The Number That Decides Whether You Work 5 More Years

How to calculate with certainty whether you can step away now or need to grind for 5 more years…

(If you're looking for my typical video – you'll find it at the bottom of the blog today. Read on!)

If you run a practice or business doing $1–10M in revenue, there’s a good chance you’ve had this thought:

“I’m doing well… but what's my exit plan?”

From the outside, everything looks solid.

The business is profitable.
You’re earning more than you ever have.
Your net worth has grown.

By most measures, you’ve won.

And yet…

You’re still deeply involved in operations.
You still carry the weight.
And you still don’t know the answer to one simple question:

How much is enough?

That question sits quietly in the background.

It shows up when you think about slowing down.
When your spouse asks about long-term plans.
When you watch someone else sell and wonder if you should.

But most founders don’t answer it.

They default to something easier:

“Let’s just do a few more years.”

The “Few More Years” Strategy

On paper, it sounds responsible.

Another few years of growth.
Another push on valuation.
Another cycle of reinvestment.

What could go wrong?

In my experience looking over financials for thousands of doctors, there is a “flattening of the curve” that happens for professionals late in their career. When normalized against inflation, the real purchasing power of your net worth doesn't grow as fast many think.

The primary impact is just using up more years of your life so that you don't have as many years of retirement to fund.

Which is sad, when you think about it.

The “few more years” decision is usually driven by three things:

Fear of not having enough
Lack of clarity
Inertia

If you don’t know what you actually need, you can’t know whether you already have it.

So you stay.

Not because it’s optimal.
But because it feels safer than guessing.

Revenue Is Not Freedom

Here’s a subtle trap I see often.

A founder earns $500K or $1M per year and assumes they’re financially secure.

But income is not freedom.

Freedom is the point at which your invested assets — not your effort — fund your lifestyle.

That’s a completely different equation.

If your lifestyle costs $400K per year and you don’t know:

Your true personal burn rate
The invested asset base required to support it
The return assumptions you’re relying on
The gap between where you are and where you need to be

… then you’re not free.

You’re successful.

There’s a difference.

The Personal Burn Rate Blind Spot

One of the most surprising conversations I have with founders revolves around spending.

Most don’t know their real annual burn rate.

They know revenue.
They know EBITDA.
They know enterprise value.

But ask them what they actually spend per year across:

Lifestyle
Travel
Insurance
Taxes
Philanthropy
Family support
Debt service

And the number is usually a guess.

In running the numbers with hundreds of doctors, on average they underestimate by 35-45%.

If you don’t know what it costs to live your life, how can you know what it takes to fund it without working?

This is where clarity starts.

Why Your Advisor Can’t Answer This for You

Most financial advisors are excellent at portfolio construction.

They optimize returns.
They diversify risk.
They allocate assets.

But they rarely anchor everything to one central question:

“What number makes work optional?”

That question requires integrating:

Personal lifestyle design
Business valuation realities
Exit timing
Capital preservation strategy
Sustainable cashflow planning

That’s not just a portfolio conversation.

It’s a freedom conversation.

And until you run that math, everything else is guesswork.

The Business Sale Assumption

Another quiet assumption many founders carry:

“When I sell the business, I’ll be set.”

Maybe.

But have you calculated what the business would actually need to sell for — after taxes, fees, and reinvestment — to fund your lifestyle indefinitely?

Have you stress-tested lower valuation scenarios?

Have you separated what you hope it’s worth from what the market might pay?

If your entire retirement plan depends on one liquidity event, that deserves more scrutiny than optimism.

Wealth on Paper vs. Wealth in Practice

There’s a psychological layer here too.

Your business may represent 70–90% of your net worth.

That’s wealth.

But it’s illiquid.

It requires your involvement.
It carries operational risk.
It fluctuates with markets and industry cycles.

Until that equity becomes diversified, income-producing capital, it doesn’t buy time.

It buys responsibility.

There’s nothing wrong with that — unless you believe it equals freedom.

What Happens When You Run the Numbers

When founders finally calculate what I call their Freedom Number, one of two things usually happens.

Either:

They realize they’re closer than they thought.

Or:

They see clearly what needs to happen to close the gap.

Both outcomes are powerful.

Because clarity changes behavior.

If you’re close, you might begin transitioning sooner.
If you’re not, you can commit to another 3–5 years intentionally — with defined targets.

The difference between drifting and deciding is math.

Capital Stewardship Matters

Let’s assume you exit.

Now what?

How will you steward that capital?

The shift from operator to allocator is not trivial.

You move from:

Controlling outcomes

Managing risk and preserving purchasing power.

That transition requires:

A clear capital preservation strategy
Thoughtful income design
Risk calibration aligned to lifestyle needs
Guardrails against overexposure

Winning the exit is only half the equation.

Protecting the freedom it creates is the other half.

You Don’t Need Motivation. You Need Specificity.

Most founders don’t struggle with work ethic.

They struggle with ambiguity.

They don’t lack discipline.
They lack precision.

Clarity around your Freedom Number answers:

How much is enough?
How far away am I?
What must come from a sale vs. invested assets?
Is staying another five years rational — or emotional?

Without that clarity, “a few more years” can quietly become ten.

With it, you regain control of the timeline.

A Different Way to Think About Success

Business success is one game.

Freedom is another.

Revenue measures the first.
Optionality measures the second.

At some point — especially between 40 and 60 — the second game starts to matter more.

The solution isn’t working harder.

It’s running the numbers.

If this topic resonates, I’ll be walking through the full framework live in an upcoming live hands on workshop where we calculate your Freedom Number step by step and explore what it means for your exit timeline.

Here is a short video with my thoughts on how this could be relevant for you: