Transitioning Your Career: Life After Professional Sports

retired athletes career

Back in 2019, I was an active athlete with more than 2,900 career wins under my belt. A seven-time Canadian Sovereign Award winner with a historic victory at the recent 2017 World Jockey Championship in Japan, I knew I had accomplished more than I could have dreamed of in my 20+ year career. Still, I was facing the reality that my professional riding career was nearing its finish line.

At that time, my impending career transition was filled with unknowns (and anxieties). But fear wasn’t an option. Years ago, I’d made a pact with myself: when the checkered flag dropped on my racing career, I wouldn’t stumble blindly into the next chapter. I’d be ready.

That’s why I spent four years preparing for that moment. I had a plan, and I was ready to start my next chapter.

Now, I’ll share a piece of that story with you, and I’ll also share several actionable strategies you can use to help make transitioning your career as a retired athlete as smooth as possible.

Reframe Your Athletic Strengths

Before my final race, the familiar feeling of anxiety twisted in my gut. It wasn’t the pre-race jitters I knew so well; I always welcomed those, as they fueled my focus.

This was a deeper feeling, as the unknown that was waiting for me beyond the finish line. Would I find meaning and fulfillment beyond the sounds of the crowd and the thunder of hooves? Could I translate the skills I strengthened over a 20+ year career in professional sports to a new arena?

The fear of starting over, of losing the identity I’d built for two decades, was real. Maybe you’re going through something similar in your life now. But, here’s how I dealt with it.

Assessing & Reimagining Your Skillset

No matter what your current career or future plans may be, years at the top of any field will build valuable transferable skills for employees and employers alike. For example, in my case, it wasn’t just about riding horses. That competitive fire, the split-second decision-making, my determination and resilience in the face of defeat? Those are real skills, and they are not industry specific.

It’s a matter of translating your existing skills into the language of a new field. As you begin assessing your options for your next career move, ask yourself the following questions.

● What problems did you solve daily in your previous role?
● How may those problem-solving skills transfer to different work?
● What are you looking to achieve in your next career step?

The problem with a career transition is that we see ourselves as “the jockey,” not “the adaptable problem-solver” or “the relentlessly goal-oriented leader.” This requires deliberate reflection to unpack the core of what made you successful. Here’s what I did:

I started journaling—not about wins, but about difficult races, setbacks I bounced back from, and moments when teamwork made a measurable difference.

When you see your reflections written down, patterns emerge that show a broader skillset: resourcefulness, communication, pressure management. Then, you’ll find yourself qualified for research jobs or businesses where those qualities are required. It’s a matter of recognizing the strengths we’ve built unconsciously by excelling in one particular domain.

The key to my transition into a speaker and coach was in deep-level planning and reframing my current skillset into another value-driven career path.

Career Transitions

Draft Your Transition Blueprint

When I started thinking about my jockey career coming to a close, I was worried about missing the camaraderie, the adrenaline rush, the purpose. Life as a retired athlete can be a tough transition—if you don’t have a plan.

What I realized was that it’s okay to feel a range of emotions—anyone making a life pivot does, just maybe without the roar of the crowd. Acknowledging those feelings was the first step.

There’s a practical side to emotions, too. They cloud judgment, and major transitions need clear thinking. I had to be honest with myself. Was I looking for something as intense and structured as racing, or a track that allowed me to build the life of my dreams on my own terms and at my own pace?

Each answer leads to a different preparation path. My advice to you is to be brutally honest with yourself about what you want, where you want to go, and what you see yourself doing day in, day out.

Building Your New Life As a Retired Athlete

Drafting a career transition plan shouldn’t be a rigid business proposal. Mine evolved, some ideas flopped, but having a structure kept me moving forward. Instead of rigid goals, I outlined desired outcomes and actionable plans in different life areas:

● Finances: Obviously important, but it’s beyond income: did I want location flexibility, was I building something to sell down the line?

● Lifestyle: No more crazy athlete schedules. But did I want something structured, 9-5? How much travel was okay? What “non-work” was crucial to keep in my life?

● Purpose: This had to be deeper than moneymaking. How did I want to impact the world, or my new work community?

Answering these, while exploring possible career paths, created the foundation for more tangible next steps. It sounds heavy, but it brings back some control when the rest of your life feels chaotic and in a state of big change.

The Long Game: Patience as a Strategy

Building a new career or shifting life direction after dedicating decades to a singular goal demands a marathon mindset, not a racer’s one. That doesn’t make it any easier. Having a great plan helps, but the hardest part is the waiting. Those were the moments doubts fill your head, when it feels like you should take a quick opportunity rather than hold out for something that truly aligns with your vision—that’s what you want to avoid.

What kept me going wasn’t blind optimism, but deliberate strategies tailored to a long-term approach. Those four years of planning gave me the foundation, but also let me embrace the reality of my next chapters being messy, and that’s okay.

Staying Motivated in the “Messy Middle”

Here’s what worked for me, framed in a way applicable to career shifters beyond sports:

● Micro-Goals: Big visions are vital, but easily become sources of frustration. I broke down my larger goals into monthly, even weekly milestones. Stanford research proves they work as motivators—just don’t forget about the big picture, though. It could be researching an industry, learning a skill, or just having a set number of networking coffees per week.

● Celebrating Non-Outcomes: Focusing purely on final wins (the new job, the business launch) makes the journey demoralizing. I found moments to celebrate effort: completing an intimidating course, making a bold outreach, or simply overcoming a bad day without quitting.

● The Accountability Network: These weren’t just supporters. I had trusted people call me on my B.S. when I wavered. But, equally important, they reminded me how far I’d come when I lost perspective.

My final race was easy compared to the four years prior. But without playing the long game, walking away feeling fulfilled rather than just relieved wasn’t likely. If you want to make a major plan, you MUST plan it out and set up goals along the way—short, mid, and long-term. It’s non-negotiable for success.

professional athletes

Your Next Winning Season

Building a life after professional sports wasn’t an ending for me—it was the start of a different kind of championship. That same discipline, work ethic, and fierce self-belief that built a racing legacy carries over to what I do now as a coach and speaker. After all, it’s about the journey.

New opportunities in your life may take longer, and the track might be unfamiliar, but your determination and drive remain your greatest advantage. This next step isn’t about replacing what was or who you were in a previous career, but exploring the victories you haven’t even imagined yet.

If you’re unsure how to get started, let me know. We’ll discuss your future together and build the right plan for your journey beyond the field, so that you can get back to what drives you.