Rethinking Transition
Why It Feels Hard and Why Starting Early Changes Everything
You’ll spend decades mastering your sport…
and 10 minutes planning what comes after it.
So is it any surprise it hits hard?
For years you’ve had structure, teammates, identity, status, and regular feedback.
Then one morning no weekly schedule arrives.
And group admin unceremoniously removes you from the team WhatsApp.
The WhatsApp cull hit me harder than any tackle ever did.
Suddenly you realise: you’re now outside the system that moulded you.
Why Transition Feels So Hard
Let’s be realistic.
It’s not your priority to plan long-term when:
you’re fighting for selection
you’re chasing a contract
you’re managing pain
you’re rehabbing
and just trying to get through the week
It’s normal to feel too busy to prepare.
But waiting years to take action is not.
Athletes come from environments built on very short feedback loops and immediate results.
Which makes thinking about a future, beyond the weekend, uncomfortable; filled with uncertainty and maybe a good dose of fear.
Because, who are you without the sport that defines you?
But the day will come when you’re no longer the pro athlete, and being prepared is in your best interest.
Most athletes try to hedge by doing “a bit of everything”: coaching, property, coffee shops, financial advice… none of these are wrong.
The problem is exploring without intention.
That’s when you drift.
And drift is quiet, subtle, and expensive, in ways most athletes don’t realise.
Here’s the truth no one says enough:
You are in the Business of You.
Your career, your decisions, your future – they’re your responsibility.
No one is building your next chapter for you.
And when the structure of sport falls away, that reality becomes very real, very quickly.
The Cost of Waiting
Professional athletes’ careers are shorter than traditional careers.
We know this intuitively, and data from Rugby Dome, and medical studies by KSSTA backs this up.
Rugby careers average between 11 to 14 years, and footballers are similar, commonly end between the ages of 34-36.
Your second career could last 30 years!
Here’s the part athletes often never fully take on board until it’s too late:
Inaction is a decision in itself, and has an opportunity cost. A big one!
Failing to take action for a year costs you roughly 7% of your available time to build your second career options.
If you wait five years to start preparing, you lose around 35% of your available time to build your next chapter, that’s a third of your runway on average, gone.
Time to experiment, prepare, network, and learn you can’t get back.
And the cost isn’t just time.
It’s momentum, self-belief, fewer opportunities, and a shrinking identity beyond sport.
Leverage Your Playing Years
When you’re still playing, your network reach is strong.
Your access is at its greatest.
This is a window most athletes waste.
Not because they’re lazy, but because they don’t realise the opportunity until it’s too late.
Ultimately, you can’t control when your career ends, but you can control whether you’ve spent the last 5 years avoiding it or preparing for it.
The Transition Flywheel
A flywheel is simple: each small turn makes the next one easier.
Effort compounds and athletes understand compounding better than most.
Transition works the same way.
Experiment → Reflect → Re-direct → Repeat
1. Experiment
Try something new, a course, a coffee chat, a shadow day, a conversation.
This is how you expand your surface area of luck, a concept Sahil Bloom writes a brilliant essay about: more reps = more opportunities.
2. Reflect
After each experience, write three bullet points:
what you enjoyed
what you didn’t
what you learned
This gives you data.
3. Re-direct
Use those insights to guide your next action.
This is a Hemingway Bridge – leaving the next step obvious, so momentum becomes easier.
4. Repeat
Effort compounds.
Short feedback loops build momentum, which accelerates clarity and direction emerges.
My Own Flywheel (And the Injury That Started It)
People often assume I had a clear plan.
That I “always knew” I wanted to be a Chartered Financial Planner.
Let me be honest, this wasn’t the case.
It started on a wet, muddy afternoon in Gloucester, when I got knocked out and broke my leg, at the same time.
Up until then, I had the confidence of someone who’d never had a serious setback.
But lying in hospital afterwards, my brutally honest thought was:
“If I can’t play again, I’m f***ed.”
No plan.
No qualifications.
No clue what I’d do outside of Rugby.
My fear became fuel.
I started experimenting, not because I had any sort of ‘light bulb’ moment. But because I knew I needed an alternative.
Coaching? Loved the strategy side of it. Zero interest in managing big groups.
But learned I liked mentoring smaller ones.
Finance?
A few tax shocks got me curious.
(When a new contract kicked in, I found myself paying more in monthly tax, than I used to take home)
Met an asset manager. Interesting. Not it though.
However, they introduced me to financial planning. It clicked immediately.
It blended a lot of what interested me:
coaching
personal finance
psychology
strategy
helping people make informed decisions
I studied between training sessions.
Passed exams.
Qualified before I ‘retired’ (couldn’t get a contract).
Those early experiments gave me options later.
That’s the flywheel in action.
Money….It’s Important
Athletes’ income patterns are unpredictable.
It accelerates, peaks, drops, and often stops suddenly.
Financial clarity mirrors emotional clarity:
Structure = freedom
Freedom = choice
Choice = calm
Spend less than you earn.
Build buffers.
Protect yourself
Invest for your future.
It will buy you the most valuable asset in transition:
Time.
Do Something Today Your Future Self Will Thank You For
If you’re still playing, don’t overthink it.
Do this:
1) Write down a list of things you enjoy doing, and that you’re interested in.
2) On Monday, message one person on social media you want to learn from. Do that every week.
3) Bonus if you contact your commercial department or a sponsor….
Because if you don’t start preparing when it’s easy…you’ll be forced to when it’s hard.
If you’ve read this and want to dig a little deeper into how to get your flywheel moving then I’m happy to have a coffee and share some insights.