Earlier this month was National 401(k) Day, and while we were busy hanging fake cobwebs and pumpkin lights in Mom’s basement, we totally missed it. But hey—every day is a great day to polish up your retirement plan! That’s why we’ve invited friends of the show Paula Pant (Afford Anything), Jesse Cramer (The Best Interest podcast), and Lacey Langford (The Military Money Show) to help us tackle the biggest mistakes people make with their 401(k)s, TSPs, and workplace plans. From missing the employer match to setting and forgetting your investments, the roundtable has you covered.
In today’s discussion, we’ll dig into the strategies and missteps that can make or break your long-term wealth. You’ll hear about overlooked features like Roth vs. traditional contributions, hidden fees in small company plans, and why “target date fund autopilot” isn’t always the perfect choice. Along the way, our contributors share personal stories, a little empathy, and a few reality checks (plus plenty of knob-tweaking jokes that we may or may not regret).
Of course, no Friday show is complete without Doug’s trivia—this week he pours us a frothy Oktoberfest special. How many Olympic-sized swimming pools could all that beer fill? Paula, Jesse, and Lacey take their best shots, and one lucky guesser takes over the lead in our year-long trivia challenge. Will it be a win, or just another empty stein? Tune in to find out.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201
Enjoy!
Our Topic: Making the most of your 401(k)
During our conversation, you’ll hear us mention:
- Employer 401(k) match
- Thrift Savings Plan
- Blended Retirement System
- Underemployment in military
- Saving for future self
- Opting out mistakes
- Credit card debt
- Lifestyle creep spending
- Finding hidden money
- Side hustles for saving
- Trying contributions experiment
- Investing without strategy
- Money stuck in cash
- Risk tolerance basics
- Diversification importance
- Need, ability, willingness
- Learning through mistakes
- Target date funds
- VTSAX and index funds
- Fees and expenses
- High-fee small companies
- Rolling over old 401(k)s
- Brokerage account options
- Roth vs. traditional
- Automatic escalation plans
Our Contributors
A big thanks to our contributors! You can check out more links for our guests below.
Lacey Langford
Another thanks to Lacey Langford for joining our contributors this week! Hear more from Lacey on her show, Military Money Show at MILMO Show on Apple Podcasts.
Jesse Cramer
Another thanks to Jesse Cramer for joining our contributors this week! Hear more from Jesse on his show, Personal Finance for Long-Term Investors – The Best Interest, on Apple Podcasts.
Learn how you can work with Jesse by visiting The Best Interest – Invest in Knowledge.
Paula Pant
Check out Paula’s site and amazing podcast at AffordAnything.com
Follow Paula on Twitter: @AffordAnything
Doug’s Game Show Trivia
- Based on the number of liters of beer these lunatics downed in Munich in 2024 over 16 days at the official Oktoberfest celebration, how many Olympic-sized pools could this beer have filled?
Mentioned in today’s show
Join Us on Monday!
Tune in on Monday when we dive into a piece that reveals the alarmingly high price of the American Dream.
Miss our last show? Check it out here: Work Less, Live More, AND Be Better at Your Job (SB1739).
Written by: Kevin Bailey
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