I FIRST MET my son through a stack of papers. Jason was ten years old, the papers read, and I owed his mom back payments for childcare.

I was shocked, but I complied. I knew his mom. (Yes, I’m gay, but don’t try to tell me all 15-year-olds don’t go through times of self-doubt.) I wouldn’t say that I was ready to be a dad back then, but I was ready to move on from the self-destruction of my early 20s, a time that consisted of near-constant late-night partying, alcohol and drug abuse, and simply not dealing with my own emotional challenges.

Soon after I met Jason, I agreed to take custody of him. Three years later, I did the same for his half brother, Chris. I’m 41 now (Jason is 25; Chris is 22),and at no point did I see any of this coming. But honestly, regardless of who you are as a parent, you never see anything coming.

Like right within that first year of raising Jason, he started giving me the dreaded one-word “fine” after I’d ask him how his day was at school.

And I believed him because he would come home and be funny and engaging, and I would walk around the house thinking that my son was the most confident kid in the world. But then I began getting reports from school. Jason is struggling. Jason is having issues with anxiety. Basically, Jason wasn’t “fine.”

Taken off guard, I initially made Jason’s struggles all about me. I was heartbroken that he wasn’t sharing things with me. Was I not open enough with him? Not present enough? Or, worse still, not cool enough?

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But then I acknowledged my feelings and came up with a plan. My son wasn’t having the best experience at school, and he needed help. My sister was a counselor, so I asked for her advice. I used my heartbreak to push myself past my anxiety (and you wonder where he gets it from) and tried to create a safe place for my child.

I Am Okay to Feel

I Am Okay to Feel

I Am Okay to Feel

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It took some discussion, but we got to the root of it. Back in my day, it mattered if you didn’t have the latest pair of Jordans. Now it’s the latest iPhone. If I didn’t get my hair cut for a month when I was ten, big deal. If Jason went a week without one, who would like his Instagram pics? It came down to cash: We didn’t have much money; other kids did. So we talked about comparisons and inadequacy and—yeah, okay, okay—I started to take him to the barber more often.

Before I had kids, I always thought surprises had to be something big. Like deciding I wasn’t going to college anymore. Or shaving off my hair. Or, ha, finding out I had a son. But when you’re a dad, almost every day holds at least one micro surprise. When the kids are younger, it’s seeing them develop some new skill. When they’re older, it’s watching them successfully (or unsuccessfully) navigate social or professional situations.

But I don’t believe there’s such a thing as a bad surprise, whether it’s macro or micro. And I’m only ever really surprised if I’m setting an expectation. When my kids defy those expectations, I could resent them for doing so—or I could do what’s actually more helpful: grow with them. Because there are all the times your kids surprise you, but then there are the times you surprise yourself and your kids help you become a better human being.

It’s like getting a fresh new pair of Jordans—or an iPhone 14—but for your soul.

A version of this article originally appeared in the November 2022 issue of Men's Health.

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Karamo Brown

Karamo Brown is the host of Karamo, a daytime talk show, one fifth of the Queer Eye crew, and the co-author of two children’s books with his son, Jason “Rachel” Brown; the latest called I Am Okay to Feel.