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 how the best financial plans aren't flashy—they're clear, flexible, and focused on what truly matters. We dive into the first cluster of lessons about money and planning, starting with the idea that clarity beats complexity every time. Fancy strategies may look appealing, but real success comes from plans that are understandable and actionable. A flexible plan, one that can adapt to life’s inevitable changes, always outperforms a rigid one.

We continue by looking at how emotions play into financial decision-making. Amy explains that emotions aren't distractions—they’re data. Recognizing fear, guilt, or excitement can lead to more empathetic and accurate planning. We don't need to know everything to make progress; staying curious and asking the right questions is often enough. That curiosity can help us avoid the traps of both overconfidence and paralysis.

As we shift toward life-focused lessons, Amy reminds us that success looks different for everyone—and that’s the point. Whether it's retiring early or spending more time with family, the plan has to fit the person. Life moves faster than spreadsheets, and that’s why regular check-ins and flexibility are essential.

Amy emphasizes that the best financial plans make room for joy. Planning isn’t about restriction—it’s about creating space for what we love, whether that’s rest, giving, or travel. Simplicity, while hard, is always worth it. And finally, a good plan isn’t static—it grows with us. It's not about being perfect; it's about evolving alongside life’s changes and building confidence as we go.

As we wrap up, we focus on three key takeaways for the new year: clarity, consistency, and curiosity. It’s not about predicting the future—it's about being prepared for it. And that preparation, rooted in simple, flexible planning, is what makes long-term success possible.

00:00 – Intro & Episode 150 Milestone

00:23 – 10 Years of Thimbleberry Financial

01:08 – Simplicity as a Core Value

02:15 – Lesson 1: Clarity Beats Complexity

03:23 – Lesson 2: Flexibility Over Perfection

03:49 – Lesson 3: Markets Don’t Care—Your Plan Should

04:33 – Lesson 4: Emotions Are Data

06:39 – Lesson 5: Stay Curious

07:22 – Lesson 6: Success Looks Different for Everyone

08:15 – Lesson 7: Life Moves Faster Than Spreadsheets

09:01 – Lesson 8: Make Room for Joy

09:31 – Lesson 9: Simple Isn’t Easy

09:57 – Lesson 10: A Plan That Grows With You

10:41 – Final Takeaways for the New Year

11:53 – Contact Info & Closing

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

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 Financial, breaking down not only what to expect at each stage but also how to make a decision that aligns with our values, personality, and financial goals.

We begin by examining the startup world—fast-paced, creative, and filled with uncertainty. It’s a space for people who love to experiment and thrive in ambiguity. The upside can be big: ownership, impact, and equity at low initial prices. But the downsides—unpredictable income, fewer benefits, and emotional strain—are just as real. Amy shares stories of clients who initially thrived in startup life but found it incompatible with long-term needs like family time or structured days.

Next, we shift to pre-IPO companies, which often represent a middle ground. These firms offer more stability than startups but still retain a sense of mission and momentum. Equity typically comes in the form of RSUs, and while there’s real potential for financial gain, it hinges heavily on IPO timing—something employees can’t always control. Amy emphasizes the importance of planning for delays, setting aside cash, and staying flexible when managing that equity.

Public companies offer clarity and predictability—stable salaries, strong benefits, and slower but more structured growth paths. For professionals seeking balance, or with greater family or financial obligations, this environment often provides the support and stability they need. The culture tends to be more formal, but that predictability can actually empower people to do their best work.

Ultimately, the conversation centers around fit—not which company is best, but which is best for us, right now. Personality, financial goals, and life stage all play a role. A startup might make sense early in a career, while a more structured setting could become the right choice later on. Amy reminds us that romanticizing a company type—or even our own preferences—can lead us astray, and encourages getting honest feedback from those who know us best.

We wrap by reinforcing that job decisions should balance financial and emotional fit. Before accepting an offer, it’s critical to understand the equity structure, total compensation, pace of work, and company culture. Especially in today’s tight job market, doing our due diligence can prevent long-term regret and position us to thrive both professionally and personally.

00:00 - Intro and Episode Setup

00:49 - Startup Culture: Opportunity vs. Chaos

03:19 - Pre-IPO Companies: Growth with Guardrails

06:08 - Public Companies: Structure and Stability

09:27 - It's About Fit: Personality and Life Stage

11:43 - Culture, Pace, and Real-Life Trade-offs

13:43 - When the Job Market is Tight

14:17 - Takeaways: Equity, Compensation, and Culture

16:44 - How to Connect with Thimbleberry Financial

16:57 - Disclaimer and Wrap-Up

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

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 family.

