Open Window's Insight Articles

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The biggest tax law since 2017 is here. The “OBBBA” reshapes tax rates, deductions, student loans, business rules, and estate planning, all while cutting social support and adding to the deficit. Our new guide breaks it all down and shows what steps might make sense for you and your family.

With fresh IRS updates, inflation-adjusted brackets, and potential legislation on the horizon, now’s an ideal time to get ahead, sidestep surprises, and keep more of the money you’ve worked so hard to earn. In this Insight Article, we highlight key tax changes, explore Roth conversions in down markets, and revisit a longtime favorite—the strategic use of Health Savings Accounts for Medicare—to help you maximize deductions, avoid penalties, and make confident, tax-smart decisions in 2025.

Do you see tax season as a chore—something to endure, not optimize? When done right, filing your tax return isn’t just about compliance, it’s a chance to celebrate the tax-smart moves you made last year and uncover new ways to maximize your future financial success. From strategic planning to hidden savings, your tax return holds valuable insights that can shape your financial future. Don’t just file—plan. Here’s how smart tax planning can put more money in your pocket now and for years to come.

Each year, the IRS reviews and adjusts specific tax provisions for inflation. Below are the latest updates for the 2025 tax year, including common income, dividend, and capital gain tax brackets. What is your strategy to make the most of these brackets (in 2025 and beyond)?

Here are the tax policies we're watching and what they could mean for the high-earners, diligent savers, and charitable givers with which we work best. Proactive and adaptable tax and financial planning remain essential, especially since political and policy landscapes could shift yet again post-2026.

Were you surprised to receive a Medicare IRMAA letter from the Social Security Administration? Beware that certain income levels can increase your Medicare premium by up to 286% - an increase called "IRMAA." And yet, some people might still pursue this increase. If you're among the 8% of all Medicare participants who received an "IRMAA" letter, here's what you need to know.

The tax policies proposed by former President Donald Trump and Vice President Kamala Harris highlight and contrast their different economic visions. Awareness of these policies and proposals is part of making an informed decision on Election Day. Although these tax proposals could have significant impacts on individuals, businesses, and the overall economy, a balanced approach in your personal planning remains a prudent way forward.

Tax changes are on the horizon with the "TCJA sunset". Within, we highlight how the rules are scheduled by law to change. Use our Comparison Guide and Personalized Checklist to review how your taxes might change with this major potential revision of tax law. Let's consider these changes together as opportunities to avoid reacting to them later as threats.

Paying taxes is part of life, but did you know that when you choose to pay them might make a difference in your tax bill, and in your quality of life? Consider these must-know facts about your taxes, especially if you owe "quarterlies" or estimated "voucher payments."

Every year, the IRS evaluates and adjusts certain tax provisions to account for inflation. Below are the latest adjustments for the 2024 tax year - including common income, dividends, and gain tax brackets.

A health savings account (HSA) provides a tax-smart way to confront the growing burden of healthcare costs while providing other unique tax advantages. Here's what you need to know towards making a lifetime of health & medical expenses tax-deductible (including most Medicare expenses).

Tax savings can be significant by targeting the “Valley of Opportunity” that appears during lower-income tax years. Life tends to present these valleys as predictable opportunities, occurring at certain times and even at specific ages. Make sure you’re prepared to act by “filling up the valley” to avoid leaving your future self, or your beneficiaries, with higher effective tax rates.

How much of your recent efforts to file this year's taxes went towards confirming last year's actions? Over the years, all that backward-looking tax reporting adds up. You can bet that the IRS is keeping track. So, if you want to come out ahead on taxes next year (and in the years to follow), make sure you're being just as forward-looking about your money as the IRS is. Here's how.

A tax-focused understanding of your finances is a crucial component of preserving and growing wealth. With tax rates set to rise in 2026, a tax-focused financial strategy is now even more crucial, regardless of your age or income-level. Here are a few tips to get around the myths we see tripping up high-earners and good savers.

Whatever your reason for giving this year, it’s important to be intentional. With a little strategic planning, your existing charitable contributions can go further, while creating tax benefits for both you and your chosen charity. A donor-advised fund can supercharge your existing giving. Here's how.

Roth accounts offer tax-free growth and tax-free withdrawals. But these benefits can be hard to come by, especially for high earners. Should you consider a tax-free Roth? We’re discussing what you need to know below.

There are three certainties in life: death, taxes, and change. Here is an in-depth review of some of the tools and techniques we can use to reduce one of those certainties: your lifetime tax bill (or beyond, through a tax-efficient transfer to heirs).

A summary of recent tax legislation, much of which was expected to be enacted in 2021, before stalling in Congress. While the final language remains uncertain, many of the proposals could become law. Ask us to show you your potential impacts in a personalized "what if" proposal.

After a tumultuous 2020 election season, inauguration day is almost here. If you are a high-earner, here are some challenges that could arise during a Biden administration.