Hello Marathoners-
There’s something about fall that always invites a moment to pause and take stock — and this season, we have plenty to be thankful for. Our journey to full independence is now complete, and while the path took a lot of energy and planning, the result has been incredibly rewarding. We’re running strong, feeling energized, and most importantly, grateful for the trust you’ve placed in us through it all.
Making the leap to stand-alone independence has been both a professional milestone and a personal one. It’s given us the freedom to operate fully on our own terms — to build the kind of client experience, technology, and investment flexibility we’ve always envisioned. And seeing how smoothly the transition went only reinforces how strong our foundation truly is, thanks to you.
I’m also excited to share that in light of our Rhode Island clientele growing so rapidly in recent years, we are in the early stages of due diligence on making RI/Providence a formal ‘outpost’ for Marathon Financial Group. More to come on that soon.
As we settle into this next chapter, our focus remains the same: providing thoughtful guidance, clear communication, and a steady hand through whatever markets bring next. And as fall turns to year-end, it’s also a natural time to revisit your financial plan — to make sure everything from tax strategies to charitable giving and cash flow are aligned heading into 2026. Small adjustments now can make a meaningful difference later, and we’re here to help you think through the best moves for your situation.
On Wednesday, we sent out an email invitation to our Year-End Investment Webinar “Marathon Mindset 2025”. This will be led by our Director of Investments, Michael Neill and conducted on Wednesday, November 5th, 4-5pm ET, via Zoom. All are welcome to attend, even if not clients, so feel free to share the invite with someone you know who might be interested in getting some perspective on markets right now.
Following the webinar, we will begin to send out year-end portfolio performance reporting (which will include YTD portfolio income & capital gains) along with market commentary and a linked recording of the webinar. Meeting windows will also be available beginning mid-November to discuss any topics further, or go through the reports deeper.
In addition, Connor and I will be checking in on any outstanding action items for 2025 financial planning, to help ensure that these items are addressed by year-end (or the 2025 tax deadline in April 2026, if applicable).
💡 A Quick Q4 Check Worth Doing
More on strategic financial planning considerations & to-do’s will be coming soon, but one area worth a quick check right now is your tax withholdings. Taking a few minutes to review how much has been withheld so far this year can help avoid any unpleasant surprises come tax time. The IRS’s online withholding estimator is a great place to start — it can help you estimate whether you’re on track or if you might owe more (or be due a refund) come filing time. You’ll just need your most recent pay stub and last year’s tax return to plug in some numbers.
If you find that your current withholdings are a little light, there’s still time to fix it. You can adjust your W-4 through your employer, or — if you’re self-employed or have investment income — make an additional estimated payment before year-end. Catching it now can help you avoid penalties later, and it’s one less surprise to deal with next spring.
As always, we’re here to help if you’d like to walk through your specific situation. A quick conversation and a few calculations can make sure everything lines up with your broader plan for the year — especially if you’ve had job or income changes, adjusted retirement contributions, exercised stock options, or realized larger investment gains.
💵 Payroll Withholding vs. Quarterly Payments: Why One Usually Wins
When it comes to paying income taxes, you generally have two paths: you can either have taxes withheld automatically from your paycheck, or send in quarterly estimated payments yourself. Both get the job done — but in most cases, it’s better to pay through payroll withholding if you can.
Here’s why:
- The IRS likes steady payments.
The tax system is “pay-as-you-go,” which means the IRS expects taxes to be paid throughout the year, not just at filing time. When taxes are withheld from your paycheck, those payments are considered evenly spread over the year — even if most of them happen later on. That gives you a built-in cushion if you’re playing catch-up. - Less hassle, fewer surprises.
Payroll withholding is automatic, so you don’t have to remember quarterly deadlines or worry about mailing payments (or logging in to IRS.gov four times a year). For many people, that convenience alone reduces the odds of underpayment penalties or missed payments. - Penalty protection.
If you find you’re underwithheld late in the year, bumping up your payroll withholding can help you avoid IRS penalties — because those withholdings are treated as if they were made evenly throughout the year. By contrast, estimated tax payments are timestamped to when they’re actually made, so missing or shorting an earlier quarter can still trigger interest or penalties. - Cash flow consistency.
Withholding smooths out your cash flow — smaller, steady payments instead of four big quarterly checks. That can make budgeting easier and reduce the temptation to “borrow” from funds earmarked for taxes.
That said, quarterly estimated payments still make sense for folks with income that isn’t subject to withholding — like business owners, freelancers, or those with large investment or rental income. But if you have access to payroll, it’s usually the cleaner, safer, and simpler route.
🧾 How the 2025 Tax Law Shift Is Already Affecting You
You may have heard chatter about the “One Big Beautiful Bill” (OBBB) that passed in July 2025 — and yes, it brings a handful of changes that are relevant this year. That said, there’s a bit of nuance in how those changes interact with withholding, reporting, and your tax bill.
