“When’s the right time to sell my business?”
Most people assume it’s about the market, the right buyer at the right time and the right price. You might imagine there will be a moment when all the stars align, when the perfect economic and business cycles match your own life. But those stars rarely line up. If you wait for perfect certainty, you may end up waiting forever.
The real issue isn’t timing the market. It’s timing yourself. Are you ready for the day you turn out the lights and shut the door behind you? Are you ready for the morning after, when the responsibilities that once shaped your daily routine are no longer there? Who are you when the title is gone, the staff stop calling, and the sign out the front no longer carries your name?
That’s the harder part. A family enterprise isn’t just an asset. It’s an identity. Letting go can feel less like a sale and more like a loss.
There is never a wrong time to prepare your business for sale. But you need to prepare yourself as well. Create a vision for what lies ahead, not just the next six to twelve months, but the next ten to twenty years and beyond. Maybe it’s mentoring. Maybe it’s philanthropy or time with grandchildren. Maybe it’s simply the freedom to do the things you’ve put off for decades. And if the desire is there, think further still: how can today’s business success translate into a long-term legacy that lasts generations?
So, when is the right time? The truth is, there isn’t one. But the more prepared you are for the next stage of life, the more likely the outcome will make sense and allow your family to move confidently into its next chapter.
By Victorian based Family Business Accredited Advisor
Robert Carson
Founder and Family Enterprise Advisor
Robert Carson is the founder of Canopy East, where he works as a family enterprise adviser and financial consigliere to some of Australia’s most successful families. Drawing on years of experience across wealth management, governance, strategy and philanthropy, he helps families navigate the complexity of succession, decision-making, and legacy. His approach goes beyond the numbers, focusing on purpose, trust, and clarity so that both the family and its enterprise can thrive across generations.
Robert writes and speaks widely on the moral tensions of advising families, the hidden costs of success, and the need for providing an environment where the next generation can learn, fail, and grow without destabilising the family. Through Canopy East, Robert blends practical expertise with a strong values lens, encouraging families to ask bigger questions about why their wealth exists and how it can be used as a force for continuity and contribution.
