#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, we share tips for handling health insurance and other logistics during your mini- ... Show More
Nov 19
2025 Holiday Gift Guide and Top Ways to Save This Season
#255: Here are 100+ holiday gift ideas across tech, kitchen, home, clothing, fitness, kids, and games. I’ll also share tools and tactics to help you find deals and spend less this holiday season.
For all the products, links, deals and more, check out the full 2025 Gift Guide h ... Show More
1h 24m
Nov 5
10 Lessons That Challenged My Thinking on Money and Life
#253: My top 10 takeaways from a retreat for high-net-worth investors, which will cover investing, managing risk, investing in your health, building meaningful relationships, parenting with purpose, and defining success in a way that goes far beyond money. Tad Fallows is the co-f ... Show More
59m 23s
Oct 2024
How To Retire w/ Christine Benz #887
Ok, here us out: retirement is a topic that we talk about all the time here at How To Money, but simultaneously we probably don’t talk about it nearly enough! How is that possible you might ask? Well, we are oftentimes discussing retirement through the lens of investing – spendin ... Show More
57m 32s
Sep 2024
How to Retire: Stay Flexible with Your Retirement Spending
<p>Christine Benz, Morningstar’s director of personal finance and retirement planning, interviews financial experts about different aspects of retirement in ‘How to Retire,’ the companion podcast to her book of the same name. In this episode, Christine sits down with senior nerd ... Show More
19m 6s
Feb 2025
3035: [Part 1] Generating Retirement Income Before Age 59 by Darrow Kirkpatrick of Can I Retire Yet
Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com.
Episode 3035:
Darrow Kirkpatrick explores various strategies, from leveraging taxable investment accounts to taking advantage of Ro ... Show More
10m 34s
Sep 2024
560: Dude ACTUALLY Withdraws From His 401(k) and Retires at 47
Did you know you can use your 401(k) to retire early? Yep, it’s possible. And today’s guest, Eric Cooper, is doing it atage 47! Most FIRE chasers search for how to withdraw from a 401(k) early but know that doing so will hit them with substantial penalties. The best way around th ... Show More
46m 39s
Oct 2024
How to Retire: Know What ‘Enough’ Means in Retirement
<p>Christine Benz, Morningstar’s director of personal finance and retirement planning, interviews financial experts about different aspects of retirement in ‘How to Retire,’ the companion podcast to her book of the same name. In this episode, Christine sits down with personal fin ... Show More
22m 14s
May 2025
207. “I’m 40, burned out, and don’t know what’s next in my life”
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 bu ... Show More
1h 16m
Aug 2024
Q&A: The Unintended Consequences of Early Retirement
#529: Anonymous, 60, recently lost her job and is worried about retirement. She owns a paid-off triplex, living in one unit and renting the others for $30,000 a year. She used her 401(k) funds to buy the triplex and now has $50,000 in retirement savings and $150,000 in cash. She ... Show More
1h 13m
Sep 2024
How to Retire: Understand the Role of Working Longer
<p>Christine Benz, Morningstar’s director of personal finance and retirement planning, interviews financial experts about different aspects of retirement in ‘How to Retire,’ the companion podcast to her book of the same name. In this episode, Christine sits down with Yahoo Financ ... Show More
17m 32s