Retirement Starts Today
Benjamin Brandt CFP®, RICP®
Do you want to spend more money & pay less taxes on your way to an even better retirement? Great news, you're in the right place!
I'll also teach you the benefits of retiring TO something, while most retirees only solve half the equation by retiring FROM something.
Tune in every Monday morning - hosted by Benjamin Brandt CFP®, RICP®.
Join my "This Week in Retirement" newsletter for the best retirement content of the week, sourced by me: https://pages.thisweekinretirement.com/newsletter
I'll also teach you the benefits of retiring TO something, while most retirees only solve half the equation by retiring FROM something.
Tune in every Monday morning - hosted by Benjamin Brandt CFP®, RICP®.
Join my "This Week in Retirement" newsletter for the best retirement content of the week, sourced by me: https://pages.thisweekinretirement.com/newsletter
Episodes
Mentioned books
Oct 12, 2026 • 18min
Four Big IRA Mistakes That You Can't Undo
Explore four IRA missteps that can trigger lasting tax consequences, from inherited-account transfers and rollover limits to 72(t) payment rules and securities handling. Tom asks how the Rule of 55 could unlock his 401(k) after leaving work at 55. The discussion also considers building a market-resistant retirement runway and finding purpose through service, family, health, and community.
Oct 5, 2026 • 1h 2min
Are Super Savers Failing in Retirement? with Andy Panko [Rebroadcast]
Andy Panko, a retirement educator and financial advisor, explores why super savers can struggle to spend their money confidently. They discuss the limits of Monte Carlo projections, flexible Social Security and Roth conversion strategies, IRMAA and charitable giving, renting in retirement, AI’s risks, and finding purpose beyond perfect spreadsheets.
Sep 28, 2026 • 28min
How to Get the Most from Your Employee Benefits [Rebroadcast]
Joe Saul-Sehy, personal finance educator, former advisor, and co-host of Stacking Benjamins, explores the often-overlooked value of employee benefits. Topics include own-occupation disability coverage, using emergency funds to self-insure, avoiding low-value supplemental policies, choosing term versus permanent life insurance, and calculating personalized coverage needs. He also shares a practical guide for navigating changing workplace benefits.
Sep 21, 2026 • 18min
Using IRAs To Reduce Estimated Tax Penalties
A late-year windfall can trigger an unexpected IRS penalty, but retirement-account withholding may offer a solution. Learn how December RMD withholding, tax safe harbors, and Form 2210 can simplify estimated taxes. Plus, a listener’s windfall question and an inspiring look at finding purpose through faith, service, and meaningful work in retirement.
9 snips
Sep 14, 2026 • 25min
6 Cases When a Roth IRA Conversion Isn't a Smart Move
Explore six situations where Roth IRA conversions may deserve a second look, including Medicare surcharges, widow’s taxes, inheritance planning, and retirement time horizons. The discussion also covers strategically funding conversion taxes and the special considerations facing super savers. Plus, a listener’s plan to bridge retirement before Social Security and a moving story about finding purpose through service.
9 snips
Sep 7, 2026 • 20min
Why I Object to 'Hitting a Number' for Retirement
Why can “hitting a number” be a dangerous retirement goal? This discussion explores personalized spending plans, sequence-of-returns risk, and building a safer runway after market highs. It also tackles whether $1 million is enough, how a low-rate mortgage affects timing, and the challenge of pre-Medicare health insurance. Plus, Kurt’s story shows how purposeful activities can shape an active retirement.
Aug 31, 2026 • 15min
The 'Open Sandwich' Generation
What happens when aging parents are gone and children no longer depend on you? Explore the freedom, grief, and unexpected responsibilities of becoming the family’s senior generation. The discussion also covers estate planning for solo agers, professional fiduciaries, healthcare decisions, and charitable beneficiaries. Plus, Judy’s creative path to a meaningful retirement through substitute teaching.
Aug 24, 2026 • 18min
Your $135,000 Retirement Risk
They unpack Milliman’s $135,000 long-term care figure and what it actually represents. They compare short, costly care episodes with multi-year care that can reach six figures. They explore sex differences in expected long-term care costs. They weigh options like using home equity, insurance, annuities, or self-funding for this tail risk.
8 snips
Aug 17, 2026 • 20min
38% of Retirees Underspend
A look at a survey showing many retirees hold back spending to avoid shrinking their nest egg. Discussion of different retirement spending shapes and the idea of a minimum dignity floor. Practical strategies for replacing lost survivor pension income without overly cutting current living. A profile of purposeful retirement activities like tutoring, volunteering, and pickleball.
Aug 10, 2026 • 18min
"New" Rules around 401K Catch-Up Contributions
A new tax rule now forces many catch-up 401(k) contributions into Roth accounts and the show walks through the 2026 numbers. The host weighs whether Roth catch-ups still make sense versus taxable savings. A listener’s clever workaround for Roth conversion timing and Medicare surcharges gets analyzed. A retired HR manager shares finding purpose tutoring kids through Reading Partners.
