A Good Problem to Have

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...

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...

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 st...

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...

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...

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 doll...

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...

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...

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 c...

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 o...

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...

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: Bitcoin Tyrone 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 y...

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...

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 ca...

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 rates The relationship between Treasuries, inflation, and mortgage-backed securities What the “spread” between mortgage rates and the 10-year Treasury really means Whether the new 50-year mort...

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 consideration...

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...