If you’re thinking about selling your practice—or you’ve already started down that road—you might find yourself wrestling with a question that keeps popping up:
“Am I really ready to do this?”
This is based on insights from a recent Fireside Chat with industry experts Steve Mountain, Sean Healy, and George Fox—who have each played key roles in the buying and selling of practices from different angles, including M&A, accounting, and acquisition.
Selling a practice isn’t just a transaction. It’s a life decision. And no matter how much money is on the table, if you’re not clear about why you’re doing it, you can wind up with something worse than regret—you can wind up with seller’s remorse.
Let’s break this down so you can move forward with clarity, confidence, and peace of mind. No second-guessing. No sleepless nights. Just a decision that feels right because it is right—for you, your family, and your future.
What Is Seller’s Remorse, Really?
Seller’s remorse happens when you make a decision that doesn’t line up with what you truly want. You might feel like you lost a part of your identity. You might question if you jumped too soon—or worse, if you sold for the wrong reasons.
Here’s what most people don’t tell you:
It’s not just about whether you sold for top dollar. It’s also about whether you made the decision with full clarity and intention.
Selling your practice is the easy part. What comes before and after is where the real work (and real freedom) lives.
Why You Might Be Considering a Sale
Let’s start with your why. You need to be brutally honest with yourself here.
Are you:
- Burnt out and running on fumes?
- Tired of managing people and handling all the day-to-day?
- Feeling like the business owns you instead of the other way around?
- Tempted by a big offer that sounds like a way out?
None of those are wrong reasons to sell.
But here’s the catch: if you’re only selling to escape, you’re setting yourself up for remorse.
The practice might be the source of your stress, but it’s also something you built. It’s part of your identity. And selling it without a clear picture of what comes next can leave a hole you didn’t see coming.
Get Clear on What You Really Want
Clarity comes before confidence.
That’s true whether you’re trying to grow your business or get out of it.
If you’re even thinking about selling, you owe it to yourself to slow down and get real clear on a few things:
1. What does your ideal life look like—after the sale?
Be specific. How do you want to spend your time? Who do you want to spend it with? What role, if any, do you want to play in the business going forward?
If you can’t paint a vivid picture of what comes next, you’re not ready to sell.
2. Are you truly done being a practice owner—or just done with how you’re running it?
There’s a difference between wanting out and needing a reset. Sometimes it’s not the business that’s broken—it’s your relationship to the business. You may need to re-structure your role, not sell the whole thing.
3. What’s driving your desire to sell?
Is it fear? Fatigue? Frustration? Or is it a real, intentional pivot toward something that lights you up?
The more honest you are here, the better your decision will be.
Mistakes That Lead to Seller’s Remorse
Let me share some of the most common mistakes I see owners make when they’re considering a sale:
1. Rushing into it
Desperation leads to bad decisions. Don’t let burnout or a tempting offer push you into a fast sale. Selling from emotion rather than strategy almost always leads to regret.
2. Letting someone else drive the process
This is your business and your decision. Advisors, brokers, and even family members may mean well—but if they’re more excited about the deal than you are, that’s a red flag.
3. Not preparing the business first
If your systems are shaky and your team relies on you for everything, your business isn’t truly sellable. Or at least, not for the price you want. That creates unnecessary stress during and after the transition.
If you’ve been treating the business like your baby instead of building it to run without you, it’s time to make some changes—before you sell.
How to Build Confidence Before You Sell
Clarity brings confidence. So how do you build that clarity?
Here’s a step-by-step approach:
Step 1: Journal your thoughts for 30 days
Each day, write down what’s coming up for you about selling—fears, hopes, dreams, hesitations. Don’t edit. Don’t filter. Just write. Patterns will emerge that will guide your decision.
Step 2: Talk to someone who’s done it
There’s no better teacher than someone who’s already been through it. Ask them what they wish they knew, what surprised them, and what they’d do differently.
Step 3: Test-drive your post-sale life
If your goal is more freedom, try stepping back from the business now to see how that feels. Take a month off. Let your team lead. See if it’s the business you’re done with—or just the way you’ve been running it.
Step 4: Work with an advisor who gets it
This isn’t the time for cookie-cutter advice. You need someone who understands the business side and the personal side. Someone who can help you explore all your options—including keeping the business and scaling it in a different way.
Selling your practice can be a beautiful, empowering decision. But only if you do it for the right reasons. Don’t let burnout, fear, or a big paycheck make the call for you. Take the time to get clear on what you really want—emotionally, financially, and personally. When you know why you’re selling and what you’re moving toward, you won’t just avoid seller’s remorse.
You’ll step into your next chapter with full confidence—and zero regrets.
At Practice Freedom U, I help practice owners like you navigate this exact decision—whether to sell, scale, or step away. It’s not just about making the numbers work. It’s about aligning your business with the life you actually want. If you’re feeling stuck or unsure, let’s talk. You don’t have to figure this out alone.
This is just a small part of what we covered in the Fireside Chat. Let me know if you want the link to the full recording.
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