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A Good Problem to Have

A Good Problem to Have

By: Tyler Olson
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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.Tyler Olson
Episodes
  • New Intern Money Series: Employer Benefits (Part 4)
    Apr 1 2026

    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 decisions, HSAs vs FSAs, group disability, life insurance, retirement matching, PTO… all things that can meaningfully impact your finances right out of the gate.

    Take an hour or two, get this right, and you’ll be setting yourself up for a much smoother intern year.

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    10 mins
  • New Intern Money Series: Disability, Life, Umbrella Insurance (Part 3)
    Mar 25 2026

    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 the long term is incredibly important.

    If you’re transitioning from medical school into intern year, this is one decision process you’ll want to understand early.

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    17 mins
  • New Intern Money Series: Private Student Loans & Debt (Part 2)
    Mar 18 2026

    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 means the strategy during residency looks very different.

    The key takeaway: during residency, your goal isn’t to crush the debt immediately. It’s to manage cash flow, understand your loan terms, and position yourself to handle the debt effectively once attending income arrives.

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    8 mins
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