Most Exits Happen When Owners Aren’t Ready. Here’s How to Avoid That

December does something funny to business owners.

You finally slow down.
The inbox quiets.
The calendar gets lighter.

And suddenly, all the things you’ve been postponing show up uninvited.

Not next quarter.
Not “after this busy season.”
Now.

Here’s the uncomfortable truth most owners never hear until it’s too late:

Very few businesses are sold when the owner wants to exit.
Most exits happen when the owner is forced to.

And forced exits don’t come with leverage, clean deals, or great outcomes.

They come with stress, discounts, and regret.

The Real Reason Most Exits Go Sideways

It’s not market conditions.
It’s not timing.
It’s not even valuation.

It’s that most owners never plan for an exit because they assume they’ll decide when it happens.

Reality has other plans.

In exit planning, we call them the 5 Ds. And they don’t care about your calendar, your goals, or your to-do list.

The 5 Ds That Force Business Owners Into Bad Exits

1. Death

Let’s not sugarcoat it.
If something happens to you tomorrow, what happens to the business?

No plan means chaos.
Chaos destroys value fast.

2. Disability

Burnout. Health scares. Injuries. Chronic stress catching up.

If you’re the engine and the engine stalls, the whole operation follows.

3. Divorce

Divorce doesn’t just divide assets. It divides leverage.

Suddenly, decisions aren’t strategic. They’re emotional. And buyers smell that from a mile away.

4. Distress

Cash flow issues. Bad financing. One rough year turning into three.

Distress doesn’t usually announce itself loudly. It creeps in quietly… until your options shrink.

5. Disagreement

Partners fall out. Family dynamics change. Vision fractures.

When alignment disappears, value follows it out the door.

Why December Is the Best Time to Face This (Quietly)

December isn’t about panic planning.
It’s about honest reflection.

You’re already reviewing numbers.
You’re already thinking about next year.
You’re already aware of what feels fragile.

This is the moment to ask:

• Could this business survive without me?
• Do I have real options if something unexpected happens?
• Am I building value… or just staying busy?

You don’t need to sell.
You don’t need to announce anything.
You just need to de-risk.

Quietly. Intentionally. On your terms.

What “Being Ready” Actually Means

Exit readiness doesn’t mean you’re walking away tomorrow.

It means:

• The business isn’t 100% dependent on you
• Financials tell a clean, believable story
• Key risks are identified and managed
• You have options instead of ultimatums

The irony?
Businesses that are exit-ready almost never need to exit.

They have leverage.
They have flexibility.
They have control.

The Worst Time to Think About an Exit Is When You Need One

Forced exits happen fast.
Prepared exits happen on purpose.

Let’s Talk Before You’re Forced To

Shield Advisory Group works with business owners to reduce risk, improve optionality, and put structure around decisions before pressure enters the room.

If this year stirred up questions you’ve been postponing, now is a good time to talk them through. CLICK HERE to book a call today.