“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: financial independence
#735: He Tried 30+ Side Hustles Before 3 Actually Paid Off, with Cody Berman
Cody Berman was 19 when he learned about financial independence, and 25 when he reached it.
There’s no trust fund here, no lucky exit. Just a brutal train commute, over 30 side hustles, and a gap between what he earned and what he spent that […]
#734: Q&A: Her Brother Owns 3 Houses — Is That Why We Have a ‘Housing Shortage’?
Is there really a housing shortage — or do we just have a lot of wealthy people buying up all the good stuff?
That’s the question kicking off this episode.
Joe and I also help a woman simplify a $1.5 million portfolio she’s managing on her own for the first time.
And we help a […]
#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?
[…]
#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 […]
#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 […]
#718: Q&A: The Goalposts Moved — Is That Actually a Problem?
As we edge closer to financial independence, a funny thing happens to the finish line: it often starts to move.
But the goalposts don’t always shift because of lifestyle inflation or uncontrolled spending.
Sometimes, they move because our vision for our wealth expands—particularly when it comes to long-term charitable giving, family legacy, […]
#708: Q&A: My Mom Is 73. She Has a House – But It Doesn’t Pay the Bills. Now What?
Joe and I are catching up in person to dive into a new set of listener questions.
From navigating the complexities of the current real estate market to strategic tax planning for retirement, this episode explores both the technical and psychological aspects of building wealth.
Whether you’re wondering how to handle a sudden […]
#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 […]
#682: 52 Tiny Improvements in 2026 [GREATEST HITS]
Grab the FREE handbook: affordanything.com/financialgoals
Today’s episode is a special rerun that’s perfectly timed for anyone looking to build stronger financial habits this year.
Originally aired on January 3rd, 2025, this episode introduces a game-changing approach to personal finance: instead of relying solely on big moves like […]