First off, it’s worth noting that the IRS declared there will be no changes to the 2025 withholding tables or key payroll forms under the new law, at least for now. That means your employer should continue following the same withholding rules in place prior to OBBB — which helps avoid mid-year chaos. But just because withholding hasn’t changed doesn’t mean your tax picture can’t shift.
Here are some of the most important provisions from OBBB that can influence what you owe — even if your withholding number stayed the same:
- SALT Deduction Cap Boost – From January 1, 2025 through 2029, the state and local tax (SALT) deduction cap is raised to $40,000 (or $20,000 if married filing separately) for many taxpayers.
- Permanent Extension of Tax Cuts / Brackets – The individual rate structure from the 2017 Tax Cuts and Jobs Act (TCJA) — which was scheduled to expire — is now made permanent under OBBB.
- Standard Deduction & Inflation Adjustments – The IRS also made inflation-based adjustments for 2025: for example, the standard deduction is higher.
- Other Phase-In Provisions – Some changes — like how tips or overtime pay are reported, and other related forms — will roll out more fully in 2026, so there’s still room for adjustments.
Because of these tweaks, even if your income, deductions, or filing status haven’t changed, your tax liability might shift subtly.
As we all know, there are lots of important numbers to keep in mind when it comes to strategic financial and tax planning. In the case of 2025 and 2026, a lot of these figures (annual limits, etc.) are changing. In response to this challenge, we’ve updated the two-page ‘Important Numbers (2025)’ summary guide. This quick reference guide covers the most important annual limits as well as figures that are commonly referred to during the year. While I’m at it, here are a few more related guides around taxes and year-end planning considerations in general:
End Of The Year Planning Issues (2025)
🔍 WSJ Insights: How Scammers Are Leveling Up (and What You Need to Know)
According to recent Wall Street Journal reporting, scammers are increasingly using AI to craft messages, impersonate voices, and build fake websites that look nearly indistinguishable from the real ones. One popular trick: creating clone sites that replicate familiar brands so perfectly that victims don’t realize anything’s off until they’ve entered their sensitive info.
Meanwhile, fraudsters are still using older—but effective—techniques like manipulating paper checks and deploying clever crypto scams.
Key Trends
- AI-powered deception is rising fast
Scammers are using generative AI to craft highly realistic emails, texts, and even voice calls. These tools help them mimic tone, vocabulary, and conversational nuance — making the scams harder to spot. WSJ - Fake websites that look exactly like the real deal
Criminals are cloning trusted brands (logos, product images, web layouts) to lure people into entering their credit-card or login credentials. The site seems legitimate until it’s too late. WSJ - Social media as scam launchpad
Platforms like Instagram and Facebook are being used to spread fake ads (e.g. “puppies for sale,” deep-discount deals) backed by overseas crime networks. WSJ - Old-school tactics are still alive
Altered paper checks are making a comeback in some circles — scammers deposit or manipulate checks and withdraw funds before banks flag the transactions. WSJ - Crypto and digital-asset fraud is evolving
With digital wealth rising, scammers are deploying new schemes targeting crypto investors — phishing, bogus token offerings, fake wallets, etc. Some even use AI to make their pitch more convincing. WSJ
How To Avoid Getting Scammed As A Busy Professional
Scam tactics evolve all the time, so vigilance is key. New tools may change the tactics, but the red flags often stay the same. If anything in your inbox, mail, or calls feels off — you’re not overreacting, you’re being smart. And as always, if you want us to help vet something, give me a shout — we’ve got your back.
🧐 WSJ “The Intelligent Investor: Why Do Smart People Do Stupid Things With Their Money?
In a recent Wall Street Journal column, behavioral economists Richard Thaler and Alex Imas reminded us that even the savviest investors fall prey to emotional decision making. For some background, Thaler won a Nobel prize in economics in 2017 for his research into the limits of rationality and self-control. In 1992 he published the classic book The Winner’s Curse. Thaler and Imas worked together to update the book, and new edition comes out October 21st.
They pointed out how easy it is to chase yield, mistreat losses, and overtrade — especially in today’s app-driven, hyper-connected investing environment.
Here’s a snippet:
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These insights reinforce why we prioritize disciplined, rules-based approaches for you: setting withdrawal strategies separate from yield hunting, avoiding overtrading, and relying on structured portfolio design. Your capital shouldn’t be hostage to our worst impulses.
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It’s Not Your Retirement Savings—It’s You
The Psychology of Retirement Income: From Saving to Spending
7 Steps to Estimating Your In-Retirement Cash Flow Needs
A Checklist for Open Enrollment Season
The Hidden Costs of Passive Investing
Can You Control Required Minimum Distributions?
Why Convert To A Roth IRA Now?
Why Mortgage Rates Might Not Keep Going Down
Markets Have Soared—What’s Next?
What We’ve Learned from 150 Years of Stock Market Crashes
Have a great weekend,
Charlie