roadmap to RETIREMENT

In this solo Roadmap to Retirement mailbag, I answer five listener and client questions: how to retire early by building a liquid, non-retirement investment pool to bridge the years before penalty-free access to retirement accounts (while still enjoying life); whether to buy a whole life policy for a friend, where I stress starting with your financial plan rather than a product; whether to buy silver, where I caution against chasing what’s been hot and suggest only a small, diversified allocation if any; how to handle being overconcentrated in one stock, where I argue that paying capital gains taxes can be worth it to reduce risk and note options like spreading sales across tax years; and whether it’s “stupid” to move and give up a low 2020-era mortgage rate, where I weigh lifestyle needs and mention refinancing if rates fall.

Thanks for listening and come back for new episodes and returning guests soon!

On this episode of Roadmap to Retirement, I talked with Jon Sheldon, founder of BelleauWood Coaching LLC in Rochester, NY, about the non-financial side of the FIRE movement—especially the purpose gap that can hit when someone retires around 45 and suddenly loses the structure and meaning work provided.

Jon explains his coaching framework built on four pillars:

We discussed how redefining success can shift priorities, and how ecosystem changes often mean adding the right relationships, not just cutting toxic ones. Jon closes with his “briefs and battle plans” approach to quicker decision-making: clarity, condition, cost, align, act, and adapt.

In this episode of Roadmap to Retirement, I sat down again with Jason Grover to talk about how financial planning shouldn’t only revolve around the vague idea of “retirement someday,” especially for younger people who need more motivating, near-term goals.

We discussed common “pipe dream” goals like buying a cottage or lake house and even retiring early, and why those goals are often achievable if you’re willing to make the sacrifices and turn them into a date-specific, dollar-specific plan. Jason emphasized that retirement planning still has to come first, particularly for young parents who want to prioritize their kids’ education.

The key point: if you neglect your own retirement, you risk becoming financially dependent on your children later. We talked about how some families get into trouble by financially supporting adult children—sometimes without the adult kids realizing the debt or financial strain it creates—and how bringing multiple generations into the planning conversation can improve transparency and behavior.

Jason and I explored why “I want to retire” isn’t enough—asking “why” helps uncover what someone actually wants, whether that’s purpose-driven work, more freedom, time with family, travel, or passion projects. When it comes to early retirement and the FIRE movement, Jason framed it as less about the size of your portfolio and more about the lifestyle you choose and how you’ll sustain it over decades, including inflation.

We discussed the broader issue of limited financial education and how debt can set people up for long-term challenges. To end the episode, there was the idea that goals are achievable when you’re serious: write them down and stay flexible enough to pivot when reality requires it.

Come back soon for another episode.

Welcome back to the Roadmap to Retirement podcast. In this solo episode, I discuss two key topics. First, the challenge some retirees face of having ‘too much money,’ a situation often resulting from decades of diligent saving and conservative spending habits. I explore strategies for making meaningful use of these funds, such as gifting to adult children or supporting charities, and also suggest indulging in personal bucket list experiences.

Second, I address the temptation and pitfalls of debt, particularly low-interest debt, urging listeners to be cautious of lifestyle creep and to consider the true cost of financing items like cars. Finally, I propose a crucial question for anyone meeting a financial advisor: ‘How long have you been an advisor, and how long do you plan to continue?’ This helps ensure you find a knowledgeable advisor who can support you long-term. Tune in for practical financial tips and strategies to supercharge your retirement savings.

Thanks for listening, come back soon for another new episode!

In our latest episode of Roadmap to Retirement, we dive into the interplay between accountants and financial advisors with Jordan Stealey, EA at Redwood Tax and Accounting.

We discuss the importance of collaboration in financial planning and tax preparation, especially around tax season. Topics include the misperceptions surrounding Qualified Charitable Distributions (QCDs), the nuances of handling RMDs, and strategies for business owners to save effectively for retirement.

Jordan also shares insights on recent changes in tax law, including the senior enhanced deduction and new rules around social security and tax deduction on car loans.

We touch on the practicalities of budgeting and how financial behavior plays a critical role in retirement planning. The episode is packed with invaluable advice to help you streamline your financial future by leveraging the unique strengths of both your accountant and financial advisor.

Come back next week for another episode!

