What Happens When Retirement Doesn’t Go According to Plan?

What if the biggest retirement mistake isn’t running out of money, but running out of options? Sean Mason uses NFL star Josh Allen’s approach to planning for an uncertain future as a springboard to discuss flexibility in retirement. The conversation explores why freedom matters more than rigid fina…

The Legacy Mistake That Can Cost Future Generations

What if the most valuable thing you leave behind isn't money at all? Inspired by the legacy of Dolly Parton, Sean Mason explores how families can pass down values, memories, and purpose alongside their wealth. The conversation covers meaningful family discussions, common estate planning mistakes, t…

Retirement's Most Trusted Rule Under the Microscope

What if the retirement rule everyone trusts could actually create unnecessary risk? This week, Sean Mason breaks down the widely known 4% rule, including why its creator recently increased the withdrawal rate to 4.7% and what that means for retirees today. Sean explains the dangers of relying on av…

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 …