Planning Season and Wild Turkeys
In this edition of the Flying Point Update, we're going to talk about the shift from tax season into planning season, why tax and financial planning are more connected than most people think, and a mid-year financial review checklist to work through while your 2025 numbers are still fresh. We'll also revisit a Perna family favorite: wild turkeys.
Top of Mind
Tax season ends and something interesting happens. The questions change.
For the past few months, the conversations in my office have been backward-looking by nature. What did you earn? What did you spend? What do you owe? These are important questions, but they're fundamentally about documenting the past. There's not much we can do to change 2025 at this point.
But now, almost on cue, a different kind of conversation is starting. Clients are asking things like: am I saving enough? Is my business structured the right way? Am I going to be okay? These are bigger, more nebulous questions, and they don't have clean answers the way a tax return does. There's no line on a form for "are you on track."
What I find interesting is how often people think of tax planning and financial planning as two separate disciplines. You do your taxes in the spring, you do your financial planning... sometime. In practice, the two are deeply connected, and the decisions you make in one area almost always affect the other.
A solo 401(k) is a good example. It sounds like a tax question, but it's actually four or five questions layered on top of each other. How do I set one up? What's the actual tax benefit? How much should I contribute? Where does that money get invested? Should contributions be Roth or traditional? Each of those questions touches both tax and planning, and the right answer to any one of them depends on the others. You can't really answer "how much should I contribute" without thinking about your cash flow, your other retirement assets, your income trajectory, and your tax bracket now versus in retirement.
This is what planning season looks like from where I sit. Good answers to the big questions almost always have tax implications. And good tax advice almost always has planning implications. The line between the two was never as clear as it seemed.
Worth Knowing
With your 2025 return either filed or extended, now is actually a great time to do a quick financial review while the numbers are still fresh. Not a comprehensive overhaul, just a few things that are easy to overlook and worth a few minutes of attention.
Review your withholding and estimated taxes. You now have a complete picture of what you owed for 2025. If April was unpleasant, the fix starts here. Pull up your W-4 and run it through the IRS withholding estimator, or take a look at whether your estimated payment schedule reflects what 2026 is actually shaping up to look like. This is the least exciting item on this list and probably the most impactful.
Check your retirement contribution levels. Are you contributing as much as makes sense given your income and goals? Are those contributions going into the right bucket? The Roth versus traditional question is worth revisiting periodically rather than leaving it on autopilot. The answer can change as your income changes, your tax bracket shifts, or your retirement timeline comes into focus. If you set up your contribution elections a few years ago and haven't looked since, now's a good time to look.
While you’re reviewing contributions, take a minute to revisit your beneficiary designations. This one gets neglected almost universally. Your 401(k), IRA, and life insurance policies all pass outside of your will, which means the beneficiary designations on file control where that money goes regardless of what your estate documents say. Life changes. Make sure the designations reflect your current intentions.
Take stock of your insurance coverage. Disability insurance in particular tends to be underowned, especially among self-employed people and business owners. If your income has grown since you last looked at your coverage, your policy limits may not reflect what you'd actually need. Same goes for life insurance if your family situation has changed.
Look at your business structure with fresh 2025 numbers. Now that the year is closed, you have real data to work with. If you've been wondering whether your current structure still makes sense, whether that's a sole proprietorship, single member LLC, or S-corp, the time to have that conversation is before another year is underway. As I covered in S-corps and Largemouth Bass back in January, the math matters more than the general advice you'll hear at a networking event.
None of these require a major commitment of time or money. Most of them just require pausing long enough to actually look. Also, do it before summer starts in earnest. Nobody ever wants to deal with these things during the summer, and then before you know it, we’re already facing the holidays. If anything on this list surfaces a question, that's what I'm here for.
Mark Your Calendar
June 15th: Q2 estimated tax payments are due. Q2 covers April 1 through May 31, with the payment due in mid-June. If you're making quarterly payments, don't let the quiet summer stretch get away from you on this one.
September 15th: Extended S-corp and partnership returns are due.
October 15th: Extended individual returns are due. If we filed an extension on your behalf, this is your real deadline. It feels far away right now. It will not feel far away in September.
Maine Wildlife Facts
We wrote about wild turkeys in the very first issue of the Flying Point Update, Summer Camp and Turkeys, back in June of last year, where we learned that they can fly at up to 55 mph. Will insisted on turkeys then, and Will is insisting on turkeys now. The only thing Will likes more than turkeys is chasing turkeys.
While Thanksgiving may feel like a good time to talk about turkeys, May is actually a much better fit, from a naturalist’s perspective. Right now, the woods are genuinely alive with them. Turkey mating season runs through April and May in New England, and the activity this time of year is something else entirely. Toms spend the winter in bachelor groups, largely separate from hens, but as the days get longer and testosterone levels rise, that arrangement falls apart quickly. Toms start gobbling from their roosts at dawn, advertising their location to any nearby hens. Gobbling is long-range communication. Once a tom gets close to a hen, the gobbling gives way to strutting, which involves puffed plumage, a fanned tail, and a dragging of the wingtips along the ground. It is, by any measure, a lot.
Jakes, which are immature male turkeys in their first year, also gobble and strut, but they're mostly just making noise. Actual breeding is typically handled by the mature toms. Jakes are essentially the younger siblings showing up to a situation they don't fully understand yet.
Will has accumulated a collection of turkey calls over the years, including a gobble call, a hen call, a crow call, and an owl call. Each call produces a different sound that turkeys respond to differently. Just the other evening, he was in the backyard with his gobble call, going back and forth with a tom hidden somewhere in the woods about a hundred yards out. Will was absolutely thrilled that he could make the tom gobble almost on command. The tom, presumably, was very confused and increasingly frustrated.
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.