I spent over a decade becoming a physician. Nobody once sat me down and explained how money actually works. By the time most of us figure it out, we've already made the mistakes that quietly cost us a decade of compounding.

In this conversation, I sit down with one of the sharpest financial minds I know to walk through exactly what every physician (premed to retired) needs to understand about money. We talk about the school decision that quietly costs a doctor hundreds of thousands of dollars, the one account every resident should be using and almost none of them are, the math behind why starting in your thirties is worth more than working twice as hard in your fifties, and the tax trap most physicians don't even know they're walking into until it's too late.

If you've ever felt like you make good money but somehow never quite feel ahead… this episode is the one.

In this episode, you'll learn:

The first financial decision a future physician makes that quietly shapes the next forty years of their life

The single account that costs you nothing today and could be worth millions in retirement, if you start it in the right window

The retirement mistake almost every successful doctor walks into without realizing it, and the simple shift that fixes it

Connect with our guest Caitlin Frederick CFA, CFP:

LinkedIn: https://www.linkedin.com/in/olearycg/

Chapters:

01:18 – Why Physicians Get Personal Finance So Wrong

04:07 – The Real Number On Medical School Debt

06:26 – Public Service Loan Forgiveness Explained

08:45 – The Undergrad Decision That Changes Everything

11:35 – The New $50K Loan Cap And What It Means

13:15 – Private Loans, Death, And Disability Risk

17:58 – The Military Scholarship Path Nobody Talks About

20:18 – The Magic Account For Residents

22:37 – The Bentley Question After Residency

24:58 – $49K At 35 Vs $317K At 55

27:22 – Why The First Million Is The Hardest

29:40 – Why Doctors Are Bad Investors

32:01 – The Internet Bubble Lesson

34:24 – The Rebalancing Discipline That Works

41:35 – Dollar Cost Averaging In Real Life

43:53 – Why Bonds Are Different From Stocks

48:30 – The Saver Mindset That Quietly Wins

53:12 – Why HSAs Are The Best Account Nobody Uses

57:50 – RMDs And The Tax Bill Waiting For You

01:04:40 – Read Your First Contract Back To Front

01:07:03 – Final Word: Focus On What You Can Control