ThimbleberryU

Amy Walls
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Financial planning is all about vision - what do you want for the rest of your life? Amy Walls of Thimbleberry Financial helps clients paint that picture every day. And it's what we will do in this podcast.

  1. 3D AGO

    Tech Burnout Blueprint: Aligning Money With Mental Health

    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 we can use financial planning to move from depletion to clarity and control. We explore how burnout rewires our ability to make decisions. Stress from long hours and mental overload shrinks our decision-making capacity. This leads to automatic, often reflexive spending as a way to cope—ordering food, shopping online, or subscribing to convenience services not out of indulgence, but survival. Many of us say we make good money, yet still feel stretched. Amy explains this disconnect through the lens of decision fatigue and lifestyle inflation as coping tools, rather than conscious choices. Then, we walk through Amy’s Burnout Blueprint, a three-pillar framework for using financial planning to support mental and emotional wellbeing. The first pillar is intentional spending. We learn to distinguish between energy-saving expenses, like cleaning services or meal prep, and stress-coping spending that signals a deeper need for rest or support. We hear how small shifts—like outsourcing chores—can buy back time and change our relationship with money. The second pillar is career pacing. Amy shows how financial clarity gives us room to pause, reassess, or even take sabbaticals. Instead of being chained to the next RSU payout or promotion, we can model what “enough” looks like and make career decisions from a place of health, not fear. The third pillar is structured downtime. Real rest requires more than intention—it requires the freedom to disconnect without guilt or financial worry. Whether it’s a full sabbatical or just a microbreak, planning for rest helps rebuild energy and perspective. We also look at underutilized workplace benefits that can support recovery and reduce costs. To wrap up, Amy leaves us with a powerful reminder: burnout isn’t a personal failure—it’s a mismatch between demands and energy. Small, intentional changes around spending, work, and rest can restore control and support our overall wellbeing. To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    20 min

  2. JAN 26

    The Shift From Saver to Spender - Transitioning Into Retirement

    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 carefully built. We start by recognizing how identity plays a major role. Many in healthcare see themselves as protectors and planners. Saving becomes a symbol of safety, and shifting to spending can feel like breaking an internal rule. With the end of scheduled shifts and steady paychecks, many experience a sense of floating—losing the rhythm they’ve followed for decades. We clarify that this unease is normal, not a sign of poor planning, but a psychological adjustment. We emphasize that the solution lies in structure. By creating an income plan that mimics the regularity of a paycheck, we restore the stability many retirees need. We walk through how to assemble an “income playbook”—a way to integrate pensions, IRAs, 403(b)s, HSAs, and savings into a cohesive plan. Each account gets a role, whether it’s for essentials or discretionary goals, and cash buffers protect against market swings. Automation is key here—turning on scheduled withdrawals and tax withholding brings back the rhythm retirees are used to. We also break down the concept of retirement into phases: go-go, slow-go, and no-go years. Spending shifts naturally, so we help clients build flexibility into their plans. Travel and hobbies may define the early years, while later stages often involve more home time or increased healthcare costs. By projecting different scenarios and using guardrails, we help people make confident adjustments as life evolves. Throughout, we stress that it’s okay to spend what you’ve saved. Retirement isn’t about hoarding your wealth—it’s about enjoying the life you worked hard to build. We suggest starting with a snapshot of your financial picture, visualizing what your days might look like, and even running a test month on future income to see how it feels. Ultimately, retirement is about shifting into a new, well-supported identity—one that still reflects who you are but in a new chapter of life. To get in touch with Amy and her team at Thimbleberry Financial, call 503-610-6510 or visit thimbleberryfinancial.com. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    19 min
  3. 10 Lessons from 10 Years at Thimbleberry Financial

    JAN 12

    10 Lessons from 10 Years at Thimbleberry Financial

    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. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    13 min

  4. 12/22/2025

    Choosing Between Tech Companies

    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. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    18 min

  5. 12/08/2025

    Caring for Aging Parents While Planning Your Own Retirement

    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. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    14 min

  6. 11/24/2025

    Why It Feels Like Everyone Has More Money

    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. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    12 min

  7. 11/10/2025

    RSUs in 2025 Explained

    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. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    18 min

  8. 10/27/2025

    T-Bill Myths on Social Media

    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. The ThimbleberryU Podcast is produced by JAG Podcast Productions - https://jagpodcastproductions.com/

    10 min
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About

Financial planning is all about vision - what do you want for the rest of your life? Amy Walls of Thimbleberry Financial helps clients paint that picture every day. And it's what we will do in this podcast.

Information

  • Creator
    Amy Walls
  • Years Active
    2019 - 2026
  • Episodes
    153
  • Rating
    Clean
  • Copyright
    © 2023-2026 Thimbleberry Financial
  • Show Website
    ThimbleberryU