by Krista Wallace, CFP®, AFC®
It’s spooky season again – no, I don’t mean the ghosts and goblins coming to your doorstep. I mean fourth quarter tax planning time.
While tax planning may not be everyone’s idea of a good time, your advisor is looking forward to a lively and decidedly less spooky conversation with you this fall.
Many taxpayers are “spooked” by taxes. The forms to collect, the records to organize, and the seemingly endless tax terminology can make the whole process feel mysterious. In fact, the confusion surrounding taxes has been comedic fodder for television for decades - from Seinfeld to Schitt’s Creek:
From Seinfeld, Season 8, Episode 5
Jerry: Write it off what?
Kramer: Jerry, all these big companies, they write off everything.
Jerry: You don’t even know what a write-off is.
Kramer: Do you?
Jerry: No, I don’t.
Kramer: But they do, and they are the ones writing it off.
From Schitt’s Creek, Season 2, Episode 6
Johnny Rose: That’s a write-off? Do you even know what a write-off is?
David Rose: Uh, yeah. It’s when you buy something for your business and the government pays you back for it.
Johnny Rose: Oh. And who pays for it?
David Rose: Nobody. You write it off.
Johnny Rose: WHO writes it off?
David Rose: I don’t know, the gov—the “write-off” people! Why are we having this conversation?
From Spooky to Smooth
Whether you’re part of the Seinfeld era or the Schitt’s Creek era, the good news is that tax planning doesn’t have to be scary.
Here’s a few ways to shift your mindset around tax season and move from spooky to SMOOTH this fall:
Start now. Begin tracking expenses and other items that may affect your tax situation. Review your 2025 tax return with your advisor so you understand the adjustments, deductions, and credits that applied to you. Your prior-year return can serve as a useful roadmap for identifying opportunities and questions for 2026.
Make a list. Write down questions, unusual expenses, or significant financial events you have encountered during the year. You do not need to know whether something is tax-related before asking about it. That is what your advisor is there to help determine.
Optimize your records. Choose one place for tax-related forms and documents. It can be as simple as a tray or folder in your office. Once everything has arrived, consider scanning the documents and saving them together in one clearly labeled digital file. Future you will be grateful.
Organize key deductions. Keep an ongoing record of charitable donations, home improvements, medical expenses, business-related costs, or other potentially significant items. Your pharmacy and healthcare providers may be able to provide annual summaries of out-of-pocket expenses. Qualified charitable distributions should also be tracked separately because they may not be clearly identified on form 1099-R from your IRA.
Think forward. Tax planning is not only about what happened this year. Consider whether you expect a major purchase, charitable gift, business transaction, retirement, or other financial event. Looking ahead may create opportunities to coordinate income, deductions, charitable giving, and other decisions more effectively.
Create a Habit. Make tax planning part of your annual financial routine. Reviewing your year-end paystub can help you determine whether you are fully using retirement plan contributions, Health Savings Accounts, and other employee benefits. Pairing that review with open enrollment can also lead to more intentional benefit decisions.
Let’s Make Tax Planning Less Spooky
You don’t need to become a tax expert OR learn what a “write-off” actually is to make thoughtful tax decisions.
Start. Make a list. Optimize. Organize. Think forward. Create a Habit.
A little planning now can make tax season feel a lot less mysterious later.