Back to School and Ocean Sunfish
It's been a few weeks since the last update, longer than usual, and that's ok. Summer got busy in the good way, and the bi-weekly schedule I'd been holding myself to slipped. Going forward I'm loosening the cadence a bit: expect this newsletter approximately every two to three weeks, rather than a strict bi-weekly clock. It's not a corporate marketing newsletter, it's just me writing when I've got something worth saying, and summer made that a little less predictable.
That said, in this edition, we'll cover a fantastic summer, a back-to-school tax checklist, and a very large fish.
Top of Mind
Today was the first day of school. Will, Frank, and Catherine all walked out the door this morning with a mix of excitement and nervousness. They’re ready for new teachers, new schools, and the particular chaos of a school-year routine. I'm happy for them. At the same time, if I’m being honest with myself, I’m a little sad that summer vacation is over.
This was a good summer. We ate more hot dogs than I can possibly count. We went camping in the back yard. We went on a whale watch. We dug for clams and caught fish and played Pokémon cards. There were video games, island treasure hunts, movie nights, and more craft projects than I knew we owned supplies for. We spent hours at the dairy barn at Wolfe’s Neck torturing the staff with endless questions. I did not get nearly as much work done as I told myself I would back in June. I'm not mad about it in the least.
I started this firm, in part, so that summers could look like this. Not zero work or a three-month vacation, just the ability to shut down the computer on a Tuesday afternoon for a clamming trip and some ice cream while making the time up some other way. That trade-off is the whole point, and it's a lot easier to make up the time when you're the one who gets to decide when to close up shop for the day!
So today felt like the actual turning point of the year, more than New Year's Day ever does. Routine is coming back, and there's real relief in that. But I'll take the disorganized, sunburned, chaotic version of summer over an efficient one every time.
Worth Knowing
Nobody wants to think about taxes in July. Now that the backpacks are out and the routine is back, here are a few back-to-school items worth a few minutes of your time:
Gather your summer camp receipts. If you paid for day camp so you could work, that expense may qualify for the Child and Dependent Care Credit, and 2026 made it more valuable. Under current tax law, the maximum credit percentage jumped from 35% to 50% for qualifying expenses, up to $3,000 for one child or $6,000 for two or more, with the exact percentage sliding down as income rises. The key distinction is day camp versus overnight camp: day camp generally qualifies, overnight camp never does, regardless of how much work you got done while your kid was away. You'll need the provider's name, address, and tax ID to file Form 2441, so it's worth tracking that down now rather than hunting for it in April. Most camps are used to supplying this information.
Check in on 529 contributions. If you're funding an education savings account, back to school is a natural prompt to check where you stand for the year and whether a top-up before December 31 makes sense for your state tax situation.
Revisit your withholding. Summer often brings irregular income (bonuses, a side project, investment activity) that doesn't get caught by your regular paycheck withholding. With routine returning, it's a good moment to pull your last pay stub and make sure you're not heading toward an unpleasant surprise or an interest-free loan to the IRS next spring. There is still plenty of time left in the year to make catch-up estimated tax payments.
S-corp health insurance. This is a little specific, but if you're an S-corp owner, check that your health insurance is actually flowing through payroll. This one trips up a lot of owners. If you own more than 2% of an S-corp and the company pays or reimburses your health insurance, that premium needs to be added to your W-2 Box 1 wages, but kept out of Boxes 3 and 5 so it isn't hit with Social Security or Medicare tax. Skip that step and the self-employed health insurance deduction on your personal return isn't available, even though you paid the premiums. It's a quick fix if you catch it now, and a much bigger headache if it surfaces for the first time when your return is being prepared.
Mark Your Calendar
September 15: Q3 2026 estimated tax payments due. Also, extended partnership and S-corp returns are due.
October 15: Extended 2025 individual returns due.
Maine Wildlife Facts
We closed out the summer with one last adventure: a full day on the water in Casco Bay, with a treasure hunt on Little Whaleboat Island. On the way out, just off Crab Island, we came across a mola mola, or ocean sunfish, warming itself at the surface.
If you've never seen one, it's a genuinely strange animal. Mola mola are the heaviest bony fish in the world, capable of topping 2,000 pounds and occasionally pushing past 5,000! They look less like a fish and more like a fish head that lost the rest of its body. Their bodies are flat and round, their fins are set far back, and from a distance the tall dorsal fin breaking the surface gets mistaken for a shark more often than you'd think.
The "sunfish" name comes from their habit of lying on their side at the surface, basking, which is exactly what ours was doing. Nobody's entirely sure why they do it. It might be to warm up after a dive into cold water hunting jellyfish, which make up a large part of their diet. It might be to invite seabirds to pick parasites off their skin. Either way, it makes them easy to spot and remarkably calm about boats getting close, which is part of why they've become a favorite sighting on Maine whale watches.
Ocean sunfish sightings in the Gulf of Maine have been on the rise over the past decade, generally attributed to warming water drawing them further north and keeping them around longer into the season. Will had his hopes set on sighting dolphins, but was happy to settle for seeing a giant, derpy-looking fish flopping its fins, and basking on the surface.
These Maine wildlife facts have been brought to you by Will (8), 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.