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.