Tax season is here, and if you're just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you're not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of your money where it belongs.

• [00:00] Why tax season mistakes are more common than you might think

• [01:00] The costly consequences of filing after the tax deadline

• [02:30] Why double-checking basic personal information matters more than you think

• [03:30] The hidden risk of missing 1099 forms in the digital age

• [04:15] How a rollover mistake can accidentally create taxable income

• [05:00] The surprisingly common issue of unsigned tax returns

• [05:30] Why simple math errors can lead to penalties or unexpected refunds

• [06:30] When free tax preparation help may—or may not—be a good option

Many tax mistakes don't happen because people are careless. They happen because people rush, assume something was already handled, or simply overlook a small detail that turns into a big issue later. One of the most common problems I see is filing past the tax deadline. Each year millions of taxpayers fail to file by the April deadline, which can trigger penalties and interest if taxes are owed. Even if you're due a refund, filing late can delay getting your money back.

Another major issue is incomplete or incorrect information on the return. Something as simple as entering the wrong bank account for a direct deposit or forgetting to include a tax document can delay processing or create unnecessary headaches. And in today's digital world, many tax forms are delivered electronically, which means it's easier than ever to overlook a 1099 if you forget about an account.

Beyond basic filing errors, many taxpayers lose money by missing deductions or not understanding new tax rules. Starting with the 2025 tax return, several changes introduced under the "One Big Beautiful Bill Act" create additional tax breaks. These include adjustments to the standard deduction, expanded deductions for certain taxpayers, and other potential opportunities many filers may not even realize exist.

I also discuss why deciding between the standard deduction and itemizing can significantly affect how much tax you owe. In recent years, higher standard deductions meant fewer people itemized their taxes. But changes to the state and local tax deduction cap may reopen the door for some taxpayers to itemize again, especially homeowners with mortgages or individuals paying higher state and local taxes.

Understanding what qualifies as an itemized deduction—from mortgage interest to medical expenses and charitable contributions—can make a meaningful difference in your tax outcome.

Two other mistakes I see regularly involve retirement and tax planning details that often get overlooked. Some taxpayers make IRA or Health Savings Account contributions but forget to report them properly on their return. That mistake can cause them to miss legitimate deductions that could reduce their taxable income.

Another issue is failing to pay quarterly estimated taxes. This commonly affects self-employed individuals, business owners, and retirees who receive income without automatic tax withholding. Without proper withholding or estimated payments, taxpayers may face penalties—even if they eventually pay the full amount owed.

The good news is that many tax mistakes can be corrected. If you discover an issue after filing, an amended return can often resolve the problem. But catching these issues before filing is always the best strategy.

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If you're approaching age 65, Medicare can feel overwhelming fast. Between Parts A, B, C, and D and the timing rules tied to each—it's easy to make a costly mistake if you don't understand how the pieces fit together.

In this episode, I walk through the Medicare "alphabet," explaining what each part does, when enrollment matters most, and how your decisions interact with the rest of your retirement plan. We also cover common questions that come up when clients transition from employer-sponsored coverage to Medicare for the first time.

Whether retirement is right around the corner or still a few years away, this episode is designed to help you avoid penalties, coverage gaps, and surprises down the road.

[00:00] Understanding Medicare Parts A, B, C, and D
[01:00] When you can delay Medicare without penalties
[02:30] How late enrollment penalties actually work
[06:00] Timing Medicare enrollment to avoid coverage gaps
[07:30] What Medicare does—and does not—cover
[10:00] Medicare Advantage vs. supplemental coverage
[14:00] How state rules can affect your long-term options

Medicare isn't just about what coverage you choose it's also about when you enroll. Missing key enrollment windows can trigger penalties that last for life, even if the mistake was unintentional. In this episode, I explain the rules around initial enrollment, special enrollment periods, and why employer coverage plays such a critical role in determining your options.

Once you enroll in Parts A and B, you still need to decide how to fill the gaps. Medicare Advantage plans and Medigap policies take very different approaches to coverage, costs, and flexibility. I outline how these options compare, what tradeoffs to be aware of, and why the "best" choice depends heavily on your health, preferences, and where you live.

Medicare decisions don't exist in a vacuum. Premiums, out-of-pocket costs, and coverage choices all affect cash flow in retirement. In this episode, I explain how to think about Medicare as part of a larger retirement strategy, not just a healthcare decision—so your plan stays aligned as you transition out of the workforce.

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Have you ever fallen victim to a RAT attack? No, not the furry kind, a Remote Access Trojan attack.

I'm discussing how cybercriminals use social engineering to target victims, and the real-world impact these threats can have on your investment accounts and personal information. I reveal the latest tactics scammers use, and, most importantly, offer practical tips to help you recognize warning signs, safeguard your accounts, and minimize your risk, whether you're an individual managing your retirement nest egg or a business owner overseeing company assets.

• [00:00] What is a RAT attack?
• [02:45] Avoid clicking unknown links.
• [06:28] Preventing fraud through active monitoring.
• [09:44] Enhancing network security strategies.
• [10:48] Tips for staying secure online.

