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A Good Problem to Have

A Good Problem to Have

By: Tyler Olson
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Summary

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

    1099 vs. W-2 Income for Doctors (Pros and Cons)
    May 13 2026

    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, and how to properly compare a 1099 offer to a traditional W-2 role.

    If you’re considering consulting income, moonlighting, or a transition away from a W-2 job, this episode should help you think through the decision more clearly.
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    16 mins
  • Money Anxiety in Residency (Even When You’re Doing Well)

    Money Anxiety in Residency (Even When You’re Doing Well)
    May 6 2026

    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 now.

    They’re doing a lot right. They’re saving, investing, tracking their spending, and making intentional decisions.

    But like a lot of people in training, it still doesn’t feel like enough.

    For Cambra: 35:38
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    49 mins
  • New Intern Money Series: Estate Planning (Part 8)

    New Intern Money Series: Estate Planning (Part 8)
    Apr 29 2026

    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 this done quickly and affordably, so it doesn’t sit on your to-do list forever.

    It’s not complicated, but it is important.
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    15 mins
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