Ask Faleskini - The Midlife Crisis Clarity Compass

How can adequate retirement planning help you get out of a midlife crisis?

Chris Maduri · August 26, 2026

Finance · Life Coach · Wellnessin

Interview with Chris Maduri

How can adequate retirement planning help you get out of a midlife crisis? — Chris Maduri

Podcast: Ask Faleskini - The Midlife Crisis Clarity Compass

August 26, 2026 · 21 min

Retiring without a clear plan can turn midlife uncertainty into a full-blown crisis, but securing guaranteed income and clarifying your long-term goals can restore total peace of mind. In this final episode of Season 6 of the Ask Faleskini Podcast, Peter Faleskini sits down…

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How can adequate retirement planning help you get out of a midlife crisis?

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Ask Faleskini - The Midlife Crisis Clarity Compass

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Key topicsNothing Coming In — The Fear That Arrives With the First Retirement WithdrawalChris Maduri has spent nearly two decades walking people from earning money to living off it, and he finds the anxiety starts with the first withdrawal, long before markets do anything. Most preparation treats retirement as a maths problem, when the harder change is that after 30 years of watching a balance grow, people now have to watch it fall on purpose. He explains how that feeling drives real decisions, from cutting spending they could comfortably afford to reaching for returns they do not need. Across 15 years and work with about 70 insurance companies, he has seen which plans hold up once people start drawing on them and which only ever worked on paper. Listeners leave able to name what is actually making them uneasy, and knowing which decisions to make before the feeling makes them.Which Retirement Plans Survived 2008, and Which Quietly Broke?Chris Maduri began his career just before the 2008 financial crisis, and spent his first years watching plans that looked solid on paper come apart under pressure. That start shaped how he judges risk: not by what a projection promises in a good year, but by what a plan still delivers in a bad one. He walks through what actually broke in 2008 for people close to retirement, why the damage landed hardest on those drawing income rather than still saving, and what the survivors had in common. Nearly two decades and about 70 insurance companies later, he can show which structures earned their place and which were sold on optimism. Listeners leave with a way to stress test their own plan against the year nobody plans for.Twelve Months to Drawdown — The Five Retirement Decisions That Get the Money Down the MountainChris Maduri compares retirement to climbing: years of preparation go into reaching the summit and almost none into getting back down, which is exactly where people get hurt. In nearly two decades of retirement planning, and as the founder of Vibrant Retirement, he has seen the final twelve months before the paycheck stops do more damage than any bad market year. He walks through the five decisions that belong in that window — when income starts, what is guaranteed, what stays invested, what covers care, and what the day after work actually looks like — and why leaving them until the last month is too late. Having worked with about 70 insurance companies across 15 years, he can say plainly which structures hold on the way down and which were only ever built for the way up. Listeners leave with a twelve-month order of operations they can start from whatever month they are in.View all topics →

About Chris Maduri

Retirement & Life Transitions Expert

Nearly 20 years Helping people prepare for retirement4 Pillars of sustainable retirement planning3 Buckets in his wealth-building approachSales Director Named by Financial Marketing Group in 2013

Chris Maduri has spent nearly two decades helping people prepare for more than retirement - he helps them prepare for the life that comes after work.

Because retirement isn't simply the day the pay cheque stops.

It can change your identity, your marriage, your relationship with your time, your health, your family and your sense of purpose. And Chris believes that's the part of retirement planning most people don't talk about.

Chris began his career just before the 2008 Financial Crisis, an experience that fundamentally shaped how he thinks about risk. Watching carefully constructed plans come under pressure taught him that assumptions can fail - and that a retirement plan needs to work in the real world, not just on paper.

But after nearly two decades in the industry, Chris has come to see that financial preparation is only one part of the equation.

The bigger question is: What are you actually retiring to?

Chris describes retirement as the "fourth quarter of life" - and, if you've done things right, a little overtime.His work explores what it takes to make that chapter meaningful: having financial confidence, maintaining your health, protecting the people you love, staying connected to a sense of purpose and knowing how you want to spend the years you've worked so hard to create.

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About this episode

Retiring without a clear plan can turn midlife uncertainty into a full-blown crisis, but securing guaranteed income and clarifying your long-term goals can restore total peace of mind. In this final episode of Season 6 of the Ask Faleskini Podcast, Peter Faleskini sits down with financial and retirement plannerChris Madurito discuss how smart financial choices can eliminate the fear of aging and underpreparation.

Key Topics Covered in This Episode:

- The Midlife Retirement Panic: Why it is never too late to start planning and how to align daily choices with future freedom.

- Income Over Raw Accumulation: Why tracking how much you spend and keep is far more critical than just chasing a net worth figure.

- Guaranteed Income for Guaranteed Expenses: Using tools like annuities to cover essential living costs so you never outlive your money.

- Sequence of Return Risk: How to safeguard your portfolio during the vulnerable 5-year window right before and after retirement.

- Balancing Equities & Guaranteed Assets: Using growth assets to combat inflation while relying on structured income for daily bills.

- The First Steps: Why spouses need to get on the same page psychologically before consulting a specialized financial planner.

How to Connect with Chris Maduri Resources & Links:

🌐 Chris Maduri's Website: https://vibrantretirement.com/

#MidlifeCrisis #FinancialFreedom #AskFaleskini #Annuities #WealthManagement #SequenceOfReturnRisk

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Peter's books

The Clarity CompassStop Midlife Burnout, Escape the Matrix, and Resolve Faleskini’s Complex

Faleskini’s complexDiagnosing the Systemic Costs of Midlife Crisis and Advancing Holistic Pathways of Resolution

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Guest: Chris Maduri

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