Beyond Limits: The Rugby Legend, My Kids, and the Email I Almost Didn't Send

For former athletes becoming more - beyond the game. Life reflections, curated weekly.

June 15, 2025 | 5-minute read:

One lesson I taught my kids came from an email I almost didn't send.

Bob Skinstad. South African rugby legend. A man who's shared conversations with Nelson Mandela.

And I almost didn't ask him on my podcast.

Most people miss meaningful opportunities not because they lack talent, but because they never hit "send."

I almost made that mistake.

We'd been connected through someone in our networks (a casual introduction that led to a surprisingly good initial conversation).

As we were wrapping up, Bob said, "Kyle, feel free to shoot me an email with how I can help."

That's when the thought crossed my mind – I wonder if I could get him on the podcast?

When Doubt Creeps In

But the doubts rushed in immediately:

This man had just given me 30 minutes of his time, getting to know me and hearing my passion for helping former athletes.

Was I pushing it after a generous conversation?

I know, I know.

This is where my anxiety kicks into full gear.

That nagging inner critic gets loud.

'Why would he choose YOUR podcast when he could go on any show he wants?'

And perhaps the deepest fear of all: What if he actually says yes, and I don't do a good job?

This man had been interviewed by professionals throughout his entire career. What could I possibly offer that hadn't been asked before?

But here's what I realized: most people think the biggest risk is getting a 'no.' But the real risk is never asking at all.

When you don't ask for what you want, you lose twice: the chance you don't take and the example you set.

I've struggled at moments in my life asking for what I want. The reasons vary—fear of rejection, feeling unworthy, not wanting to impose. I think we all face this at times.

37 Seconds of Courage

All these thoughts swirled in my mind before I hit send.

I hesitated.

Considered the rejection.

But I sent it anyway.

Courage isn't the absence of fear. It's hitting send anyway.

It took exactly 37 seconds of courage to write that email. The return? Immeasurable.

But when it comes to what I'm doing with United After Sport, something deeper drives me. The passion pushes me past the discomfort.

The reply came faster than expected (he said yes).

Everything changed.

I still remember that moment vividly. Walking out of the bedroom, pumped to share the news.

My wife and kids looked up, curious.

"Bob Skinstad is coming on the podcast!"

"Who's that?" they asked in unison. 🤣

I couldn't blame them. I didn't know who Bob was either (as rugby is not the biggest of sports here in the US).

Of course, the kids went right to YouTube. "Let's look him up!" Then we sat on my bed with their iPad and watched some highlights.

I could tell they now understood why it mattered so much. When kids see all the search results, they get it.

In that moment, something shifted. What began as my personal achievement transformed into something deeper.

I never expected a podcast recording to create a moment of connection with my children. Yet there we were, huddled together, watching rugby clips, bonding over something that had once been just my thing.

Over the following weeks, my kids kept asking: "When is Bob coming on the podcast?"

They weren't just remembering his name. They were invested in something that mattered to me.

The Plot Twist

Then came the plot twist.

Twenty-four hours before the scheduled interview, I got sick. Really sick.

I remember lying in bed, thinking, "I just need to power through this."

But something in me thought: "You owe it to yourself and to Bob to show up at your best."

The fear crept in immediately.

What if he doesn't respond when I ask to reschedule?

What if this was my one chance?

Sometimes asking for what you need is just as important as asking for what you want.

Another email. Another moment of vulnerability.

So I sent it anyway.

Her response? "No problem at all, Kyle. Let's find another date when you're feeling better." It was actually his admin who responded and suggested new times almost immediately (what a relief!).

Then came a moment I'll never forget. My son looked at me and said, "I'm proud of you, hun."

Why hun? Longer story for another day, but wow. Straight to the heart.

One email doesn't just change opportunities. It could change how your children see you.

The real question wasn't whether Bob would say yes. It was whether my kids would see their dad as someone who goes after what matters to him.

Before recording, I mentioned to Bob how excited my kids were about the interview. At the end of our conversation, he looked at the camera and said, "Kyle, you can tell your kids we did it."

A small gesture from him. A meaningful moment for my family.

To wrap things up, we recorded a short thank you video afterward. My kids, in perfect unison, saying "Thanks Bob!" I sent it over to him – a simple way of bringing things full circle.

What Your Kids Are Really Learning

Will this interview be the one that makes my podcast take off? Will episode five with Bob Skinstad be the tipping point that launches my show into the stratosphere?

Who knows.

Who cares.

The metrics, the downloads, the subscriber count – none of that matters against the backdrop of what really happened here.

Maybe it's just where I am in life – this stage of parenting where I'm more attuned to these fleeting moments of connection.

Maybe they won't even remember this years from now (perhaps only fragments will remain in their subconscious – some vague memory of me pursuing something I cared about).

But for me? This will always be a perfect memory I'll carry with me.

Sometimes the win isn't measured in listeners, but in the eyes of your children when they see you go after something that matters.

Your actions teach your children more than your words ever will.

As a parent, I realized my children were witnessing an important lesson:

The worst outcome isn't rejection. It's never knowing what could have been.

But here's what really matters: It's not about having courage. It's about choosing courage.

The Ripple Effect

I wonder how many opportunities we miss by overthinking. How many emails remain unsent. How many doors stay closed because we never knocked. I know I've had my fair share.

And I wonder about the unseen ripples of our courage – how one act of bravery might create unexpected moments of connection with those we love most.

Hit send.

Cheers,

Kyle

P.S. Happy Father's Day to all the dads reading this. One thing I appreciate most about my own father is how he has led by example. He showed me that courage isn't loud – it's quiet moments of doing what's right when no one's watching.