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.