Thoughts on Thursday: A Reason to Stand in the Rain

TL;DR: I left my job to pursue what lights me up: building Loop Athlete, coaching my community and being present for the moments that matter with my family. The spark is back. I've found my reason to stand in the rain.

A few weeks ago at Disney World, the sky cracked open. One of those Florida storms that doesn't ask permission, it just arrives, loud and proud. People ducked into the nearest building, show or shop, mickey ponchos appeared out of nowhere, and the rain came down in sheets. But here's what struck me: no one was mad. No one left. The music still played on. Laughter still carried. We were drenched and delighted because we had a reason to stand in the rain.

That sentence hit me hard: Do you have a reason to stand in the rain?

I realized I'd been weathering a storm without a reason that moved me anymore. Not because the work wasn't meaningful and not because the people weren't great, because oh so many were (more on that next week). But the spark that gets you up early and keeps you up late, the one that makes long hours feel like a privilege instead of a penalty, had dimmed. I was chasing shelter, not the magic.

So I made a decision. I stepped out of the role I'd been holding and back into my purpose: creating an environment for more effective and empathetic coaching at scale, developing and driving growth alongside my co-founders at Loop Athlete, and returning to the field with the Windsor-Essex athletes who've shaped me as much as I've shaped them

This is a love letter to that choice.

What the Rain Taught Me

Storms don't decide whether we stay or go. Reasons do. At Disney, the reason was simple: shared joy. Magic you could feel in the centre of your chest and back between your shoulder blades. The rain didn't kill it; it amplified it. Everyone had already decided, "We're here for this."

That's how I want to live my days. Not avoiding storms, but choosing my storm and choosing the reason that makes it worth it.

• Developing better coaches through the rain. The messy, beautiful and intentional kind of coaching that grows people. Loop Athlete has acknowledged the need for specific coaching to deal with all the individuals we coach. Every person needs to be seen, heard, and know they belong. We can't coach everyone the same way and expect different people to thrive.

• My family is my umbrella. They give me the strength to shield and shut out the world when we need to. They don't hide me from the weather; they help me stand in it on purpose, giving me the clarity, support, and connection to do hard things together.

• Windsor-Essex is my home field. These kids, these communities, these extra sessions and late nights on the field, they're not just where I coach, they're why I coach. This is where I belong, where I can develop the coaches who will see, hear, and help every athlete find their place.

The New Zealand All Blacks have a saying: "Leave the jersey in a better place than you found it." It's about uplifting not just your team, but the entire tradition and everyone who comes after. That's what I'm choosing. Developing Loop Athlete gives all coaches and leaders the tools they need, while I continue working on the front lines to uplift this community. To leave coaching, education, and development in a better place than I found it.

Coming Home (In Every Way That Matters)

Here's what no one tells you about chasing success: sometimes it takes you away from your reasons for wanting it in the first place. I've watched too many sunsets alone on the field and missed too many bedtime stories for Zoom calls that could've been emails.

My daughter is four. Four is magic. Four is "watch this, Dad" a hundred times a day. Four is questions about everything and dance parties in the kitchen. Four doesn't come back. Neither does five, or six, or sixteen. I want to be there for all of it, not just the convenient parts.

And my wife? She's been the anchor through every storm, holding down everything while I chased ambitions that took me away more than toward. She never complained, just carried on. She deserves a partner who's present, not just productive. Someone who shares the load instead of adding to it. Someone who models for our daughter what a real partnership looks like: two people choosing each other and their shared mission, daily.

And these Windsor-Essex kids? They're writing their own stories right now. The kid from Tecumseh who's discovering she's faster than she thought. The goalkeeper in LaSalle who's learning that leadership isn't volume, it's consistency. The team representing our community, competing at the highest level, figuring out how to lose on Tuesday and show up better for it on Thursday. These aren't just athletes; they're my neighbors' kids, my community's future. They deserve a coach who's fully present, not checking emails during water breaks.

Coming home means:

• Waking up with and walking my daughter and her scooter to school every day (making time to pick her up too)

• Being the partner my wife deserves, more often present for dinner, bedtime, and the thousand little moments that make a family

• Building something (Loop Athlete) as a business at scale that helps more coaches and kids while still being there for ours

• Choosing presence over presence of mind, being in the moment, more often

• Re-prioritizing my own health, both physical and mental, letting go of bad habits and building new routines that reflect my priorities and align with my schedule 

• Making time for family activities, creating saturday mornings that belong to us and not everyone and everything else

Empathetic Coaching at Scale (What That Actually Means)

I've spent years on touchlines and in team rooms watching how small conversations change careers. A timely question. A reframed failure. A moment where an athlete finally feels seen. That's empathy in action. It’s not soft or vague, it's notably specific and it's performance fuel.

