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.