Want to sell your business one day? It sounds cool, right?
But too many of us barrel into selling without thinking hard about what comes next. We focus on the terms and the lawyers and the due diligence, in service of the financial windfall on the other side.
Yet when the deal is signed and the funds transferred, a whole load else is transferred too.
Last year I sold the social media agency I started when I was 22 for 7 figures, after 10 years of owning it. I got my perfect deal and knew it was right. But even so, there were parts of the aftermath I had no idea would happen.
While they were all good problems to have, a heads up might have been nice. After 18 months of journaling, figuring it all out and even writing a book about entrepreneurship, here’s what I wish I knew before I sold — the things no one tells you about the personal side of selling your business.
It’s lonely at the top
Hardly anyone knows what it’s like to sell their business because hardly anyone has done it. Hardly anyone is close. So the number of people you can talk to about your sale, when planning or reflecting on one, is tiny.
Friends and family members will support, sure, but the details from experience or the advice that can make all the difference might not come from your existing circles. Those who have sold their business can be useful, as long as their stories guide and inspire rather than scare or warn.
My broker was a godsend. But if I knew then what I know now, I’d talk to more people who had been there and done it.
You can’t anticipate how you will feel
I visualized my sale before it happened. I journaled from my future self, planning what I’d do the week after completion. I even wrote myself a pretend check and imagined it all coming true. Whilst the check matched up, the rest was different.
When you sell, if you sell, you don’t know how you will feel. So rather than trying to predict, get comfy with not knowing.
I had to remind myself every day, “This is new, this is different, and that’s OK.” If you’re a Type A personality, used to handling many responsibilities at once, you might struggle to feel fine not knowing who you are, what’s next and how to spend your time.
But here’s the cool part: that blank space holds answers to your next steps that you couldn’t have predicted.
There’s loss as well as gain
When I sold, I thought about how much I would gain. The headspace, the cash, the free time. The experience, the kudos, the right to do whatever I wanted.
I didn’t think at all about what I would lose and how strange that would feel.
Without a company, you might not be needed. Someone else is running the show and your team reports to them. You won’t be summoned for emergencies. You’re old news, you’ve jumped ship and that’s the end of that.
While losing your team and clients might feel fine, losing being needed, as well as the identity that came with your old company, might not be.
Ego creeps in to tell us this is bad. But really, it’s needed. We’re the caterpillar turning into the butterfly — and to do that, you have to shed your old self.
Small problems appear bigger
Without the company you used to run, you might find you have far fewer problems. But that, in itself, is a problem. In the absence of big problems, small ones appear bigger. Whilst before you could happily tackle multiple fires at once, now the most trivial of issues might stress you out.
What marks a significant decision now isn’t so clear cut. Instead of hiring, firing and cost per conversion, now it’s holidays, adventure and leisure. Your comfort zone shrinks as well as the level of complexity you can handle.
Realizing this feels strange; the wartime CEO needs war. Where are those challenges you used to love to hate, and why do you miss them so much?
You might not know who you are
“What do you do?” is the simplest opening line, but in the post-exit haze it can have you running for cover. I trialed a bunch of different answers. “I just sold my business” works, but not forever. “I’m retired” makes me sound ancient.
There’s no answer reflective of the complexity of your situation and the truth is, the asker of the question doesn’t want an essay. You might find you avoid meeting new people so you don’t have to engage.
Facing an identity crisis and not knowing who you are or what you do might rush you into deciding what’s next, but that’s not the answer. Being happy to not know is. Laughing in response to being asked where you work, or simply rolling your eyes at LinkedIn when it asks you to “update your current position” for the second time this month.
You have to believe you’ll figure it out.
You don’t know what’s next
Once they have established that you don’t know who you are and you don’t work anywhere, their next question will be, “what’s next?” Past colleagues, friends and family members will all ask this question. Even your buyer probably asked you during the sale. What is next?
The truth is that you probably won’t know, nor should you feel like you have to. You wouldn’t ask a toddler where they want to go to high school. You wouldn’t ask a new partner where you’re spending your wedding anniversary.
We’re back to baby steps here. Taking it all in and testing all the waters before committing. I tested many ways forward rather than committing straight away. You’ve just won all this freedom. Now isn’t the time to give it back.
If you think you might want to sell your business one day, consider that it’s more than a transaction of assets and shares. Whatever you think you will feel and want to do might not match up with reality. You’ll feel loss as well as gain. You won’t know how to answer questions that once rolled off the tongue.
You’ll trade the known for the unknown, and the future might be unclear. What you do with that is up to you.
