Today, we look at the first five of ten common estate planning pitfalls that many people either ignore or misunderstand, and we lay out the real-life consequences of those mistakes. Estate planning is important not in terms of wealth, but in terms of reducing stress and preserving relationships when someone passes away. Whether or not someone is wealthy, a proper estate plan can prevent delayed decisions, misallocated assets, and elevated emotions for surviving loved ones - during a very stressful time.

The first pitfall we tackle is not having a will at all. If someone dies without a will, their state—not their estate—decides who inherits what, based on legal formulas that ignore personal relationships or intentions. These formulas differ by state and often don’t align with what people assume will happen.

Next, we highlight the danger of outdated documents. Many people who think they’re covered by old wills or plans don’t realize that state laws or life changes—like moves, marriages, or children—can render those documents ineffective. We share a story of a family who thought they were protected, only to find out their paperwork didn’t align with their current state’s laws.

Then, we move into beneficiary designations, which can override a will because they’re treated as contracts. If those designations are outdated, such as naming an ex-spouse, the wrong person could end up with assets, regardless of what the will says. This is why reviewing beneficiaries regularly is crucial.

The fourth pitfall is unfunded trusts. Setting up a trust isn’t enough—it has to be funded, meaning the assets need to be formally moved into the trust. Without doing this, the trust is an empty safe, and the probate process still applies. We discuss a case where a well-intentioned trust ended up being completely ineffective because it wasn’t properly funded.

Finally, we address the lack of incapacity planning. Many people forget to prepare for a scenario where they’re alive but unable to make decisions. Without healthcare directives or powers of attorney, families may have to go to court just to pay bills or make medical decisions—adding legal stress to already emotional situations.

We wrap up by reiterating the importance of having clear, updated, and legally valid documents in place—not just for your sake, but for those you care about. In Part 2, we’ll continue with the next five pitfalls to avoid.

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 a topic that’s becoming more and more urgent: how healthcare professionals can financially prepare for the possibility of career burnout. We know from data and personal experience with clients that burnout is hitting this sector hard—over 50% of healthcare professionals report symptoms, and a significant number are considering stepping away from their roles entirely. So, we tackle this issue head-on, not from a medical standpoint, but from a financial planning perspective.

We start by emphasizing that prevention is key. Just like in medicine, the best remedy for burnout is early action, and that begins with building a solid financial foundation. We explore how consistent savings habits—even when it feels unnecessary—can offer crucial flexibility down the line. Setting aside 20% or more of each paycheck, creating an emergency fund with 6–12 months of expenses, and maintaining liquidity outside of retirement accounts are all smart, actionable steps. We also stress the importance of not delaying financial planning because you assume higher income gives you more time to catch up later. That’s a trap we see too often.

Next, we look at how to create income flexibility if burnout leads to reduced hours, a role change, or even early retirement. We talk through the importance of evaluating disability insurance—especially with mental health in mind—and how thinking ahead about possible career pivots like consulting or teaching can reduce stress. We also dive into the importance of building passive income streams and using investment strategy to bridge income gaps without needing active work.

For those considering early retirement, we advise updating retirement plans immediately to identify any needed changes, recalibrating spending, and optimizing the timing of account withdrawals to minimize taxes. We also cover how to smartly use pensions and healthcare benefits, especially when considering stepping away. Timing really matters here, and small adjustments can have outsized financial impacts.

Finally, we go over tactics to manage financial obligations during a career break—reducing debt, refinancing, and communicating with lenders. We talk about using COBRA, marketplace insurance, and HSAs to maintain healthcare coverage. The bottom line is that being proactive with money gives healthcare professionals the power to make the best choices for their well-being—financially and mentally—before burnout forces their hand.

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 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.