Curated articles and podcasts from trusted financial experts and real retirees.
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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...
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...
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 ...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
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...
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 ...
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...
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...
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...
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...
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 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&...
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...
James addresses a listener's question regarding Social Security strategies in retirement. Sasha, aged 59, seeks advice on when to start collecting Social Security, considering her husband's benefits a...
James explores the nuanced aspects of Roth IRAs, shedding light on intricacies that can confound even experienced investors. Through a listener question from Manfred, a retiree contemplating a $50,000...
 Tax loss harvesting is a strategy that investors use to reduce their tax bill. However, there are many misconceptions about tax loss harvesting, including when it's valuable and how to do it ef...
James walks through a framework of how you ensure that your legacy goals include more than just leaving a chunk of money to your kids when you're gone. He explains the key concepts that can help your ...
Have you ever wondered if purchasing an annuity makes sense for you? There are two conflicting opinions from financial advisors: some advocate for annuities while others advise against them. James exp...
401(k) account management is an option for anyone with a 401(k) – no matter how close or far you are from retirement. Even if you have some basic investment knowledge, you might want to consider...
Gen Xers still have some time – but not a ton – to plan for retirement....
Ready for Retirement is on a mission to be the most valuable source of retirement information in the world. In that light, we’re making some changes. The biggest change is that rather than James...
Dr. Riley Moynes, author and creator of a popular TED Talk joins James to discuss his own retirement which led him to become the author of The 4 Phases of Retirement. While Dr. Moynes was financially ...
Retirement is not just about financial readiness; it's also about finding purpose, passion, and personal growth. James and guest Cynthia Meyer debunk the arrival fallacy, the illusion that reaching re...
Joining the ranks of 401(k) millionaires can be withing your sights with these four strategies....
In 2010, Nobel Prize winners Daniel Kahneman and Angus Deaton found that happiness rises with income up to about $75,000 a year*. After that, more income doesn’t increase happiness. However, ......
Multi-national organized networks of criminals know how to get to vulnerable people. Learn how to stop them....
Beneficiaries will pay less in 2025 for Medicare Part D prescription and Medicare Advantage plan premiums....
Discover the most affordable car insurance options in Maine for 2024. Compare rates from top providers like Auto-Owners, State Farm, and Geico, and learn how to lower your premiums through discounts, ...
We live in an area where the value of houses has appreciated quite a bit, and ours is paid off. We do not have an LTC policy, having heard poor experiences and reviews. But, depending on how long we c...