Courtney (40) and Ray (41) have spent their entire adult lives in the structure of military life—but with retirement on the horizon, they’re about to face a future filled with choices for the first time.
For Ray, that means walking away from the rank, routine, and pension he’s built for over 20 years and entering a civilian job market he knows little about. ... Show More
Yesterday
247. "We’re in our 40s — with nothing saved"
Ramit Sethi of I Will Teach You To Be Rich talks to Stephanie and Chris, an early-40s couple with three young children, two of whom have special needs. Chris is a professor, and Stephanie, an RN, has recently cut back her hours due to burnout. Despite Chris’s confidence that “it’ ... Show More
1h 37m
Feb 3
246. "We’re drowning in debt, but bought another house"
Ramit Sethi of I Will Teach You To Be Rich talks to Melissa and Tony, a couple who immigrated from Mexico with big dreams and an even bigger work ethic. In less than a decade, they've built a net worth of nearly $900,000. But beneath the surface of their impressive paper wealth, ... Show More
1h 49m
Jan 27
245. "We make 6 figures. Why am I hiding fast food purchases?"
Ramit Sethi of I Will Teach You To Be Rich talks to Grace and James, a couple from Ireland, aged 38 and 37, who have been navigating immense challenges. James was diagnosed with cancer and underwent a year of treatment, while Grace managed a difficult pregnancy and maternity leav ... Show More
2h 5m
Jul 2025
Mini Retirements: How to Take a Break Sooner That Could Also Boost Your Career and Income with Jillian Johnsrud
#239: Why wait until you're 65? It's feasible for almost anyone to take a mini retirement and when done right, it can also fast-track your career and income. Learn how to plan one, negotiate time off, manage costs, avoid pitfalls, and make it work if you’re self-employed. Plus, w ... Show More
1 h
Aug 2024
Navigating Your Twenties: How to Stop People Pleasing, Take Control of Your Bad Habits, Find What Makes You Happy & *ACTUALLY* Follow Your Dreams
<p>This week's episode Kenzie sits down with Twenty Whatever to record another episode on navigating your twenties. The girls are talking financial literacy, relieving stress, following your dreams, taking the harder path, how to stop people pleasing, and following your ... Show More
51m 26s
Jul 2025
Your Future Self is Begging You To Listen to This Episode (Let's Talk How Much Super You'll Really Need)
Trying to figure out how much super you actually need? Yep, it’s confusing. With all the numbers, charts, and retirement buzzwords flying around, it’s no wonder most of us throw it in the “deal with it later” pile. But future you? They’re going to be so glad you tuned in. This we ... Show More
39m 58s
Apr 2025
227. How to Stop Caring What People Think with Mel Robbins
You know that little voice in your head that says, “What will they think?” The one that’s held you back from hitting publish, setting a boundary, or even just being yourself? Yeah, we’re done with that. In this episode, I sit down with the iconic Mel Robbins to talk about how to ... Show More
1h 22m
Jan 2025
#896 - 3.25M Q&A - Marriage Plans, Beautiful Women & Chris Bumstead
I hit 3.25 million Subscribers on YouTube!!
To celebrate, I asked for questions from YouTube, Twitter and Instagram, so here’s another 90ish minutes of me trying to answer as many as possible.
Expect to learn my thoughts on the Fin vs The Internet episode, what my favorite band I ... Show More
1h 41m