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A Good Problem to Have

A Good Problem to Have

By: Tyler Olson
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About this listen

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
  • Post-Training Career Paths: The Devil is in the Details
    Jan 7 2026

    In this episode, I talk through the reality of choosing a post-training career path and why the decision between academics and private practice is rarely as simple as it sounds. There are meaningful pros and cons on both sides, and the real story lives in the details of contracts, culture, expectations, and incentives.

    You’ll hear about:

    • Why academics and private practice each cover a wide range of real-world experiences
    • How financial structure, partnership terms, and equity risk show up in private practice
    • What to watch for around research time, call responsibilities, and compensation in academics

    The goal is not to tell you which path is better. The goal is to help you understand what you are walking into so you can choose the environment that aligns with your values, your priorities, and the kind of work life you want to build.

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    10 mins
  • “What Percentage of Income Should I Save for Retirement?”
    Dec 31 2025

    I walk through the popular “save 20% of your income for retirement” guideline and why that number is only a starting point. The real conversation is about your life, your priorities, and the tradeoffs you want to make. In this episode:

    • Why 20 percent is a rule of thumb, not a rule
    • The role of employer retirement contributions
    • How lifestyle choices shape your savings rate
    • Early retirement goals
    • Why cost of living & inflation matter more than a single number
    • Situations where saving less than 20% still works
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    9 mins
  • The Wisdom of Making Less Than Optimal Money Decisions
    Dec 24 2025

    This episode is about something we do not talk about enough in personal finance: the freedom to choose what feels right, even when it is not the most optimal decision.

    Using two real student loan examples, I explain how to evaluate tradeoffs between investing, debt payoff, and mental health, and why progress should feel good.

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    16 mins
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