Retirement Redzone, The Last Mile episode artwork

EPISODE · Jun 15, 2026 · 56 MIN

Retirement Redzone, The Last Mile

from Money On Tap · host Ben Brayshaw & Seth Krussman

Ten straight up weeks, then a sharp pullback — and if you’re two to five years on either side of retirement, the fear is real. This is the Retirement Red Zone: the last mile into and out of your retirement date, and the most fragile window in your entire financial life.This week on Money On Tap, Ben Brayshaw and Dan Michelon turn last week’s market-history conversation into a practical playbook for anyone near retirement: how to avoid the paralysis that wrecked so many retirements in 2008–2009, and what to actually do right now.What you’ll learn:Why a 35-year-old and a 65-year-old should do the opposite thing in a pullbackThe accumulation-to-distribution switch most people don’t know existsWhat history says: after 40 sharp selloffs since 1980, markets were higher 75% of the time a year laterSequence-of-returns risk — why the first five years decide everythingBuilding a 1–3 year retirement runway with ~4% cash and T-billsRebalancing a 60/40 that drifted to 75/25Diversifying away from a top-10 that’s now 40% of the S&P (8 of them tech)Buffered ETFs — a 20% buffer with a 12–15% cap, explainedFoundational income, annuities, and the tax-aware withdrawal piece most firms skipPlus Money In The News:Consumer prices rose 4.2% annually in May — the highest in three years (CNBC, Jeff Cox)Elon Musk poised to become the first trillionaire — and just how much a trillion dollars really isA top JP Morgan strategist’s four ways to prep your portfolio for “considerable danger” (David Kelly)Mentioned on air: Our short sequence-of-returns risk video — watch it at brayshawfinancial.com.Read the companion blog: brayshawfinancial.com/blogSchedule a free consultation: app.greminders.com/t/9f3ce72e/initialconsultaFull Money On Tap episode library: brayshawfinancial.com/money-on-tapContact UsPhone: 855-226-8551Email: [email protected]: 116 South River Road, Bedford, NH 03110Web: brayshawfinancial.comWhat is the retirement red zone, and why does it matter? The retirement red zone is the roughly ten-year window covering the five years before and the five years after your retirement date. It matters more than almost any other period because of sequence-of-returns risk: a major market downturn while you’re beginning to withdraw income can permanently damage the plan, even if the market later recovers. Two people who invest identically but retire a few years apart can end up with opposite outcomes based solely on timing. Navigating the red zone means shifting from maximizing gains to mitigating losses — stress-testing the plan, building a cash runway, rebalancing, diversifying, and adding guardrails like buffered ETFs and guaranteed income.

Ten straight up weeks, then a sharp pullback — and if you’re two to five years on either side of retirement, the fear is real. This is the Retirement Red Zone: the last mile into and out of your retirement date, and the most fragile window in your entire financial life.This week on Money On Tap, Ben Brayshaw and Dan Michelon turn last week’s market-history conversation into a practical playbook for anyone near retirement: how to avoid the paralysis that wrecked so many retirements in 2008–2009, and what to actually do right now.What you’ll learn:Why a 35-year-old and a 65-year-old should do the opposite thing in a pullbackThe accumulation-to-distribution switch most people don’t know existsWhat history says: after 40 sharp selloffs since 1980, markets were higher 75% of the time a year laterSequence-of-returns risk — why the first five years decide everythingBuilding a 1–3 year retirement runway with ~4% cash and T-billsRebalancing a 60/40 that drifted to 75/25Diversifying away from a top-10 that’s now 40% of the S&P (8 of them tech)Buffered ETFs — a 20% buffer with a 12–15% cap, explainedFoundational income, annuities, and the tax-aware withdrawal piece most firms skipPlus Money In The News:Consumer prices rose 4.2% annually in May — the highest in three years (CNBC, Jeff Cox)Elon Musk poised to become the first trillionaire — and just how much a trillion dollars really isA top JP Morgan strategist’s four ways to prep your portfolio for “considerable danger” (David Kelly)Mentioned on air: Our short sequence-of-returns risk video — watch it at brayshawfinancial.com.Read the companion blog: brayshawfinancial.com/blogSchedule a free consultation: app.greminders.com/t/9f3ce72e/initialconsultaFull Money On Tap episode library: brayshawfinancial.com/money-on-tapContact UsPhone: 855-226-8551Email: [email protected]: 116 South River Road, Bedford, NH 03110Web: brayshawfinancial.comWhat is the retirement red zone, and why does it matter? The retirement red zone is the roughly ten-year window covering the five years before and the five years after your retirement date. It matters more than almost any other period because of sequence-of-returns risk: a major market downturn while you’re beginning to withdraw income can permanently damage the plan, even if the market later recovers. Two people who invest identically but retire a few years apart can end up with opposite outcomes based solely on timing. Navigating the red zone means shifting from maximizing gains to mitigating losses — stress-testing the plan, building a cash runway, rebalancing, diversifying, and adding guardrails like buffered ETFs and guaranteed income.

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Retirement Redzone, The Last Mile

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This episode was published on June 15, 2026.

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Ten straight up weeks, then a sharp pullback — and if you’re two to five years on either side of retirement, the fear is real. This is the Retirement Red Zone: the last mile into and out of your retirement date, and the most fragile window in your...

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