Student Loan Planner

Student Loan Tax Bomb: What Forgiveness in 2026 Really Means for You

If you started repaying federal student loans around 2001-2006 and have been on a 20, 25, or 30-year income-driven repayment plan, you’re right on the doorstep of forgive

The “Pay Down Debt vs. Invest” Math Has Shifted

Should you prioritize paying off your student loans or is it smarter to focus on investing? With interest rates changing dramatically since the days of ultra-low 3% loans

Why You Shouldn’t Panic About Forgiveness Counts Being Rolled Back

This is a two-for-one episode. We’ll start by digging into the mailbag and answering questions you sent in. Then we’ll get to the topic filling my inbox with panicked ema

Student Loan Payments Are Going Up

You’re coming off years of low or no student loan payments, only to face 10-20x jumps seemingly overnight. We get into why payments are up so sharply, what to do (and not

The Student Loan Borrower Tax Rate Is Too Dang High

If you’re on an income-driven repayment plan, you might be paying a marginal tax rate that rivals (or exceeds) those in high-tax countries. We walk through exactly how th

Why You Should Get an Old Person Hobby as a Student Loan Borrow

Summer’s winding down and, let’s be real, if you’ve got kids, you’re counting the minutes until school starts. But whether you’re squeezing in that last vacation or pieci

Are you on track to retire? Why that’s the wrong question

Most people who care about money — especially those with big student loans — eventually end up worrying, "Am I on track to retire?" But that’s not the right question. Tod

New Grad Student Loan Hacks

If you're coming out of professional school this fall, here's the quirk in your favor: you almost certainly didn't borrow after July 2026, which means you still have acce

The Post July 1 World of Student Loans

Servicers started sending official 90-day notices on July 1, and roughly 6 million borrowers are still sitting on SAVE trying to figure out what comes next. Learn what th

What Would An AI Bubble Mean for Student Loan Borrowers?

AI hype is everywhere — and it’s about more than AI taking over your job. It also affects the stock market, your investments, and even your student loan paydown strategy.

RAP Strategies 2.0

The new RAP plan has gotten plenty of criticism, but it might not be all bad news for every borrower. Learn where RAP could help, where it could hurt, and why the right s

Student Loans Post-July 1

We just got back from the NASFAA conference in Washington, D.C., and there's a lot to unpack. From the launch of the Repayment Assistance Plan (RAP) and what it means for

Why "AUM Fees are Bad" is a Marketing Ploy

Scroll through any financial feed, and you'll eventually hit the same pitch: AUM (assets under management) fees are a ripoff, and only foolish high earners pay them. We t

Are you a "SHENRY"?

You've heard of HENRYs, high earners who are not rich yet. But what if you're a high earner with six figures in student loan debt on top of it? That's a SHENRY, and the p

Repayment Assistance Plan

A brand new income-driven repayment (IDR) plan is coming, and the rules are stricter than anything borrowers have dealt with before. We break down what we know about the

New Rules, Forgiveness Updates, and PSLF Lawsuit Watch

Since the One Big Beautiful Bill, the final student loan regulations have started landing, and we're seeing the real-world fallout in consultations every single day. We b

Changes to Grad Plus Coming This Year in 2026

Grad PLUS loans are going away, and the phase-out is going to create one of the strangest stretches in the history of student loan financing. If you're enrolled in a grad

"What Now?" Listener Questions Answered

The new federal student loan regulations are about to throw a wrench into grad and professional borrowers’ repayment options, and we’re tackling some of the most pressing

Will AI Kill Student Loan Advising?

Everyone's wondering whether AI is coming for their job (or wallet), so it's fair to ask how close AI tools are to replacing a real human student loan advisor or even you

Predicting the Future of the Tax Bomb

What happens when forgiven student debt becomes taxable income again? That’s the “tax bomb” we’re breaking down this week — why it’s coming back, who could get caught by