Finding Time to Reconnect

October 24, 2025
Time Freedom Theo sporting his FC Porto gear during our epic one-month trip to Portugal in 2023

“Hey…Dad? You want to have a catch?”

It’s the iconic question from the 1989 film Field of Dreams that captures all the complexities of a father-son connection so simply. I’ve appreciated my connection with my own father more over the years since I first saw that movie at thirteen years old.

I’ve had some catches with my son, but we’ve connected in other ways too: trips to the park to climb trees or play frisbee, visits to our friends Jim and Linda’s house to watch the kids run around, our big family trip to Portugal in June 2023.

Then things shifted. About a year ago, right around his fourteenth birthday, everything changed. I’m no longer the one he chooses. Now Theo prefers to hang with friends. It goes in phases—first school friends who play online games, then heading to the fields with his soccer team to kick the ball around, later a group of mountain biking friends who like to build jumps together.

When I share this conundrum with my friends, the feedback I receive is that “it’s normal.” “Theo’s a teen who’s focused on learning who he is. He’s pulling away for now, but he’ll come back,” they say.

I still don’t like it.

But fortunately, I have the time to work on finding a solution. I’ve tried different strategies from books I’ve read, therapists I’ve seen, and parenting coaches I’ve worked with. So many of these ideas haven’t worked. Boy, how I wish there were a magic bullet.

One thing that has worked is what’s essentially thirty minutes of forced togetherness. We must hang out as a family. As far as what we do together, my wife and I let Theo choose.

Sometimes we watch Brooklyn 99 together. Many nights we sit in his room and watch him do funny things in a game of FIFA (a soccer video game). Lately, we join him outside after dark to rebound soccer balls that he fires at the goal in our back yard.

As I retrieve balls, I don’t get a lot of details on what’s going on inside our teenage boy’s brain. But we get snippets, and that’s better than nothing.

I’ll keep doing it while he still wants to. And I’ll keep trying new things.

I haven’t found the solution for reconnecting with my son. But I’ve got a wonderful wife who’s in this with me. And I’ve got time to keep at it.

In Time Freedom, I write about how so many of us struggle alone with big money mistakes we’ve made. I believe a lot of us think that we’re the only ones struggling at home too. Family dynamics are tough. They often feel insurmountable. But if the challenges at home are important enough for you to want to fix, the best thing we can do is find time to keep trying.

I love you, buddy.

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