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.

In this episode, we tackle a difficult but crucial topic: what to do when someone passes away. While it’s not a conversation most people want to have, planning ahead can save significant stress and confusion for those left behind.

We start with the immediate steps that need to be taken. First, a legal pronouncement of death is required, which is usually handled by hospital or hospice staff, but in cases of a home passing, 911 or hospice must be called. Then, notifying immediate family and close friends becomes a priority. This can be overwhelming, so enlisting help to spread the word is essential. Arranging transportation of the body, securing the deceased’s home and belongings, and taking care of any pets are also critical early tasks.

Next, we move into handling financial and legal matters. Obtaining multiple copies of the death certificate is key, as most financial institutions require them. Locating the will or estate documents helps determine whether probate is necessary. If the deceased’s assets were solely in their name, probate is likely required. However, if assets were jointly owned or placed in a trust, probate may be avoided. It's important to notify key institutions—banks, investment custodians, mortgage lenders, pension providers, Social Security, and credit card companies—to avoid complications like continued payments that may need to be repaid.

Probate can be a time-consuming and public legal process, so we discuss three common scenarios:

1. If assets are solely owned, probate is required to legally transfer them.
2. If assets are jointly owned, probate is not needed, and the co-owner retains full ownership.
3. If a trust is in place, assets can be distributed per the trust’s instructions without probate, saving time and legal fees.

After probate (or if it’s not required), the final steps include distributing personal belongings and assets, closing remaining accounts, and handling final taxes. Supporting family members emotionally and financially is also critical, as unexpected financial burdens can arise even with the best planning.

The best way to ease this process is by planning ahead. Having an updated will or trust, maintaining a list of financial accounts and key documents, using a password vault, and discussing final wishes with loved ones can help ensure a smooth transition. Regularly reviewing beneficiary designations on accounts and property is also essential to prevent unintended complications.

While this is a difficult conversation, taking steps now can relieve significant stress later. If you need guidance, Thimbleberry Financial can help.

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

In this episode, we dive into the 83(b) Election—a tax strategy that can have significant financial implications for individuals who receive stock as part of their compensation. While it might sound technical, understanding how it works can be crucial for employees, particularly in startups and the tech sector.

The 83(b) Election allows recipients of stock grants to pay taxes on the stock's value at the time of the grant rather than waiting until it vests. If the stock appreciates over time, this decision can result in substantial tax savings, as the taxable income is locked in at a lower rate. However, it’s not always the best choice, and there are key risks to consider. Once the election is made, it cannot be reversed, and the taxes must be paid upfront, regardless of future stock performance.

Amy walks us through a real-world example with a hypothetical client, Emily, a software engineer who receives 10,000 shares of restricted stock. If she files the 83(b) Election when the shares are valued at $1 each, she pays taxes on $10,000. Four years later, if the stock is worth $10 per share, she avoids paying income tax on $100,000 when the stock vests, benefiting from long-term capital gains treatment instead. Without the election, she would be taxed on the stock’s higher value at vesting, potentially leading to a much larger tax bill.

We also discuss how 83(b) applies to stock options using another hypothetical client, Mark, a doctor in the healthcare field. If Mark exercises his options early while the stock is at $2 per share and files an 83(b) Election, he eliminates the income tax liability at vesting and benefits from capital gains treatment on future gains. Without filing, he would owe income tax on the difference between the strike price and the stock’s value at vesting, which could lead to a massive tax burden.

However, the 83(b) Election is not for everyone. Key risks include leaving the company before stock vests, the stock declining in value, or not having the cash available to pay the upfront tax. Timing is also critical—filing must be completed within 30 days of the grant or exercise, with no exceptions. The process involves submitting a signed election form to the IRS via certified mail, providing a copy to the employer, and attaching the form to the tax return for that year.

Ultimately, the 83(b) Election can be a powerful tax-saving tool, but it requires careful consideration. If you’re receiving stock as part of your compensation, understanding this option and consulting a financial professional can help determine if it’s the right move for you.

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

In this episode, we dive into one of the most delicate yet essential discussions families need to have: aging and finances. It’s not just about planning for the future—it’s about ensuring clarity and peace of mind for everyone involved. Many parents assume their children are only interested in their inheritance, while adult children are more focused on logistics—whether their parents are financially secure, who will make decisions, and what kind of support will be needed.

