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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. 

Outline of This Episode

• (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!

Resources & People Mentioned

• 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)

Connect with Dr. Daniel Crosby

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

Connect with Benjamin Brandt

• 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.

Outline of This Episode

• (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

Resources & People Mentioned

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

Connect with Benjamin Brandt

• 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

Subscribe to Retirement Starts Today on

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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.

 

Connect with Benjamin Brandt

• 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

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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. 

Outline of This Episode

• (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

Resources & People Mentioned

• The Retirement Podcast Network
• Website: Stacking Benjamins

Connect with Joe Saul-Sehy

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

Connect with Benjamin Brandt

• 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

Subscribe to Retirement Starts Today on

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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. 

Outline of This Episode

• (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.

Resources & People Mentioned

• 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

Connect with Peter Lazaroff

• Peter's website

Connect with Benjamin Brandt

• 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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Can you be fired after announcing your retirement? It's a question that raises eyebrows and stirs concern for anyone nearing the end of their career. A recent article highlights the legal and financial implications of being terminated after sharing retirement plans, and it’s a scenario more common than you might think.

Employers often operate under at-will employment laws, giving them broad rights to terminate employees, even after a retirement announcement. But what does that mean for you? Understanding protections like ERISA and the Age Discrimination in Employment Act can make all the difference in navigating this tricky situation. It's not just about legalities—financial stability, severance packages, and health insurance come into play too.

On top of that, announcing retirement at the wrong time could mean missing out on potential benefits or buyouts. Striking a balance between professional courtesy and protecting your financial future is essential. When it comes to planning for life after work, the timing and approach of your announcement could impact everything from your wallet to your peace of mind.

Outline of This Episode

• (0:00) Introduction
• (0:29) Yahoo Finance article discussion
• (1:11) At-will employment laws explained
• (2:08) Legal considerations: ERISA and age discrimination
• (3:57) Financial steps after unexpected termination
• (7:47) Protective measures to stay on track
• (10:05) Client story: Announcing retirement too early
• (12:12) Listener questions: What to retire to
• (13:04) Crafting a fulfilling retirement plan
• (17:27) Taking small risks to find post-career purpose

Resources & People Mentioned

• The Retirement Podcast Network
• Yahoo Finance Article by Christy Bieber – Discussing legal and financial challenges of being fired after announcing retirement
• Freedom for Fido – A charity building shelters and fences for dogs in need

Connect with Benjamin Brandt

• 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

Subscribe to Retirement Starts Today on

Apple Podcasts, Stitcher, TuneIn, Podbean, Player FM, iHeart, or Spotify

Click here to work with us!

Are you spending too little in retirement, worried you might outlive your savings? Many retirees struggle to strike the right balance, often holding back on enjoying the wealth they’ve worked a lifetime to build. I’ll show you how to overcome those fears and spend with confidence while still planning for the future.

What about real estate? Whether you’re thinking about renting instead of owning, leveraging home equity for long-term care, or even investing in rental properties, the right approach can make all the difference. I’ll share practical insights to help you figure out what works best for your lifestyle and financial independence.

Retirement is your chance to live on your terms, free of unnecessary stress and worry. By understanding the psychology of spending and making thoughtful decisions about your biggest assets, you can enjoy the freedom and security you’ve earned. Let’s get started. 

Outline of This Episode

• [0:00] The Start of 2025
• [1:50] Spending Struggles in Retirement
• [4:40] Connecting with Your Future Self
• [6:12] Underspending Biases and Longevity Risk
• [12:01] Real Estate in Retirement
• [14:10] Renting vs. Owning
• [16:10] Home Equity for Long-Term Care

Resources & People Mentioned

• The Retirement Podcast Network
• Morningstar Article: Tips to spend less or more in retirement by Samantha Lamas.
• Benjamin Brandt’s Book: Retirement Starts Today.
• Capital City Wealth Management: Benjamin Brandt’s financial planning firm.

Connect with Benjamin Brandt

• 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

Subscribe to Retirement Starts Today on

Apple Podcasts, Stitcher, TuneIn, Podbean, Player FM, iHeart, or Spotify

What does it mean to live a life of purpose? I talk with Jordan Grumet, aka Doc G, host of the Earn & Invest podcast, about how his work as a hospice doctor shaped his understanding of purpose and regret. His new book, “The Purpose Code,” offers insights on how to live with intention and meaning.

We talk about the difference between "Big P" and "Little P" purpose and why focusing on grand goals often leads to frustration. Jordan shares how the terminally ill reflect on their lives, emphasizing the courage it takes to prioritize what truly matters.

This conversation is about using time, money, and energy to create a fulfilling life. Whether you’re planning retirement or redefining your goals, Jordan’s perspective can help you focus on what lights you up and brings you joy. 

Outline of This Episode

• [1:42] Purpose and Regret: Lessons from terminally ill patients
• [3:40] The Purpose Paradox: Tackling anxiety in finding purpose
• [5:50] The Role of Courage: Overcoming barriers to meaningful living
• [8:40] The Trap of “Enoughness”: When financial goals fall short
• [14:00] Winning Life: Filling your calendar with what matters
• [17:10] The Purpose Code: A guide to living intentionally

Resources & People Mentioned

• The Retirement Podcast Network
• Book: The Purpose Code (Available January 7th, 2025)
• Podcast: Earn and Invest
• Book: Taking Stock: A Hospice Doctor’s Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life

Connect with Jordan Grumet

• Jordan Grumet’s Website: jordangrumet.com

Connect with Benjamin Brandt

• 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

Subscribe to Retirement Starts Today on

Apple Podcasts, Stitcher, TuneIn, Podbean, Player FM, iHeart, or Spotify

Originally aired February 2024:

There are two ways to mess up retirement: run out of money or die with regret. Oftentimes, people in the retirement space only focus on the running out of money part.

In an effort to help you live an even better retirement, today’s retirement headline discusses the regret part. Join me to learn five expenses that retirees wish they had spent more money on so that you can learn from their mistakes.

Stick around to hear the answer to our listener question: Is there one person who can help develop a comprehensive retirement plan? Or do you need to have an investment advisor, a financial advisor, a tax advisor, and an estate planning attorney? Find out the answer by pressing play.

For more information, visit the show notes at https://retirementstartstodayradio.com/5-expenses-retirees-wish-they-spent-more-money-on-rebroadcast 

Originally aired March 2024:

There are many ways that could threaten your financial security in retirement. Knowing the common issues can ensure that you don’t fall into the traps.

Today’s financial headline comes from Yahoo Finance and is called 8 Ways Baby Boomers Become Poor in Retirement. Listen in to learn what they are so that you don’t drive yourself into the poorhouse.

For more information, visit the show notes at https://retirementstartstodayradio.com/8-ways-to-become-poor-in-retirement-rebroadcast