A Good Problem to Have

In this episode, Noah shares the story behind KaufCare, a direct acute care practice designed to bridge the gap between urgent care and the emergency room.We discuss what it takes to launch a medical business, how he evaluated the financial viability of the idea, and the realities of stepping away from traditional employment. We also talk about risk, liability, burnout, and the type of physician who may be well-suited for entrepreneurship.If you've ever wondered what it looks like to create your own path in medicine, this conversation is for you.

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 paying, preserve cash flow, and trust that your buyback request will ultimately be approved?In this episode, I walk through both approaches, explain the factors worth considering, and share what I've seen from clients navigating the process.

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 wondered whether an S-Corp is truly saving you money or just adding another layer of administration and stress, this episode is for you.Financial advice for quality of life-focused physicians: www.olsonfp.com

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 why the “best” fee model is rarely as simple as the internet makes it sound.But more importantly, I explain what actually matters when choosing someone to trust with your financial life.

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 a way that protects your future flexibility.We cover intentional spending, avoiding overcommitment, and how to create a lifestyle that gets better without trapping you into needing maximum income forever.

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.

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

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.

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 about making sure you’re ready for it.

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 it.This isn’t about perfection. It’s about building a little bit of stability, one step at a time.

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 worse, building debt without realizing it.This isn’t about being perfect. It’s about being aware.Because the habits you build now are the ones that scale when your income does.

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.

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.

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.

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 return matters, how to potentially qualify for $0 payments, when consolidation might make sense, and how these decisions can affect Public Service Loan Forgiveness down the road.If you’re about to start residency, this episode will help you make a few smart moves now that can simplify your finances during training.

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 life.We dig into how they built serious momentum, why they’re leaning toward paying down a low-rate mortgage anyway, and how to think about the tradeoff between maximizing dollars and minimizing stress.

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%. If you’re not, you’re behind. If you can’t, you’re doing something wrong.But is that really true?

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 and how to avoid them.We discuss why the “I deserve it now” mindset can quietly create long-term pressure, and why focusing on the so-called boring fundamentals gives you the freedom to spend and invest with confidence later.If you want your new income to create stability instead of stress, this conversation is for you.

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.

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

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.

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.

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

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.

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

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.

Too many doctors get pushed into insurance they never needed. In this episode, I explain how I evaluate disability insurance, why independence matters, and what residents need to know about Guaranteed Standard Issue (GSI) coverage before their window closes.

Starting fellowship is a huge milestone and a stressful financial transition.In this episode, I walk through eight practical money moves every new fellow should be thinking about, from emergency savings and disability insurance to student loans, taxes, and avoiding expensive short term mistakes.The goal is simple.Stay steady now so future you has more options later.

In this episode, I sit down with my friend and colleague Tyrone Ross to talk through something that a lot of people are curious about but still feel unsure how to approach: BitcoinTyrone has been studying, teaching, and building in this space for more than a decade, and what I appreciate most is the way he brings clarity without hype.We get into the basics in a way that actually helps you form your own opinion, answering questions like:What is Bitcoin? Why does it matter? How should regular people think about it? And where does it fit within a real financial plan?

In this episode of A Good Problem to Have, I sit down again with my friend and fellow planner, Ronnie Colvin, to walk through one of the most common (and most confusing) topics physicians ask us about: life insurance.We break it down into the three questions you actually need to answer:Do you need life insurance? - we talk through who is financially impacted if you weren’t here, how debt and co-signers factor in, and why the answer looks different for a single resident versus a married attending with kids.If you do need it, what kind? - we cover why term life insurance is the right starting point for nearly everyone, where permanent insurance can serve a specific purpose later on, and why you should be cautious of anyone pushing complex policies early in your career.How much coverage do you need? - the rules of thumb you’ll find online are all over the place. We walk through how we actually calculate this using real client examples, from income replacement to childcare costs to Social Security survivor benefits.Other takeaways you’ll hear:Why getting insurance while you’re young and healthy can save you a huge amount over your lifetimeHow a health change can make you uninsurable or dramatically increase your premiumsThe problem with “term to age 80” and other policies that look cheap up front

In this episode, I address a common question I receive from prospective clients: "What is the value of working with a financial planner?"It's a valid concern, especially when considering the investment of both time and money involved. That's why I focus on how effective financial planning can significantly enhance your life in these three critical areas.Time: how effective financial planning can save you countless hours of analysis and decision-makingTaxes: the importance of strategic tax planning and how it can lead to substantial savings over your careerProtection: various ways to protect your assets, including the right insurance coverage and account types that can safeguard your financial future

In this episode, I’m joined by Matt Graham, founder of MBSLive.net and writer for Mortgage News Daily, to unpack what’s driving interest rates today.We discuss:Why the Fed doesn’t directly control mortgage ratesThe relationship between Treasuries, inflation, and mortgage-backed securitiesWhat the “spread” between mortgage rates and the 10-year Treasury really meansWhether the new 50-year mortgage is a smart idea (or a costly mistake)

You might think that a high income means you can spend freely, but without monitoring, you could find yourself in a tough spot.No matter your financial situation, having a system in place to monitor your spending can lead to healthier financial habits and a more relaxed mindset around money.

Join us as we focus on the question a lot of doctors face at some point in their lives: "Can I afford to install a pool in my backyard?"We explore real-life cases from the past summer, discussing different factors that influence this decision beyond just the initial cost. Some highlights from the episode:The hidden costs of pool ownership, including maintenance and safety considerationsThe importance of understanding asset location and allocation when it comes to funding major purchasesThe pros and cons of using home equity versus selling taxable assets to finance a poolStrategies for cash flow and redirecting funds to meet financial goals

While a guaranteed salary can provide much-needed financial stability as you transition into your new role, there are important factors to consider before signing on the dotted line. Some highlights from the episode:The benefits & drawbacks of guaranteed salaries (including financial security and time to build your patient panel)Key considerations regarding time commitments and the potential consequences of leaving earlyThe importance of understanding your income expectations and patient volume requirements once the guarantee period endsTax implications, especially if your guaranteed salary is structured as a forgivable loan, and how to prepare for potential tax bills

In this episode, I dive into the topic of student loans, specifically focusing on the implications of having $150,000 in debt. You'll learn about two main options for managing student loans: staying within the federal loan system or refinancing with private lenders. We outline the benefits and drawbacks of each approach, including the potential for lower interest rates through refinancing and the safety net provided by federal loans.

In this episode, we discuss the exciting (yet overwhelming) transition from training to attending-hood, specifically focusing on that first attending paycheck. Some highlights:- How to pay off credit card debt effectively- The importance of building an emergency fund- Tips for maximizing your 401(k) or 403(b) contributions---------Financial planning for physicians: https://www.olsonfp.com

Welcome to the first episode of A Good Problem to Have! I'm your host, Tyler Olson, and in this episode, I introduce myself and share my journey in the financial planning field, specifically focusing on the unique challenges faced by physicians.Since 2005, I've dedicated my career to helping individuals navigate their financial landscapes, and in 2018, I launched my own practice to better serve my clients. With a deep understanding of the financial hurdles that come with a medical career—such as student loans, delayed earnings, and the behavioral impacts of financial decision-making—I aim to provide actionable insights tailored for doctors.In this episode, I discuss the concept of "good problems" in financial planning, like having a 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 life.---------Financial planning for physicians: ⁠https://www.olsonfp.com⁠