fewer.

What is “my number” when selling a business?

Your number is the amount you need, after tax and fees, to fund the life you want once the business is sold. It’s different from your business valuation, which reflects what the business might fetch on the open market.

Do I need a financial planner if I already have an accountant?

Yes, and the two roles are different. Your accountant and corporate finance adviser focus on the sale itself and the business’s value. A financial planner focuses on what the proceeds need to do for you personally, once the deal completes.

How much should I sell my business for?

There’s no single right answer, because it depends on your own number rather than the market alone. Knowing your number in advance means you can judge whether an offer genuinely meets your needs, rather than guessing under pressure.

What happens to the money after I sell my business?

That depends on your plans, but proceeds are often used to fund retirement, new ventures, or family priorities. A financial planner helps structure this in advance, so the money is working for you as soon as the sale completes rather than sitting undecided.

Posted on: 19th August, 2026
Posted by: The Chesterton House Team
Chesterton House Financial Planning Ltd
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