Thursday Deep Dive: Tax Moves Before Year-End

Thursday is my strategy day, and in Q4 that means taxes. I pull the year-to-date ledger, categorize any transactions the bookkeeper flagged, and line them up against the tax projection spreadsheet. The goal is to understand the story before the CPA meeting, not during it.

Tax-loss harvesting is the headline move, but I start with the basics. Are estimated payments on track? Have I maxed employer plans, HSAs, and the solo 401(k)? Are charitable contributions batched to hit standard deduction thresholds? The boring checklist usually delivers more savings than the exotic strategy.

Once the fundamentals are handled, I look at timing. Can I accelerate deductions or defer income without hurting cash flow? Do I have credits expiring? Thursday is the sweet spot for scheduling calls with advisors because everyone is still in work mode and the week has context.

Documentation is my secret weapon. Every note of intent, every receipt, every explanation of why a position was harvested goes into the tax folder. When questions pop up in April, future me can answer them in seconds.

If you are new to proactive tax planning, build a shared spreadsheet with your accountant. Drop Thursday observations there, tag open questions, and keep a running tally of action items. You’ll arrive at year-end with less dread and more clarity.