After 100 episodes of diving into the messy, hilarious, emotional and utterly human world of retirement, I return with the rawest and most powerful episode yet. This milestone isn't a celebration; it's a challenge. A wake-up call. A bold invitation to stop drifting, stop delaying, stop hiding behind old identities… and finally step into the second half of life with honesty, courage, and intention.

This episode strips retirement down to what it really is: not money, not timing, not spreadsheets, but the ongoing evolution of you. Who you are when the job title disappears. Who do you dare to become next? And what you're no longer willing to tolerate in the life you have left.

• The biggest insight 100 episodes have revealed about human beings and retirement

• Why retirement isn't actually about retirement, it's about identity

• The hidden question sitting under nearly every conversation I have ever had

• Why most people drift through the second half of life instead of designing it

• How self-honesty becomes the true starting line of retirement

• Why courage, not money, is the single biggest predictor of a fulfilling future

• What it really means to write the next chapter of your life on purpose

👉 Answer the only question that truly matters:

What are you no longer willing to tolerate in the second half of your life?

Write it down.
Say it out loud.
Let it change something.

Because that answer is your starting line, your compass, your invitation to evolve.

Season 7 begins soon — with a fresh blend of interviews, solo episodes, and deeper dives into the emotional, behavioural, and wildly human side of retirement. Expect honesty, humour, science, challenge… and more than a few loving kicks up the backside.

If you want to retire well in 2026, you don't need a ten-year spreadsheet, a suitcase full of pensions, or a perfectly colour-coded life plan. You need five human foundations: clarity around your money, health that actually supports your freedom, purpose that wakes you up in the morning, people you want in your corner, and the courage to take action.

In this episode, I strip away the fluff and break down what actually moves the needle... the things your future self will thank you for getting right now, not "one day."

• Why your "vibes-based" retirement plan needs to become a real plan

• How financial clarity — not wealth — creates confidence and choice

• Why health is the core engine of your next chapter (not a side quest)

• How to explore purpose without pretending golf is a personality

• The huge role relationships play in your retirement experience

• Why courage — not spreadsheets — is the final unlock

1️⃣ The Money Plan (not the one in your head)
You don't retire on vibes — you retire on numbers, clarity, and confidence.
Know what you've got, how it's structured, and what it can actually do.

2️⃣ Your Health (so you can enjoy the freedom you've worked for)
No point having time and money if you're exhausted, aching, or stuck on the sofa.
Small, consistent actions → big retirement quality.

3️⃣ Purpose (you need something to wake up for)
Work gave you identity, rhythm, and direction.
Retirement requires you to create it — not wait for it to appear.

4️⃣ Relationships (your real retirement portfolio)
Remove work, and the room gets quiet fast.
Build connection intentionally: tribes, friendships, laughter, people who energise you.

5️⃣ Courage (the part no one likes to talk about)
Fear keeps people in holding patterns: waiting for "readiness," waiting for a sign.
Confidence doesn't precede action — it comes from it.

👉 Pick one of the five pillars and make a visible move.

• Book the financial planning call

• Start a consistent walk routine

• Try a new hobby or project you've always avoided

• Message someone you miss and reconnect

• Commit to one brave retirement decision you've been postponing

Don't wait for certainty. Do the human thing that moves life forward.

In the season finale, I tear up the traditional retirement rulebook and replace it with a bold, human, and rebellious manifesto for the second half of life. The old rules — work 40 years, aim for "enough," play it safe, slow down — were never designed for modern retirees who want meaning, energy, experiences, connection, and agency.

This episode lays out The New Rules of Retirement — ten powerful principles for anyone who refuses to drift through retirement and instead wants to design it boldly, live it fully, and leave a legacy that's felt as much as it's funded. This is your encore… so make it loud.

• Why the old retirement rules are outdated, limiting, and designed for a different era

• Ten modern, human-first principles for living boldly after work

• Why retirement isn't the end — it's the starting line

• How to prioritise time, meaning, purpose, and memory dividends over fear and preservation

• Why confidence comes before clarity, and flexibility beats perfection

• The truth about retirement as an emotional journey, not just a financial event

• How to shape a legacy through impact, stories, and how you live — not just what you leave

👉 Write your own new retirement rule.
Just one. Something that becomes a north star for how you want to live the next chapter.

Examples:

• "I spend without guilt when it brings me joy."

• "My time is my greatest asset."

• "I will not shrink my life to fit someone else's expectations."

• "I choose connection over busyness."

• "The second half of my life will be better than the first."

Write it. Repeat it. Live it.

• The New Rules of Retirement — Dan's Season 6 manifesto

• Episode references:

  • Episode 4: Time Isn't What You Think It Is

  • Episode 9: The Retirement Reinvention Curve

  • Episode 10: Modern Software, Ancient Hardware

  • Episode 11: The Retirement Focus Ratio

• My sketches, book, and newsletter

This episode wraps Season 6, a season dedicated to human-first retirement, emotional truth, and challenging the defaults. If these conversations have sparked anything in you, share them with someone who needs a more rebellious, honest, and liberating view of retirement.