Retirement With/On Purpose

Trevor introduces a new format by interviewing retired North Carolina clerk of court Susan Hicks to explore the emotional and practical transitions of life after work. Susan shares firsthand insights on the challenge of shifting from a rigid career schedule to managing an open slate of retirement time, emphasizing that finding purpose can come from simple, flexible daily goals and community servic...

Trevor Lawson addresses the complex financial and emotional challenges of passing down real estate, particularly cherished vacation homes, to the next generation. With approximately $25 trillion in real estate expected to transfer to heirs by 2048, Trevor outlines five essential strategies to minimize capital gains taxes and avoid family conflict. Key insights include the benefits of a step-up in...

How do retirees optimize tax-deferred growth and portfolio longevity? Host Trevor Lawson evaluates three distinct approaches for 2026: delaying withdrawals until year-end to maximize tax-deferred compounding , taking distributions early in the year to eliminate penalty risks and facilitate Roth IRA conversions , or utilizing a systematic monthly or quarterly "installment" method to mitigate market...

Trevor Lawson tackles a timely and often expensive issue for retirees and business owners: the surge in underpayment penalties for estimated taxes. With penalty rates nearly doubling since 2021, Lawson explains how taxpayers with non-withholding income—such as investment gains, self-employment earnings, or Roth IRA conversions—can inadvertently trigger interest-based charges by failing to pay taxe...

Trevor Lawson explores flexible alternatives to the traditional 529 plan for families wary of tying up funds exclusively for higher education. While acknowledging the 529's tax advantages and new provisions for Roth IRA rollovers, Trevor evaluates the pros and cons of taxable brokerage accounts, Roth IRAs, custodial accounts (UGMA/UTMA), and cash-value life insurance. The discussion emphasizes the...

Trevor Lawson revisits one of the most critical technical threats to a stable retirement: sequence of returns risk. By examining the work of retirement specialist Dr. Wade Pfau, the episode breaks down how the timing of market downturns—specifically in the years immediately surrounding one's retirement date—can have a more profound impact on portfolio longevity than average long-term returns. Laws...

Trevor Lawson explores the "mattering span," a critical but often overlooked dimension of retirement planning that focuses on the deep human need to feel seen, valued, and essential. Drawing on insights from author Jennifer Wallace, Lawson defines the "mattering crisis" as the destabilizing loss of purpose and social connection that occurs when the structure of a career is removed. The episode hig...

Trevor Lawson explores the significant communication gap between parents and their heirs regarding estate planning and inherited wealth. While nearly all families recognize the importance of these discussions, a Fidelity study reveals that nearly half have yet to engage in them, often due to the discomfort of discussing mortality. Trevor emphasizes that proactive communication is essential to ensu...

Trevor Lawson explores the unique financial and logistical strategies necessary for a successful retirement without children. With child-free adults representing over 20% of those in their 50s and 60s, Lawson emphasizes the importance of building a "support team" of legal proxies or geriatric care managers to handle medical and financial decisions when you cannot. The discussion details critical s...

Trevor Lawson discusses the unique financial and logistical considerations for adults navigating retirement without children. Because child-free individuals lack a traditional family safety net, Lawson emphasizes the necessity of proactively building a support team of legal proxies or professional geriatric care managers to handle medical and financial decisions. The conversation covers critical s...

Want to build a million-dollar balance in your 401(k)? It all starts with the power of compound interest—why starting early and getting the full employer match is crucial. Learn to put contribution increases on autopilot, save aggressively (the millionaires' average is over 17% of pay) , and why maintaining a separate emergency fund prevents costly 401(k) loans and penalties. We also cover how to...

You've budgeted for travel and groceries, but are you prepared for the sneaky, rising costs that can derail a well-laid retirement plan? Learn why healthcare and wellness could be the "big tamale" of your retirement spending, with costs rising faster than general inflation. We also explore the hidden costs of home maintenance and modifications , rising insurance premiums , the expense of multi-gen...

