A Good Problem to Have

A Good Problem to Have

Tyler Olson

Episodes 37
Avg. Duration 14m
Activity Highly Active
Since Oct 2025
Latest Episode Jun 2026

Publishing Details

Schedule
Weekly
Format
Episodic
Consistency
100%
Hosting
anchor.fm

Contact & Outreach

About This Podcast

In this show, I discuss the concept of "good problems to have" as a physician (like having a significant surplus in your checking account) and the importance of addressing these situations thoughtfully. My goal is to make financial planning concise, useful, and relevant to your unique life.

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Recent Episodes

PSLF Buyback: What Happens While You Wait?

Jun 10, 2026 8m

A lot of physicians are facing the same thing right now: waiting on PSLF buyback while trying to decide what comes next.Do you keep making payments as a hedge against uncertainty?Or do you stop…

S Corp Tax Savings: What You Need to Know

Jun 03, 2026 13m

In this episode, I break down the mechanics of reasonable salary decisions, how retirement contributions affect business profits, and the ethical side of aggressive tax planning.If you’ve ever…

Financial Advisor Fees Explained: Commissions, AUM, Flat-Fee

May 27, 2026 15m

In this episode, I break down the three most common ways financial advisors get paid: commissions, AUM fees, and flat fees. Learn why compensation structures matter, where conflicts can show up, and…

The Real Cost of Upgrading Your Lifestyle Too Fast

May 20, 2026 13m

In this episode, I talk about why emergency medicine doctors face a unique financial challenge after training, why “can I afford it?” is the wrong question to ask, and how to think about spending in…

1099 vs. W-2 Income for Doctors (Pros and Cons)

May 13, 2026 16m

In this episode, I walk through the pros and cons of 1099 income for doctors, including retirement planning opportunities, solo 401(k)s, tax considerations, malpractice insurance, health insurance,…

Money Anxiety in Residency (Even When You’re Doing Well)

May 06, 2026 48m

Today, I’m sitting down with Dylan and Cambra, a couple navigating residency life, a growing family, and the constant tension between saving for the future and actually enjoying life right…

New Intern Money Series: Estate Planning (Part 8)

Apr 29, 2026 14m

In this episode, I walk through why having a will & power of attorney in place matters, even if you’re just starting out and don’t feel like you have much to protect.We also talk about how to get…

New Intern Money Series: Investing (Part 7)

Apr 22, 2026 15m

If you’re in residency, investing is not about maximizing returns or building massive wealth.It’s about creating the habit.Future you is going to have a lot more income to work with.This phase is…

New Intern Money Series: Emergency Funds (Part 6)

Apr 15, 2026 6m

In this episode, I walk through why an emergency fund matters, how to approach it on a resident salary, and where to actually keep the money so it’s working for you but still accessible when you need…

New Intern Money Series: Cash Flow (Part 5)

Apr 08, 2026 15m

Most new doctors don’t have a money problem. They have a visibility problem.If you don’t know what’s coming in, and you don’t know where it’s going, it’s really easy to end up saving nothing… or…

New Intern Money Series: Employer Benefits (Part 4)

Apr 01, 2026 10m

In this episode we’re talking about employer benefits. You’re going to get that packet. That PDF. And your first instinct might be to ignore it.Don’t.There’s real value in there. Health insurance…

New Intern Money Series: Disability, Life, Umbrella Insurance (Part 3)

Mar 25, 2026 16m

In this episode, we’re diving into insurance for new doctors, with a focus on disability insurance. Even though your resident salary might be modest, protecting your ability to earn an income over…

New Intern Money Series: Private Student Loans & Debt (Part 2)

Mar 18, 2026 7m

In part two of this eight-episode post-Match series, we’re talking about private student loans. Unlike federal loans, private loans don’t come with the same protections or forgiveness programs, which…

New Intern Money Series: Federal Student Loans (Part 1)

Mar 11, 2026 19m

In this first episode I walk through one of the most important financial steps you can take right now: managing your federal student loans before residency begins.We talk about why e-filing your tax…

A Couple’s Perspective: How to Manage a $250,000 Gift w/ $3 Million Net Worth

Mar 04, 2026 55m

In this episode, I sit down with Joe and Josie, a healthcare couple I’ve known anonymously for years, to talk through a decision that sounds simple on paper and gets way more interesting in real…

How Much Does Your Savings Rate Matter? (with Ronnie Colvin, MS, CFP®)

Feb 25, 2026 13m

In this episode, Ronnie and I dig into one of the most common and most misunderstood questions in personal finance:"How much should you actually be saving?"You’ve probably heard the rule - save 20%.…

2 Common Pitfalls Doctors Fall Into as Their Income Jumps

Feb 18, 2026 20m

Going from a trainee salary to an attending income is one of the biggest financial inflection points in a physician’s life. In this episode, I share two mistakes I see early-career physicians make…

Why You Want Good Judgement in Your Financial Decisions

Feb 11, 2026 7m

Financial planning is often framed as numbers, projections, and optimization, but those are only part of the picture.In this episode, I discuss AI in financial advice and explain why experienced…

Filing Taxes With Student Loans: What Physicians Need to Know

Feb 04, 2026 10m

In this episode of A Good Problem to Have, I walk through how your tax choices can directly impact your student loan payments, especially if you’re pursuing PSLF.Whether you’re in training or already…

Preparing for Relocation Costs

Jan 28, 2026 17m

In this episode, I talk about relocation expenses and why they consistently catch physicians off guard, even though we all know the moves are coming. The challenge is not just the cost. It's the…

Frequently Asked Questions

How many episodes does A Good Problem to Have have?

A Good Problem to Have has published 37 episodes since October 2025, covering topics in Education.

Is A Good Problem to Have still active?

A Good Problem to Have is currently highly active with new episodes weekly. Average episode length is 14m.

How do I contact A Good Problem to Have for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for A Good Problem to Have, including email and social media links.

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