What happens when the two co-hosts stop being polite, start being honest, and publicly debate the money moves they still don't agree on? We throw open the doors on four of our favorite friction points:

Simple index-fund investing versus "modest complexity"
Whether high school personal finance classes are actually helping
What to make of the new 530A Trump accounts
Taking Social Security at 62 versus waiting

The fun here is that neither of us is playing a character. Jackie comes in swinging for simplicity, practical execution, and "please stop overcomplicating this for normal people," while Bill makes the case for curiosity, customization, and not sleepwalking through important financial choices. Along the way, we swap real stories about helping kids with 401(k)s, seeing bad default investments in the wild, what personal finance education gets wrong, and why Social Security advice may be more nuanced than the "always wait until 70" crowd admits. It's a reminder that thoughtful disagreement can sharpen your own plan faster than blindly copying someone else's.

.

=== SUPPORT THE SHOW ===

📩 Sign up for our newsletter

🌐 Visit Catching Up to FI website

🔗Connect with us

☕ Like what you hear on Catching Up to FI? Support the show at "Buy Me a Coffee"

🎙️We love hearing from you! Record a Voice Message with your feedback or question Record a Voice Message with your feedback or question

.

===DEALS & DISCOUNTS FROM OUR TRUSTED PARTNERS===

📈 Boldin (formerly NewRetirement): Retirement planning software that's like having a financial advisor at your fingertips. You can get started with the free version or choose the premium option (PlannerPlus) and get a 14-day free trial. 👉🏼 Be sure to use this link to get started: Go.boldin.com/catchingup

Personal Finance Club: Use code CUTOFI to get $30 OFF any investing course

Nectarine: Advice-Only and Flat-Fee Hourly Fiduciary Financial Advisors (Catching Up to FI will be compensated by Nectarine if you use our affiliate link, which creates an incentive and conflict of interest. We are not current clients or employees of Nectarine.)

For a full list of current deals and discounts from our partners, sponsors and affiliates, click here: catchinguptofi.com/our-partners

.

RESOURCES MENTIONED ON THE SHOW

Check your social security estimates

Mike Piper's Open Social Security Calculator

Next Gen Personal Finance

Trump Accounts

.

⏰ Related Episodes

Is Your 401(k) a Mess? Do This Now (Step-by-Step Guide) | Bill & Jackie | 205

These New Rules Will Change The Way You Think About 529 Plans | Patricia Roberts | 193

Celebrating Financial Literacy Month with Next Gen Personal Finance | Tim Ranzetta | 072

Social Security Made Simple | Mike Piper | 054

.

If you enjoyed this episode, please follow the show on your podcast player and leave us a rating and review. If you want to watch, be sure to subscribe to our YouTube Channel. This helps others find the show and keeps us creating great content for you!

.

📌Disclaimer: Our content is for general education and information purposes only. We are not providing financial, legal, or tax advice. Always do your own research or consult a professional before making important decisions.

You don't have to use dating apps. But if you do - some tips!

Life Kit

Move Faster Than the Messaging Vortex

The AI-powered Podcast Player