ThimbleberryU

If you're in healthcare and you've changed hospitals, you have a 403(b) at the employer you left. What should you do with it? For many healthcare professionals it isn't a one-time question. It comes back with every move. Amy Walls lays out the four options, leaving the account where it is, moving it into the new employer's plan, rolling it into an IRA, or cashing it out, and how to compare the old...

If you're in tech and a recruiter just handed you a better offer, there's a number standing in the way of an easy yes, whatever's still unvested in your current RSU grant. It's easy to treat that number as a straight loss and let it decide the whole conversation for you. Amy Walls walks through how to put a number on what you'd leave behind, when an upcoming vest date should change your start date...

If you're in healthcare or academia and retirement is coming into view, you've probably gotten a form asking whether you want to annuitize your 403(b), and it's not obvious what you're actually agreeing to. This episode breaks down what annuitizing really means, why it's usually permanent, and how it compares to keeping the account invested instead. Amy Walls walks through why not every 403(b) can...

If you're in tech and exercised incentive stock options, you may have discovered that holding the shares can trigger Alternative Minimum Tax, even though you never sold anything and never saw a dollar of cash. Amy Walls breaks down why that phantom income creates a real tax bill, and why that bill isn't gone for good, it becomes a credit you can recover. This episode walks through how the minimum...

If you’re in healthcare or academia and you already have a CPA, it’s easy to assume your tax and financial picture is fully covered. It isn’t, and this episode explains exactly where the line falls. Amy Walls breaks down the real difference between tax preparation and tax planning, why accounts spread across multiple hospital systems or universities, 403(b)s, 457(b)s, and pensions, need someone co...

Higher mortgage rates quietly changed the math on one of the most argued questions in personal finance. If you’re in tech, with a mortgage, RSUs, and real money to deploy, the answer isn’t as obvious as it used to be, and the stakes are higher than a simple rate comparison suggests. In this episode, Amy Walls walks you through how to weigh a guaranteed return against an uncertain one, what extra m...

This episode focuses on a question that follows many professionals in academic medicine, healthcare, and research: “Can I actually retire?” Jon Gay and Amy Walls explain that the stress behind this question often does not come from a lack of money. It comes from a lack of visibility. Retirement accounts, pensions, 403(b)s, 457 plans, IRAs, and Social Security all produce separate statements. But n...

In this episode of ThimbleberryU, Jag and Amy talk about the difference between simple investing and ignoring your portfolio. This is especially for those of you working in tech, where it is easy for much of your financial life to become tied to the same industry without realizing it. Your paycheck may come from tech. Your RSUs or stock options may depend on your company’s performance. Your future...

In this episode of ThimbleberryU, you'll hear why reducing chaos for the people you love is one of the most practical and caring financial steps you can take. It is not a topic most people want to face, but it is one almost every family eventually has to deal with. For healthcare professionals, financial life can get complicated quickly. You may have old retirement plans from different hospital sy...

In this episode of ThimbleberryU, we talk about what a giant IPO like SpaceX could mean for a personal investment portfolio. The conversation starts with common questions many investors ask when a major private company gets ready to go public. Am I missing out? Is my index fund going to own it? Am I exposed to something I do not understand? Amy explains that many people assume an index fund owns t...

In this episode, we talk about what it means to move beyond simply earning a strong paycheck and start building wealth with real intention, especially for people in tech who are in the middle or later stages of their careers. We start with the idea that success can remove urgency. Early on, financial decisions feel obvious because everything is new and growing. Later, income is steady, accounts ar...

Today, Amy and Jag look at a financial risk that is easy to ignore because it does not feel urgent in the moment: the cost of doing nothing. In this episode, we focus on how delays in financial decisions can quietly create long term consequences, especially for healthcare professionals who are used to acting quickly at work but may postpone choices in their own financial lives. The central idea is...

Careers in technology change as professionals move into their 40s and 50s. Early in a tech career, rapid change feels exciting. New tools, companies, and opportunities create momentum. Over time that same pace can begin to feel heavy. Many professionals start asking different questions. They wonder how long their skills will stay valuable, whether companies will continue to seek their experience,...

