The Income Question Every Retiree Must Answer

What happens in retirement when the paychecks stop? This episode explores why guaranteed income is such a critical piece of retirement planning and how it can help support essential expenses while shaping investment and tax strategies. Sean Mason discusses the balance between guaranteed and non-gua…

What If You Could Retire Sooner Than You Think?54

What if the only thing standing between you and retirement is a fear that may not match the numbers? Sean Mason discusses why so many people believe they need to work longer, even when retirement may already be within reach. He explores common concerns about running out of money, the difference bet…

The Retirement Threat You Can't Control

What if the biggest threat to your retirement isn't the market, but decisions being made in Washington? With ongoing uncertainty around Social Security and proposals inspired by Australia's retirement system, Sean Mason discusses the risks retirees can't control and the strategies they can. He expl…

Warren Buffett Went to Cash. Should You?

What if playing it safe with your retirement savings creates a different kind of risk? Inspired by Warren Buffett's massive cash position before retiring, Sean Mason explores why moving money out of the market isn't always the straightforward decision it seems. He discusses the difference between e…

Think You're Too Old for a Roth Conversion? Think Again

Could a successful IRA become a tax headache later in retirement? Sean Mason unpacks a real-world scenario involving an 80-year-old retiree facing a massive required minimum distribution (RMD) and the tax consequences that follow. He explains how RMDs can impact Social Security taxation, Medicare p…

The Retirement Rules That May No Longer Work

What if the retirement strategies that got you here are the very things holding you back? Sean Mason discusses why many long-standing financial habits may no longer fit today’s retirement landscape. From outdated portfolio models and changing tax laws to shifting views on long-term care and debt, h…

Pay Taxes Now or Later? The Roth Conversion Question

Could a strategy designed for Gen Z also reshape retirement planning for boomers? Sean Mason explores why Roth accounts are gaining momentum across generations, from young investors embracing Roth IRAs to retirees considering Roth conversions. The conversation examines the tradeoffs between paying …

The Retirement Freedom Everyone Is Chasing

What does financial freedom really look like once the paychecks stop? In this episode, Sean Mason connects America’s 250th birthday celebration with the retirement goal of financial independence. He discusses why retirement is about more than leaving a job, how confidence comes from understanding y…

The Retirement Conversation Your Family Can’t Afford to Skip

What happens when the person who has always managed the family finances is suddenly no longer there? Sean Mason explores why retirement planning should be a family conversation, not a private one. Drawing on real-life experiences, Sean and Casey discuss the importance of involving spouses and adult…

The Roth Rule Change That Could Reshape Retirement Planning

Could moving Roth IRA money back into a workplace retirement plan ever make sense? Sean Mason explores a proposed rule change that would allow Roth IRA assets to roll into employer-sponsored Roth plans and breaks down the situations where it might help—or where it may not. The conversation covers e…