Retirement Starts Today

Most people focus on saving for retirement, but what happens when you actually get there? Retirement isn't just about having enough money—it's about managing risks that can threaten your financial security and lifestyle.

In this episode, we explore Five Key Retirement Challenges (and Solutions), inspired by a Kiplinger's Personal Finance article by Walt West. From unexpected market downturns to rising healthcare costs, these challenges can catch retirees off guard if they're not prepared.

We break down each challenge—financial instability, healthcare expenses, taxes, inflation, and estate planning oversights—and discuss practical strategies to navigate them. Learn how to structure a flexible withdrawal plan, prepare for long-term care costs, use tax-efficient strategies like Roth conversions, and ensure your estate plan protects your loved ones.

Plus, we tackle a listener question about using a MIGA ladder strategy to bridge the gap until Social Security—offering insights into the pros and cons of annuities in a retirement portfolio.

If you want to retire with confidence and avoid costly missteps, this episode is a must-listen. Whether you're years away from retirement or already in it, understanding these key challenges and their solutions can help you make smarter financial decisions for the road ahead.

• (0:00) 5 Key Retirement Challenges (and Solutions)
• (1:17) Retirement headline: Kiplinger's article on retirement challenges
• (1:42) Challenge #1: Financial instability
• (4:09) Challenge #2: Healthcare and long-term care costs
• (6:33) Challenge #3: Taxes in retirement
• (7:33) Challenge #4: Inflation's impact on retirement income
• (8:32) Challenge #5: Estate planning oversights
• (10:25) Listener question: MIGA ladder strategy for retirement income

• The Retirement Podcast Network
• Kiplinger's Personal Finance "Five Key Retirement Challenges" by Walt West
• Fidelity's Healthcare in Retirement Report

• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

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Most people plan for retirement by focusing on their savings and investment returns—but what if some of the most important decisions happen after you stop working?

In this episode, I sit down with Jeremy Keil, also known as Mr. Retirement, to discuss the three biggest mistakes retirees make—mistakes that can cost them financial security, tax savings, and peace of mind.

From misunderstanding the best time to take Social Security to underestimating how long retirement will last, we break down the key oversights that can derail even the best-laid plans.

Jeremy and I dive into why retirement age and Social Security claiming don't have to go hand in hand, how to accurately gauge your longevity to avoid outliving your money, and the crucial difference between optimizing for next month's income versus planning for a lifetime of financial security.

Whether you're a few years away from retirement or already in it, this conversation will challenge the way you think about your financial future and equip you with strategies to make smarter decisions.

• (0:00) Intro
• (1:19) Mistake #1 – Tying retirement to Social Security
• (4:05) Mistake #2 – Underestimating longevity
• (8:41) Planning for an earlier retirement than expected
• (13:50) Mistake #3 – Optimizing for short-term income over long-term security
• (19:20) Where to find more from Mr. Retirement

• The Retirement Podcast Network
• Mr. Retirement YouTube Channel
• Longevity Illustrator Tool

• Connect with Jeremy Keil AKA Mr Retirement on LinkedIn

• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

Get the book - out now!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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Many retirees enter their golden years with the goal of financial security, but what if the biggest risk isn't running out of money—it's not spending enough of it? A surprising new study reveals that retirees are withdrawing just 2% a year from their savings—barely half of what's traditionally considered safe.

This cautious approach might seem responsible, but it often leads to unnecessary frugality, missed experiences, and larger-than-expected tax burdens later in life. The hesitation to tap into personal savings, even when there's plenty available, raises an important question: What's stopping retirees from spending with confidence?

Research shows that retirees feel much more comfortable spending guaranteed income from sources like Social Security and pensions while being reluctant to withdraw from their own investments. This behavioral tendency can leave money unspent for decades, only to be forced out later through required minimum distributions (RMDs) that create tax inefficiencies. Meanwhile, large inheritances often arrive too late to make a meaningful impact on the next generation.

