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.

In this episode of ThimbleberryU, we dive into a common and costly mistake that often undermines the effectiveness of the backdoor Roth IRA strategy. We begin by establishing that the strategy itself is sound—used by high-income earners to legally sidestep income limits on Roth IRA contributions—but the pitfall lies in the tax return process, particularly in how the transaction is reported to the IRS.

We walk through how the strategy works: First, an individual makes a non-deductible contribution to a traditional IRA. Then, they convert those funds to a Roth IRA. The key here is that the contribution was already taxed, so the conversion should be non-taxable. The mistake happens when this sequence isn’t reported properly. We discuss how custodians like brokerage firms don’t know your tax strategy or income limits and cannot flag these issues for the IRS. So, if you're not proactively involved, you risk the IRS treating the conversion as fully taxable.

We unpack the three IRS forms involved: Form 1099-R (reports the conversion but not the tax status), Form 5498 (shows the IRA contribution but often arrives too late to help with timely tax filing), and most importantly, Form 8606 (tells the IRS the contribution was non-deductible and prevents double taxation). We emphasize that most errors occur because Form 8606 is either filed incorrectly or not filed at all. Without it, the IRS assumes your entire IRA is pre-tax, meaning future withdrawals will be fully taxed—even if you already paid taxes on that money.

Using a real-world example, we show how someone like “Jill” can end up paying taxes and penalties she didn’t owe, all because her CPA didn’t receive the full picture. This reinforces the importance of owning the communication and documentation process. We stress the need for record-keeping, proactively communicating with your CPA, and double-checking your return to ensure Form 8606 is present and correct.

In closing, we make it clear: the IRS isn’t malicious here—they can only go by what's filed. It's up to each of us to ensure our tax reporting matches our financial strategy. If you're going to use the backdoor Roth, you need to take responsibility for the reporting piece or work with an advisor who helps manage that process effectively.

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 a topic that often catches even financially savvy people off guard—estimated taxes. Many assume taxes are fully handled through paycheck withholdings, but we unpack why that assumption can lead to nasty surprises, especially for professionals in tech and healthcare.

We start by defining what estimated taxes are: quarterly payments made directly to the IRS when withholding isn’t enough to cover total tax liability. This often applies to small business owners, but also to high-income W-2 employees who receive RSUs, ESPP income, large bonuses, or mid-year raises. Amy shares real-life examples of clients whose withholding fell short, either because RSUs were taxed at a flat 22% while their actual bracket was higher, or because payroll systems didn’t account for mid-year raises, leading to unexpected tax bills and underpayment penalties.

We then explore the IRS’s pay-as-you-go approach. If you've underpaid during the year—even if you pay in full by April—you could still face penalties. Jag and Amy emphasize how the system annualizes income, so a raise in July can retroactively affect your tax liability starting in January. This is where estimated taxes kick in, sometimes unexpectedly after filing the previous year’s return.

To determine whether you're subject to these payments, we explain the IRS safe harbor rule: if you pay 90% of your current year’s liability or 110% of the prior year’s, you generally avoid penalties. We walk through the process of calculating your total tax liability, subtracting what’s already been withheld, and deciding how to handle any shortfall—either through increased paycheck withholding or quarterly payments to the IRS and state.

Amy reminds us that overpaying gives the IRS an interest-free loan, so it's often best to aim for accuracy. Tools like financial planning software and coordination with a CPA can make this process manageable. The key is to review and adjust quarterly so you’re not blindsided come tax time.

We close with key takeaways: estimated taxes aren’t just for freelancers, income changes—whether yours or a spouse’s—can affect your liability, and proactive planning with a financial advisor and CPA helps avoid surprises. Most importantly, working with both professionals ensures smoother execution and better results.

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

In this episode, we pick up where we left off—diving into the second half of the top ten estate planning mistakes people make and how to avoid them. Trusts are where we pick up the conversation, and we emphasize that they are tools, not one-size-fits-all solutions. Using the wrong trust, or one that isn’t necessary, can actually create more problems than it solves. We stress the importance of intentionality—choosing the right tool for the right issue, and understanding the specific goals and laws relevant to each person’s situation, especially given varying state estate tax thresholds like Oregon’s low $1 million.

From there, we explore how conflicting or vague instructions can derail even well-meaning plans. When wills, trusts, and beneficiary designations don’t align, chaos can follow. “Fairly” and “equally” may seem interchangeable, but they’re not, and those subtle differences can lead to confusion, resentment, or even legal battles. We also caution against naming just one child with the “plan” that they’ll distribute assets informally—that’s a recipe for tax issues and strained family dynamics.

Ignoring taxes is another frequent oversight. Many people don’t realize how estate planning decisions can trigger income, capital gains, or estate taxes. Planning won’t erase taxes, but it can eliminate nasty surprises. We revisit digital assets too—crypto, photo storage, password managers—emphasizing that if no one can access them, they may as well not exist. These assets require thoughtful handling, not just from a distribution standpoint, but also accessibility.

Finally, we tackle the often-overlooked issue of naming the wrong fiduciary. This isn’t an honorary role—it’s a job. Too often people pick fiduciaries based on birth order, guilt, or assumptions rather than capability and willingness. We share stories illustrating how the wrong choice can create unnecessary complications, and how the right person isn’t always the obvious one. Jag shares how he's not at all upset that his brother is in charge of their parents' estate.

To wrap, we recap all ten estate planning pitfalls discussed across both episodes and remind listeners to align legal documents, assets, and intent—while working with professionals who know how to navigate the complexity.

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