How To - Get Smart About Retirement

Should You Use Your Retirement Savings to Start a Business?

If you’re going to try, here are some ideas on how to do it safely.

money.usnews.com Apr 26 2026

7 Medicare Part D Costs to Prepare For

Here’s how to find a lower cost Medicare prescription drug plan.

money.usnews.com Apr 26 2026

Investing When the World Feels Crazy: Expert Strategies

Here's how to manage portfolio risk in uncertain times, without losing your cool. Because "a well-built plan ... should not follow the news cycle."

kiplinger.com Apr 25 2026

561: Freedom After 50: The 80% Rule That Could Change Your Retirement Timeline with Jordan Grumet, MD

What if waiting until you're "fully ready" for retirement is actually costing you some of the best years of your life? Topics covered in this episode: The controversial "retire at 80%" framework Why m...

howardbailey.com Apr 25 2026

559: How Dopamine Shapes Your Motivation, Happiness, and Purpose in Retirement with Michael Long

Today, I'm excited to welcome Michael Long to the podcast. Michael is a physicist-turned-writer and the co-author of the international bestseller The Molecule of More. His work explores one of the mos...

howardbailey.com Apr 25 2026

557: By the Numbers: The Fragile Decade That Could Make (or Break) Your Retirement

What if the real retirement risk zone isn't during retirement… but the five critical years before and after it begins? In this episode, you'll learn about: Pre- vs. post-retirement sequence of returns...

howardbailey.com Apr 25 2026

Financial Mistakes High-Income Professionals Should Avoid with Amanda Harrell

An interview with FPL's Amanda Harrell, where we talk through how to handle a 401(k) rollover without blowing up your Backdoor Roth IRA, whether direct indexing is really worth it, and what to think a...

whitecoatinvestor.com Apr 23 2026

Social Security Benefit Cuts? What the Latest Projections Mean for Your Plan

Social Security benefit cuts are a real risk but not certain. Here’s what projections show, and how to plan your retirement accordingly. The post Social Security Benefit Cuts? What the Latest Projecti...

boldin.com Apr 22 2026

Will Your Retirement Income Trigger the IRMAA This Year? (Plus, 6 Ways to Avoid it in the Future)

Medicare costs can spike if your income triggers the income-related monthly adjustment amount. Here's what to expect in 2026 and how to avoid it in the future.

kiplinger.com Apr 22 2026

Trump Accounts Are Coming. How Should Employers Prepare?

Employers are already getting questions from employees about Trump Accounts. Here’s how they work, what they mean, and how to prepare before the details finalized.

forbes.com Apr 22 2026

Listener Questions: How Do I Create a Diversified Portfolio?

Roger Whitney breaks down how to create a diversified portfolio by explaining the core principles of diversification and asset allocation, then answers listener questions on topics like using allocati...

share.transistor.fm Apr 22 2026

I'm 74 With a Beloved Dog, But I Don't Trust My Adult Kids to Care for My 'Third Child' If I Die. What Should I Do?

We asked estate planners how to protect his one-year-old dog when his heirs aren't up to the task.

kiplinger.com Apr 21 2026

Bloomberg Businessweek story on retirement advice featuring r/retirement

Hello, I'm a reporter, often writing about aging. I wrote a story for Bloomberg Businessweek with advice from people who have retired about how to do it right. I wanted to share, because I had a very ...

reddit.com Apr 21 2026

Physician Spending Guilt During Retirement: How to Make the Most of Your Hard-Earned Money

Physicians have gotten better about entering retirement with serious financial muscle. Yet many still struggle with peace about actually spending ... Read more

physicianonfire.com Apr 21 2026

The Retirement Question Every Couple Asks: Can We Afford It? - 578

"Chase and Ryder" are 56 and 55 with $5 million saved and huge pensions the day they retire. So why are they so nervous about pulling the trigger? That's today on Your Money, Your Wealth® podcast numb...

purefinancial.com Apr 21 2026

4 Retirement Risks Business Owners Often Overlook

Retirement can be hard for business owners who've tied up their net worth — and sense of purpose — in one company. Find out how to make your exit successful.

kiplinger.com Apr 17 2026

Listener Questions: What Should I Be Doing When I'm Two Years from Retirement?