We explore how this dual role adds emotional and financial weight. Many healthcare professionals become the “go-to” child in the family, shouldering time off work, travel, coordination, and often direct financial support. But as Amy reminds us, we can’t pour from an empty cup. Our ability to help others long-term depends on preserving our own financial health first.

We talk through the major financial decisions that come up—care settings for aging parents, sibling coordination, insurance gaps, and legal documents. There’s often an assumption that Medicare will cover long-term care, but it doesn’t, which leads to unexpected financial strain. Amy also highlights the importance of separating finances, documenting contributions, and maintaining clear records to protect relationships and ensure fairness.

A major theme we come back to is boundaries. Just like in an emergency on an airplane, we must put on our own oxygen mask first. For financial health, that means building a plan for ourselves before helping our parents. That clarity allows us to make better decisions, communicate expectations with siblings, and avoid jeopardizing our own retirement.

We also recognize the strengths healthcare professionals already bring—assessment, planning, communication, and monitoring. These are the same skills needed to manage a family’s financial and care responsibilities. Amy urges listeners to apply their professional mindset to this personal challenge.

Finally, we lay out five concrete next steps: gain financial clarity for both generations, start those tough conversations early, prioritize your own retirement, coordinate insurance and estate planning, and build a team of advisors, including financial planners and elder law attorneys. Sustainable care means both generations are supported—and planning ahead is the only way to get there.

00:00 - Intro
00:14 - The Sandwich Generation in Healthcare
00:49 - Emotional and Financial Weight of Caregiving
02:24 - Financial Decisions When Parents Need Support
04:59 - Sibling Dynamics and Hidden Costs
05:48 - Helping Without Sacrificing Your Retirement
08:33 - Applying Professional Skills to Family Finances
10:42 - Five Concrete Next Steps
12:21 - Sustainable Care Across Generations
12:42 - How to Contact Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

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 see online is rarely the whole picture. People share the new boat or vacation, not the credit card debt, parental help, or stress behind the scenes.

We also talk about how older stats around side hustles — like claims that 50% of people have them — still influence how we think today, despite more accurate 2025 data showing only 25% of adults actually have one. And affluence is often funded by invisible resources like family wealth or debt, which makes comparisons misleading and self-defeating.

Psychologically, we’re wired for social comparison, but our brains focus upward. We look at those doing better, rarely at those with less. That creates ever-shifting benchmarks for “enough,” raising the bar as others share their wins. On top of that, algorithms feed us more of what we engage with — usually success stories — which can skew our sense of what’s normal.

Amy walks us through the reality: the national savings rate is low (4–5%), emergency funds are thin (1 in 5 adults can’t handle a $100 surprise), and credit card debt is at an all-time high in 2025. Even those who look like they have it all together might be stretched thin.

Why does this all sting so much? Because we’ve tied our identity to our finances. Falling behind feels like failure. It hits at our self-worth and creates a stress loop: we feel behind, we spend to catch up, and that spending adds more stress. It’s emotional and financial burnout.

So how do we break the cycle? First, redefine goals based on our own needs. Track progress against your own goals — like building savings or reducing debt — not against someone else’s vacation photos. Curate your feeds to remove content that sparks comparison. Write down what “enough” looks like for you in terms of comfort, flexibility, and fun. Celebrate quiet wins like financial stability, and be cautious of lifestyle creep when your income rises.

Lastly, Amy reminds us to stay curious instead of competitive. Learn from others without turning it into a race. Real wealth and well-being come from clarity, control, and peace of mind — not what someone else posts online.

00:00 – Intro
00:35 – Why social media skews our perception
01:30 – Debt and side hustle myths
03:00 – Why we compare ourselves psychologically
04:50 – The illusion of success online
05:50 – What’s really going on financially nationwide
06:50 – Why it hurts to feel behind
07:40 – The emotional and financial cost of comparison
08:45 – How to reset your goals
09:40 – Avoiding lifestyle creep
10:25 – Final takeaways and closing

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

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 over a period of years. Amy compares this to being promised jelly beans in the future—enticing but only valuable once they’re actually in your hands.

