Ready For Retirement

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 highlights the importance of aligning financial plans with personal goals, maint...

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 your life look like without constraints? What actually matters most to you? A...

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, increasing payments by 8% annually after full retirement age.3. Leverage spousal ...

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 deciding whether to hold or sell vested shares and how this decis...

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 explains that by managing withdrawals and Roth conversions strategica...

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 did Ben decide to retire when he was in his peak earning years?What are the st...

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 challenges related to spending, travel, and family dynamics. Qu...

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 never been happier. James and Elaine discuss how she found her footing i...

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 concerns➡ How his perspective on life and giving back has shifted➡ How he and his wife prepa...

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 focusing on giving back, retirement can be quite fulfilling. An...

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 importance of remaining flexible and trying new things as retirees explore who...

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. Get all the details in today’s episode.Questions answered:How ...

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 distributions.James encourages Gary to reassess his investment strategy, particularly the bond funds in his Roth IRA, and align his tax planning with his broader financial goals. By doing this, Gary could make more informed decisions that support his retirement goals and charitable aspirations.Questions ans...

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 why there is no one-size-fits-all answer. When it comes to having a mortgage in retirement, math and spreadsheets can help with part of the question, but emotions and personal values should be considered too.Questions answered:Should you pay off your mortgage as you head into retirement, especially...

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 in in retirement. Is there a tax strategy that would put her in a lower tax bracket? James explores some often-overlooked tax strategies that can save retirees thousands in retirement, especially for those like Jodie with diverse portfolios.Questions answered:How could my home be part of m...