Morning,
Is it not wild how September always sneaks up on us? Backpacks are stuffed, lunch kits are lost by day two, and the kitchen calendar suddenly looks like an air-traffic control tower. With kids back in school, we fall back into routines – some comforting, some chaotic, all reminders that seasons shift whether we’re ready or not.
Business ownership works the same way. Days grow shorter, leaves surrender their color, and we’re reminded that everything – in nature, in markets, in life – is built on cycles. Growth. Maturity. Renewal. And eventually, succession.
At Henderson Family Wealth, we work with enterprising families who know wealth is more than capital. It is strategy. It is stewardship. It is the discipline of investing not just for today’s returns, but for tomorrow’s resilience. Nowhere is this more evident than in the season of succession.
The coming wave
I’ve written about this before, but it’s a theme worth revisiting. According to the Canadian Federation of Independent Business (CFIB), over $2 trillion in business assets are expected to change hands in the next decade as three-quarters of Canadian business owners plan to exit. Yet only 1 in 10 have a formal succession plan.
The reasons for stepping away are human: retirement (75%), burnout (22%), or simply wanting to step back (21%). But the obstacles are systemic. Half of owners cannot find a suitable buyer. Many struggle to even measure the value of what they’ve built. And too often, the business itself is still too reliant on them – fragile without the founder at the helm.
Cycles in markets and life
Markets remind us of seasonality too. Since 1928, September has been the weakest month for the S&P 500, with an average decline of 1.2%. Bond yields are climbing globally as fiscal imbalances weigh heavily. Economic data signals both resilience and fragility.
Howard Marks puts it simply: “the danger isn’t in cycles themselves, but in failing to recognize them.”
And as T.S. Eliot wrote in Four Quartets:
“To make an end is to make a beginning. The end is where we start from.”
That is the essence of succession.
Preparation, not clinging.
Renewal, not resistance.
When “success” isn’t enough
Here’s the hard truth.
When asked, most owners say they have a successful business. They’re proud of what they’ve built: customers, employees, profits, a strong balance sheet. Yet when it comes time to sell, many are stunned. It’s a jarring thing to hear your baby called ugly.
Even after years of success, some can’t sell at all. Why? Because they built something successful, but not significant.
A significant company is valuable, transferrable, and resilient. It aligns to business, personal, and financial goals. It is designed to endure.
The gap in planning
Research by the Exit Planning Institute highlights the disconnect:
- 61% of owners say a transition strategy is important.
- 80% have no written plan.
- 95% have no plan for their life post-exit.
The result? Owners who are unprepared, vulnerable to involuntary exits, and often left with regret.
Three challenges stand out:
Unpreparedness. Too many treat succession like selling a house — a quick facelift before the sale. But exit strategy is business strategy. Every decision today either strengthens or weakens what you’ll pass on.
Involuntary exits. Half of exits are forced by death, disability, divorce, disagreement, or distress. Without resilience beyond the founder, the business cracks under pressure.
Lack of holistic planning. Seventy-five percent of owners regret selling within a year – not because of the deal itself, but because they never defined what came next.
The urgency of intention
Succession planning isn’t something you cram 18 months before retirement. It’s like buying school supplies the night before classes start — technically possible, rarely pretty, and usually missing the one thing you’ll need most.
To ignore succession is to risk being forced out. To embrace it is to build resilience through people, process, and culture that survive beyond the founder.
This is where intention matters most. It’s why we walk alongside families and business owners in this season — ensuring transitions are not rushed events, but carefully designed passages. Preparing the next generation. Protecting employees. Preserving purpose. Aligning goals so the transition is not just a sale, but a succession.
The real question
Because, in the end, the seasons will change with or without us. The question is whether we’re caught off guard by the frost, or whether the roots we’ve planted are strong enough to carry new growth.
Too many owners confuse a successful business with a significant one. A successful business provides income, lifestyle, and pride of ownership. A significant business goes further: it is transferrable, valuable, and resilient. It serves the owner’s personal, financial, and family goals – while standing strong enough to endure without them.
Think of it as the difference between eating the harvest and planting seeds.
Success feeds today. Significance endures tomorrow.
Have a fantastic week!
Be well and enjoy the moments,
Derek Henderson