In this episode, we tackle one of the most significant financial decisions tech professionals face: knowing when and how to walk away from a job—whether that's to retire or move to another opportunity—especially when equity compensation is in the mix. We emphasize the mental and financial distinction between retiring permanently and transitioning to a new firm. Retirement means permanently stepping away from income and needing a long-term strategy to generate cashflow from your assets. Switching firms, on the other hand, is temporary unemployment with the potential for new income and equity.

We walk through how to determine readiness for either scenario. For retirement, it’s essential to assess total wealth, stress test sustainable spending, and build a reliable paycheck from assets. For switching jobs, we need ample cash reserves and liquidity, as job searches are unpredictable in length. Equity compensation plays a central role—particularly what we leave behind. We highlight the importance of reviewing company plan documents to understand if retirement will trigger accelerated vesting or forfeiture of RSUs.

When it comes to timing, especially for those with stock options or RSUs, planning ahead is critical. If possible, we want to spread taxable events over multiple years to manage the tax burden more efficiently. We also discuss evaluating whether to hold or sell company stock after departure. The decision hinges on one’s financial goals, income flexibility, and risk tolerance. Behavioral aspects come into play too—avoiding regret by making informed, goal-aligned choices and not falling into the “shoulda, coulda, woulda” trap.

Taxes are unavoidable, but they can be managed with proper planning, especially when dealing with capital gains, ordinary income, and potential AMT from equity compensation. We stress the importance of integrating equity compensation into a long-term financial plan, using it to meet both short-term liquidity needs and long-term diversification goals.

Company-specific events like IPOs, mergers, layoffs, or vesting schedules can all influence the decision to leave. Evaluating those triggers through the lens of your goals helps in deciding whether to act now or wait. Lastly, we return to the value of working with a financial planner and the need for intentionality. Walking away—whether to retire or transition—is rarely simple, and it's okay to find the decision hard.

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

In this episode, we confront a truth many couples avoid: one partner will likely outlive the other. Statistically, especially in heterosexual relationships, it’s often the woman. That fact shapes the financial, emotional, and logistical choices couples need to make as they plan for retirement. We talk about why it’s essential to create a shared plan—one that not only protects assets, but gives peace of mind to both people involved.

We open by acknowledging that in many relationships, one person traditionally handles the finances. If that person passes first, the surviving partner can be left not only grieving, but scrambling to understand the financial puzzle. Amy shares how often she hears from women who feel anxious and uncertain when they’re suddenly in charge. These women aren’t incapable—they just haven’t been part of the process.

The heart of our conversation is about empowering both partners to be part of financial planning. Amy outlines the three big areas where questions tend to show up: understanding the financial picture, handling the emotional baggage around trust and confidence, and building knowledge to make informed decisions. It’s not about control—it’s about shared responsibility and kindness. We highlight how reframing conversations away from aging and death toward security and love can help bring both partners to the table more comfortably.

We also touch on how crucial it is for the financially involved partner—often men in older generations—to help build a bridge of understanding and trust. Amy uses the metaphor of setting up a tent: it takes both people holding up their corner to make the structure stand. We talk practical next steps, including setting up regular financial check-ins, building a “what-if” folder with key documents and passwords, and ensuring both partners feel respected and heard in these discussions.

Ultimately, we conclude that it’s never too late to get involved, and one of the most powerful legacies anyone can leave behind is a partner who feels confident to navigate life after loss. This isn’t just about money—it’s about care, connection, and preparing for a future that’s secure for both people in the relationship.

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 step behind the curtain of financial planning to unpack what makes a financial plan succeed—and just as importantly—what can derail it. We kick things off with a discussion about structure and intentionality. Amy Walls explains how her team at Thimbleberry Financial organizes their schedules to be proactive and client-focused. By setting clear availability and reserving space for strategic planning and internal work, they're able to show up fully prepared for client meetings and respond effectively in between.

We then explore how life events, especially the big and unexpected ones, impact planning. Medical diagnoses, large expenses, home changes, or receiving an inheritance—all of these can affect a financial strategy. We emphasize the importance of timely communication: the sooner we know, the better we can adjust the plan. Amy also reminds us that “big” is subjective. Our financial mindset and values shape how we define major changes, and that’s part of the data that matters, too.

Speaking of data, we clarify that every document request serves a purpose. Whether it's retirement summaries or tax returns, we ask only for what might improve the accuracy and depth of our advice. Sometimes, those pieces of information reveal benefits or pitfalls that clients weren’t even aware of, significantly shifting their trajectory. Taxes, in particular, often catch people off guard, and without returns in hand, it’s tough to diagnose the real issue.

As we dig deeper, we confront ambition versus reality. When clients want to retire early but aren’t on track for a more standard goal, we stress the importance of honest evaluation. If you're not ready to make the changes needed to hit the baseline, it's not useful to explore stretch goals. It’s not about being harsh—it’s about using everyone’s time wisely and avoiding decision fatigue.

We close by highlighting what a successful client-advisor relationship looks like. Clear communication, timely data, and realism about trade-offs are essential. When clients are engaged, responsive, and honest about what's possible, we can offer not just sound advice, but advice that truly improves lives. Financial planning works best when both advisor and client show up ready to collaborate with transparency and intention.

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