Ready For Retirement

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 philosophical take as he tackles Drew’s question. He demonstrates how to determine when Drew and his wife will be in a good position to fully retire. He also challenges listeners to assess their spending and saving habits and to strike a balanc...

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 three-step test to determine your retirement readiness.

By pulling together principles from the 4% Rule, straight-line projection, and a Monte Carlo analysis, you can assess whether your portfolio can sustain your desired lifesty...

Jennifer, 54, plans to retire soon. Her husband, 70, is retired, on Social Security, and dealing with some severe health issues. Jennifer worries about possibly becoming single in retirement, which could result in a higher tax bracket for her. 

Jennifer is considering whether to convert her traditional accounts to Roth to lower future taxes or to change her contributions to Roth 403b, even if it means paying more taxes now...

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 money and offer tax deferral on growth until withdrawal. When taking out funds, the principal is tax-free, but earnings are taxed at ordinary income rates. 

He explores strategies for tax-efficient withdrawals. He also touche...

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, finances become more complex. More money means more decisions and more chances to make mistakes or miss out on opportunities. That's where a quality advisor can come in handy. They help you steer clear of b...

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 flow? 

James explores the nuances of home ownership as an asset versus an investment. He considers cash flow and leverage as he looks at Ray’s three options – sell, rent, or borrow – while emphasizing aligning financial decis...

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 provides some general guidelines that can be helpful for anyone with similar gnarly tax strategy challenges in retirement. 

In this episode, we’ll cover the extent to which required distributions will be an issue, what you need to alleviate tha...

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 things to consider when it comes to gifting and inheritance: your gifting goal, whether you have a strong desire to see the assets gifted within your lifetime, the tax implications of various types of gifts, and what to do with assets y...

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 into account?” 

James explores several factors that could positively and negatively impact a survivor’s tax liability and what to consider when creating a Roth conversion strategy. 


Questions Answered: 
How can Roth convers...

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 sources, including pensions, 401k, property sales, and Social Security, they estimate their monthly expenses at $7,500. James analyzes their situation, emphasizing the balance between annuity stability and investment flexibility...

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 first bucket. With $1.6 million in assets and pension incomes, they aim to retire in 2026. 

James analyzes their needs, income sources, and portfolio and lays a foundation for their Bucket #1. It's crucial to br...

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 significant tax hit due to long-held appreciable value. 

James explains weighing the immediate tax consequences against the risk of holding onto underperforming assets. He also provides a framework for assessing risk, identifying o...

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 to a listener’s question about where to invest as he anticipates an early retirement. James walks through the steps of Root’s Sequoia System to explore options for early retirement scenarios.

Questions Answered: 
How does ...

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 implications are drastically misunderstood. I explore the three common mistakes people make when applying this rule and how to avoid them.

Questions Answered:
How do RMDs impact the 4 percent rule?
Does the 4 percent...

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 retirement will bring lasting happiness. 

Having structure in retirement and pursuing your passions is vital to feeling fulfilled. Although it's easy to fall into comparing our retirement experiences to those...

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 security benefits. 

James analyzes Sammy's current financial situation and offers guidance on approaching the tax planning aspect of her retirement strategy.

Learn:
How to determine how much to convert from an ...

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’s retirement.

Understanding Social Security strategies to avoid potential losses during retirement is important.

James explains the intricacies of spousal benefits, detailing how they are calculated based on the primary earne...

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 stock-to-bond conversation.

Learn how to determine the appropriate amount to have a bond ladder and whether you should own individual bonds or bond funds as a part of that ladder.

Questions Answered:
How do ...

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 portfolio.

Responding to a listener’s inquiry about early retirement, James dives into the potential impact of market timing on retirement outcomes. 

Learn three actionable strategies:

• Ensure a reasonable initial withdrawal rate.
• Implement a suitabl...