Should I Sell My Business? The Question That's Been Keeping You Up for 6 Months
Should I sell?
That question is living rent-free in your head right now, isn't it?
It wakes you up at 3am. Follows you through every meeting. You're at dinner with your family and you're not really there, you're running through the same mental loop you've been stuck in for months.
You've made the lists. Had the conversations with your spouse. Maybe looked at valuations. Run the numbers in your head a hundred times.
And still. You don't know.
I've been hearing this question my entire adult life.
As a PA in Los Angeles, I heard high-profile patients wrestle with it. Successful, brilliant people who couldn't see their way forward.
I watched my father struggle with it, running a multi-generational plumbing and HVAC business, wondering how and when he should exit.
My physician mentor contemplated this question for years trying to decide if he wanted to sell vs partner with the next generation physician owner.
My husband and I have battled this question in our own ventures.
And now I guide business leaders through this exact question using decision-making frameworks, neuroscience, and strategic planning.
Here's what I've learned after decades around this question: when you've been asking "should I sell?" for months and still can't answer it, you're usually asking the wrong question.
Here's What's Actually Going On
When you're chronically stressed, which you are if you've been stuck on this for 6 months or more, your brain can't think straight.
Your prefrontal cortex (the part that helps you see options, weigh scenarios, think long-term) goes offline.
Your amygdala, threat detection center, takes over. When that's running the show, everything feels like a crisis. Stay and suffer, or sell and walk away from everything you've built.
That's not strategic thinking. That's survival mode.
I saw this with my high-profile patients. People at the top of their fields who couldn't think clearly about their own businesses. I heard it in my dad's voice at the dinner table. I've felt it myself, that fog where you can't tell if you're thinking clearly or just reacting to stress.
You can't make a good decision from survival mode.
What You're Really Asking
When you say "should I sell?" I think what you're really asking is:
How do I stop feeling crushed by this weight?
How do I get my life back?
Is there ANY version of this that doesn't require me to give up everything?
Your brain can't answer those questions when it's in panic or reaction mode.
That's why we have to step back first.
When you create distance, physically get out of your environment, give your brain space, that strategic part comes back online.
Suddenly you can see options. You can think. You're not just reacting.
It's not magic. It's how your brain works.
Let Me Tell You What Happened
A few months ago, a medical practice owner called me.
"I'm done. I need to sell. I'm calling buyers this week."
I could hear it, exhausted, defeated, at the end of her rope.
I'd heard that exact tone before. From patients. From my dad. From my mentor. From myself in moments of desperation.
I asked: "Have you looked at what your practice is worth?"
Long pause.
"No. I just know I can't keep doing this."
I felt that. Been there myself.
We set up a VIP day. When we stepped back and looked at the whole picture:
She didn't hate her business. She hated that 60% of her time was operations, billing, scheduling, HR drama, and only 40% was patients.
She wasn't stuck in a bad business. She was stuck in the wrong role.
We built three scenarios:
Sell everything - Exit completely
Hire a COO - Someone runs operations, she focuses on patients
Partial exit - Sell to partner, keep seeing patients
We mapped what each would actually look like. The money. The time. Her daily life.
Her shoulders dropped. First real breath all day.
"I thought I only had one option. Turns out I had three."
She began exploring hiring a COO partner.
Two months later: working with patients (what she loves), someone else handling operations (what was killing her).
She texted: "I almost sold the thing I love because I couldn't see another way."
So Here's What I Want You to Hear
The question isn't "should I sell?"
It's: "What do I actually want my life to look like—and what needs to change to get there?"
Sometimes that's selling. Sometimes it's restructuring your role. Sometimes it's bringing in help so you can do what you're actually good at.
But you can't see any of that when your brain is in survival mode.
After decades around this question—watching patients struggle with it, seeing my mentor and father both wrestle with it, battling it myself, and now helping leaders navigate it—I know this:
Stepping back isn't optional. It's how your brain needs to work to make this decision.
When you telescope out, your brain can think again. You can see options. You can choose from clarity instead of desperation.
This is what I do now. I combine 20 years of clinical practice, growing up around family business, building my own ventures, and studying neuroscience and decision frameworks to help leaders step back, understand what's happening in their brain, and build a roadmap forward.
If This Sounds Like You
If you've been circling this decision for months, it's not because you're not smart enough or decisive enough.
It's because you're too close. Your brain literally can't do what you're asking from where you're standing.
This is what my VIP Strategy Days are for.
We telescope out together. Build three real scenarios with 90-day action plans. You choose based on what aligns, not just financially, but with the life you want.
You walk out knowing exactly what you're doing next.
Here’s to clarity on your next move,
Kasey
P.S. Your answer might be different from my client's outcome. But you won't know until you step back and look at the whole picture.