We kick off part one of our two-part series by exploring how gamification can make saving money feel less like a chore and more like a motivating challenge. Even high-income earners often feel stuck when it comes to saving, not because they lack discipline, but because they’ve already checked the big boxes—maxed out retirement accounts, built up emergency funds—and then don’t know what to do next. Without a plan, spending creeps in to fill the gap. So we look at how to turn savings into a game—something with rules, progress, and rewards—to reignite momentum.

We clarify that knowing you should save doesn’t automatically lead to action. That’s where gamification steps in. Tools like Qapital show that users who engage with automation and gaming strategies save more and stay more engaged. We also reference employer-based incentives like those offered through Secure 2.0, where bonuses are tied to increased retirement contributions.

One easy place to start is by automating just one transfer—no matter how small—to reduce decision fatigue. Then, to make it stick, we frame savings as something familiar and motivating. For example, we explore the idea of treating savings like a “debt to your future self,” flipping a psychologically powerful habit like debt aversion into a positive financial behavior.

Amy shares a client case study of a high-earning couple who couldn’t get traction with savings—until they started treating their savings goal like a debt that needed to be paid off. That mindset shift helped them redirect thousands per month into future-focused goals.

Then we move into more playful territory, introducing practical games to get people started. These include “Level Up” savings, where every $500 or $1,000 milestone brings a sense of progress; “No Spend” challenges, focused on key problem areas like Amazon or takeout; and visual trackers like progress bars stuck on the fridge. Even simple things like rounding up purchases and transferring the change can reinforce good habits.

The big takeaway is to pick one area where spending tends to leak—Amazon, dining out, etc.—and pair it with one of these gamified saving techniques. You can even stack methods for greater impact. The key is to make saving easier, more visual, and more rewarding—so it becomes a behavior you actually want to continue.

In part two, we’ll dive deeper into building out a full gamified system with recovery plans, rewards, and design tips. For now, we encourage listeners to find just one game that resonates and start today.

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 common and costly mistake that often undermines the effectiveness of the backdoor Roth IRA strategy. We begin by establishing that the strategy itself is sound—used by high-income earners to legally sidestep income limits on Roth IRA contributions—but the pitfall lies in the tax return process, particularly in how the transaction is reported to the IRS.

We walk through how the strategy works: First, an individual makes a non-deductible contribution to a traditional IRA. Then, they convert those funds to a Roth IRA. The key here is that the contribution was already taxed, so the conversion should be non-taxable. The mistake happens when this sequence isn’t reported properly. We discuss how custodians like brokerage firms don’t know your tax strategy or income limits and cannot flag these issues for the IRS. So, if you're not proactively involved, you risk the IRS treating the conversion as fully taxable.

We unpack the three IRS forms involved: Form 1099-R (reports the conversion but not the tax status), Form 5498 (shows the IRA contribution but often arrives too late to help with timely tax filing), and most importantly, Form 8606 (tells the IRS the contribution was non-deductible and prevents double taxation). We emphasize that most errors occur because Form 8606 is either filed incorrectly or not filed at all. Without it, the IRS assumes your entire IRA is pre-tax, meaning future withdrawals will be fully taxed—even if you already paid taxes on that money.

Using a real-world example, we show how someone like “Jill” can end up paying taxes and penalties she didn’t owe, all because her CPA didn’t receive the full picture. This reinforces the importance of owning the communication and documentation process. We stress the need for record-keeping, proactively communicating with your CPA, and double-checking your return to ensure Form 8606 is present and correct.

In closing, we make it clear: the IRS isn’t malicious here—they can only go by what's filed. It's up to each of us to ensure our tax reporting matches our financial strategy. If you're going to use the backdoor Roth, you need to take responsibility for the reporting piece or work with an advisor who helps manage that process effectively.

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 topic that often catches even financially savvy people off guard—estimated taxes. Many assume taxes are fully handled through paycheck withholdings, but we unpack why that assumption can lead to nasty surprises, especially for professionals in tech and healthcare.

We start by defining what estimated taxes are: quarterly payments made directly to the IRS when withholding isn’t enough to cover total tax liability. This often applies to small business owners, but also to high-income W-2 employees who receive RSUs, ESPP income, large bonuses, or mid-year raises. Amy shares real-life examples of clients whose withholding fell short, either because RSUs were taxed at a flat 22% while their actual bracket was higher, or because payroll systems didn’t account for mid-year raises, leading to unexpected tax bills and underpayment penalties.

We then explore the IRS’s pay-as-you-go approach. If you've underpaid during the year—even if you pay in full by April—you could still face penalties. Jag and Amy emphasize how the system annualizes income, so a raise in July can retroactively affect your tax liability starting in January. This is where estimated taxes kick in, sometimes unexpectedly after filing the previous year’s return.

To determine whether you're subject to these payments, we explain the IRS safe harbor rule: if you pay 90% of your current year’s liability or 110% of the prior year’s, you generally avoid penalties. We walk through the process of calculating your total tax liability, subtracting what’s already been withheld, and deciding how to handle any shortfall—either through increased paycheck withholding or quarterly payments to the IRS and state.

Amy reminds us that overpaying gives the IRS an interest-free loan, so it's often best to aim for accuracy. Tools like financial planning software and coordination with a CPA can make this process manageable. The key is to review and adjust quarterly so you’re not blindsided come tax time.

We close with key takeaways: estimated taxes aren’t just for freelancers, income changes—whether yours or a spouse’s—can affect your liability, and proactive planning with a financial advisor and CPA helps avoid surprises. Most importantly, working with both professionals ensures smoother execution and better results.

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

In this episode, we pick up where we left off—diving into the second half of the top ten estate planning mistakes people make and how to avoid them. Trusts are where we pick up the conversation, and we emphasize that they are tools, not one-size-fits-all solutions. Using the wrong trust, or one that isn’t necessary, can actually create more problems than it solves. We stress the importance of intentionality—choosing the right tool for the right issue, and understanding the specific goals and laws relevant to each person’s situation, especially given varying state estate tax thresholds like Oregon’s low $1 million.

From there, we explore how conflicting or vague instructions can derail even well-meaning plans. When wills, trusts, and beneficiary designations don’t align, chaos can follow. “Fairly” and “equally” may seem interchangeable, but they’re not, and those subtle differences can lead to confusion, resentment, or even legal battles. We also caution against naming just one child with the “plan” that they’ll distribute assets informally—that’s a recipe for tax issues and strained family dynamics.

Ignoring taxes is another frequent oversight. Many people don’t realize how estate planning decisions can trigger income, capital gains, or estate taxes. Planning won’t erase taxes, but it can eliminate nasty surprises. We revisit digital assets too—crypto, photo storage, password managers—emphasizing that if no one can access them, they may as well not exist. These assets require thoughtful handling, not just from a distribution standpoint, but also accessibility.

Finally, we tackle the often-overlooked issue of naming the wrong fiduciary. This isn’t an honorary role—it’s a job. Too often people pick fiduciaries based on birth order, guilt, or assumptions rather than capability and willingness. We share stories illustrating how the wrong choice can create unnecessary complications, and how the right person isn’t always the obvious one. Jag shares how he's not at all upset that his brother is in charge of their parents' estate.

To wrap, we recap all ten estate planning pitfalls discussed across both episodes and remind listeners to align legal documents, assets, and intent—while working with professionals who know how to navigate the complexity.

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

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.

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.