Parenting Teenage Boys: The Real Struggle, Heart-to-Hearts, and

How We Grow Together

Are you parenting teenage boys? Ever feel like you’re constantly balancing between tough love and tenderness—and sometimes dropping the ball? Let’s get real about the messy, rewarding truth behind raising lads in today’s wild world.

Welcome back, Runpreneur community! Currently deep in my mission to push beyond day 4,292 of the Runpreneur Challenge—aiming to cover 40,075km and raise £1,000,000 in support of children’s causes. But today’s topic hits even closer to home: my journey as a dad doubling as a marathon runner, and what it really means to guide teenage boys as a father.

The Unfiltered Truth: Parenting Isn’t Perfect

Let’s not sugarcoat it—parenting teenage boys is, quite frankly, incredibly challenging. There’s no how-to manual for navigating hormone-fuelled moods, growth spurts that suddenly see my son towering over me, and the overwhelming sense that every day, the world they’re entering is shifting faster than I can keep up.

Recently, life gave me one of those classic “fly in your mouth” moments—literally in the middle of a father-son conversation. These interruptions sum up parenting, don’t they? Unexpected, unglamorous, but totally real.

Learning Together: Heart-to-Heart Conversations

My eldest is fourteen now. He’s an amazing lad—taller, stronger and, on shorter distances, a better runner than me at his age. But if I’m honest? I haven’t been telling him enough how proud I am. I always default to the tough love: be a role model, teach resilience, push him to be the best version of himself.

But sometimes, that backfires. The other day, we had a real heart-to-heart. He opened up about the pressure he feels—pressure I never meant to pile on. It hit me: while I thought I was encouraging him, he was hearing that his best wasn’t yet enough. That’s the kind of generational pressure I desperately want to break.

Dads, Listen Up: Less Pressure, More Praise

There’s such a temptation to focus on what our boys can do better—to shape them into future leaders, winners, those who grab every opportunity. But sometimes I forget: our sons look up to us simply for who we are, not what we accomplish. Praise is the fuel they need. I rarely give enough.

I made a promise—to him and to myself—to say I’m proud more often and to remind him he has nothing to prove. His worth isn’t measured in wins or medals, but in giving his best and embracing who he is.

Facing Fear of Failure—Together

This became crystal clear with his running. Gifted though he is, his anxiety before races is huge—three years as the under 16 winners, now the pressure mounts. I urge him to run, thinking it builds resilience, but deep down he’s scared to disappoint me. When he said so, I reassured: I don’t care about placings. All I want is for him to set his own targets and race himself, not others.

This is the lesson I’d share with every parent: help your teenager set their own standards. Don’t let them feel like they could ever let you down—they can’t. All we want is for them not to let themselves down by holding back from their potential.

Real Talk: Balancing Tough Love and Kindness

Yes, there’s time for tough love. But if we forget the compassion, we risk losing our connection. Every father, especially with teenage boys, needs to balance being a motivator with being a loud, proud cheerleader. I’m working on this, and if you’re reading, maybe we’re on that journey together.

Join Me On My Mission

As I run every single day—barefoot, and beyond 4,292 days—I’m doing it for a cause close to my heart: saving children’s lives, hoping to reach £1,000,000 raised.

If the ups and downs of parenting teenage boys resonate with you, drop your thoughts below, or reach out. I’m always here to share experiences and learn with you.

Like, comment, and share if you believe in raising strong, proud sons—without the weight of perfection. Subscribe to follow my journey, and remember: every day, every mile, every lesson is for a better tomorrow—for my sons and for children everywhere.

Stay positive, stay happy—and parent with love!