The Succession Crisis Nobody Wants to Plan For

Five observations from Jamie Dimon's latest warning — and what it means for the business owner who still hasn't named a successor

Jamie Dimon has been saying it for months: the American Dream is slipping out of reach. But a new JPMorgan Chase report gives that warning something it didn't have before — a number attached to it. And the number is sobering for anyone who owns a business and has quietly told themselves "I'll figure out my exit eventually."

Here's what stood out to me, and why I think this is less a finance story than an alignment story.

1. The planning gap is enormous — and it's not a knowledge problem

Chase surveyed 1,000 business owners and found that 70% say they're in the early stages of succession planning. Only 8% have reached an advanced stage. That's not a small gap — that's almost everyone stuck at the starting line.

I don't think most owners are stuck there because they don't know succession planning matters. They're stuck because succession planning forces you to answer harder questions first: Who am I without this business? What do I actually want the second half of my life to look like? Those aren't spreadsheet questions. They're identity questions — and most owners have never built the kind of life outside the business that makes those questions answerable.

2. This is a bigger wave than most owners realize

The report points to roughly 12 million businesses — representing nearly $10 trillion in assets — expected to change hands over the next decade. Other estimates run from 2.3 million to 6 million business transitions by 2035. The exact number depends on who's counting, but the direction is the same: an entire generation of owners is aging out of the businesses they spent decades building, at the same time.

That scale matters because it means the market for buyers, successors, and capital is about to get crowded. The owner who waits until year nine of a ten-year window to start planning isn't just risking a rushed exit — they're competing with millions of other owners doing the exact same thing, at the exact same time, for the exact same pool of buyers.

3. The paralysis runs from Main Street to the C-suite

What struck me most wasn't the small-business data — it was the reminder that this dysfunction isn't confined to the corner hardware store. A recent analysis found that at more than a third of S&P 500 companies sampled, the CEO and CFO were both sitting in the retirement window at the same time, with no clear succession plan disclosed.

If the leaders of the most sophisticated, best-resourced companies in the world are avoiding this conversation, it's not a sophistication problem. It's a human one. Nobody — regardless of the size of the business — wants to sit down and plan for their own obsolescence. That takes a level of self-awareness and surrender that most leadership training never touches.

4. Closures aren't happening because businesses fail — they're happening because owners run out of time

This is the line that should stop every business owner mid-scroll: research cited in the report suggests a meaningful share of small-business closures over the next decade are avoidable. Not because the business isn't viable. Because the owner ran out of time before finding a buyer or a successor.

Think about what that means. A business someone built for twenty or thirty years — one that provides jobs, serves customers, maybe even carries a family name — closes not because it stopped working, but because its owner never got around to answering the question of what comes next. That's not a market failure. That's a planning failure, and it's the kind of failure that compounds silently for years before it becomes irreversible.

5. The rare success story is a story about community, not solo grit

The report's bright spot is Nicole Williams and the Cowrie Collective — six Black women entrepreneurs in San Francisco who pooled their businesses into a shared retail space rather than each trying to grow alone. It worked because Williams didn't try to build, or transition, by herself. She recruited partners, brought in outside coaching, and used the structure of a shared enterprise to do something most solo owners never manage: plan on purpose, instead of by default.

That's the pattern I see over and over in my own work with business owners. The ones who actually build a plan for their exit are almost never the ones who tried to do it alone in their own head. They're the ones who brought their business decisions into the light — with a coach, a partner, a board, someone who could see what they couldn't see about their own blind spots.

Why this is an alignment problem, not just a business problem

Here's what I keep coming back to: a business owner who can't plan an exit is usually an owner whose calendar, marriage, and business have been running on autopilot for years — with no margin left over to think past the next quarter, let alone the next decade. Succession planning isn't really a late-career task you tack on when you're "ready to retire." It's the natural output of a life that's already in alignment — where your business serves your life instead of consuming it, where you and your spouse are actually talking about what's next, and where you've built in enough space to think clearly about decisions this size.

If you're reading this and quietly realizing you don't have a plan — you're not alone, and you're not behind in some unusual way. You're behind in the same way 92% of the owners in that survey are behind. The question isn't whether you're behind. It's whether you're going to start closing that gap now, while you still have runway, or wait until the runway runs out.

If you want a clearer picture of where the misalignment actually lives in your business, marriage, or calendar, take the free 3-minute Alignment Quiz. It won't write your succession plan for you — but it will show you exactly where to start.