Retirement Rescue: The Money Mistakes of Every Decade

Whatever you've done, there's a very good chance you can recover. That's the message of this week's show — and then Ben and Dan get specific, decade by decade, about the mistakes that quietly sink retirements and the moves that rescue them.In this week's Money On Tap, Ben Brayshaw and Dan Michelon walk through the money mistakes of every stage of life. The 20s and 30s: waiting to invest, lifestyle inflation, and treating insurance as a nuisance instead of what it really is — protection of your ability to retire. The 40s — the squeeze years: turning off the 401(k) match to pay the bills (walking away from free money), getting too comfortable with debt, and skipping the tax planning that builds tax-free assets for later. The 50s — the catch-up years: catch-up contributions, the HSA "triple threat," the backdoor Roth, and the fear-driven mistake of going too conservative too soon. And in retirement itself: the light-switch move to cash, target-date funds past their date, scattered old 401(k)s, chasing a "number" instead of an income, and the biggest one of all — no plan for a health change.What you'll learn:Why your 20s and 30s are the most powerful investing decade you'll ever get — and what lifestyle inflation really costsInsurance reframed: insuring well-being, not events — and why long-term care planning protects the healthy spouseThe 401(k) match rule for the squeeze years: never walk away from free moneyWhen to shift from investment planning to retirement planning — and why the goal is an income number, not a total numberThe catch-up toolkit for your 50s: 401(k) and IRA catch-ups, the HSA triple threat, and the backdoor RothWhy "too conservative too soon" quietly loses money backwards — and how segmentation puts risk and security in one strategyThe bucket strategy in action: a real case of a 60%-bond portfolio, a 4.5% withdrawal rate, and a first-home gift — rescuedFoundational expenses: the income planning step most people skip before retiringThe health-change plan: estate documents, powers of attorney, and why waiting can mean it's too late to signPlus Money In The News:Alphabet set for a blockbuster quarter as AI bets collide with spending fears — why this AI buildout isn't the dot-com eraPhased tariffs on generic drugs: 90% of U.S. prescriptions are generics, and most aren't made hereFidelity's new number: retirees may need nearly $186,000 for healthcare — up 7.5% in a yearWant the Retirement Rescue white paper? Email us at [email protected] and we'll send it over.Read the companion blog: https://www.brayshawfinancial.com/blogSchedule a free consultation: https://app.greminders.com/t/9f3ce72e/initialconsultaBrowse the full Money On Tap library: https://www.brayshawfinancial.com/money-on-tapContact UsPhone: 855-226-8551Email: [email protected]: 116 South River Road, Bedford, NH 03110Web: brayshawfinancial.comSecurities and advisory services offered through Osaic Wealth, Inc., member FINRA/SIPC. All other services offered through Brayshaw Financial Group, LLC are independent of Osaic Wealth, Inc. Osaic Wealth, Inc. and Brayshaw Financial Group do not provide tax or legal advice. Figures cited are as of the air date, drawn from sources believed reliable, and subject to change. Past performance is not a guarantee of future results.Is it too late to fix my retirement at 50?No — the 50s are the catch-up years by design. Catch-up provisions let you contribute above the standard limits to 401(k)s and IRAs, the HSA offers triple tax advantages for future healthcare costs, and a backdoor Roth can build a tax-free bucket even if your income is too high for direct contributions. Pair those with a segmented "bucket" strategy — instead of retreating to CDs and cash — and most late starts can still be rescued. The first step is knowing your income need, not chasing a number.