Welcome to The Roadmap to Retirement, this episode I am flying solo. As a way to kick off the new year, let’s talk about financial planning best practices, tips and smart money moves.

Learn about the Mexican fisherman story, and the importance of financial goals aligning with one’s desired lifestyle rather than merely accumulating wealth. I want to caution against relying on market predictions, and stress the importance of a well-thought-out investment philosophy that can withstand market fluctuations. Practical advice for managing your investments includes aligning risk with your life stage, adopting a conservative approach for short-term goals, and avoiding the pitfalls of frequently checking investment performance.

This episode is also a discussion towards the emotional impact of losing money through different scenarios like gambling, stock investments, and accidental loss, highlighting the psychological aspects of financial decision-making.

Lastly, I want to introduce the concept of our client communication schedule to ensure proactive and meaningful interactions between financial advisors and their clients, helping to stay ahead of any issues and making informed decisions. Tune in to secure your financial future and enable a fulfilling retirement lifestyle.

As always, thank you for listening. We have exciting plans for 2026 – more solo sessions and some with new topics and guests!

Welcome back to the Roadmap Retirement Podcast! Kicking off the new year strong with a new guest – Jesse Cramer, who transitioned from a mechanical engineer to a financial planning and wealth management professional. We dove into Jesse’s journey, including his podcast, ‘Personal Finance for Long-Term Investors,’ and discussed the unique financial planning perspectives that come from his engineering background.

We explored the challenges faced by detail-oriented clients, especially engineers, and how their methodical approach impacts financial planning strategies. We also discussed the dynamic nature of financial planning, the pitfalls of relying solely on the 4% rule, and the importance of maintaining flexibility in retirement plans. Additionally, we touched on the topic of estate planning and the benefits of having open conversations with beneficiaries.

Thank you for listening, make sure to tune in for new episodes, topics and guests!

Welcome back to the Roadmap Retirement Podcast, returning for a second time, I am talking with Alex Wesdorf today to talk about the often-avoided topic of disability insurance.

This episode explores the critical need for disability insurance, especially for self-employed individuals and W2 employees who might not fully comprehend their existing benefits. We discuss real-life scenarios, such as the impact of injuries and the undervalued risk of cognitive issues. Highlights include the inadequate default benefits provided by employers, the importance of considering future medical costs, and how critical insurance can be in shielding your family’s financial future.

We also touch on the crucial role that employers play in educating their employees about available benefits and provide actionable advice: review your benefits booklet and consult with a financial advisor to ensure you’re adequately covered. This episode is a comprehensive guide to understanding why disability insurance should be an integral part of your financial planning.

Welcome back to the ‘Roadmap to Retirement’ podcast, where we delve into financial tips, investment strategies, and smart money moves to supercharge your retirement savings. Today, I’m joined by Tom Harris, someone whose career and perspective on retirement resonate with many of our clients.

Tom shares his journey from a career in operations excellence and leadership development in Rochester to his current semi-retired status. He emphasizes the importance of understanding one’s motivations and impact as a leader, reflecting on the generational shifts in workplace culture and expectations over the past few decades. From the command-and-control styles of his early career to the more flexible and balanced approaches of today, Tom provides a broad perspective on leadership and career development. He advocates for redefining retirement, seeing it more as financial freedom and a journey rather than a final destination.

He encourages young professionals to always be learning, to seek out mentors, and to build relationships. Tom’s own experiences and insights offer valuable lessons for both those nearing retirement and those just starting their careers.

Thank you for listening and stay tuned for new episodes, guests and topics!

Welcome to another episode of the Roadmap to Retirement Podcast! I’m joined once again by Matthew Jarvis. In this episode, we dive into the complexities of retirement planning, with a particular emphasis on tax strategies. We shed light on recent changes in tax laws, such as the increase in the state and local tax (SALT) cap from $10,000 to $40,000, and new provisions for charitable contributions. We also discuss the importance of proactive tax planning to avoid unexpected tax bills in retirement. Additionally, we touch on intriguing topics like the financial impacts of gambling and the essential role of meaningful activities post-retirement. For younger listeners aiming for early retirement, we recommend exploring resources like Tim Ferris’s ‘Four-Hour Work Week’ and the ‘Mr. Money Mustache’ blog. Whether you’re close to retirement or just starting to plan, this episode is packed with valuable advice to help you build a secure and enjoyable future.