There are an estimated 2,200 cyberattacks every day, or one every 39 seconds. Global financial damages from cybercrime are projected to rise from $9.5 trillion (2024) to an estimated $10.5 trillion in 2025. It's no longer a matter of if, but when, the next attack will happen.

Most RAT attacks begin with "social engineering", that is, psychological manipulation designed to get you to act against your best interest. This can look like an email or text from what appears to be a trusted company (think Schwab, Amazon, or EZ Pass), urging you to click a link or download an attachment.

Do not click these links or download unknown files, even if the message creates a sense of urgency or familiarity. Even a simple PDF can be the Trojan horse that installs malware without you noticing.

Once delivered, the RAT malware quietly installs itself, evading your detection. It can come bundled with software downloads, or even through "drive-by" downloads, just visiting a compromised website can infect your device without any clicking at all.

Recently, cybercriminals hacked a client's phone and attempted to transfer money from their investment account. Because my team actively monitors accounts and receives real-time alerts from Schwab, we caught the fraudulent activity before funds were lost. But not everyone is so lucky, if hackers compromise your credentials and accounts aren't closely watched, money could be transferred out, leaving you to face a lengthy investigation to recover your hard-earned savings.

Most successful attacks don't involve sophisticated hacking, they leverage human error. Train yourself (and if you're a business owner, your staff) to recognize phishing emails and suspicious texts. Verify unexpected requests directly with the company, never through the provided links.

Implement "least privilege" access, using strong, unique passwords and two-factor authentication for every account. For investment platforms and email, enable notifications for any account activity, so you're alerted instantly to suspicious changes.

Secure remote connections with a Virtual Private Network (VPN) and avoid unsecured public Wi-Fi. If you must work remotely, use your cell phone's secure hotspot rather than free Wi-Fi at a coffee shop. And never log on to bank or brokerage accounts on shared or public networks.

Constant vigilance is your shield. Regularly monitor account activity and set up a system of alerts. Layer your security by combining access controls, firewalls, and regular updates. Always verify new contacts or software installations, adopt a "zero trust" mindset: trust, but always verify.

Stay One Step Ahead

No single solution can prevent all RAT attacks, but a combination of awareness, good digital habits, and layered security makes a world of difference. Being informed is your best defense. Activate two-factor authentication, review your notifications and account alerts, and approach every digital interaction with a healthy dose of skepticism.

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A listener recently wrote in with a common and important retirement planning question: If I'm already maxing out my 401(k), can I also contribute to a traditional IRA in the same year? The short answer is yes—but whether it makes sense, and how much benefit you receive, depends on your income, tax situation, and long-term goals.

In this episode, I break down how traditional IRA contributions work alongside employer-sponsored retirement plans, when those contributions are deductible, and what options are available if your income is too high for a deduction. We also explore alternative strategies, including Roth IRA contributions and backdoor Roth conversions, so you can decide how best to use your annual IRA "coupon."

This episode is especially helpful if you're trying to balance tax savings today with tax flexibility in retirement and want to avoid common mistakes that can complicate your plan later.

[00:00] Whether you can contribute to a 401(k) and IRA in the same tax year
[01:55] The tax-deferral benefits of contributing to a traditional IRA
[03:55] When a traditional IRA contribution is tax deductible
[05:00] Income limits that affect IRA deductions
[07:00] Using non-deductible IRA contributions correctly
[10:00] Roth IRA contribution limits and income phaseouts
[11:45] How a backdoor Roth IRA strategy works
[13:30] Choosing the right IRA strategy for your situation

Even if you are already maxing out your 401(k), contributing to a traditional IRA can provide additional tax advantages. The primary benefit is tax deferral. Dividends, interest, and capital gains generated inside an IRA are not taxed in the year they occur. Instead, taxes are deferred until you withdraw the money, potentially years or even decades later.

This can be especially powerful if you do not need the money right away. With required minimum distributions now starting at age 73—and increasing to age 75 for those born in 1960 or later—many investors have a long runway for tax-deferred growth.

Whether your traditional IRA contribution is deductible depends on two main factors: whether you or your spouse are covered by an employer-sponsored retirement plan, and your adjusted gross income (AGI). Coverage includes plans such as a 401(k), 403(b), 457, SIMPLE IRA, SEP IRA, or pension plan.

For 2026, married couples filing jointly can fully deduct a traditional IRA contribution if their AGI is below $129,000, with deductions phasing out completely by $149,000. For single filers, the full deduction applies below $81,000 and phases out by $91,000. If neither spouse is covered by a workplace plan, the contribution is fully deductible regardless of income.

If your income is too high to deduct a traditional IRA contribution, you still have options. One approach is making a non-deductible IRA contribution. While this does not provide a tax deduction upfront, your investments can still grow tax deferred. However, this strategy requires careful recordkeeping to properly track taxable and non-taxable portions when withdrawals begin.

Another option is contributing to a Roth IRA, if your income falls within Roth contribution limits. Roth IRAs offer tax-free growth and tax-free withdrawals, making them attractive for long-term planning. For those whose income exceeds Roth limits, a backdoor Roth IRA may be an option, provided there are no other pre-tax IRA balances that would trigger pro-rata taxation.

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