Waiting for the stars to align? Your family's legacy might pass you by

There’s a particular moment in every family business journey when the question of selling the enterprise moves from the distant horizon to the kitchen table. It’s rarely a straightforward decision. In fact, for many Australian family business owners, the timing of a sale often feels completely out of sync with the business’s growth cycle, the prevailing economic winds, or the evolving plans and aspirations of the family itself. If you’re grappling with this conundrum, you’re not alone—and the path forward is rarely linear.

"It's not in the stars to hold our destiny but in ourselves"- Julius Caesar, Shakespeare

The reality is that life doesn’t always wait for the perfect market window. Retirement, health concerns, or a sudden shift in family dynamics can force the issue, making the sale of the business less about seizing opportunity and more about managing necessity. This timing dilemma is one of the most common, and most challenging, aspects of transitioning out of a family business. Owners find themselves weighing personal needs against the cold logic of market conditions, and sometimes, there simply isn’t a neat overlap.

Consider the business’s growth cycle. The ideal, of course, is to sell at the crest of a growth wave, when future profits are visible, and buyers are eager. But what happens when family circumstances dictate a sale during a period of expansion, or worse, during a downturn? Selling mid-growth can feel like walking away from untapped potential, while selling in a slump risks leaving hard-earned value on the table. The temptation to wait for “just one more good year” is ever-present, but the risks of delay—changing markets, shifting regulations, or unforeseen family events—can quickly erode that rationale.

Layer on top the unpredictability of the economic environment. We’ve all seen how quickly recessions, inflation spikes, or interest rate rises can sap buyer enthusiasm and dampen valuations. Even the most robust businesses can find themselves struggling to attract serious offers when the broader market is jittery. For family owners, this can mean accepting a lower price than they’d hoped for, or worse, being forced to hold on longer than planned and weathering the stress and uncertainty that comes with it.

Then there’s the family itself. Family businesses are, by their nature, deeply personal. Each member brings their own vision, ambitions, and risk appetite to the table. It’s not uncommon for one generation to be hungry for growth, while another is ready to cash out and diversify. These diverging interests can make consensus on timing elusive.

Emotional attachment adds another layer of complexity: for many, the business is more than an asset; it’s a legacy and a testament to years of hard work. The desire to protect that legacy can delay important decisions, sometimes to the detriment of both the business and the family’s financial wellbeing. Letting go can feel like a betrayal of tradition, but holding on too long can erode value, especially if the next generation isn’t prepared or willing to step in. Succession planning, or the lack of it, is often decisive. Too many families are forced into a sale by unforeseen circumstances, like a health crisis or sudden loss, and without early, clear planning, owners may have to accept less-than-ideal terms. The best outcomes come from planning well in advance, with contingencies for the unexpected.

Another often-overlooked risk is owner dependency. Businesses that rely heavily on the founder’s skills, relationships, or reputation are harder to sell and often fetch lower prices. If a sale is forced by unforeseen circumstances, and the owner must exit quickly, the business may struggle to stand on its own. Building a strong management team and institutionalising key relationships can help mitigate this risk, but it takes time and foresight.

Tax and regulatory changes are ever-present wildcards. Shifts in tax law or compliance requirements can have a material impact on the net proceeds from a sale. Owners who aren’t monitoring these changes may find themselves caught off guard, with less to show for their efforts than anticipated. Regular reviews with trusted advisers can help families stay ahead of the curve and make informed decisions, even when the timing isn’t perfect.

Ultimately, the most successful family business transitions are those grounded in early, honest conversations—both within the family and with professional advisers. Proactive planning allows families to align on their goals, prepare for the inevitable ups and downs of market cycles, and maximise value when the time comes. It’s not about waiting for the perfect moment—because it rarely arrives. It’s about being ready, as a family, to seize the best opportunity available, with eyes wide open to the trade-offs involved.

Selling a family business is never just a financial transaction. It’s a deeply personal crossroads, shaped as much by emotion and family dynamics as by market forces or business cycles. If the timing feels off, you’re not alone. But with open communication, strategic planning, and a willingness to adapt, families can navigate these complexities and write the next chapter of their story with confidence and purpose. To have an open discussion about your family's business and succession plans, please contact Canopy East

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