Discover the Best Insights for Every Stage of Retirement

Top 30 Middle-Class Retirement Towns in U.S. 2024

GOBanking Rates ranks the best retirement havens with an eye toward affordability and…...

Alight Partners With Holistic Wellbeing and Fertility Support Services

The firm is growing its Alight Partner Network with Journey and Carrot Fertility...

Solving the Portability Puzzle with Allianz Life’s Ben Thomason

Considerable resources have been devoted to solving the challenge of portability in…...

Vestmark, BlackRock Partner to Strengthen Custom Model Portfolios

BlackRock will provide standard and custom RIA custom model portfolios through Vestmark platform...

Managed Accounts Get More Personal in PGIM RetireWell/iJoin Deal

New offering raises bar on personalized advice at scale to help savers reach retirement goals...

Tax-Savvy In-Plan Roth Conversions and Inherited IRA Withdrawals - 497

Should David in Ohio use 457 funds to do an in-plan Roth conversion in his 403(b) plan, and should he hire a financial advisor? Chris in DC needs a retirement and Roth conversion spitball analysis, an...

Should We Always Pull From our Brokerage Account First in Retirement? (Hint: No)

Patrick and Mary will soon both be retired. They are curious about what their withdrawal strategy should be as they balance various retirement accounts, including a pension, IRAs, and a brokerage acco...

How to Overcome Fears of Spending in Retirement

Ben has been a saver his entire life, which helped position him for an early retirement at the age of 53. Yet, he faces a big challenge. Having maintained his modest lifestyle, Ben’s comfortable...

Unexpected Retirement: Finding Happiness and New Adventures

Elaine didn’t decide to retire at age 57, but changes in her company meant an early retirement for her. Being caught off guard, she didn’t feel emotionally prepared to make the shift, even...

Facing Health Challenges in Retirement and Learning to Reconnect with Your Spouse

After his father lost healthcare coverage in retirement and had to pay for a major health event with savings, Derek was highly motivated to ensure sufficient coverage in retirement. He even considered...

How to Thrive in Retirement by Embracing the Unknown

Chris has been retired for a little over a year while his wife has continued to work. Now that Chris has “tried on” retirement and found the fit good, his wife will likely join him within ...

The Benefits of a Retirement Community and How to Find Your Purpose in Retirement

Meet Joe Sullivan, who found the first few years of retirement very difficult. Community is important to Joe, but he wasn't getting sufficient, routine social interaction to make meaningful connection...

Am I Too Old for Roth Conversions? 3 Things to Consider

Gary is a 73-year-old with $8 million in savings. Despite having substantial assets, he’s concerned about missed opportunities for Roth conversions as he faces significant required minimum distr...

3 Key Factors to Consider Before Paying Your Mortgage Off in Retirement

Connor plans to retire soon and wonders if he should pay off his mortgage of $300,000 or invest those funds, especially since he has a low interest rate. James gives a detailed response and reveals wh...

Pre-Retirement Tax Planning: Things to Know to Save Big in Retirement

Retirement tax planning should begin well before retirement. Listener Jodie, with over $2 million in assets in various types of accounts, is concerned about the high tax bracket she anticipates she be...

Social Security Demystified: Calculating Taxation, Provisional Income, and the Tax Torpedo

Listener Michael asks about how Social Security is taxed, the rationale behind the 50% and 85% tax thresholds, and the implications of these taxes on Social Security and IRA withdrawals. James respond...

The Roth Conversion Sweet Spot: Maximize Retirement Savings (And Avoid Costly Mistakes)

Listener Nael opens up a discussion about Roth conversions. There are benefits to doing Roth conversions, but can you do too many? Are there any downsides to Roth conversions? Reaping the tax benefits...

How to Estimate Your Tax Bill in Retirement (And How to Pay it)

David has a question about taxes in retirement: When you’re retired and no longer getting a regular paycheck from which your employer withheld tax payments on your behalf, how do you estimate th...

Retirement Income Strategies: IRA vs. Brokerage Withdrawals (The Tax-Smart Choice for Retirees)

Mark asks a common question – What should I do regarding my withdrawal strategy? Should I first pull from my brokerage account or my IRA? There is no one-size-fits-all answer, but James provides...

Planning for Large Costs in Retirement | Beyond the 4% Rule

Listener Sherry asks a good question: How do large, one-off expenses (like a new roof, new car, etc.) fit in the 4% Rule? James explains the concept of the 4% Rule and its limitations while demonstrat...

Early Retirement Health Insurance Strategies | Roth Conversions vs. ACA Subsidies

Healthcare subsidies are like a tax break and should always be optimized, right? That seems like an easy question that should have a straightforward answer. But the correct answer is, “It depend...

