When Is the Right Time to Sell Your Business if You’re Thinking About Retirement?

When Is the Right Time to Sell Your Business if You’re Thinking About Retirement?

For many small business owners, the idea of retirement sits on a distant horizon, a “someday” thought rather than an active plan. But unlike a salaried role where retirement can be as simple as giving notice, exiting a business requires strategy, time, and preparation. Leaving it too late can carry serious risks, both financial and personal.

So, when is the right time to sell your business if retirement is on your radar?

Don’t Wait for a Crisis

One of the most common, and costly, mistakes business owners make is delaying the decision until a negative life event forces their hand. Illness, divorce, or burnout can hit unexpectedly, turning what could have been a carefully planned exit into a rushed sale at a lower value.

Health issues, for instance, not only affect your ability to run the business but also your capacity to be present and involved in the sale process, which is vital. Divorces or family disputes can complicate ownership structures, distract from performance, and muddy negotiations. These triggers shift the power to the buyer, often resulting in reduced offers or abandoned deals.

Good planning helps avoid these scenarios. Ideally, the decision to sell should come from a position of strength, while the business is healthy, profitable, and you’re in control.

Start the Process Early

Preparation is everything. From cleaning up financials to identifying growth opportunities that will appeal to a buyer, getting a business sale-ready takes time. Most business sales, even smooth ones, can take six to twelve months from listing to settlement.

Planning for retirement should begin two to three years out from your ideal exit. This gives you time to:

• Increase profitability and reduce reliance on you as the owner.
• Strengthen systems and team structure.
• Resolve any legal, lease, or supplier complications.
• Maximise your valuation through strategic improvements.

Early preparation also gives you the chance to choose your successor or buyer on your own terms and avoid rushed negotiations. However if you havent prepared and stioll need to sell, being on the market can give you the momentum to put some of the above into place while you are listed for sale.

Be Available During the Sale

A business sale isn’t a passive process. Owners play a crucial role throughout, from meeting with prospective buyers to answering detailed operational questions and providing key information to lawyers, accountants, and brokers.

If your plan involves retiring to a remote beach during the sale, think again.

Buyers want to see a cooperative and responsive seller, especially during due diligence. If you’re unavailable, vague, or disengaged, you risk undermining confidence in the business and in you. Being present, calm, and well-prepared will directly influence both your sale price and how smoothly the deal progresses.

The Takeaway

The best time to sell your business is before you need to. Retirement may be the end goal, but the journey toward it should start long before you hang up your keys.

Don’t let poor timing or unforeseen life events dictate your exit. With proactive planning and clear intent, you’ll not only safeguard the value of your business — you’ll also give yourself the freedom to walk away on your own terms.

Because the goal isn’t just to retire,  it’s to retire well.