Spring Miles and American Goldfinches
In this edition of the Flying Point Update, we're going to talk about training data and finding the signal in the noise, dig into the actual mechanics of estimated tax payments before the June 15th deadline, and hear from the naturalist team about American goldfinches.
Top of Mind
I ran my first 5k of the season a few weeks ago. After a long winter and a tax season that leaves little room for serious training, my result was what it was. Plenty of room for improvement. Which is, if I'm being straightforward about it, exactly the information I needed.
What followed was probably an inevitable consequence of having a Garmin watch and too much post-tax-season mental energy: I went deep on training data. Heart rate variability, cadence, VO2 max estimates, recovery scores. It's genuinely impressive how much a running watch will tell you if you let it. It's also very easy to feel like every number needs attention and every metric needs optimizing.
Most of it, I've concluded, is either vanity or noise. Interesting to look at, not particularly useful to act on. There's also a version of this that's less about data and more about ego — chasing a pace that looks good on Strava rather than one that actually builds fitness. I've been guilty of this. If you’re not familiar with Strava, it’s just athletics focused social media masquerading as data analytics. A run that feels embarrassingly slow at the right heart rate is doing more work than a fast one that leaves you wrecked for three days.
The signal, once I stopped chasing everything, turned out to be pretty simple: heart rate. Specifically, learning to train at the right heart rate zones consistently rather than just running by feel or chasing pace.
Pace, it turns out, is mostly a derivative of a well-trained heart. Focus on the right input long enough and the output takes care of itself. The data was never the problem. Knowing which data to ignore was.
Most data is like this, whether you're tracking miles or managing a business. The hard part is rarely finding more information. It's figuring out which two or three numbers actually matter and ignoring the rest.
And now I'm going to stop philosophizing and spare you the overly obvious LinkedIn-style analogy.
Worth Knowing
Q2 estimated tax payments are due June 15th, which makes this a good moment to talk about how estimated taxes actually work, because the system is genuinely confusing and the confusion is at least partly the IRS's fault.
Most people call these "quarterly" payments, which implies four equal periods spread evenly across the year. That's not what they are. The actual schedule looks like this:
Q1: January 1 through March 31, due April 15th
Q2: April 1 through May 31, due June 15th
Q3: June 1 through August 31, due September 15th
Q4: September 1 through December 31, due January 15th of the following year
Q2 covers two months. Q4 covers four months but isn't due until the following January. None of it maps to what a normal person would call a quarter. The IRS has never offered a satisfying explanation for this, and I've stopped expecting one.
The more useful thing to understand is safe harbor. Safe harbor is the mechanism that protects you from underpayment penalties even if your payments turn out to be less than what you actually owe. Here's how it works: if you've paid in at least 100% of last year's total tax liability across your withholding and estimated payments, you won't owe an underpayment penalty regardless of how large your final bill turns out to be. If your prior year adjusted gross income exceeded $150,000, that threshold bumps up to 110%. You can also satisfy safe harbor by paying at least 90% of your current year’s tax liability.
This matters because it changes how you should think about estimated payments. You're not necessarily trying to predict exactly what you'll owe. You're trying to make sure you've met the safe harbor threshold so that the penalty question is off the table. Once you've done that, any remaining balance due in April is just a balance due, not a penalty situation.
Once you understand safe harbor, there's a separate question worth thinking about: how much do you actually want to pay throughout the year beyond the minimum required to avoid penalties?
There are two reasonable camps here. The first pays just enough to satisfy safe harbor and settles up with the government at tax time. This means potentially larger April bills, but you hold onto your cash throughout the year. The second pays more aggressively throughout the year so that tax season is a non-event. Smaller bills in April, or even refunds, but less cash on hand during the year. Neither is wrong. They reflect different preferences around cash flow and how much you enjoy writing large checks in April. Worth noting that the second camp requires a little more active management throughout the year — you're looking at actual results as they develop rather than just relying on safe harbor calculations as a baseline. The important thing is knowing which camp you're in and making sure your payments actually reflect that intention rather than just defaulting to whatever you did last year.
A few things worth checking before June 15th: do you know what your 2025 total tax liability was? That number is on your return, and it's your baseline for calculating safe harbor. Are your 2026 payments on track relative to that number? If your income has changed significantly, are you adjusting accordingly, or are you on autopilot from last year's vouchers?
If you miss the June 15th deadline, it's not the end of the world. You're not going to tax jail. The IRS will assess some interest on the underpayment, but the amounts are generally modest. Pay what you can when you can, and get back on track for Q3. Chronic underpayment throughout the year adds up, but a missed quarter is a minor inconvenience, not a crisis.
If you're unsure where you stand, this is worth a quick conversation before the deadline rather than after.
Mark Your Calendar
June 15th: Q2 estimated tax payments are due. Q2 covers April 1 through May 31.
September 15th: Extended S-corp and partnership returns are due, along with Q3 estimated tax payments.
October 15th: Extended individual returns are due. If we filed an extension on your behalf, this is your real deadline. It feels far away. It will not feel far away in September.
Maine Wildlife Facts
Will has appointed himself the official defender of our bird feeder. Squirrels, dogs, and several very confused turkeys have all been firmly redirected away from the feeders this spring. He takes the role seriously. The birds, for their part, seem largely unaware that they have a dedicated security detail.
The current favorites at our feeders are the American goldfinches, which Will has been watching closely. He noticed a few weeks ago that they look completely different than they did in the winter, which led to a research session that the rest of the naturalist team participated in with varying degrees of enthusiasm.
Male goldfinches go through one of the more dramatic seasonal color changes of any common feeder bird. In winter, they're a dull olive-yellow, easy to overlook. By late spring, the males have molted into their breeding plumage: bright lemon yellow with sharp black wings and a black cap. Right now, in early June, they're at peak color. Will has strong opinions about which birds at the feeder are the best looking, and the goldfinch is currently at the top of that list.
Goldfinches are among the strictest vegetarians of any North American bird, eating almost exclusively seeds. This is part of why they're such reliable feeder visitors and also why they nest later than almost any other songbird in Maine, often waiting until late June or July when thistle and other seed plants are producing. They actually use thistle fibers to line their nests, timing reproduction around plant availability in a way that most birds don't.
One detail that got the whole team's attention: goldfinches are sometimes targeted by brown-headed cowbirds, which lay eggs in other birds' nests and let the host raise their chicks. The goldfinch diet is so seed-heavy, though, that cowbird chicks typically don't survive it. Frank found this grim justice satisfying.
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.