One of the most common questions I hear from business owners is, “How do I know if it’s the right time to sell?”
And to be honest, it’s never as simple as checking a box or circling a date on the calendar. Selling a business isn’t like selling a car or a house. This isn’t just an asset, it’s something you built, poured yourself into, sacrificed sleep for, argued with your spouse about, and missed events for. It probably shaped you more than anything else outside your family.
So, if you’re feeling conflicted about when to sell, that’s normal. I’ve never met a business owner who came to this decision without at least a little hesitation, curiosity, or concern.
What I’d like to do here is walk you through how real business owners tend to make the decision - not in theory, but in real life.
Let’s talk about the signs you may be ready, the reasons owners sometimes wait too long, and how to think about timing in a way that feels smart and confident, not rushed.
First, let’s talk about how it feels
Most owners don’t wake up one morning and suddenly decide to sell. Instead, the thought shows up quietly, and it’s usually emotional at first:
“I love this business, but I don’t love running it anymore.”
“I’m proud of what we built, but I’m tired.”
“I want to enjoy life a little before I’m too old to.”
“I have other ideas and passions, and no time to pursue them.”
“I don’t want to look back and wish I didn’t wait too long.”
If you’ve caught yourself having thoughts like those, you’re not alone. And there’s nothing wrong with you, it doesn’t mean you’re giving up. It usually means you’re evolving.
Your relationship with the business shifts
In the early days, your business needed you. It consumed you. It stretched you. You built it with sweat and grit and stubbornness.
But eventually, it becomes something different. It becomes a valuable asset, not just a job or mission. It becomes something that could live without you, and that’s usually when the question of selling starts to make sense.
I often see three mindsets, and many owners will recognize themselves in at least one:
Mindset 1: “I feel ready for something else.”
You’re not burned out, you’re just done. There’s a difference.
You may still enjoy parts of the business, but your energy is shifting. You think more about time, flexibility, and new ideas than reinvesting into this chapter.
That’s a healthy signal, not a negative one.
Mindset 2: “I’m tired, and it’s catching up with me.”
You still care, but the enthusiasm has faded. The thought of tackling the next growth phase feels heavy, not exciting. That’s a sign to start planning, because owners who wait until they’re fully burned out often let value slip before they act.
Mindset 3: “The business is doing well, and I don’t want to risk the momentum.”
One of the hardest things in entrepreneurship is quitting while you're ahead. But often, the best exits happen from a position of strength, not exhaustion or decline.
Now let’s talk about the business itself
Personal readiness is only half the timing equation. The other half is how well the business can stand on its own.
Ask yourself:
Can the business run day-to-day without me?
Are the financials clean and consistent?
Is revenue predictable, not erratic?
Do we have good people in place?
Would a buyer see opportunity here, not just legacy?
If those answers lean toward “yes,” you might be closer to ready than you think.
If some are “not yet,” that doesn’t mean you shouldn’t sell, it just means you may want to plan ahead to make the process smoother and maximize value.
And then there’s the market
No one can perfectly time the market, but here’s what we do know:
There are cycles. There are windows. There are times when buyers are active and capital is available. And there are times when waiting can cost you, in valuation multiples, buyer demand, or lending conditions.
The mistake is thinking you should wait for the “perfect” market. The perfect market doesn’t exist. But good markets do, and if your personal readiness and business readiness line up during one, that’s when magic happens.
When owners regret timing, and when they don’t
Let me share something I see often:
Most owners don’t regret selling. They regret not preparing sooner so they could sell at the right time.
I’ve never had someone say, “I wish I had waited until I was more tired.”
But I’ve heard many say, “I stayed one or two years too long.”
They waited until stress built up, the business plateaued, or momentum softened. Timing is much easier when you’re not operating from depletion.
So how do you actually decide?
Here’s a simple place to start:
Ask yourself, “If someone made me a fair offer today, would I feel relieved, excited, or disappointed?”
Relief → You're closer to ready than you think
Excitement → Timing may be ideal
Disappointment → It’s likely not yet time, but planning still matters
Then ask yourself one more honest question:
“If I stay, am I doing it because I still love it or because I don’t know what comes next?”
Selling isn't running away, it’s moving forward.
What to do if you’re not sure yet
You don’t need to decide today. Really, you don’t. But there’s tremendous value in simply starting the conversation early, even if you don’t plan to sell for a year or two.
Planning at the right time gives you:
Clarity
Control
Better terms
Less stress
Higher value
Planning under pressure rarely produces the same result.
The goal isn’t to rush you. It’s to make sure you have options when you want them, not when circumstances force your hand.
A good rule of thumb
If you’re thinking about selling regularly, not just occasionally, you’re already in the early phase of transition. That’s the moment to get informed and explore your options - privately, calmly, and without commitment.
You earned the right to sell from a position of strength, clarity, and confidence. You don’t have to make a decision today, but you do deserve to understand your timing, your value, and your options.
If this sounds like you…
I’d be happy to talk through where you are and what timing might look like for you, whether you’re thinking about selling soon or just beginning to wonder.
No pressure. No obligation. Just a conversation between someone who’s built something and someone who helps owners move to their next chapter smoothly and successfully.
You don’t need to decide. You just need to start exploring.
And that’s something we can do together.