Kissing My Daughter and My Business Goodbye

Control is overrated—until you don’t have any.

The spring my daughter Hannah was finishing high school was the same spring I was trying to sell my business. We were both ready to move on with our lives.

I’m a writer turned rabbi turned entrepreneur turned financially illiterate CEO. My brother says I’m impulsive. I prefer frolicsome.

Trying to sell my company to corporate guys in white shirts and blue sportcoats was surreal. My banker said I should look more interested. But how? They kept talking about my “predictable ARR” and “smooth CAGR.” Who the hell cares? In a moment of desperation, I asked the investors to silently build balloon hats with a partner, which we do in our program to teach teamwork to children. A few chuckled, gamely fumbling with pipe cleaners and twisty ties; others checked their phones. They learned who I was, and I learned who should and shouldn’t own an after-school organization.

Hannah and I would both discover our fate during the last week of March, when we were on spring break with several thousand of her best friends and a dozen other befuddled parents. We would learn which colleges wanted her, and which businesses wanted me.

We’ve all waited for news before—job interviews, pregnancy tests, the moment after you say, “I love you” and wait to hear something back. Waiting means giving up control. You’ve done everything you can; now it’s out of your hands. Hannah found stress relief at the beach with her friends and our resort’s lax drinking policies. I found mine by signing my name for snacks and cocktails instead of paying with real money.

Hannah was our brilliant child. Our boys are no dummies, and I love them both beyond words, but have you ever met a male teenager? They try to sneak beer out of the house in leaking backpacks. They think “but it’s not mine” is plausible deniability.

Hannah excelled in her coursework and after-school activities, including dance, violin, and Mandarin. One of the boys in her language class was flabbergasted to learn that my blonde, blue-eyed, nine-year-old daughter spoke English too.

Hannah deserved to attend whatever school she wanted, but the process seemed so arbitrary. She had already received a rejection from a place that Trish and I thought was a shoo-in. What if she was rejected by more?

I was worried about my own future too. I loved my business, but it had grown beyond me. When we were in a few dozen schools I was effective. At 500 schools, I was clumsy but harmless. But now, with 1,000 locations and growing, I was over my head and needed experienced leaders. It was time to let it go.

Two days into the trip, Hannah’s top choice, the University of Southern California, emailed to say, “Fight on, Trojan, you’re in.” And a few days after that, my top choice, a mission-driven group out of Canada, who looked hilarious wearing balloons on their heads, said, “We’d love to partner with you, eh?”

And that was that.

Oscar Wilde wrote that there are two tragedies in life: One is not getting what one wants, and the other is getting it. For Hannah, getting what she wanted was pure joy.

It was more complicated for me.

When Hannah was three, she thought I knew everything. When my business was three, my team thought I knew what I was doing. Both kept me worried but sure of my role.

But now what? In a few months, neither my daughter nor my business would need me anymore. I wouldn’t have a daughter to see off in the morning or a team to work with in the afternoon. I would have nowhere to go, nothing to do. Would Trish and I celebrate our freedom and have breakfast naked? Or would we sit at a lonely dinner table, staring at our phones, waiting for a text that says, “I’m fine. Stop texting.”

The week before she left, I dreamed that Hannah and her friends were jumping off a foggy pier in Lake Michigan. I called after them; they swam away laughing. I called her name, but nothing came back. I woke up feeling like I’d already lost her.

These days Hannah’s having the time of her life. I think she even goes to class. As for me, I went from being a CEO in a button-down shirt wondering how to build a business to a guy in sweatpants wondering how to use a semicolon. And I couldn’t be happier.

My new CEO still calls once or twice a month to ask how I’d solve one problem or another. I talk longer than she needs me to, and she humors me. Hannah calls sometimes too, between activities. We talk a little longer than she means to, and I hang up smiling.

Sometimes I still think about that dream—the foggy pier, Hannah and her friends jumping into the lake, swimming away laughing. I call her name, and now she turns, waves, and keeps swimming.

She’s fine. So is my company. And so, finally, am I.