Are you ready to retire?
Are you ready to retire?

J Hirtle The Last Storyteller

Jim Hirtle talks with financial planner John Becker about practical steps to build confidence in the five years before and after retirement. They discuss risks, spending habits and why even modest earners may still create a secure, dignified later life with realistic planning.

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43:44•10 Jun 2026

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Countdown to a Confident Retirement with John Becker

Episode Overview

The “retirement red zone” – five years before and five years into retirement – is a critical window to check risk, spending and overall strategy.
Relying only on high stock returns can be dangerous; early losses in retirement can seriously damage long‑term income.
Many workplace 401(k) plans offer limited options, so some people may benefit from in‑service rollovers and guidance from a fiduciary.
Retirement risk includes long‑term care needs, tax traps and Medicare costs, not just market swings.
Even those living paycheque to paycheque may build a workable retirement plan with discipline, realistic expectations and professional advice.

“Are you disciplined enough to compartmentalise that spending when every day is Saturday now?”

How do people find strength in their journey to sobriety? For many, money worries sit right alongside cravings and old habits, and that’s exactly where this conversation plants its flag. Poet and storyteller Jim Hirtle sits down with financial planner and author John Becker to chat about his book *Countdown to a Confident Retirement: What to Do Five Years Before and Five Years Into Retirement*.

The tone stays friendly and down‑to‑earth, with Jim approaching the topic as a brand‑new retiree who still feels like he’s on a “long weekend” rather than fully out of the workforce. John breaks down what he calls the retirement “red zone” – those crucial years either side of your retirement date – and why they matter so much for long‑term security.

He explains risks like big early‑retirement market losses, long‑term care costs, and the danger of “every day is Saturday” spending. As he puts it, “Are you disciplined enough to compartmentalise that spending when every day is Saturday now?” You’ll hear clear, practical talk about 401(k)s, in‑service rollovers, balanced portfolios, and why many people may need a second opinion from a fiduciary rather than just trusting a generic workplace plan.

There’s also a strong message of hope for those living paycheque to paycheque: careful saving, social security, and a realistic plan can still make a dignified retirement possible. Jim keeps things light with jokes about being a lifelong cheapskate and not wanting “70 to be the new 40”, while John shares real‑life examples of clients on very different incomes to show how habits and planning beat flashy salaries.

If money has always felt too intimidating, or you’ve avoided looking at your 401(k) the way you once avoided your own reflection, this chat might be the nudge you need to ask: what small step could I take today towards a calmer, more confident future?

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