Ready For Retirement

Roth conversions are almost a buzzword today, with many people jumping into them like they’re a guaranteed fix for tax worries—much like rushing into surgery hoping it will solve all your problems. But just like surgery, Roth conversions require careful consideration, and they’re not always the right solution. Before deciding to convert, it’s essential to understand why not to do it.

Here are some key reasons to skip—or at...

Meet Sarah—a retiree with a multi-million-dollar portfolio, no mortgage, and all her income needs covered by Social Security. Yet, she hesitates to furnish her newly expanded home, fearing it would “waste” money. In this episode, James unpacks Sarah’s story to explore why so many of us struggle to spend, even when we're financially secure.

James explores concepts like:
- The Purpose of Money: Money is a tool, not ...

Are you delaying retirement, working for "just one more year" to feel ready? In this episode, Ari and James dive into goalpost planning—the tendency to postpone retirement over financial or emotional uncertainties. Learn how to prioritize life goals over arbitrary benchmarks, like saving $1M or following a generic 60/40 portfolio strategy.

🎙️ Highlights from the conversation:

• The emotional challenges of leavi...

In today’s episode of Ready for Retirement episode James covers when to adjust your portfolio as retirement nears—a crucial step for balancing growth and security. If adjustments happen too late, market downturns could delay your plans; if too early, you might miss out on potential growth.

The focus is on reallocating stocks to more stable investments like bonds as you approach the time you’ll need to start drawing from yo...

Meet Ari Taublieb 👋 If you didn’t already know, Ari and I work together at Root Financial, and we thought it was finally time to launch a podcast series together.

In our very first episode, we dive into a topic that many people shy away from: talking to your parents about money. Whether it’s discussing their estate plans, long-term care, or the tough conversations around wealth, these talks can feel awkward—but they’re ab...

Roth IRAs offer great tax-free income benefits, but to make the most of them in retirement, here are seven things you need to know:

1. Contribution Limits: In 2024, you can contribute up to $7,000 annually ($8,000 if 50+), across both Roth and traditional IRAs.
2. Access to Contributions: You can withdraw your contributions at any time, tax-free and penalty-free. Only earnings are subject to penalties if withdrawn early.
3. The F...

Have you thought about what moving to a new state might mean for your retirement budget and lifestyle? In this Ready for Retirement episode, the focus is on preparing for an out-of-state retirement. James outlines three essential considerations for retirees planning a move:

1. Housing Costs and Expenses: From property values and local property taxes to potential capital gains from selling a current home.
2. Overall Cos...

Many dream of retiring early, but you would be surprised to learn that many people who retire early regret doing so. James reveals five things that lead people to regret early retirement and provides practical tips to avoid these pitfalls.

He explains why many individuals who retire before 65 struggle due to a lack of planning, overly conservative investment strategies, and failure to envision life beyond work. He highligh...

James sits down with someone who’s financially set to retire—mortgage paid off, kids through college, and investments in place—but he’s still grappling with one big question: what’s next?
Instead of focusing solely on financial strategies or retirement planning, James gives him some unexpected advice: start journaling. This led to a deeper conversation about finding purpose beyond optimizing your portfolio.

What would ...

For many, Social Security makes up a large portion of their retirement income, so it’s important to know how to maximize your Social Security benefit. James explains how Social Security works, diving into some important foundational aspects. He then explains four key strategies for maximizing benefits:

1. Work for 35 years to avoid zero-income years in the calculation.
2. Delay benefits, if possible, until age 70, incr...

ames responds to a question from Chris regarding restricted stock units (RSUs) and how to avoid costly mistakes when managing them. He explores whether it’s wise to hold onto company stock or diversify for a safer financial future. He breaks down how RSUs work, from vesting schedules to the tax implications of receiving stock as part of your compensation package. He also explains the critical considerations you should make when dec...

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 account. They've been using tax gain harvesting to minimize taxes and plan to eliminate gains by 2024. A key question is whether to withdraw from their IRAs or brokerage account first, considering their state’s tax exclusion. James ex...

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 portfolio has continued to grow and has nearly doubled in value. James and Ben discuss the challenges of making mindset shifts and the proactive steps Ben has taken to encourage himself to spend more.

Questions answered:
How d...

Monique aspired to retire early, and while she had faithfully saved throughout her working years, she wasn’t sure if she had enough to retire. After getting assurance from professionals, she took the plunge and quit working. Monique and James talk about the first two years of her retirement – how she’s been able to focus on her health and pursue some hobbies she didn’t have time for previously. Monique also shares some surprising c...

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 though she knew that her family would be fine financially.

One year into her retirement, she found her groove by focusing on her family, building new relationships, trying new things, and staying physically active. Today she says she’s ...

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 leaving the job he loved for one with better healthcare and retirement benefits.

Derek shares his retirement journey with James, including:

➡ Decisions he made pre-retirement
➡ How he addressed healthcare conce...

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 year. In his conversation with James, Chris, who could be described as goal-oriented and one who likes to be prepared, talks about the pros and cons of retirement. He’s found that by staying flexible, maintaining an adventuresome spirit, and f...

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 connections while living in rural Virginia. He found his groove once he moved to a retirement community in Florida.

James and Joe discuss the phases of retirement and what those phases have looked like for Joe. Joe emphasizes the i...

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 doing all the talking, he’s inviting people like you to be part of the show. Some of you have real-life retirement advice to share. Others of you have questions that James can address. Ready for Retirement is poised to be a place for both. ...