Retirement Rescue: The Money Mistakes of Every Decade copertina

Retirement Rescue: The Money Mistakes of Every Decade

Retirement Rescue: The Money Mistakes of Every Decade

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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 costs
  • Insurance reframed: insuring well-being, not events — and why long-term care planning protects the healthy spouse
  • The 401(k) match rule for the squeeze years: never walk away from free money
  • When to shift from investment planning to retirement planning — and why the goal is an income number, not a total number
  • The catch-up toolkit for your 50s: 401(k) and IRA catch-ups, the HSA triple threat, and the backdoor Roth
  • Why "too conservative too soon" quietly loses money backwards — and how segmentation puts risk and security in one strategy
  • The bucket strategy in action: a real case of a 60%-bond portfolio, a 4.5% withdrawal rate, and a first-home gift — rescued
  • Foundational expenses: the income planning step most people skip before retiring
  • The health-change plan: estate documents, powers of attorney, and why waiting can mean it's too late to sign
Plus 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 era
  • Phased tariffs on generic drugs: 90% of U.S. prescriptions are generics, and most aren't made here
  • Fidelity's new number: retirees may need nearly $186,000 for healthcare — up 7.5% in a year
Want the Retirement Rescue white paper? Email us at info@yourmoneyontap.com and we'll send it over.Read the companion blog: https://www.brayshawfinancial.com/blog
Schedule a free consultation: https://app.greminders.com/t/9f3ce72e/initialconsulta
Browse the full Money On Tap library: https://www.brayshawfinancial.com/money-on-tapContact Us
  • Phone: 855-226-8551
  • Email: info@yourmoneyontap.com
  • Office: 116 South River Road, Bedford, NH 03110
  • Web: brayshawfinancial.com
Securities 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.

  • What is value investing and why is it working again in 2026?
    Value investing means buying strong, profitable, often dividend-paying companies at sensible prices and holding them patiently — the approach built by Benjamin Graham and made famous by Warren Buffett and Charlie Munger. It struggled while near-zero interest rates favored growth stocks, but higher rates flipped the equation: in 2026, value sectors like energy (~20%), industrials (~17%), and healthcare (~15%) are outpacing the S&P 500's roughly 8–9%. The appeal is simple — instead of borrowing to chase growth, these companies pay shareholders real income today, and reinvested dividends compound over decades.
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