But here's the tension: empathy usually scales poorly. It's personal, contextual, and time-intensive. Meanwhile, sport is chaotic and calendar-crushed. That's why we built Loop Athlete to make those micro-moments repeatable and trackable without losing the human core.

Empathetic coaching at scale means:

• Turning reflection into routine, not a once-a-season survey

• Making feedback a loop, not a lecture, athlete voice up, coach guidance back, parent clarity alongside

• Moving from mystery to measurable with progress you can see, not just feel

• Building psychological safety without lowering standards. Honesty + Accountability = Growth

• Helping that volunteer coach in Belle River have the same tools as the academy director in Toronto and those across the border. 

This isn't about replacing coaching. It's about amplifying it. It's me on the field with a team in Tecumseh on Tuesday night, and also me helping a coach in Amherstburg facilitate better check-ins on Thursday morning. Same heartbeat, bigger reach.

Why I Walked Away (And What I'm Walking Toward)

I'm grateful for the work I've done and the people I worked with. Truly. But gratitude and alignment aren't synonyms. The line I kept hearing in my head was simple: "Are you building the thing only you can build?"

For me, that answer is now yes.

• Building Loop Athlete, fully. Long hours are back, but they're the right kind—the kind that make you lose track of time because you're in love with the problem.

• Back on the grass, where I belong. Sessions that challenge and change. Old school grit with new school methods. Human first, high performance always.

• Present for what matters. I want my daughter to see her dad create, serve, and care. To see me stand in the rain on purpose, not by default. I want to coach her team one day and actually know her teammates' names because I've been around. I want my wife to have a partner who's all-in on our life, not just visiting between meetings.

• Investing in Windsor-Essex. This community gave me everything. Time to give back, not with a check, but with time, energy, and expertise.

My future isn't a retreat. It's an advance with clearer coordinates and better reasons.

The ROI of Sleepless Nights

I've done the up-at-1:00 a.m. prep and the dawn practice. The caffeine math. The spreadsheets on flights and the recruiting calls in parking lots. I'm not trading that life for serenity, I'm trading it for significance.

When the work is aligned, sleepless nights don't drain you; they invest in you. When the mission is clear, long hours don't feel like a burden; they feel like a vote for what matters. When you're building something for your community and your kid can watch, exhaustion becomes fuel.

I'm voting. With my calendar. With my energy. With my craft. And this time, my family, my future and community are on the ballot.

What This Means for Athletes, Parents, and Coaches

If we work together in any capacity, here's what you can expect from me:

1. Clarity > Comfort. I'll tell the truth kindly and expect the same in return.

2. Consistency > Intensity. We'll build habits that hold under pressure.

3. Process > Posturing. No gimmicks. Just work, reflection, adjustment, repeat.

4. Belonging + Demands. You are welcome and you will be challenged.

5. Receipts of Progress. Not vibes. Visible growth. The loop will show it.

6. Community First. We're building something bigger than wins and we're building better future leaders for Windsor-Essex.

And if you're a coach or a club leader, Loop Athlete isn't another report card. It's a conversation engine. It keeps the main thing the main thing: the athlete's growth. It's especially built for clubs like ours that are community-driven, passion powered and heart-centered.

The Disney Test

I keep coming back to that moment in the rain. No one panicked. No one needed a committee meeting or a perfect plan. We had already decided what we were there for. That's the test: If the storm hit right now, would you still want to be here?

I can say yes again.

Some people feel the rain. Others just get wet. I want to learn from it, dance in it, and build with it with people who are here for the same reason.

And now, when the rain comes, I know exactly where I want to be standing: on a field in Windsor-Essex, with kids who are learning to love the game, building something that matters with my co-founder and best friend and close enough to home that I can still make bedtime.

An Invitation

If you're an athlete in Windsor-Essex: you matter to me. Your growth is my mission. If you're a parent: let's raise these kids together, ask better questions than "Did you win?" If you're a coach: let's trade ego for evidence and build this community up. If you're a club: let's create environments where hard things are normal and growth is a guarantee.

And if you're reading this wondering whether it's time to make your own move, ask yourself the only question that mattered to me:

Do you have a reason to stand in the rain?

Mine is clear: it's the kid who needs one more rep, the parent who needs to understand the journey, the community that deserves excellence, the four-year-old at home who needs her dad to show her what purposeful work looks like, and the woman who's stood by me through every pivot who deserves a husband who's building something sustainable, not just successful.

If your answer is yes, I hope I see you out there, drenched, grinning, and doing the work that matters. Maybe on a field in Tecumseh, maybe at the arena in Lakeshore, maybe at a park in Windsor. I'll be the one full of passion, positivity and probably a full to do list, but absolutely no regrets.

With Love, Passion and Purpose,

Ryan

PS: If you want to bring empathetic coaching at scale into your team or club, reach out. I'm building Loop Athlete with sleepless-nights-level love and I'd be honoured to stand in the rain with you. Especially if you're from around here. This is home.