“Joe, how much did you spend on your wedding?”
That’s how this episode kicks off, and it sets up the theme running through everything else.
Joe and I help a couple figure out if their plan to retire together in […]
Tag: retirement planning
#730: Q&A: We Have $1.5 Million. Can We Stop Now?
What does it actually mean to have “enough” — and how do you know when it’s time to stop optimizing and start living?
This week’s questions all circle the same tension: how do you keep building financial security without losing the years you’re supposedly securing it for?
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#728: Q&A: What $2.4 Million at 37 Actually Looks Like (It’s Not What You Think)
What happens when a sudden $850,000 inheritance turns into eight different account balances, three rental properties, and one very big decision about your future?
When grief, real estate, and a six-figure windfall collide all at once, the fastest way to make an expensive mistake is to rush […]
#726: Q&A: She Has $884K Saved — So Why Can’t She Retire?
What happens when you look at a $862,000 portfolio and realize early retirement might actually be out of reach?
When a mountain of ticker symbols, account balances, and unexpected life updates come hitting you all at once, your money plan can quickly start to look like a complete mess.
#720: Q&A: When the “Right” Decision Feels Harder Than The Math
Why is the finish line of financial independence so much scarier than the starting line?
While the early stages of accumulating wealth are full of possibility, approaching the moment where work becomes optional can trigger an unexpected wave of financial anxiety, causing many to stall out right at the edge of freedom.
Joe […]
#710: Q&A: He Wants to Die With Zero – Here’s How to Spend $1M Without Running Out
Joe and I tackle questions about the complexities of early retirement at age 60 and the most efficient withdrawal strategies for lifelong security.
This episode explores both the technical and psychological aspects of “spending down”—from balancing Social Security timing with your investment accounts to deciding if you should spend every last penny before you’re […]
#706: Q&A: The Case for NOT Paying Off Your Student Loans
What do student loans, early retirement, and Airbnb have in common?
They’re the three questions we’re tackling in today’s episode, and each one forces you to think about uncertainty, flexibility, and whether the “right” financial move on paper is actually the right move for your life.
Joe and I answer three listener questions. KJ […]
#703: First Friday: Jobs Are Up. So Why Does the Economy Feel Worse?
This month’s jobs report looks strong on the surface, with 178,000 jobs added and unemployment ticking down—but a closer look tells a more complicated story. When I compare it against other data like job openings and layoffs, it still points to a slower, low-hiring environment, raising the question: is this […]
#701: What Retirement Planning Gets Wrong with Jamie Hopkins
In this episode, I am joined by Jamie Hopkins, a leading retirement researcher and finance expert, to debunk the myth of the “magic number.” We explore why retirement planning is a dynamic process of constant adaptation rather than a static goal.
Jamie explains the psychological and mathematical flaws of focusing solely on a […]
#700: Q&A: A $30K Promotion Near FI, Learning Put Options, and Scaling a 16-Unit Portfolio
Should you take a $30,000 raise right before you retire? It’s the kind of question that forces you to ask what you’re really optimizing for—money, or something else entirely.
In this Q&A episode, Joe and I answer three questions: Melanie is four years from FI but a high-stress job with a big raise just opened […]
