Tax Season Hangover and Eastern Red-Backed Salamanders
In this edition of the Flying Point Update, we're going to decompress from tax season, talk about why surprise tax bills are usually not actually surprises, and learn about Big Nights and Eastern Red-backed salamanders.
Top of Mind
April 15th was yesterday. I'm tired.
Tax season is always a mix of things I love and things I would happily skip. The client conversations are genuinely great. People are engaged, asking real questions, paying attention to their finances in a way that leads to good decisions. I learn something new almost every year, and this one was no exception.
The chaos, on the other hand, is a feature I could do without, but kind of comes with the territory. Documents arriving in waves, the annual last-minute scramble, extensions filed on behalf of clients still gathering their paperwork. It's a lot, and it compresses into a very short window. None of it would be manageable without Anna, who holds the house and kids together every year while I disappear into the tax hole. She deserves more than a mention in a newsletter, but it's a start.
Now that the dust has settled, I'm doing what I do every spring: thinking about what went well, what didn't, and what I want to do differently next year. Better systems for document collection. Earlier conversations with clients whose situations are more complex. Clearer communication about deadlines before they're a week away. The work is always better when it's less reactive. This is also an area that I’d love to hear from clients on.
This is also the part of the year I genuinely look forward to. Tax season is backward-looking by nature. You're documenting what already happened. The spring and summer are when I get to shift gears toward forward-looking work: financial planning, business analysis, conversations about what clients are trying to build and how to get there. It's a different kind of thinking, and I find it energizing after months of living in the past.
More on that in issues to come. For now, I'm going to drink some coffee and enjoy the short window of quiet before school vacation starts later this afternoon.
Worth Knowing
Every April, I have a few tough conversations around large tax bills. I completely empathize. No one likes surprise bills. The silver lining is that most “surprise” tax bills can be avoided . In most cases, the math was there all along. What's missing is the visibility and adjusting to changing circumstances.
Almost every large April tax bill traces back to one of two things.
The first is withholding that isn't calibrated to your actual situation. If you're a W-2 employee and your withholding was set up years ago and never revisited, it may not reflect your current income, filing status, or deductions. Life changes, and the W-4 you filled out in 2018 probably doesn't reflect your life in 2026. A few minutes with the IRS withholding estimator can tell you whether you're on track or heading for a gap. It takes a few minutes, but the payoff next April is worth it.
The second is estimated taxes that were never paid, or that weren't adjusted as income grew. This one hits self-employed people and business owners most often. If your income went up significantly in 2025 but your estimated payments were based on 2024 numbers, the shortfall accumulates quietly all year and shows up as a lump sum in April. The fix isn't complicated, it just requires paying attention and updating the math when things change. Paying only safe harbor estimates could still leave you with a large bill.
There's a third issue worth naming, though it's more situational, and the heart of an overly complicated tax system: income from one source can affect what you owe on income from another in ways that aren't always obvious. A strong investment year might push you into the 20% long-term capital gains bracket, or trigger the 3.8% Net Investment Income Tax on top of that. A retirement distribution might make your Social Security taxable, or phase out a deduction you were counting on. Even something as straightforward as a side consulting engagement can push your income past the threshold for a deductible IRA contribution, which is a particularly frustrating discovery in April when it's too late to do anything about it. Each of these interactions is knowable in advance. They just require looking at the full picture before year-end rather than after.
If April was unpleasant this year, the good news is that you have twelve full months to do something about it. We can look at your withholding, review your estimated tax obligations, and set up a better baseline for 2026. The conversation is easier in April than it is next March.
Mark Your Calendar
June 15th: Q2 estimated tax payments are due. Q2 covers April 1 through May 31. If you're making quarterly estimated payments, mark this one down.
September 15th: Extended partnership and S-corp returns are due.
October 15th: Extended individual returns are due. If we filed an extension on your behalf, this is your actual deadline. Six months sounds like a long time, and then suddenly it isn't.
Maine Wildlife Facts
One of the more remarkable calendar events happens on the first warm rainy nights of the spring season, when nighttime temperatures climb above 40 degrees and the ground is wet. On those nights, amphibians of all shapes and sizes emerge in large numbers to migrate to their breeding pools. Naturalists call these events "Big Nights." Thanks to the rain earlier this week, we just had what was probably the biggest Big Night of the year.
Eastern Red-backed salamanders are one of the most common vertebrates in Maine's forests, which surprises most people because they're so rarely seen. They spend most of their lives under rocks, logs, and debris, emerging at night and after rain. We keep what Will and Frank have formally named the "salamander farm" in the backyard, which is, in practice, a pile of old bricks and a rotting stump that turns out to be excellent salamander habitat. After a good rain, you can reliably find several tucked underneath.
The red-backed salamander comes in two color forms: the familiar striped version with the reddish-orange stripe down the back, and a solid dark form called the "leadback." Both are the same species.
What makes these salamanders genuinely unusual is that they don't have lungs. They breathe entirely through their skin, which is why moisture matters so much to them. A dry salamander is in trouble. They also skip the aquatic larval stage entirely, hatching from eggs as fully formed miniature salamanders, which makes them unusual among salamanders and allows them to thrive far from standing water. Skin-breathing also means that oils and chemicals from human hands can interfere with their respiration, which is why we have a firm look-but-don't-touch policy with the salamander farm. If you do need to handle or move one, rub your hands in the dirt first to neutralize the oils. This rule is more enthusiastically followed by some members of the naturalist team than others…
If you want to learn more about Big Nights, participate in seasonal counting, or help shepherd amphibians across roads to their breeding pools, check out Maine Big Nights. It’s not uncommon to see volunteers out and about during big nights.
These Maine wildlife facts have been brought to you by Will (7), Frank (4), and Catherine (2), Flying Point Advisors' on-staff naturalists.
Questions about any of this? Just reach out - I read every email and love hearing from you. Thanks for reading. You'll hear from me again in about two weeks.
-Mike
Disclaimer
The Flying Point Update is provided for general educational and informational purposes only. The content in this newsletter reflects my thoughts and observations on tax, accounting, and financial planning topics, but should not be considered personalized tax, accounting, or investment advice for your specific situation.
Tax laws are complex and change frequently. The information presented here is based on current tax law as of the publication date and represents general concepts that may not apply to your circumstances. Every individual and business has unique factors that affect their optimal tax and financial planning strategies.
Before making any financial decisions or implementing any tax strategies discussed in this newsletter, please consult with a qualified tax professional, CPA, or financial advisor who can evaluate your specific situation. If you'd like to discuss how any of these topics might apply to your circumstances, I'm always happy to chat.