The Exit Trap: Why Waiting to Plan Quietly Removes Choice

Reflections on legacy, responsibility, and planning with the end in mind

This post explores a pattern I see often among business owners and leaders: planning for the end is postponed not because people don’t care, but because growth and responsibility demand attention now. Over time, that delay quietly reduces choice—long before anyone intends to exit.

I recently met a business owner whose company is growing fast.

They had reached $300,000 in revenue in their first year and were on track for $600,000 the next. Energy was high. Opportunity felt wide open. Naturally, their attention was on scaling—new clients, new systems, what the business could become.

They were already imagining a future sale.

But when we talked about preparation, they waved it off gently.
“I’ll deal with that in a couple of years.”

The comment stayed with me—not because it was careless, but because it was familiar.

Around the same time, an exit-planning colleague said something that has echoed in my mind ever since:

“Most companies need at least three years to be ready.”

Not three years todecideto sell.
Three years to beready for the option.

That distinction matters more than most people realize.

The trap isn’t failing to plan — it’s assuming there’s time

Many business owners assume exit planning begins when selling is imminent.

But for many, “later” quietly becomes too late.

Not because the business failed.
Not because the owner stopped caring.
But because the business evolved around them instead of beyond them.

According to the Exit Planning Institute,70–80% of businesses that go up for sale don’t sell as planned. Owners often receive less than they expected—or discover that the business can’t support their retirement or family goals at all.

The reasons are rarely dramatic:

• The business depends too heavily on the owner

• Knowledge and relationships aren’t transferable

• Structure never caught up with growth

• A health issue or life event forces timing no one chose

This isn’t recklessness.
It’s what happens when responsibility compounds faster than planning does.

Growth can mask fragility

When a business is growing, it’s easy to assume strength.

Revenue is up. Clients are coming in. The owner is deeply involved. From the inside, everything feels alive and moving forward.

But growth can hide a different reality:
that the business worksbecauseof the owner, not independently of them.

That distinction doesn’t matter—until it suddenly matters a great deal.

A business that can’t function, transfer, or be valued without its founder hasn’t failed. But it has quietly narrowed its future options.

This is the exit trap.

Not a lack of ambition.
Not a lack of intelligence.
But a delay in planning for an end that feels distant—until it isn’t.

Exit planning is really about responsibility and continuity

Despite the name, exit planning isn’t primarily about selling.

It’s about asking different questionsnow:

• What does this business need to survive me?

• Who or what depends on it continuing well?

• How much of my personal security is tied to something only I can hold together?

These are not transactional questions.
They’re responsibility questions.

For many owners—especially those also supporting families, aging parents, or employees—these decisions sit at the intersection of work, legacy, and care.

Planning with the end in mind doesn’t mean rushing toward it.

It meansbuilding a business strong enough to give you choices:

• To sell

• To step back

• To slow down

• To continue with intention

Choice is the real asset.

What waiting quietly takes away

The cost of delay is rarely obvious at first.

Nothing breaks.
Nothing collapses.
There’s no alarm.

But over time:

• Options narrow

• Timelines harden

• Pressure replaces intention

When planning is deferred long enough, decisions stop being chosen and start being forced.

That’s when owners discover they’ve built something impressive—but not something flexible.

The goal isn’t to reach the finish line faster.

It’s to avoid waking up one day and realizing the finish line is the only option left.

Planning with the end in mind isn’t about predicting the future.
It’s about respecting how quickly responsibility compounds—and how quietly choice can disappear when preparation is postponed.

Because “someday” doesn’t usually arrive all at once.

It arrives through constraint.

If you’re building something others depend on—employees, family, or both—this question matters earlier than it feels comfortable to admit.

And if this way of thinking resonates, I invite you to stay connected. This space is about money and business, yes—but more fundamentally, it’s about responsibility: how it’s carried, how it grows, and how to build structures that can hold it over time.

Toward greater clarity,
Sarah

References:

• Exit Planning Institute, State of Owner Readiness Report 2025: https://exit-planning-institute.org/state-of-owner-readiness

• BizBuySell, Q2 2025 Insight Report: https://www.bizbuysell.com/insight-report/