Rethinking the 2% mindset means understanding what keeps retirees locked into ultra-conservative spending habits and finding ways to turn savings into income that feels reliable. A simple shift—such as automating monthly withdrawals or adjusting expectations around financial security—can open the door to a more fulfilling retirement. The money was saved to be spent, and spending it well can be just as important as saving it wisely.

Spending too little can be just as costly as spending too much. With the right approach, retirees can enjoy their wealth now while keeping future financial security intact.

• (0:00) Why Retirees Spend Far Less Than They Could
• (1:46) The study: Retirees underspending their savings
• (3:33) Why the 2% problem exists
• (6:10) The impact of underspending on taxes & an inheritance
• (8:11) The role of financial planning & behavioral coaching
• (9:20) Possible solutions: Turning savings into reliable income
• (11:04) Listener question: A simple withdrawal plan

• The Retirement Podcast Network
• David Blanchett – Head of Retirement Research at PGIM DC Solutions
• Michael Finke – The American College of Financial Services
• Die With Zero by Bill Perkins – Book on intentional retirement spending

• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter
• Work with Benjamin: https://retirementstartstoday.com/start

Get the book - out now!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

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For decades, you've been focused on saving—watching your retirement accounts grow, sticking to a budget, and making smart financial decisions to ensure a secure future. But now that the time has come to actually enjoy your hard-earned money, spending it feels... unsettling.

You're not alone. Many retirees struggle with the mental shift from accumulation to decumulation, even when their financial plans show they have more than enough. The fear of running out, coupled with conflicting financial advice, makes it tough to confidently transition into this new phase of life.

Today we explore strategies for overcoming the retirement spending fear, based on an insightful Forbes article by Tim Maurer. We'll break down his three-step approach: phasing into retirement instead of stopping abruptly, redefining "work" to maintain purpose and fulfillment, and structuring an investment portfolio designed specifically for retirement withdrawals.

Plus, we'll tackle a listener question about Social Security spousal benefits and the implications of early filing. By the end of the episode, you'll gain a clearer understanding of how to embrace your retirement, spend with confidence, and fully enjoy the wealth you've built.

• (0:00) The fear of spending in retirement
• (1:19) The "Retirement Cycle of Fear"
• (3:13) Step 1: Phase into retirement gradually
• (5:15) Step 2: Keep working, but redefine it
• (7:20) Step 3: Build a portfolio for spending
• (10:14) Listener Q – Social Security & spouses
• (14:30) Final thoughts (how to thrive in retirement)

• The Retirement Podcast Network
• Tim Maurer's Forbes article – Overcoming the fear of spending in retirement.
• Daniel Crosby's The Soul of Wealth – A deep dive into money and psychology.

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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A lot of retirees assume their tax situation gets simpler once they stop working, but that's not always the case. There are plenty of ways high-net-worth retirees end up paying more than they need to—sometimes without even realizing it.

Maybe it's interest and dividend income getting taxed at higher rates, or IRA withdrawals happening earlier than necessary. Maybe it's something as simple as missing the right way to report charitable giving. These things add up, and over time, they can quietly eat away at retirement savings.

Some of the biggest inefficiencies show up on tax returns in ways people don't always expect. Social Security benefits taken too soon, mutual funds kicking off surprise capital gains, or estimated tax payments falling short and triggering penalties—it all matters.

There are ways to structure income, investments, and withdrawals to keep more of what's earned, but they take a little planning. The goal isn't just to minimize taxes for the sake of it, but to make sure every dollar is working as efficiently as possible.

Most of these inefficiencies can be fixed with a few small adjustments. Some require a different way of thinking about income in retirement, others just mean taking advantage of tax rules that are already there. Either way, it's worth a closer look. A little awareness now can mean thousands saved over the years.

