The Hidden Emotional Side of Selling a Business
Before I started working as a broker, I made a trip over to Victoria to meet the team at Chinook. As they walked me through what it takes to succeed in this business, one comment stuck with me: “Only about 20% of this job is content knowledge, the rest is emotion management.”
At the time, I thought that was absurd. Business is numbers. ROI is calculated, not felt.
But we forget that behind every business are humans. And humans have emotions.
Having worked in the industry now, I can say that statement was dead-on. Every deal is different, and the 80/20 split varies depending on the owner’s situation and the complexity of the sale, but make no mistake: a big part of this work is acting as a pseudo business therapist.
It’s not something you’ll see on a billboard and most owners wouldn’t even admit they need it. But for most people, selling a business is deeply emotional. And having an experienced, unbiased third party to help manage that emotional ride can make or break a deal.
So let’s pretend we’re in therapy, grab your metaphorical tissue, and let’s talk about how emotions can quietly sabotage a business sale, and what to do about it
Why Selling is So Emotional
If you’ve never owned a business, hearing someone call it their “baby” might sound dramatic. But there’s some truth to it.
When you’ve poured blood, sweat, and tears into something for years or decades, selling it can be akin to leaving your baby on the front porch of a stranger’s house. It’s not just a transaction, it’s a letting go of a piece of you. The process can dredge up all kinds of uncomfortable emotions: fear about what comes next, anxiety over losing your sense of identity, guilt about leaving your staff and customers, or even anger when a buyer doesn’t see the value in what you’ve built.
Whether you like it or not, your business is a reflection of you. So don’t be surprised if trying to sell it stirs up some complex feelings. Feelings your friends, family, or even your therapist might not fully understand.
How Emotions Derail Deals
The Valuation Trap
One of the most common ways emotions derail a deal? Valuation disagreements.
Most founders overestimate what their business is worth. And honestly, it’s understandable. You’ve put your life into this thing. You’ve sacrificed weekends, sanity, and maybe even your health. It should be worth millions, right?
But markets don’t care about how hard you worked. Buyers are going to look at your financials, your profit margins, and how your business stacks up against others in your industry. That’s what drives a fair market valuation. Not the number of years you put in, how many all-nighters you pulled, or how much hair you lost getting here. It should matter, but it doesn’t.
Unclear Motivation = Deal Risk
The second big derailment? Lack of clarity around why you’re selling.
If you’ve ever worked with a broker, they’ve probably grilled you on this question. And with good reason. If you don’t have a solid reason for selling, or a clear plan for what comes next, you’re more likely to panic when the process gets messy (and trust me, it will). Deals take months, and when you hit the inevitable bumps, uncertainty can cause you to pull the plug, wasting your time, your team’s time, and the buyer’s time.
Plus, buyers want confidence that you’re not offloading a lemon. If you can’t articulate why you’re selling, they’ll start to wonder what you’re not telling them.
Other Emotional Landmines
Beyond valuation and motivation, there are plenty of smaller emotional triggers that can cause a deal to go up in flames. Sellers sometimes get offended by the due diligence process, especially when buyers start asking what feel like intrusive or nitpicky questions. Personality clashes between buyer and seller can sour the relationship before it ever reaches closing. And often, sellers unconsciously delay transition planning, not because the details are complex, but because they’re simply not ready to let go. These emotional undercurrents may not show up on a balance sheet, but they can be just as fatal to getting the deal done.
Advice for Sellers
If it’s your first time thinking about selling a business, how do you prepare yourself for the emotional roller coaster ahead?
I’m not going to tell you to meditate or channel your inner Spock and suppress all emotions. But there are a few things worth thinking about before you go to market, things that can save you time, money, and heartache.
Build a Trusted Team
Selling a business is never a solo mission. You need people in your corner who can give you objective, market-based advice. People who will tell you what’s normal, when to push back, and when to accept a tough reality.
Everything in the process is still your decision. But when emotions are running high (and they will), having a grounded team to keep you focused can be the difference between getting to the finish line and walking away frustrated and poorer.
Whether it’s your accountant, lawyer, or business broker, they’ll each have a valuable perspective to give as you work through this big transition.
Talk it Out Early and Don’t Bottle it Up
Just like your mom told you, you should always talk about your feelings. Cliche? Maybe. But it’s still true.
Whether it’s with friends, family, mentors, or your broker, say what’s on your mind. Voice your fears, doubts, and hesitations. The earlier they come out, the better. If you don’t address them early, they tend to surface later, right when the pressure is highest. And at that point, even something small can be enough to derail the entire deal.
Know Your “Why” and Think About Life After The Sale
Even if no one’s pressing you for an answer, take time to reflect on this: Why are you selling? What does life look like after the sale?
Are you genuinely ready to step away, or are you just chasing a hypothetical payday? Are you excited about what’s next, or do you feel lost at the thought of letting go?
If you’re on the fence, that uncertainty will eventually catch up with you, often at the worst time. Deals fall apart when sellers haven’t fully committed to the decision, and backing out late in the game can burn bridges with serious qualified buyers and end up costing you unnecessary stress and dollars.
Be Open To Feedback on Value and Process
The truth is, selling a business involves compromise. You’re trying to get strangers to agree on the value of something that’s part numbers, part story, and part emotion. It’s not going to go exactly how you imagined.
That’s why it’s critical to stay open to feedback, whether it’s from your broker, accountant, or lawyer. You don’t have to take every piece of advice, but don’t shut it down because it’s uncomfortable. Any critique is meant to help you get to the best possible deal, not to tear down what you’ve built.
Exit Plans Start On the Inside
Selling a business isn’t just a financial decision, it’s an emotional one. It marks the end of a chapter you’ve likely poured years of your life into. And even if you’re ready on paper, you might not be ready in your gut.
That’s why emotional awareness matters just as much as deal mechanics. It’s what helps you navigate tough conversations, handle surprises, and stay grounded when things inevitably get messy.
The best deals happen when owners are clear-eyed about what they want, supported by the right team, and open to where the process takes them, even if it doesn’t look exactly like they expected.
So if you're thinking about selling, do your homework. But also, do your inner work. Though it might not show on your financials, it’s often what gets the deal done.