You've spent years building your 401(k), but what happens to that money when you're no longer here? Most people don't realize that their beneficiary designation on their 401(k) or Roth 401(k) overrides their will, making it critical to keep it updated! In this episode, we explore how your retirement savings pass to your designated heirs outside of probate, and why it's essential to name both prima...

"What do I do with my 401(k)?" You've worked hard and saved diligently into your 401(k), but now that retirement is here, what comes next for that nest egg? Don't make a costly mistake by defaulting to a choice that could trigger a huge tax bill! In this episode, we break down the three most common options for your 401(k) when you leave an employer—from leaving it in place to a tax-free rollover—a...

Many people start collecting Social Security benefits before their full retirement age, often out of fear the program will change, but this can lead to penalties if they later return to work and exceed a certain income limit. This episode, Trevor outlines two ways to exercise a "do-over" on your Social Security claim. The first is Withdrawal of Benefits, which allows you to cancel your application...

Continuing the series on frequently asked retirement questions, Trevor Lawson explores the common query, "Where should I retire?" He reveals the top five U.S. destinations— Florida (ranked number one for low taxes and funding for seniors), Minnesota (for its healthcare and low crime rate), Colorado (for its active lifestyle and tax-friendly conditions), Wyoming (for low crime, sunshine, and low ta...

In this episode, Trevor Lawson tackles one of the most frequently searched retirement questions: "How much do I need to retire?" Inspired by a framework provided by ChatGPT, he outlines a seven-step process to calculate your retirement savings goal. The steps include estimating your annual spending in retirement, estimating the length of your retirement, factoring in inflation, considering guarant...

In the second part of the series on annuities, Trevor Lawson uses a framework from a Morningstar article by Christine Benz to help listeners determine if an annuity is a suitable tool for their retirement plan. Trevor discusses key questions to consider, such as whether you need guaranteed lifetime income to hedge against longevity risk, especially since pensions are becoming less common. He also...

In the first part of a series on annuities, host Trevor Lawson aims to demystify this often misunderstood financial instrument. Drawing on insights from a Morningstar article, he defines a basic annuity as a contract with an insurance company where a lump sum of money is given in exchange for a stream of income over a lifetime. Trevor explains that annuities are gaining favor as a replacement for...

In this episode, Trevor Lawson reflects on the first half of the year by providing a mid-year outlook for the market and economy, based on a publication from the Capital Group. He notes that the global landscape is undergoing a fundamental restructuring, leading to increased volatility and a lack of clear direction for investors and companies. The Capital Group has revised its 2025 GDP growth proj...

In this episode, Trevor Lawson concludes the mini-series on cognitive biases by examining how they influence the decision of when to claim Social Security benefits, often leading individuals to underestimate their life expectancy. Drawing on an article by Rick Kahler, Trevor discusses how the availability heuristic, shaped by immediate examples like untimely deaths or media coverage, can lead peop...

In this episode, Trevor Lawson resumes the series on cognitive biases, focusing on hindsight bias. He defines it as a psychological phenomenon where individuals believe they accurately predicted an event after it occurred, often leading to overconfidence. Trevor shares a personal anecdote about Meta stock to illustrate how this bias can affect investment perceptions. He explains that hindsight bia...

In this timely episode, Trevor Lawson interrupts the cognitive biases series to dive into "The Big, Beautiful Bill," a sweeping piece of legislation under the Trump administration. Drawing from a CNBC article, Trevor breaks down the key provisions and their potential impact on personal finances. He discusses the permanency of the 2017 tax cuts, including the increased standard deduction and a sign...

In this episode, Trevor Lawson delves into recency bias, a cognitive bias where individuals overemphasize recent experiences, even if they aren't the most relevant. He provides relatable examples, such as the perception of current mortgage rates as astronomically high due to recent historical lows , and the tendency to invest heavily in sectors that have recently performed well, like the large-cap...

In this episode, Trevor Lawson begins a multi-part series on cognitive biases, focusing on how they impact investment decisions. Drawing from an article by Signature Investment Advisors, Trevor introduces "high watermark thinking," where investors use their portfolio's highest value as a mental reference point, making market dips feel like losses even with overall positive long-term returns. He ex...