In this episode, Roger Whitney breaks down essential elements you need to consider before and during retirement. From understanding inflation risks to strategic asset reallocation, this episode offers...

share.transistor.fm Apr 15 2026

This Early Retirement Strategy Could Be a Huge Mistake

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on whether a popular early retirement strategy could actually blow up your financial plan, today on Your Money, Your Wealth® podcast number 577. Red...

purefinancial.com Apr 15 2026

6 Scary Retirement Risks (and How to Vanquish Them)

From the cost of long-term care to outliving your savings, aging is full of risks that are almost too scary to contemplate. Here's how to face them fearlessly.

kiplinger.com Apr 13 2026

I'm a Financial Adviser: This Could be the Single Biggest Threat to an Otherwise Solid Retirement Plan

You'll most likely need long-term care as you age. Not planning for it puts your assets and your family's peace of mind at risk. Here's how to tackle the beast.

kiplinger.com Apr 12 2026

Forget 'Trust Reveal' Parties: This Is How to Successfully Transfer Wealth

Wealth transfer isn't about dramatically revealing the size of an inheritance. It's about communicating your story and preparing heirs to uphold shared values.

kiplinger.com Apr 11 2026

How to Pay Taxes in Retirement and Avoid IRS Penalties

Paying taxes in retirement means managing income streams, quarterly deadlines, and the IRS safe harbor, without an employer doing it for you. The post How to Pay Taxes in Retirement and Avoid IRS Pena...

boldin.com Apr 09 2026

I'm a Financial Adviser: This Is How to Ensure Your Kids Never Hear, 'We Might Lose the House'

Instead of seeing retirement planning as a game of optimizing returns, try to view it as building a plan that keeps your family steady when life punches first.

kiplinger.com Apr 08 2026

Listener Questions: Should I Take Social Security Early and Invest It?

In this episode of the Retirement Answer Man, Roger Whitney explores the critical decision of when to claim Social Security benefits, weighing the pros and cons of taking them early versus delaying. T...

share.transistor.fm Apr 08 2026

How to Tackle the Nowhere-to-Be Thing in Retirement and Make a Winning Play With Your Time

Too much free time in retirement can come as a shock after decades of working. How can you ensure you don't overfill your days or let too many drift by?

kiplinger.com Apr 05 2026

How To Improve Your Home’s View With Foresight and Patience

In a previous post, I debated whether it’s better to buy a home with a bigger lot or an amazing view. One key point was that unlike increasing livable square footage, it’s nearly impossible to create ...

financialsamurai.com Apr 05 2026

How to decide what matters in downsizing?

We are looking to downsize from a 4500sf home. Naturally, that will mean giving up space, but we’re having a hard time prioritizing. Every room in our current home is spacious and we have lots of stor...

reddit.com Apr 02 2026

The Retirement Account Contribution Order: Get More From Every Dollar You Save

The contribution order for retirement accounts can affect how much your money compounds tax-free. Here’s how to prioritize for tax efficiency. The post The Retirement Account Contribution Order: Get M...

boldin.com Apr 02 2026

Emotional Intelligence and Money: Are You Making the Right Decisions with Your Investments?

Money is not all about numbers and analysis. Emotions can help and hurt your financial security. Learn how to be an emotionally intelligent investor. The post Emotional Intelligence and Money: Are You...

boldin.com Apr 02 2026

Capital Gains Tax Brackets: How Income Pushes Your Rate Higher

Capital gains tax can cost more than you expect when investment profits stack on top of ordinary income. Here’s how to plan around it. The post Capital Gains Tax Brackets: How Income Pushes Your Rate ...

boldin.com Apr 02 2026

How to Make Smarter Investment Decisions (Taxes, Fees, Risk)

Answering listener questions about whether it makes sense to sell a legacy investment for a lower-cost option and how to think through that tax tradeoff, how to choose tax lots in a taxable account, a...

whitecoatinvestor.com Apr 02 2026

Die With Zero: Are You Giving Your Kids Too Much? - 575

Joe Anderson, CFP® and Big Al Clopine, CPA spitball on how to build your own retirement AND support your kids financially, today on Your Money, Your Wealth® podcast number 575. "Lloyd and Diane" in Mo...

purefinancial.com Apr 01 2026

Listener Questions: Should I Move My 401K into an IRA When I Retire?