We walk through vesting schedules, with one-year cliffs and subsequent payouts over several years being the norm. The concept of “golden handcuffs” comes into play, where employees lose unvested RSUs if they leave a company, adding a layer of retention-driven strategy from employers. We also dig into the tax implications, emphasizing that there’s no tax when RSUs are granted—but they are taxed as ordinary income once they vest. Many people mistakenly assume the company’s withholding covers the full tax liability, but that’s often not the case, especially for high earners.

The conversation gets technical but clear, explaining how the timing of selling RSUs affects how gains are taxed—short-term gains being taxed as ordinary income and long-term gains benefitting from lower capital gains rates. We debunk the myth of “double taxation” with a simple timeline that separates the grant date, vesting date, and eventual sale date, highlighting how only the gain beyond vesting is taxed again.

We then explore the decision of whether to hold or sell RSUs. It depends on individual circumstances, but key factors include overall exposure to the company through salary, stock, and other equity compensation. Concentration risk becomes a big deal, especially if both partners in a household have RSUs at the same company.

Common mistakes include underestimating tax obligations, overconcentration in employer stock, and failing to plan for tax bracket changes due to RSU income. On the opportunity side, we point to strategic uses of appreciated RSUs—such as charitable donations and goal-based selling. With RSUs becoming more common outside of tech and market volatility remaining high, understanding your vesting schedule and strategy has never been more important.

We wrap up by encouraging listeners to treat RSUs as part of a broader financial plan, not just as a bonus or windfall. Intentionality is key, and professional planning can help manage risk and make the most of these powerful compensation tools.

00:00 – Intro & RSU Basics
01:23 – What Are RSUs and Why Do Companies Offer Them?
02:43 – Vesting Schedules Explained
04:11 – Tax Implications at Vesting
07:29 – Capital Gains on RSUs
09:10 – Myth Busting: Are RSUs Double-Taxed?
10:00 – Should You Hold or Sell RSUs?
11:12 – Risk Exposure and Concentration
13:20 – Common Mistakes with RSUs
14:06 – RSU Opportunities and Strategic Planning
14:52 – Why RSUs Matter in 2025
15:39 – Final Takeaways on RSU Strategy
16:31 – How to Contact Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

In this episode of ThimbleberryU, we dive into the hype and misinformation around Treasury bills (T-bills) that’s been circulating across social media platforms. We’ve all seen the claims: “risk-free,” “better than savings accounts,” “Warren Buffett approved,” and “perfect for retirement.” But are they really that simple? Amy Walls from Thimbleberry Financial breaks down what’s true, what’s misleading, and what actually matters when it comes to investing in T-bills.

We start by clarifying what T-bills actually are—short-term loans to the U.S. government, ranging from four weeks to a year. You buy them at a discount, and the difference between the purchase price and the face value at maturity is the interest you earn. While social media often touts them as risk-free, we explore why that’s only partially true. T-bills carry almost no credit risk, but they do carry inflation risk—if inflation outpaces your return, you're effectively losing money.

Next, we tackle the common claim that T-bills always outperform savings accounts and CDs. In some market conditions, that’s accurate—especially since T-bills are exempt from state and local taxes—but not always. High-yield savings accounts or promotional CDs can sometimes be more competitive. The idea of “guaranteed returns” is also addressed; while T-bills pay a set amount, they don’t roll over automatically, which means you need to be actively involved to maintain any momentum.

We also discuss the often-referenced Warren Buffett angle. Yes, Buffett uses T-bills—but only as a parking lot for cash while waiting on bigger investment opportunities. He doesn’t treat them as a core piece of his long-term strategy, and neither should the average investor without considering context and goals.

When it comes to retirement planning, T-bills can be part of the equation—but they aren’t universally ideal. They work for retirees focused on capital preservation, but younger investors risk missing out on growth if they lean too heavily on T-bills. We emphasize that T-bills are a tool, not a one-size-fits-all solution. Again, diversification of investments is key.

The takeaway is clear: T-bills can serve a purpose—whether as a component of a cash reserve or a conservative bond alternative—but only when used with intention and in alignment with a broader financial strategy. Social media often oversimplifies investments for the sake of attention. We encourage listeners to approach these decisions thoughtfully and critically.

