For many business owners, the retirement plan is simple: build the business, sell it, retire on the proceeds. The trouble is that real life rarely follows the plan. A health scare, a partner leaving, a slow sale or a market fall can derail years of work at the worst possible time.

A "what if?" plan doesn't predict the future. It asks the hard questions now, while you still have time and choices, so one unexpected event doesn't decide your retirement for you.

Here are six questions every business owner in the last five to ten years before retirement should be able to answer.

1. What if your health changes before you're ready to step away?

If you couldn't work for six months, would the business keep running, and would you still have an income? Review your income protection, total and permanent disability and trauma cover, and ensure it still matches your debts and lifestyle.

Just as important is who can make decisions if you can't. An enduring power of attorney, and clear authority over your business bank accounts and entities, can stop the business from stalling.

2. What if your business partner dies, falls ill or wants out?

Without a plan, you could end up in business with your partner's family, or scrambling to find the money to buy them out. A buy-sell agreement, often funded by insurance, sets out what happens to each owner's share and where the money comes from. Make sure your shareholder or partnership agreement says the same thing.

3. What if the business sells for less, or takes longer to sell?

If the sale is your whole retirement plan, a soft market or a buyer pulling out can push your retirement back years. Building wealth outside the business spreads that risk.

Superannuation can be a tax-effective way to build wealth outside the business. For 2026–27, the general concessional contributions cap is $32,500 and the general non-concessional contributions cap is $130,000. Depending on your age, total super balance and other eligibility requirements, you may also be able to bring forward future non-concessional contribution caps.

4. What if the tax rules change before you sell?

 They already have. From 1 July 2027, the 50% capital gains tax discount will be replaced with cost base indexation and a 30% minimum tax on capital gains. If you plan to sell a business or other assets in the coming years, the timing and the value of your assets on 1 July 2027 may make a real difference to your tax bill.

Small business owners may also be able to use the small business CGT concessions. For example, the small business retirement exemption has a lifetime limit of $500,000, and if you're under 55 the exempt amount must be paid into super. These concessions have strict conditions, so plan well before you sign a sale contract.

5. What if markets fall just as you retire?

 A market fall in the first few years of retirement can hurt more than the same fall later on, because you're drawing money out while values are down. Depending on your circumstances, maintaining an appropriate cash reserve and structuring your portfolio around when funds are likely to be needed may reduce the risk of having to sell growth assets during a market downturn.

6. What if something happens to you?

 Your Will doesn't automatically cover your super or your family trust. Both are controlled differently. A complete estate plan should cover:

• your will and enduring power of attorney;
• your superannuation death benefit nominations;
• the future control of trusts and companies; and
• how the business will be transferred, sold or wound up.

Building your "what if?" plan

A good plan brings your business, tax, super, insurance and estate planning together, because a decision in one area affects the others. Start with three steps:

• Set your retirement target. Write down your preferred retirement timeframe and income goal, including what you expect the business sale or ongoing business income to contribute.

• Test the key risks. Work through each of the six scenarios above and identify the questions you cannot answer confidently.

• Prioritise the gaps. Address the risks with the most serious consequences first, which may include insurance, succession arrangements, decision-making authority and business agreements.

How Count Gold Coast can help

Our Wealth Management team works alongside our tax and accounting specialists to help align your retirement, tax and business exit strategies.

To arrange a "what if?" planning conversation, contact the team on 1300 667 897 or at [email protected].

General advice warning: This article contains general information only and does not take into account your objectives, financial situation or needs. Consider whether the information is appropriate for you and seek personal financial advice before making any decisions. Count Gold Coast's financial advisers are authorised representatives of Count Financial Limited ABN 19 001 974 625, AFSL 227232. 

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