September 15 and October 15 are the two extension deadlines that bookend the fall. If those are the only times you hear from your accountant, that’s a problem.
Most business owners and executives we meet think they’re paying too much in taxes because they need a better accountant. Usually, what they actually need is a planner, not just a preparer. A preparer looks backward and reports what already happened. A planner works with you before December 31, while there are still decisions to make.
Same profession, very different relationship.
Most of the moves that shape your tax bill have to happen before year-end. Once the calendar flips, your CPA can report what happened, but they can’t change it. That’s why we say the same thing every year: friends don’t let friends wait until February to find a CPA.
This year there’s one more reason to say it now. We have room for 10 new clients before the 2027 tax season. Once those are filled, new clients go on a waitlist.
Why February Is Too Late
February feels responsible. Your W-2s and 1099s have arrived, you send everything over, and you’re ahead of the April rush. Then the number comes back, and there’s nothing left to do but pay it.
That’s because by February, the year you’re filing for has been closed for more than a month. The decisions that move the number were available in October: income, investments, purchases, entity structure, retirement plans, real estate. By then, most of those windows have shut.
We wrote about this in more depth earlier this year, including two client examples where timing made a six-figure difference. The short version: the earlier your CPA knows what’s happening, the more they can do about it.
What’s Still on the Table Before December 31
Not all of these will apply to you. But if any of them sound like your year, now is the time to talk about it.
- A big income year. A bonus, a business sale, a banner commission year. When income spikes, timing matters: pushing some income into next year, or pulling deductions into this one, can change how much gets taxed at your highest rate.
- Selling an asset. Real estate, a business interest, or appreciated stock. How and when you exit affects what you owe, including depreciation recapture on real estate.
- Owning a business. Owner pay, retirement plan contributions, and equipment purchases all come with year-end timing.
- Charitable giving. Giving appreciated assets, or bunching several years of gifts into one, can change your tax picture.
- Roth conversions. A lower-income year can open a window that closes on December 31.
- Estimated taxes. A fourth-quarter check-in helps you avoid an underpayment surprise in April.
For more detail on the business side, Cooper Westbrook’s year-end tactics for business owners and partners goes deeper.
Why We Cap New Clients
Planning-first work takes time, and our current clients are counting on it. We work with business owners and executives on tax planning, accounting, and wealth management, with the idea that those things should work together. So every new relationship starts with discovery conversations* and a real look at the whole picture. We’d rather do that well for a limited number of people than squeeze everyone in before April.
(* Or “disco calls” as we call them. Our Chief Relationship Officer, Katie, is still sourcing a sparkly ball to hang in her office.)
That also means we’re selective about fit. One of these spots is likely a good match if:
- You own a business, work in commercial real estate, are a partner or top executive in your field, or have a financial life with several moving parts
- You want someone looking ahead with you during the year, not only filing in the spring
- You’re open to your tax, accounting, and investment decisions being made together
We’re probably not the right fit if you’re mainly looking for the lowest price on a return, you’d prefer advice from several separate professionals, or you’d rather hear from your CPA once a year. All of those are reasonable choices. They’re just not how we work.
You Probably Know Someone
This is the part where we ask for your help.
Think about the people in your life who fit one of these:
- They only hear from their accountant between February and April
- They got a tax bill last spring that caught them off guard
- They started a business, sold a property, or had a big income year in 2026
- They say “I should really get someone to look at this” every October, and then don’t
- Their CPA and their financial advisor have never talked to each other
That last one is easy to miss. When tax and investment decisions get made in separate offices, it’s easy for no one to check whether they work together. (We call that the hidden coordination tax.) At Tannery Company, CPAs and wealth advisors work under one roof, so those conversations happen while there’s still time to act on them.
Send them this post. A forward in the fall is worth a lot more to them than a referral in March.
What Starting Now Looks Like
When you start in the fall, the work happens while it can still make a difference. By the time your documents come in next spring, the plan is already built, and filing is just the last step.
If you’d like one of those 10 spots, schedule a discovery call. The first conversation is about whether we’re a fit, for you and for us.
Consider this your friend telling you not to wait until February.