00:00 – Introduction & T-Bill Hype on Social Media
00:47 – What Are T-Bills, Really?
01:46 – Are T-Bills Risk-Free?
03:00 – T-Bills vs. Savings Accounts and CDs
03:53 – “Guaranteed Returns” – Fact or Fiction?
05:08 – The Warren Buffett Argument
06:00 – Are T-Bills Good for Retirement?
07:13 – Using T-Bills Strategically
08:43 – The Real Lesson on Financial Tools
09:25 – How to Connect with Thimbleberry Financial

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

In this episode of ThimbleberryU, we continue our discussion on gamifying savings by shifting from the “why” to the “how.” Last time, we explored the psychology behind gamification. Today, we walk through the specific steps to design a savings game that’s personal, sustainable, and motivating.

We begin by stressing the importance of having a vivid goal. It’s not enough to have a vague intention—our goals need to be visualized, named, printed, and emotionally connected to. Once the goal is in place, we choose a structure that fits our personal motivation style. For some, it's a streak counter; for others, it’s hitting milestones, unlocking levels, or incorporating random rewards. The key is to tailor the game mechanics to what actually drives us.

Next, we build structure around the game by defining clear rules—written rules—to eliminate ambiguity and reduce the temptation to bend the system. Amy emphasizes the importance of including predefined exceptions so we can respond to life’s inevitable hiccups without feeling like we’ve failed. Automation plays a huge role in eliminating friction; it ensures that we follow through without having to rely on willpower.

We also talk about the power of accountability. Whether it’s a partner or a regular financial check-in, accountability helps us track wins, adjust strategies, and stay committed. And because humans respond to incentives, it’s critical to build a reward ladder. These rewards should be meaningful but proportionate—ideally no more than 10% of what we’re trying to save. We also look at the value of experience-based rewards, which generate longer-lasting satisfaction than material purchases.

To ground the theory, Amy shares a story about “Alex,” who gamified her weekday lunch spending. By creating a simple challenge, defining her rules, and building in smart rewards and penalties—including donating to a “liked but not loved” charity—Alex turned a small change into a sustainable habit.

When setbacks happen, we encourage listeners not to see them as failures. Reset the streak, learn from the moment, and evaluate whether the original goal was realistic. Symbolic penalties and honest reflection can help restore momentum.

We wrap up with a lightning round, debunking the idea that gamification is childish or time-consuming. It’s backed by behavioral science and can be managed with minimal effort through automation. Finally, we suggest starting small, being flexible, and aiming for traction—not perfection.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.

We kick off part one of our two-part series by exploring how gamification can make saving money feel less like a chore and more like a motivating challenge. Even high-income earners often feel stuck when it comes to saving, not because they lack discipline, but because they’ve already checked the big boxes—maxed out retirement accounts, built up emergency funds—and then don’t know what to do next. Without a plan, spending creeps in to fill the gap. So we look at how to turn savings into a game—something with rules, progress, and rewards—to reignite momentum.

We clarify that knowing you should save doesn’t automatically lead to action. That’s where gamification steps in. Tools like Qapital show that users who engage with automation and gaming strategies save more and stay more engaged. We also reference employer-based incentives like those offered through Secure 2.0, where bonuses are tied to increased retirement contributions.

One easy place to start is by automating just one transfer—no matter how small—to reduce decision fatigue. Then, to make it stick, we frame savings as something familiar and motivating. For example, we explore the idea of treating savings like a “debt to your future self,” flipping a psychologically powerful habit like debt aversion into a positive financial behavior.

Amy shares a client case study of a high-earning couple who couldn’t get traction with savings—until they started treating their savings goal like a debt that needed to be paid off. That mindset shift helped them redirect thousands per month into future-focused goals.

Then we move into more playful territory, introducing practical games to get people started. These include “Level Up” savings, where every $500 or $1,000 milestone brings a sense of progress; “No Spend” challenges, focused on key problem areas like Amazon or takeout; and visual trackers like progress bars stuck on the fridge. Even simple things like rounding up purchases and transferring the change can reinforce good habits.

The big takeaway is to pick one area where spending tends to leak—Amazon, dining out, etc.—and pair it with one of these gamified saving techniques. You can even stack methods for greater impact. The key is to make saving easier, more visual, and more rewarding—so it becomes a behavior you actually want to continue.

In part two, we’ll dive deeper into building out a full gamified system with recovery plans, rewards, and design tips. For now, we encourage listeners to find just one game that resonates and start today.

To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com.