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After 18 Years: What Selling Your Company Actually Feels Like

Every founder fantasy ends the same way:

“One day I’ll sell this thing and finally relax.”

You picture the wire hitting, a big exhale, maybe a beach, maybe a stupid car, and some kind of permanent relief.

What actually happened for me after 18 years was a lot more complicated:

Relief, yes.
But also grief.
A weird emotional vacuum.
And the sudden realization that the thing that ran my life, calendar, and identity was just… gone.

This is what it actually felt like.

1. The Decision to Sell

It wasn’t one moment. It was a slow accumulation.

The year before the sale, a few things were true at the same time:

The business was mature and stable.
The system was deeply embedded in real operations.
I was tired in a way vacations don’t fix.

It wasn’t “I hate this.” It was:

I’ve been carrying this thing on my back for almost two decades.
Every new contract, every new integration, every new regulatory shift piles on more responsibility.
It’s not just a product; it’s a promise to entire states, agencies, and people.

At the same time:

Market conditions were decent.
There were potential buyers who understood the space.
I knew that if we were going to sell, it had to be from a position of strength, not after burnout had wrecked everything.

So the decision was a mix of:

Timing: the company was in a good place externally.
Opportunity: serious interest from buyers.
Self-awareness: I didn’t want to become the bitter, exhausted founder who hangs on too long and resents his own product.

It wasn’t some Hollywood “aha” moment. It was me finally admitting:

“I’ve taken this as far as I want to personally.
It deserves to keep going. I don’t necessarily want to keep doing this for another 10 years.”

2. The Sale Process: Not Fun, Not Glamorous

The sale process is basically:

Run your business and live inside a multi-month audit at the same time.

Even high level, the pattern is the same:

NDAs
Initial conversations
LOI (Letter of Intent)
Due diligence (the grind)
Negotiations around everything:
- price
- structure
- earn-outs
- roles
Closing mechanics

Due diligence is where the fantasy dies:

They want to see:
- contracts
- financials
- customer concentration
- renewal histories
- code risk
- infra risk
- legal risk
They ask the same questions 5 different ways.
You realize how much of your company lives in your head and has to be turned into paperwork.

You’re still:

Running operations
Keeping customers happy
Trying not to slip on performance while people are digging through everything.

It’s exhausting. It’s necessary. It’s not “dealmakers with cigars and champagne.” It’s a spreadsheet and PDF marathon.

3. Closing Day: Not the Movie Version

People imagine:

Huge party
Fireworks
Tears of joy
Life instantly different

Closing day for me felt more like:

A long build-up
A bunch of signatures
Some logistics
And then…

“Okay. That’s it. It’s done.”

There was some relief, yes:

The transaction is real.
The risk is transferred.
The thing you’ve been working toward is no longer hypothetical.

But at the same time:

No one hands you a new identity.
There’s no automatic sense of “completion.”
There’s just… silence.

It’s like finishing a marathon alone on an empty street. You stop running, but your body and brain are still in “keep going” mode.

The void after selling

4. The Weird Emptiness

This is the part nobody talks about.

For 18 years:

My calendar was structured by the company.
My decisions were filtered through:
- “What’s best for the business?”
- “What’s best for the customers?”
My sense of usefulness came from:
- solving fires
- making calls
- shipping things
- supporting the team

After the sale:

The Slack pings stop.
The email volume drops.
People don’t ask you for decisions anymore.
The system keeps running… without you.

That “weird emptiness” is:

Losing the constant pull of a demanding machine.
Realizing how much of your day was reactive energy.
The sudden absence of “I’m needed.”

You don’t just lose a job.
You lose the gravity well you’ve orbited for nearly two decades.

5. What I Expected vs What Actually Happened

What I expected:

A big sense of closure
Clear “chapter end” feeling
Freedom, mentally and physically
Maybe boredom in a good way

What actually happened:

My body was still wired for:
- urgency
- surveillance of risk
- scanning for what might break
I kept:
- waking up thinking about edge cases
- mentally checking on systems I no longer owned
The “freedom” felt… disorienting.

I thought:

“Exit = permanent exhale.”

What I got was:

“Exit = my brain running the old playbook with nothing to attach it to.”

Huge difference.

6. The First Week After

The first week after not being “the person” anymore was bizarre.

