Yesterday, I was talking to a client who is also a good mate.
He was a bit flat and struggling to get back into the swing of things this year.
Here’s what he said:
“Peter, do you know anyone who would buy my business.”
Now, I’ve heard this before. Many times. It’s a stage most business owners reach at some point, especially after they’ve worked their butts off to build something successful. But then, success starts to feel like a double-edged sword.
Here’s the context of his business:
- Annual revenue: a few million dollars
- Margins: not bad, but not amazing
- Profits: $500k–$700k per year (before taxes and lifestyle expenses)
- Outlook: not “rich,” just comfortable
- Frustration: growing resentment for the business
- Options: Selling would only generate a 2-4X multiple of profit, which doesn’t feel like enough to justify the effort he’s put in
He’s in what I call the “golden handcuffs” phase.
You’ve built a solid 7-figure business, and on paper, you’re killing it.
But when you sit with a beer late at night, staring at your profit numbers… you realize it doesn’t feel as good as you thought it would.
It feels like a job.
You’ve got a few options:
- Sell the business — but the payout isn’t enough to retire, and it doesn’t feel like a fair reward for all the years of hustle.
- Keep grinding — but how long can you do that before burning out?
- Step back — hire a CEO/GM and reclaim your time… but you worry the business might no run so well without you at the helm.
The frustration, the stuck feeling, the “is this all worth it?” questions — it’s common.
So, I gave him some things to think about, and I want to share them with you, too.
If you’ve ever felt like this — like your business owns you more than you own it — these questions might help you gain some clarity:
1. What’s your F-off number?
You can’t work toward financial freedom without knowing what that number is.
What’s the dollar amount that would make you feel ready to walk away or at least not HAVE TO work?
2. How long would it take to hit that number?
If you keep running your business as it is today, how long will it realistically take to hit that freedom number?
Are you okay with that timeline?
3. Could a sale get you there faster?
If you sold today, would you hit your number?
If not, what changes could you make to the business to increase its value before selling?
4. Do you actually want to sell?
Be honest with yourself:
Do you want to sell, or do you just want to stop running the business?
There’s a big difference.
5. If money weren’t the issue, what would you do?
Imagine you already had your f-off number in the bank.
Would you still run the business because you love it?
Or would you bolt the second you hit your goal?
6. Could another opportunity get you there faster?
Is there another business idea that excites you more?
Could it have higher potential than what you’re doing now?
(Just remember — every new venture eventually becomes a job, too.)
7. What if you stepped back?
What would happen if you hired a CEO/GM or key leaders to take over the day-to-day?
Could you step back to 1–2 days a week and still pull in 80% of the profits?
These questions aren’t easy. They require some careful thought.
But here’s the truth I’ve seen time and time again:
“I want to sell my business” is almost never about the money.
It’s about something deeper.
Maybe you’re bored.
Maybe you’re burned out.
Maybe you feel stuck in the weeds, managing instead of building.
The good news? There’s a way out that doesn’t always involve selling.
It could be hiring the right people.
It could be creating systems to step back.
It could even be starting a side project that lights you up.
Whatever the solution is, the goal is this: You want to love your business again.
Because when you do, the idea of selling won’t even cross your mind.
If this resonates, let’s chat.
Sometimes, just having an outsider look at your financials or operations can help you see opportunities you’ve been missing.
Here’s an overview of getting the foundations in place: https://www.peterwesley.me/post/the-trade-contractor-operating-system
As always, I’m here to help.