A Good Problem to Have

Tyler Olson
  • 4.8 (4)
  • EDUCATION
  • UPDATED WEEKLY

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.

  1. 1D AGO

    Why You Want Good Judgement in Your Financial Decisions

    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 judgment still plays an essential role in helping people identify priorities, uncover blind spots, and make decisions that truly align with their values. Whether you’re a DIY investor, someone who uses AI tools, or someone considering professional guidance, this conversation will help you think more clearly about how each piece fits into your financial life.

    8 min

  2. FEB 4

    Filing Taxes With Student Loans: What Physicians Need to Know

    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 an attending, decisions like filing jointly versus separately, filing on time versus filing an extension, and even which repayment plan you’re on can change your monthly payment by thousands of dollars a year. Some topics of discussion: Why this gets especially tricky for married borrowersHow community property states complicate everythingWhy this is one of those situations where working with a student-loan-aware CPA really mattersHow tax filing timing can be used strategically to manage income-driven repayment calculationsWhy many physicians need to rethink plans like SAVE if PSLF is the goal

    11 min

  3. JAN 28

    Preparing for Relocation Costs

    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 timing, the repetition, and the fact that it shows up alongside student loans, low income, and already tight cash flow. Even if saving is limited, or debt is unavoidable, knowing what's coming can make the transition easier to manage mentally and financially.

    17 min

  4. JAN 21

    Blockchain & Bitcoin: A Practical Conversation with Tyrone Ross

    In this episode, I’m joined again by my friend and colleague Tyrone Ross. This isn’t about hype, predictions, or telling anyone what they should or shouldn’t invest in. It’s about understanding what’s actually happening in the background and why this technology keeps showing up in the financial system whether we like it or not. We talk about the real world utility of blockchain, why it's still expensive and frustrating to move money, and what “better rails” actually means. We also discuss why banks, institutions, and regulators are paying attention now, how stablecoins fit into the picture, and what role Bitcoin may or may not play in a thoughtful investment strategy. Nothing in this episode is about going all in. It’s about learning, reducing fear, and understanding how new financial technology is slowly becoming part of everyday life.

    30 min

  5. JAN 14

    $500k in Student Debt to $1mil in Net Worth: Six Steps to Get There

    In this episode, I walk through a practical 6-step path for physicians who are starting their careers with significant student debt and want to build toward a 7-figure net worth. This stage can feel slow, frustrating, and uncertain, but with the right structure, discipline, and priorities, the transition from negative net worth to financial momentum is absolutely achievable. You’ll learn: How to choose a repayment approach that actually fits your lifeWhy protecting yourself with cash reserves and insurance comes firstHow lifestyle guardrails help prevent overspending as income risesWhy investing early matters, even while paying off debt

    16 min

  6. JAN 7

    Post-Training Career Paths: The Devil is in the Details

    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 experiencesHow financial structure, partnership terms, and equity risk show up in private practiceWhat to watch for around research time, call responsibilities, and compensation in academicsThe 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.

    10 min

  7. 12/31/2025

    “What Percentage of Income Should I Save for Retirement?”

    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 ruleThe role of employer retirement contributionsHow lifestyle choices shape your savings rateEarly retirement goalsWhy cost of living & inflation matter more than a single numberSituations where saving less than 20% still works

    9 min

  8. 12/24/2025

    The Wisdom of Making Less Than Optimal Money Decisions

    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.

    16 min
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Ratings & Reviews

4.8
out of 5
4 Ratings

About

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.

Information

  • Creator
    Tyler Olson
  • Years Active
    2025 - 2026
  • Episodes
    20
  • Rating
    Clean
  • Copyright
    © Tyler Olson
  • Show Website
    A Good Problem to Have

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