Everything You Need to Know About Medicare: Q&A with a Medicare Expert

Drew Shockley of MOVE Health Partners joins James to address questions about Medicare. He overviews the Medicare system, explains Parts A, B, C, and D, and breaks down what Medicare does and doesn&rsq...

How to Prepare for Retirement Within 5 Years: 401k, Savings & Investment Changes

Graham and his wife are in their early 50s and plan to retire in 5 years. He wonders if they should continue maxing out their 401ks, how their investments should change, and what they should do with s...

How to Know When You Should Stop Saving for Retirement (and What to Do Next)

Drew, a burnt-out, financially responsible 40-something father of two, hopes he can scale back from his stressful job and still be okay when it’s time to retire. James offers a practical and phi...

3 Simple Steps to Determine If You Can Retire

How do you know if you can retire? It seems straightforward, but the answer is far from simple. Beyond portfolio balances and age thresholds, there are other things to consider. James explains his thr...

Lump Sum vs. Annuitization: Tax Implications for Your Non-Qualified Annuity

Joe is planning for retirement and wants to minimize his tax burden, especially on the interest earned from his three annuities. James explains that non-qualified annuities are purchased with post-tax...

At What Age Should I Work with a Financial Advisor?

Deciding to work with a financial advisor is about more than how much you've stashed away. It's also about determining whether an advisor's benefits outweigh the costs. In your higher earning years, f...

Sell, Rent, or Borrow? Best Ways to Use Home Equity in Retirement

Listener Ray is wondering what to do with his home as he embarks on a nomadic, van-life journey in retirement. Should he sell it to finance his travels or retain it for potential appreciation and cash...

Pay ZERO Capital Gains Tax vs Roth Conversions in Retirement: How to Determine Which is Best

Listener Drew asks about a tax strategy for juggling capital gains and Roth conversions. While it can be a complicated question – especially when large accounts are involved – James provid...

Tax-Smart Strategies for Wealth Transfer: Secure Your Family's Future

James responds to listener Jerry’s question about the optimal time to distribute inheritance or charitable gifts: before or after passing away. James walks listeners through four important thing...

Roth Conversion Strategies to Protect Your Spouse's Future Tax Burden

A listener says, “Eventually, one spouse will pass before the other, which will often catapult the survivor into a significantly higher tax bracket. Shouldn’t a Roth strategy take this int...

Should I Fund my Retirement Needs by Purchasing an Annuity?

Jason and his wife face a crucial decision: whether to purchase an annuity or pursue traditional investments as they prepare for a full-time, slow-travel retirement. With a diverse array of income sou...

How Should I Invest Bucket #1 of my Retirement Portfolio (3 Bucket Strategy)

The "Three Bucket Strategy" is a popular retirement income planning method. The first bucket covers immediate expenses in retirement. Listeners John and Donna are seeking advice on constructing their ...

At What Point Should I Take the Tax Hit on Unrealized Gains?

Benjamin, nearing retirement at 65, faces a familiar dilemma with his taxable account housing expensive mutual funds. Despite their underperformance, converting to low-cost index funds entails a signi...

Maximize Your Early Retirement: Should You Save to 401k or Brokerage Accounts?

Typical retirement strategies assume a retirement age of over 60. With an earlier retirement goal, a careful look is required to determine what strategies will create the best outcome. James responds ...

Safe Withdrawal Rate Myths: Debunking 3 Common 4% Rule Mistakes

The 4% rule helps us understand how much we can safely take out of our portfolio each year without running out of money in retirement. Yet, as simple as the 4 percent rule seems, the practical implica...

What's the Right Roth Conversion Amount to Avoid a Tax Nightmare in the Future?

Sammy, a 51-year-old retiree, is seeking advice on how much she should convert from her traditional IRA to a Roth IRA each year to avoid jumping tax brackets and minimize the taxation of her social se...

How to Maximize Social Security Spousal Benefits

James addresses a common concern for a couple approaching retirement through a listener’s question. Listener Rob plans to collect Social Security early at 62, raising questions about his wife&rs...

Bond Ladders in 2024: How to Build a Bond Portfolio for Your Retirement

As one listener prepares for an early retirement, James discusses the situation, covering how to build a bond ladder based on non-retirement funds. James provides a different way of looking at the sto...

3 Ways to Protect Against Sequence of Return Risk in Retirement

James explores the concept of sequence of return risk in retirement planning. Most people are unaware of how risky this is, as it doesn’t become an issue until you begin living off your portfoli...

Should We Sell Stocks to Make a Large Purchase?

Should you sell long-term stocks for a real estate investment? I walk through one listener’s question and explain what you need to consider before making such a decision. Aside from the obvious&...

Am I Crazy For Paying My Financial Advisor $25k/year?

When you’re doing well financially, paying advisor fees might seem unnecessary. So do you need an advisor if you’re already in a good place? Having a successful retirement isn’t just...