On paper, I had:

Time
Space
No more direct responsibility for:
- payroll
- contracts
- midnight outages

In reality, the first week felt like:

Phantom limb syndrome:
- Reaching for a dashboard I no longer had access to
- Thinking “I should check on X” and then remembering: that’s not my role anymore.
A weird mix of:
- relief
- restlessness
- a low-level “what now?” hum

Things I did notice pretty quickly that I didn’t miss:

The constant mental checklist running 24/7.
The feeling that any day could blow up because of:
- a regulatory change
- a contract crisis
- an outage

Things I did miss:

The team
The sense of being in the loop
Knowing exactly what my role in the world was every day

7. Identity Loss: Who Are You Without the Company?

For 18 years, if someone asked:

“So what do you do?”

The answer was easy:

“I run [company]. We do [X] for [Y].”

After the sale, that vanished overnight.

Now what?

“I used to run…”
“I sold…”
“I’m figuring out what’s next…”

It’s uncomfortable how fast:

You go from central to optional.
The thing you built becomes “the product” and “the platform,” not “your baby.”

If you tie your identity too tightly to:

“I am the founder”
“I am the CEO”
“I am the architect of this system”

…then selling feels partly like killing off a version of yourself.

I had to relearn:

How to describe myself without leaning on the company as a crutch.
How to value my skills outside that specific context.

It’s not instant. It’s not clean.

8. Financial Reality (Without Numbers)

I’m not dropping specific numbers, but I’ll say this:

It was meaningful.
It was the result of 18 years of work, not a lottery ticket.
It wasn’t some fantasy “never think about money again, disappear to an island” outcome.

Founders don’t talk about this enough:

You can have a good exit and still:
- feel a gap between the myth and the reality
- feel the weight of “was that the right trade?”
- still need to figure out what you’re doing next

Money solves financial stress.
It does not solve:

Purpose
Identity
Direction

If you go into an exit thinking:

“Once the money hits, everything internal will magically resolve,”

you’re setting yourself up for a hard crash.

9. Regrets?

Do I regret selling?

No.

If I dropped back into that exact situation, with the same:

personal state
company maturity
market context

I’d make the same call.

What I would do differently:

Start emotional prep earlier
- Not just the legal and financial prep.
- Actually ask:
  - “Who am I without this?”
  - “What do I want the next chapter to look like?”
Structure more space after the sale on purpose
- Instead of assuming “I’ll naturally relax and reset.”
- Be intentional about:
  - decompression
  - reflection
  - not instantly jumping into “the next thing” to fill the void.

I don’t regret stepping away.
I do think we under-estimate how much decompression time is healthy after nearly two decades in one seat.

10. The “Now What?” Question

After 18 years building one thing, you don’t just:

Flip into “normal life”
Or immediately land the perfect next mission

The “now what?” phase looked like:

A lot of quiet that felt wrong at first
Experimenting with:
- ideas
- advisory roles
- new projects
Realizing:
- I’m not done building, but I am done carrying another 18-year grind on my back in the same way.

It took time to:

Separate:
- “I’m good at building systems and companies”
- from
- “I have to recreate the exact same structure of responsibility I just left.”
Decide:
- What tempo I want my life to run at now
- What problems are worth caring about enough to commit again
- How to use what I learned without re-trapping myself

If you’re expecting a neat bow like:

“And now I do X and it’s perfect,”

that’s not how this works.

The honest version is:

Selling after 18 years is not the end of the story.
It just hands you a blank page again.
And you have to write the next chapter deliberately instead of by accident.

The real “exit” isn’t the transaction.

It’s when you stop needing your old company to define who you are
and start using that experience as raw material for whatever comes next.

Context → Decision → Outcome → Metric

Context: 18-year single-system founder/CEO, $12M+ revenue, 588 people at peak, zero contract losses in 12 years, and personal fatigue that vacations could not fix.
Decision: Sell from a position of strength while uptime, renewals, and audit posture were solid—before resentment or burnout degraded the product.
Outcome: Clean exit, platform kept running, staff retained, customers stable. Emotional decompression became the real project.
Metric: Zero customer churn tied to the sale; uptime held; contract renewal rate stayed above 95% during and after diligence.

Anecdote: The Pre-Sale Drill That Saved Diligence

Two months before LOI, we ran a fake diligence sprint: every director had to produce evidence (contracts, runbooks, DR tests, audit trails). We found three gaps—expired SLAs, missing schema docs for an integration, and an undocumented batch job. Fixing those before buyers asked changed the tone of diligence from defensive to “here’s the binder.” It also proved to the team that the system was in shape to hand off.

Mini Checklist for Founders Considering a Sale

Build a single evidence binder: uptime reports, DR tests, security controls, architecture diagrams, and renewal history.
Run a mock diligence with your own team and fix the gaps before outsiders find them.
Decide what you want your life to look like after closing; the blank page shows up fast.
Plan a decompression window on purpose—if you don’t, the calendar will refill itself.