So, you’re thinking about selling your business. Maybe you’ve had a few conversations with a broker, poked around some valuation calculators, or even fantasied about the moment the wire transfer hits your bank account. Freedom. A new chapter. No more Slack messages at 10 p.m. Bliss, right?

Hold up. Let’s be real for a second.

Selling your business isn’t like selling a house. You don’t just stick a ‘For Sale’ sign in the yard, let a broker handle the paperwork, and collect a tidy sum at closing. No. This is your business. Your legacy. The thing you’ve bled for, stressed over, built from nothing. You don’t just sell it — you transition out of it. And if you don’t take the emotional side seriously, you’re in for one hell of a wake-up call.

The Thought That’s Lodged in Your Brain Right Now

Right now, you’re probably thinking: I’ll hire a broker, they’ll find a buyer, and we’ll get a deal done. Simple.

Except it’s not.

Because if you don’t get your head straight before you start this process, you’ll either:

1. Walk away with a deal that doesn’t feel as good as you thought it would.

2. Sabotage the deal midway through because you weren’t actually ready to let go.

3. Sell — and then feel completely lost afterward.

    

I don’t want that for you.

So, let’s talk about what actually happens when an entrepreneur sells their business — and how to make sure you come out of it without regrets.

You’re Selling More Than Just a Business

When you tell people you’re selling your business, what they hear is: You’re cashing out and sailing off into the sunset.

What you’re actually doing is: Selling an identity, a routine, a purpose, and a massive chunk of your brain space.

That’s why so many founders get hit with a gut-punch of regret post-sale. It’s like a band breaking up. You go from being the frontman, making things happen, to… what, exactly? Sitting at home, wondering why your inbox is so quiet?

The businesses that sell for real money — the kind where you walk away feeling proud — aren’t just businesses. They’re machines that don’t need you anymore. And that’s a tough pill to swallow.

The “Holy Sh*t” Moment That No One Warns You About

Every founder I’ve spoken to who’s sold their business has had a moment.

It usually happens when the deal is real — not just hypothetical. The buyer is in. The money is about to change hands. And suddenly, the entrepreneur is staring at their business like a parent dropping their kid off at university for the first time.

What if they don’t run it the way I would?What if my team leaves?What if I hate life after this?

If you don’t prepare for this moment, you might kill your own deal — without even realising it.

How to Actually Get Ready (Hint: It’s Not Just About the Money)

1. Get Clear on What’s Next

If you think you’ll just “figure it out” after selling, think again. The best exits happen when you have a compelling reason to leave — not just “I’m tired” or “It’s time.”

Ask yourself:

• What will my days look like post-sale?

• Am I building another business?

• Will I invest, advise, travel, learn?

   

If you don’t have a clear next step, you’ll be tempted to drag your feet — or worse, blow up the sale last minute.

2. Stop Thinking Like a Business Owner — Start Thinking Like a Buyer

Buyers don’t want a business that relies on you. They want a business that runs smoothly without you.

Before you sell, ask yourself:

• Can my team run this without me?

• Are my systems documented, or am I the human Google of my company?

• Does the business have growth potential, or am I the bottleneck?

   

The more detached you are, the higher the valuation — and the easier it will be to walk away.

3. Talk to Someone Who’s Been Through It

There’s a reason top athletes don’t retire without a plan. They’ve seen what happens when people go from “all-in” to “nothing.” Same with entrepreneurs.

Find someone who’s exited before. Ask them:

• What surprised you most about selling?

• What do you wish you had done differently?

• How did you fill the gap post-sale?

   

Learn from their hindsight. It’ll save you a world of regret.

Final Thought: This Is More Than a Paycheck

If you’ve built something valuable, you deserve to sell it on your terms. But that means taking this seriously before the process starts.

This isn’t a house sale. This isn’t a stock trade. This is your business.

And when you sell, you want to walk away knowing you did it right.

So, are you actually ready? Or do you need to have a real conversation about what comes next?

🔥 Let’s Talk 🔥

If this hit home, let’s have a conversation. No fluff, no sales pitch — just a real talk about what your exit could actually look like.

Because selling your business should feel like freedom, not a funeral.