Leaving Behind What Might Have Been


In honor of my baby boy’s 25th birthday, I wanted to share a piece of our mother-son story. Perhaps you’ll see your own little one in my grown boy, and perhaps you’ll see your own hopes reflected in mine. Whatever you may see, I hope you’ll see that my love for my boy is a constant, no matter how our paths diverge.

My son Connor has always wanted to hit the road. When he was four, he told us he would drive a dinosaur dump truck when he grew up. He wanted to see the world from a big rig — but as he grew older, I insisted that he follow a predictable path from high school to college to professional career. In a million small ways, he declared his intention to leave my wishes behind and follow his own path, and I wish I would have acknowledged his plan so much earlier.

The practice of leaving

My tow-headed boy

When he was six years old, Connor declared he was running away. He walked out the front door of our home in Orlando, carefully crossed the street, looked back at me in the doorway, and said, “I don’t like it here. I’m going to find a better place.” I grabbed his shoes and five dollars and came back to the door. I said, “You might want your shoes and some money to get dinner at McDonald’s.” He came back.

When he was 11 years old, he declared that our house was too uptight. He spent as much time as possible at his buddy’s house. I knew that he enjoyed the freedom of this home with a young mom who was cool and casual in a way I have never been. That was good until the day he told me that they walked to 7-11 to get a bedtime snack at 11:00 p.m. Then I had to pull the plug on time spent there.

When he was 16 years old, he declared that he was going to live with his dad. My heart broke. His dad and I had been divorced for about 18 months at that point, and Connor was not happy at the large suburban high school in our neighborhood or with my house rules. I could see that this might be a good time for him to reconnect with his dad in a different environment. And it was. Until it wasn’t. He came back.

When he was 18 years old, he declared he was an adult and I could no longer tell him what to do. I pointed out that I financially supplied his life, so until he changed that I could assert some expectations. Not long after graduation from high school, he packed his stuff and left. For several weeks, I had no idea where he lived. He resurfaced with a plan to lease an apartment when he turned 19.

Now he is 25 years old, and he is leaving again. This time, it is to follow his dream.

Happy in his big rig

Finally, Connor is going to pursue what he declared would be his dream job when he was just a pre-schooler: driving big trucks. He is a truck driver, and for weeks at a time, he’ll be on the road to places I won’t know, with people I’ll never meet. What could have been resolved early on was instead delayed a few years because of my unwillingness to support his dream. He knew what his path was, but I failed to accept that reality.

My Connor has never chosen the path that I would have chosen for him. I pushed hard to make him think about college, but his dreams have always been different than the ones I had for him. I pictured my little tow-headed boy living what I expected; I did not picture him as a shaved, pierced, and tattooed driver of a big rig. I have had to redraw my image of him, of what I expected him to be, and I wish I would have listened to his dreams much sooner. It would have prevented so much struggle for both of us.

I share this to encourage you to see your children as reflections of what you have taught them, not as duplicates of who you are. Leave behind regrets for what might have been and embrace their dreams.

As Connor sets off on another “leaving,” I still make sure he has his shoes and money for dinner. I hope he remembers all the life lessons I have shared. I tell him every time we chat how much he is loved, and I pray for his safe travels. Always, always I make sure he knows he can come back home at any time, no matter where his dreams take him.


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Born in Wisconsin, Chris moved South with her family, first to Richmond, Virginia, and then to Birmingham when she was 12. She loves being a girl raised in the South, and her only remaining Midwestern traits are a love for the Packers and a fondness for bratwurst. In 2010, Chris reconnected with Christopher, a former Birmingham-Southern College classmate, after a random meeting in the cereal aisle at Publix. They married in 2011, not realizing that they were bringing together a perfect storm of teenage angst with their three children. Today, Chris is the center support that keeps the seesaw of her family balanced, leading a blended family of three young adults and enjoying an empty nest. Before the pandemic, most days were busy managing client relationships for a corporate event production company, but after six months of unemployment, she has become the parish administrator aka “the church lady” for her church. When she's not working, she loves reading a rich historical novel, volunteering with her sorority, and planning their next wine-tasting excursions.