Explore how meaningful travel experiences, storytelling, and thoughtful planning can enhance your retirement journey. In this episode, Roger answers listener questions on managing retirement accounts,...

share.transistor.fm Apr 01 2026

The Two-Lifetime Challenge: How to Fund Your Retirement and Theirs

When you have a child with a disability, your money has to last twice as long. Here is the blueprint for a century of financial security.

kiplinger.com Mar 30 2026

Is Your IRA Rollover Stuck in Neutral? This Simple Mistake Can Cost You a Lot of Money

Rollover IRAs can end up stuck in cash, while abandoned 401(k)s can be parked in a cash-like Safe Harbor IRA. Here's how to put your money back to work.

kiplinger.com Mar 28 2026

Is Your Cash in the Wrong Spot? Find Out Before It Costs You!

Jeremy Keil explains how putting your cash in the wrong spot could prevent you from earning thousands in interest during your retirement. Many retirees spend a lot of time thinking about how to get be...

keilfp.com Mar 27 2026

556: By the Numbers: Could the Government Tax Your Roth IRA in the Future? What if Congress Changes the Rules?

If you convert to a Roth today, could Congress change the rules tomorrow — and should that fear stop you from taking action? In this episode, you'll learn: The truth about retroactive Roth taxation Wh...

howardbailey.com Mar 27 2026

How To Build A 10-Million-Dollar 401(k) From A Wealth Manager

Dream of a fabulous retirement? How to actually build a $10 million 401(k) from a top wealth manager all while saving taxes and building finanical freedom.

forbes.com Mar 26 2026

Will Environmental Hazards Make a Mess of Your Estate Plan?

Careful estate planning is vital if property you own could be contaminated. Here's how to avoid handing your beneficiaries a huge legal and financial burden.

kiplinger.com Mar 25 2026

The Surprising Habit That Leads To Happiness

Generosity leads to happiness. Learn different ways to practice generosity and how to teach it to those who matter most to you.

forbes.com Mar 25 2026

Why Even the Best Retirement Calculator is Wrong

Roger Whitney explores why retirement planning software—especially Monte Carlo simulations—can give a false sense of confidence if misunderstood. He explains what these tools actually measure, the hid...

share.transistor.fm Mar 25 2026

What an Annuity Really Is (The “Tell It to Me Like I’m Tired” Version)

An annuity is basically you telling your money: “Stop wandering around and pay me like rent every month.” And your money says, “Okay, fine,” and does it. ? The Three Types (Explained Like Family Membe...

community.aarp.org Mar 25 2026

555: By the Numbers: The Anchors of Retirement Confidence, Part 4 — Building a Retirement That Can't Break

Join us as we continue our "Anchors of Retirement Confidence" series, where we discuss four areas of retirement uncertainty plus strategies designed to replace your anxiety with clarity and control. I...

howardbailey.com Mar 25 2026

How to Get More Money in Your Retirement Accounts

You don't need to be the smartest doctor in the room to understand how to get more into your retirement accounts. But I'll explain it anyway. The post How to Get More Money in Your Retirement Accounts...

whitecoatinvestor.com Mar 24 2026

When Should You Take Social Security? (Don't Screw This Up) - 574

Joe Anderson, CFP® and Big Al Clopine, CPA focus on Social Security claiming strategies as part of the retirement spitballs, today on Your Money, Your Wealth® podcast number 574. Bijou Plutus and her ...

purefinancial.com Mar 24 2026

Beyond the 183-Day Rule: How to Protect Your Retirement Wealth After Moving to a Cheaper State

While a move can protect your legacy, many retirees stumble at the finish line by ignoring the strict state residency tests used to challenge their new status.

kiplinger.com Mar 23 2026

A Market Crash Isn't Your Greatest Retirement Risk: The Real Threat Lies Closer to Home

Retirees are conditioned to think that market risk is the main threat to their future, but here's the real danger — and how to bring it under control.

kiplinger.com Mar 22 2026

The Simple Legal Document Families Need to Protect Their Kids (But Don't Know About)

When parents are absent, caregivers may not be able to make emergency decisions for a child without a Delegation of Parental Authority. Here's how to set it up.

kiplinger.com Mar 21 2026

6 Ozzy Osbourne Lyrics Retirees Should Live By

The Prince of Darkness not only knew how to rock out, but he also imparted a great deal of wisdom on living in the moment and finding serenity that can guide retirees during their greatest set.

kiplinger.com Mar 20 2026

Claim the 'Founder' Title After 55: Launch a Business Without Jeopardizing Your Retirement

Older founders are three times more likely to succeed than 30-year-olds. Here's how to leverage your expertise while navigating the "Medicare gap" and self-employment taxes.

kiplinger.com Mar 20 2026