• (0:00) Inefficiencies on Rich Retirees' Tax Returns
• (4:07) Top tax inefficiencies: Interest, dividends, and premature IRA withdrawals
• (6:52) Charitable distributions, Social Security timing, and phantom capital gains
• (9:33) Capital gains, charitable intent, and avoiding underpayment penalties
• (12:24) Listener question: Travel spending habits of wealthy retirees
• (19:05) Listener question: Callable CDs and interest rate risk
• (21:16) Closing thoughts and practical takeaways

• The Retirement Podcast Network
• Kiplinger's Article
• TurboTax Safe Harbor Guide
• Fidelity Charitable

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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Most people plan for retirement by focusing on their finances—building up a nest egg, securing passive income, and minimizing taxes. But what if that's only part of the equation? Many retirees find themselves financially secure yet feeling unexpectedly lost, disengaged, or even unhappy. The truth is, money alone doesn't guarantee a fulfilling retirement.

Dr. Daniel Crosby explains how work naturally provides purpose, engagement, relationships, and growth—key elements we often lose in retirement without realizing it. Without a plan to replace them, retirees risk dissatisfaction, depression, and even health issues.

The good news? By proactively designing your retirement around these five pillars—positive experiences, engagement, relationships, meaning, and growth—you can create a life that is just as rich in purpose as it is in financial security.

Whether it's through hobbies, social groups, volunteering, or personal growth, Dr. Crosby shares how to build a retirement that keeps you mentally, emotionally, and socially fulfilled for decades to come.

• (0:00) Introduction
• (1:30) The unexpected struggles of retirement
• (2:40) The five facets of a meaningful life
• (6:23) How to intentionally rebuild purpose after retiring
• (9:50) The hidden danger of loneliness in retirement
• (14:30) Why purpose-driven money decisions matter
• (22:50) A hilarious twist: How Elon Musk "stole" from Dr. Crosby!

• The Retirement Podcast Network
• Dr. Daniel Crosby's Book – The Soul of Wealth (Amazon)
• Dr. Daniel Crosby's Podcast – Standard Deviations (Podcast)
• CDC Report on Loneliness & Health Risks (Report)

• Chief Behavioral Officer bio
• His Twitter/X: @danielcrosby
• His LinkedIn: Dr. Daniel Crosby

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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Many people fear running out of money in retirement, assuming they'll struggle financially once they stop working. But a recent Gallup poll shows 80% of retirees have enough to live comfortably, despite concerns about Social Security, longevity risk, and pension declines.

Why the difference between expectation and reality? Many retirees find their expenses drop, Medicare covers more than expected, and Social Security plays a bigger role in their income.

However, many still claim Social Security early, leaving money on the table. By making strategic choices, like delaying Social Security and managing retirement savings wisely, you can secure a more stable, stress-free future.

If you're anxious about your retirement income, you're not alone—but retirees before you have found their finances more stable than they expected. By taking the right steps now, you can be part of that 80% who enjoy a confident retirement.

• (0:00) Concerns vs. Reality
• (1:30) The Gallup poll and retirement reality
• (5:00) The Social Security dilemma and when to claim
• (9:10) The shift from pensions to 401(k)s
• (11:17) Listener question: Pros and cons of 55+ communities
• (18:30) Why renting before buying can save you money
• (21:00) Final takeaways and episode wrap-up

• The Retirement Podcast Network
• Gallup poll on retirement confidence
• 55+ community comparison site
• Emile Hallez' Investment News retirement article

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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Listen in to this BONUS episode as Canadian CFP and host of the Your Retirement Planning Simplified Podcast, Joe Curry, interviews me (Benjamin) about:

• The non-financial aspects of retirement planning
• Shifting from a scarcity to an abundance mindset
• Retiring to something rather than from something
• and embracing creativity to design a fulfilling post-career life

Key insights include overcoming spending anxiety, identifying passions, building social connections, and planning purposefully for a no-regrets retirement. With actionable insights and a focus on mindset, this episode is perfect for those looking to simplify and enrich their retirement journey.

Enjoy!

Resources:

Joe Curry's website and podcast

Joe Curry on LinkedIn

Book: Be Your Future Self Now by Dr. Benjamin Hardy

• Inspiration for understanding and connecting with your future self to create a fulfilling retirement.

• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Subscribe to the newsletter: https://retirementstartstodayradio.com/newsletter

Get the book - out now!Retirement Starts Today: Your Non-financial Guide to an Even Better Retirement

Subscribe to Retirement Starts Today onApple Podcasts, Spotify, Pocket Casts, TuneIn, Podbean, Player FM, or iHeart

Click here to work with us!

Employee benefits are one of the most overlooked aspects of financial planning. We often check a few boxes during open enrollment and move on—but are we truly maximizing what's available to us?

This week, we sit down with Joe Saul-Sehy, host of Stacking Benjamins, to uncover the hidden value in workplace benefits. From disability insurance pitfalls to term vs. whole life insurance, Joe walks us through key strategies to ensure we're not leaving money (or protection) on the table.

Joe also introduces a powerful HR benefits guide, a resource designed to help us navigate workplace perks with confidence. Whether it's understanding own-occupation disability insurance, avoiding junk policies, or knowing when to self-insure, this conversation is packed with actionable advice. If you've ever wondered whether you're making the most of your benefits—or if you're just blindly accepting what's offered—this episode is for you.

• (0:00) Maximizing Workplace Benefits
• (2:32) Disability Insurance: Are You Really Covered?
• (6:50) The Truth About Accidental Death Policies
• (10:30) How Your Emergency Fund Can Replace Certain Insurances
• (14:50) The Hidden Costs of Small-Dollar Insurance Policies
• (18:00) Term vs. Permanent Life Insurance: What's Right for You?
• (24:20) How Much Life Insurance Do You Actually Need?
• (27:40) The Ongoing Evolution of Workplace Benefits & Joe's HR Guide

• The Retirement Podcast Network
• Website: Stacking Benjamins

• Twitter: @AverageJoeMoney
• Instagram: @StackingBenjamins
• LinkedIn: Joe Saul-Sehy

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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What if you could turn those green numbers in your investment account into retirement income while paying as little in taxes as possible? That's exactly what we're covering today with Peter Lazaroff, Chief Investment Officer at PlanCorp. We're tackling the challenge many of us face: managing deferred gains in our portfolios and figuring out the smartest ways to reduce the tax hit as we transition to retirement.

Peter and I talk through a range of strategies for handling concentrated stock positions, whether it's selling off winners gradually, taking advantage of tax-loss harvesting, or exploring more advanced options like exchange funds or a 351 exchange. These aren't just dry financial concepts—they're real, actionable ideas that can help you simplify your portfolio and make the most of what you've saved. And trust me, simplifying your financial "closet" can feel like a huge weight lifted.

We also talk about the emotional side of investing. Why does it feel so hard to part with stocks that have been good to us? Whether it's an attachment to the company or pride in your early picks, Peter shares why these feelings matter and how to move past them to make decisions that better serve your long-term goals. Stick around—you won't want to miss the insights he has to share.

• (0:20) Peter Lazaroff's Options for Reducing Taxes on Deferred Gains Pre-Retirement
• (01:46) Why retirees need to manage large brokerage gains.
• (03:10) The emotional challenge of selling winning stocks.
• (05:20) Risks of concentrated stock positions and diversification.
• (09:00) Tax-loss harvesting and direct indexing strategies.
• (14:30) Simplifying portfolios with the 351 exchange.
• (18:40) Portfolio simplicity and enjoying retirement income.

• The Retirement Podcast Network
• Peter Lazaroff's Book: "Making Money Simple" – www.peterlazaroff.com/freebook
• Peter Lazaroff's Website – peterlazaroff.com
• The Long Term Investor Podcast – thelongterminvestor.com

• Peter's website

• Become a Client: www.retirementstartstoday.com/start
• Get the Retire-Ready Toolkit: http://retirementstartstodayradio.com/
• Follow Ben on Twitter: https://twitter.com/retiremeasap
• Join the newsletter: https://retirementstartstodayradio.com/newsletter
• Dive deeper into retirement planning with Ben at www.RetirementIncome.University

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