Posted August 14, 2026

Hoping to Retire in Five Years? As a Business Owner, Here Are a Few Questions You Should Be Asking Now

In our recent blog, is your business really your retirement plan, we looked at a question many business owners never properly ask themselves: would somebody actually want to buy your business when the time comes to retire? If that article left you thinking about your own plans, the next question is equally important: what should you be doing now?

Five years may sound like a long time, but when it comes to retirement and succession planning, it can disappear remarkably quickly. The decisions made during the final years before retirement can have a significant impact on both the value of your business and your personal financial future.

If you are hoping to retire in the short or medium term, these are a few questions you should ask yourself and our opinion on what you should be doing about it.

How Much Is My Business Actually Worth?

Many owners have a figure in mind when they think about the value of their business. Unfortunately, that number is often based on turnover, hearsay or something a competitor supposedly sold for. The reality is that business value is usually driven by industry, profitability, risk and future earnings potential. A business generating reliable profits with strong systems and a capable team will often attract more interest than a larger business that relies heavily on its owner. Understanding what your business might realistically be worth today gives you time to improve areas that could affect a future sale. The majority of businesses are valued based on their adjusted EBITDA, we hope to write a blog in the future on valuing your business and calculating your EBITDA.

Who Would Buy My Business?

A surprising number of business owners haven’t considered who their likely buyer would be. Would the business appeal to a competitor looking to expand? Could the management team eventually buy it? Is there a family member who may want to take over? In many sectors, there is also an increasing number of private equity-backed groups looking to acquire and consolidate smaller businesses. For the right business, this can create significant opportunities, but buyers will still be looking for strong profits, good systems and a business that is not reliant on the owner.

Different exit routes require different planning. Understanding your most likely buyer can help shape decisions around structure, investment and succession over the coming years.

Could the Business Operate Without Me?

This is often the most revealing question of all. If you took three months away from the business tomorrow, what would happen?

Would clients continue to be looked after? Would sales still be generated? Would staff have the authority and confidence to make decisions?

Many successful businesses are heavily dependent on their owners. That isn’t necessarily a problem while you’re actively involved, but it can significantly reduce the attractiveness of the business to potential buyers. Reducing owner dependency is often one of the most effective ways to improve business value.

Do I Have Enough Wealth Outside the Business?

Many business owners have spent years reinvesting profits back into their company rather than investing in a pension or other investments which could be used to fund retirement. As a result, a significant proportion of their wealth may be tied up in a single asset. The challenge is that business sales can take time, valuations can fluctuate and circumstances can change. Having pensions, investments or other assets outside the business can provide flexibility and reduce reliance on achieving a particular sale value at a particular point in time. For many owners, retirement planning should involve looking beyond the business itself and look at your overall personal wealth.

Is the Business as Tax Efficient as It Could Be?

The years leading up to retirement can create valuable planning opportunities. Whether you’re considering selling the business, passing it to family members or gradually stepping back, it’s worth reviewing your tax position well in advance. Waiting until a transaction is imminent often limits the available options. Early planning can make a significant difference to the amount of wealth ultimately retained after tax.

Do I Have the Right Team for the Next Stage?

A strong management team is beneficial for any growing business, but it becomes particularly important when retirement approaches. Potential buyers will want to be certain that the business can continue operating successfully after the current owner leaves. Likewise, if succession is likely to come from within the business, developing future leaders takes time. The strongest succession plans rarely happen overnight.

What Does Retirement Actually Look Like?

Many owners spend years planning their exit but very little time planning what comes afterwards.

Do you want to retire completely? Work part-time? Become a consultant? Spend more time with family? Travel? The answer may influence the type of succession or exit strategy that makes the most sense for you. Retirement planning isn’t simply about leaving the business, it’s about understanding what you’re working towards.

Start Planning Before You Need To

The best retirement outcomes are usually the result of careful planning, not last-minute decisions. Owners who start asking these questions five years before retirement typically have more options, greater flexibility and more time to make improvements that enhance both business value and personal financial security.

If you haven’t already read our article is your business really your retirement plan, it’s a useful starting point for understanding whether your business is likely to deliver the retirement you’ve been hoping for.

At Whitesides Chartered Accountants, we work with owner-managed businesses to help them understand their options, improve business value and plan confidently for the future. Whether retirement is five years away or fifteen, starting the conversation early can make all the difference.