We discuss a situation many couples imagine will be simple but rarely unfolds that way in real life: retirement timing. Many couples picture both partners stepping away from work at the same moment and beginning the next chapter together. In healthcare households, however, careers often evolve differently. Physical demands, shift schedules, burnout, or changes in job roles can lead one partner to...

In this episode, we take a closer look at Employee Stock Purchase Plans and ask a simple but important question: are they worth the effort? Many people in tech see ESPPs during open enrollment, feel overwhelmed by the language, and quietly opt out. Why does that happen? Well, ESPPs sit in an awkward middle space. They are not large enough to feel exciting like salary, bonuses, or RSUs, but they ar...

In this episode, we talk about the tax time bomb hiding inside retirement accounts for healthcare professionals. We focus on clinicians who have done everything right:.you saved consistently. You deferred income. You maximized our 403(b) and 457(b) plans. But we explain how those smart decisions can create large tax consequences later in retirement. Here's the core issue. Decades of tax deferral d...

In this episode of ThimbleberryU , we dig into why tax season can feel particularly overwhelming for tech professionals and how to approach it with less stress and more predictability. We focus on the common sources of tax complexity, equity compensation and bonuses, and offer a simple framework for making tax season less dramatic and, ideally, boring. We start by exploring how tech income is rare...

In this episode of ThimbleberryU , we explore the concept of building and maintaining confidence under uncertainty , especially for healthcare professionals who are already accustomed to high-stress environments. The financial world often mirrors the unpredictability of healthcare. Policy changes, staffing shortages, and burnout are compounded by volatile markets and alarming news cycles. Our focu...

In this episode of ThimbleberryU , we dive into an increasingly common experience for those working in the tech industry: burnout. We begin by acknowledging that tech burnout is unique—fast-paced roles, unpredictable compensation, constant decision-making, and job instability combine to create chronic stress. Amy Walls shares how burnout shows up not only emotionally, but also financially, and how...

In this episode, we explore the emotional and structural challenges that come with transitioning from a lifetime of saving to actually spending in retirement. We focus especially on healthcare professionals—nurses, physicians, and leaders—who have spent their careers making cautious, life-impacting decisions and who now face a very different kind of responsibility: using the money they’ve carefull...

In this milestone episode of ThimbleberryU , we celebrate 150 episodes and the 10-year anniversary of Thimbleberry Financial. Amy Walls reflects on a decade of advising clients and the timeless lessons she’s learned—lessons that go beyond finance and into life, meaning, and the value of simplicity. We open by anchoring the episode in Thimbleberry’s core values, especially simplicity. Amy stresses...

In this episode of ThimbleberryU , we explore a fundamental question for professionals in tech: Which type of company is the right fit for your current stage in life and career? Whether it's a startup, a pre-IPO company, or a public corporation, each environment offers its own opportunities, challenges, and financial implications. Jag walks through the trade-offs with Amy Walls of Thimbleberry Fin...

In this episode of ThimbleberryU , we dive into the growing challenge facing healthcare professionals—the balancing act of caring for aging parents while still preparing for their own retirement. We’re talking directly to those in the “sandwich generation,” especially nurses, physicians, and hospital leaders who are used to caregiving professionally and now find themselves extending that care to f...

Today, Amy Walls and Jag dive into why it feels like everyone around us has more money, more freedom, or more upgrades than we do — and why that perception is often just that: perception. Social media plays a huge role in this feeling. The constant exposure to curated highlight reels makes it easy to believe others are winning financially, while we’re falling behind. Amy points out that what we se...

In this episode of ThimbleberryU, we reset the conversation around RSUs—restricted stock units—and bring it back to the basics while adding context relevant to 2025. We start by defining what RSUs are: a form of equity compensation that incentivizes employees to remain at a company and contribute to its long-term success. These units don’t hold any value until they vest, which typically happens ov...