The emotional side of selling that nobody warns you about.
When my family’s business sold at the end of 2023, I was ready. Genuinely, fully, completely ready. I had been working toward it, planning for it, and I knew it was the right move. Zero doubt.
And then the day it was officially done, I just sat in my car for an hour and felt really strange.
It wasn’t sadness exactly. It wasn’t regret. It was more like a quiet identity shift that hit me all at once. If I’m not the person who runs that business anymore, then who am I right now? What do I do on Monday? Also the feeling of…oh crap now I have to tell my staff.
Nobody warned me about that part. Not because it would have changed my decision, but I would have felt a lot less alone in the moment if someone had.
It’s Not Just a Transaction
The thing that trips up most business owners when they start thinking about selling is that they approach it as a purely financial event. And it is that. There are numbers and negotiations and legal documents and all the rest.
But it’s also this deeply personal thing where you’re handing over something you built, grew, or poured yourself into for years. Something that has shaped your identity, your schedule, your friendships, your sense of purpose.
No matter how ready you are, that transition is going to feel like something.
For some people it feels like relief. For some it feels like grief. For most of us it’s a weird cocktail of both that doesn’t really have a name.
The Identity Question
Here’s what I wasn’t prepared for: how much of my identity was wrapped up in being a business owner. Not just professionally. Personally. When people asked “what do you do,” I had an answer. When I woke up in the morning, I had a purpose. When I made decisions about my time or my money, they were filtered through the lens of the business.
Then one day that lens was gone and everything looked different. Not bad. Just different. And different takes some getting used to.
I’ve talked to other owners who’ve been through this and they all say some version of the same thing. It’s not that they miss the stress or the 70-hour weeks. It’s that they miss having a thing. A place to put their energy. A reason to be needed.
The Relationship Part
The other thing nobody talks about is the relationships. When you own a business, you’re connected to people in a really specific way. Your employees, your vendors, your clients, your community. When you sell, those relationships shift. Some stay. Most change. A others just quietly fade away.
That part caught me off guard more than I expected. Not because I didn’t know it would happen, but because knowing it intellectually and feeling it emotionally are two very different things.
If You’re Thinking About Selling
If you’re thinking about selling your business someday, here’s what I want you to know about the emotional side of it.
It’s normal to feel weird after. Even if you’re thrilled. Even if it was everything you wanted. The transition is real, it takes time, and that doesn’t mean you made the wrong call.
Start thinking about your identity outside the business now. Not because you need to have it all figured out before you sell, but because having even a rough sense of what comes next makes the landing so much softer.
Talk to other people who’ve been through it. The number one thing that helped me was hearing someone else say “yeah, I felt that too.” It’s incredibly normalizing.
If you’re a business owner thinking about what comes next and you want to talk to someone who’s been through it, come find me at ExitsWithErin.com.
Erin Fitzpatrick is a M&A Advisor with Voyage Acquisitions and also provides business coaching and consulting services. She helps business owners grow their businesses, plan their exits, and figure out what comes next. You can reach her at hello@exitswitherin.com.