Someone called into the show last week and said:

"It started at $120K… now it's $150K."

He wasn't talking about a one-bedroom rental in NYC (though he could've been). He was talking about his student loans.

Let me walk you through it, because his situation is way more common than you'd think.

Name: Robert

Age: 26 (NY)

Income $8.5K/mo

Debt $150K (6.25%)

Expenses $6K/mo

Savings $19K

Assets $67K

Our auditee went to law school and even graduated a semester early to save money. However, he still walked out six figures deep in student loans. Crazy right? Not really, this is completely normal for lawyers (including my sister)! He also recently passed the bar and is about to get licensed. He moved to Manhattan for a compliance job at a bank, has $67K invested, and after all his bills, he's still got a couple grand left over every month. Most people can’t say the same!

Robert is winning, yet he doesn't feel like it, which is much more common than 6 figures in student loans as a lawyer. There’s a problem though…

It’s not his income, savings, assets, or motivation. He feels stuck. Every month that extra $2,000 lands in his account and he freezes on the same question:

“Do I hammer these loans down as fast as I can, or should I be investing that money instead?”

So I laid out three ways he could play it.

1️⃣ Nerf the debt. Contributing every extra dollar to the loans will make him debt-free in a few years.

Pros: For most people, this is the most optimal solution from a psychological perspective. Debt is stressful for most and paying them off feels incredible — like beating Elden Ring on your 50th try.

Cons: The extra payments could make more exponentially more money elsewhere. This is known as opportunity cost 👇

2️⃣ Minimum payments only. Every month, he makes minimum payments and invests the rest of his money into the stock market

Pros: $2K/mo into an S&P 500 index fund instead. After 21 years with an average return of 10%, that’s roughly $2 million.

Cons: He pays the bank ~$60K in total loan interest along the way. Potentially lower quality of life. He might be side-eyeing that loan balance every time he opens the app for the next two decades, slowly destroying his soul (just like fighting Elden Ring/Dark Souls bosses).

3️⃣ Split it. Send about a grand at the loans and a grand into investments.

Pros: Debt's gone ~10 years early and he's still stacking market gains — kills more stress and the FOMO at the same time. Ends up north of $1.2 million and gets to sleep at night.

Cons: Slightly lower ceiling than going all-in on stocks (Option 2 wins on a pure spreadsheet). Slower debt payoff than Option 1. No clean dopamine hit — you trade both extremes for a steadier ride.

I asked Robert to rate his loan stress from 1-10, and he looked at me like I'd asked him to relive middle school with the bowl cut (maybe I’m speaking for myself). This debt is stressing him out. Yet, he also feels like he’s missing out on all the amazing gains from the stock market. This is why we lean toward option 3, as it does a good job addressing both concerns.

TLDR: It’s called Personal Finance for a reason. While option 2 may be the most optimal solution from a numbers perspective, it is not the best solution for Robert’s situation.

Have a question? Ask it on our brand spankin new subreddit, and I will answer you personally!

Talk soon,

— Imran