At the same time, adult children often think their parents only want to talk about maintaining independence or that they’re unwilling to discuss financial matters. In reality, many parents want to share their wishes but struggle with how much detail to provide. Some are hesitant because they fear their preferences may be ignored or overridden. Others want to pass on their financial values, ensuring their wealth is used to support family members or causes they care about.

The key to bridging these communication gaps is to approach the conversation with curiosity rather than control. Keeping discussions casual and starting with shared goals—like ensuring the family is prepared—can help ease tension. If starting the conversation feels awkward, using a real-life example (or even a made-up one) can make it more natural. A financial professional can also be a valuable resource in facilitating these discussions, helping to clarify complex topics like estate planning and long-term care preferences. Amy explains how this might work.

A structured yet informal family meeting with a financial advisor can ensure that everyone understands the financial landscape, responsibilities, and expectations. Whether it’s deciding who will handle the bills, managing digital assets, or simply settling who gets a sentimental ceramic cat, these discussions help eliminate surprises and prevent misunderstandings down the road.

The bottom line: these conversations don’t have to be overwhelming. By starting small, approaching with curiosity, and focusing on shared goals, families can navigate aging and financial planning with confidence. And if it all feels too daunting, professionals like Amy Walls at Thimbleberry Financial are available to help guide the process.

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, Jag and Amy delve into the benefits and functionality of virtual financial advising, a model that Thimbleberry Financial has embraced fully. Amy explains how their transition to a 100% virtual advisory model was initially born out of necessity during the COVID-19 pandemic but has since proven to be a more efficient and effective way to serve clients. Catering to their tech-savvy and healthcare-focused clientele, this approach has saved time and made financial planning more accessible.

Amy highlights the seamless integration of technology into their services. Through secure platforms like Microsoft Teams, they maintain interactive sessions where screen sharing and real-time guidance ensure clients remain engaged and understand every aspect of their financial plans. This virtual method also allows for greater flexibility, enabling clients to meet from home, work, or even while traveling within the U.S.

Despite initial misconceptions, Amy dispels the myth that virtual advising is less personal. She emphasizes that trust, communication, and understanding—not physical proximity—build connection. Clients still receive the same personalized care and attention, from initial consultations to ongoing check-ins. The virtual format even enhances convenience, as meetings can adapt to clients’ schedules without the burden of commuting.

Amy recounts how the virtual model benefits clients, particularly busy professionals, who appreciate the efficiency of hopping into meetings without interrupting their day. She also notes the technology’s role in maintaining client relationships even when they relocate, a challenge in pre-pandemic times.

For anyone hesitant about the virtual format, Amy assures listeners that technology simplifies the process without sacrificing the personal touch. Thimbleberry Financial’s approach is designed to integrate seamlessly into clients’ lives, helping them achieve their financial goals confidently and efficiently.

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 detailed case study centered on Stan and Jan, a fictitious couple navigating the complexities of retirement planning with a focus on creating income, simplifying finances, and leaving a meaningful legacy. With $5 million in assets—$3 million in qualified accounts like IRAs - and 403(b)s and $2 million in taxable accounts—they are financially secure but face challenges in optimizing their retirement strategy.

We begin by addressing their primary goal: replacing Stan’s paycheck as he retires. Given their modest spending of $100,000 annually, the focus is on balancing stability, flexibility, and efficiency. Strategies include leveraging Stan’s Social Security at age 70, drawing from qualified accounts to manage required minimum distributions (RMDs), and addressing the 10-year fixed distribution requirements from certain accounts. Consolidating multiple accounts into a single IRA for administrative simplicity is another point of emphasis.

Once income is stable, we explore aligning their investments with their goals. A mix of bond ladders, dividend-paying stocks, and liquid investments ensures consistent income while managing risk. We emphasize a conservative-to-moderate approach for near-term needs, with some growth-focused investments to combat inflation and support their longer-term financial stability.

Taxes play a significant role, and we discuss strategies like Roth conversions before Stan’s RMDs begin, allowing funds to grow tax-free for future needs. Charitable giving through Qualified Charitable Distributions (QCDs) and donor-advised funds offer opportunities to support causes while reducing taxable income. For family, gifting up to $19,000 per year per recipient tax-free enables Stan and Jan to enjoy seeing their loved ones benefit from this money during their lifetime.

Ultimately, this case study highlights that retirement planning is about more than just numbers—it’s about aligning financial strategies with personal values and creating a fulfilling, stress-free retirement. Whether simplifying accounts, managing taxes, or crafting a legacy, thoughtful planning helps ensure a meaningful and secure future. Having "enough to retire" may only be the first piece of the puzzle.

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