Selling the Business That Built Our Life: The Emotional Reality of Starting Over

We think about blowing up our lives and starting over all the time. In our heads it's clean and exciting, a decision made, a new chapter begun. In reality it's time consuming, tedious, and emotionally complicated in ways you don't anticipate until you're standing right in the middle of it.

Selling our auto repair business and moving to Italy sounds simple in one sentence. It is not simple in one sentence.

The Seinfeld problem

I keep thinking about Seinfeld. How Jerry went out on top, ending the show at its peak rather than waiting for the decline. But then I ask myself: are we at the top right now? How would I even know? You never recognize the peak until you're looking back at it in the rearview mirror. "That was when we had it." It's always ago.

The truth is, you'll never know with certainty if you're making the right decision. All you can do is make the best call with the information you have at the time and then keep moving.

What about our employees?

This is the part that keeps me up at night. Are we abandoning them? It feels like we are. But I also know that if something better came along for any of them, I would want them to take it without hesitation. I hope they'd feel the same way about us. I think they would.

The vulnerability of the sale process

Selling a business means exposing your financial soft underbelly. Anyone serious enough to pay top dollar isn't going to take your word for it. They want financials, equipment records, profit margins, spending history, all of it. It's uncomfortable and invasive and completely necessary if you want to get what the business is actually worth.

And it's worth something. We spent ten years getting it right. Building policies and procedures, putting the right people in the right roles, dialing in the marketing, upgrading equipment, creating systems. We didn't know it would take ten years. We had no real expectation of the timeline, honestly. Our only original goal was to give customers a genuinely positive experience. Everything else grew out of that.

The strange success of working yourself out of a job

Here's where we are now: after ten years, we've built something that doesn't need us for day to day operations. That's supposed to feel like the goal and in some ways it does. But it also means we've worked ourselves out of a job. And if we're being honest with each other? We're both a little bored.

So the options are: blow everything up and start over with a new shop, stay the course and slowly start declining, or sell and do something else entirely. We know we want something else. But that leads to a harder question, has this business defined me? Will I feel lost without it?

I can't answer that yet because I'm not living it yet. What I can say is that I don't want the answer to be yes. The business defines our livelihood right now, as it should, but I don't want it to define who I am on the other side of this.

Being a steward, not just an owner

One thing I think about more than the money or the logistics is this: we are stewards of something the community depends on. We bought this shop from the second generation of ownership. We're not related to the original founders, but we feel the weight of that history. Finding the right buyer, someone who will take care of the customers, the employees, and the reputation we've built. It all matters more to us than squeezing out the highest possible price.

This community deserves to keep having this service. Making sure that happens is part of our responsibility as we walk out the door.

The sheer volume of what comes next

Listing. Marketing. Finding a buyer. Negotiating. Closing. And inside each of those steps are a dozen smaller steps. It's a lot really a lot and I feel the pressure of it constantly. What's next? And then what's next after that?

We're figuring it out one step at a time. And we're bringing you along for all of it.