THE MOST PAINFUL CONVERSATION I HAVE WITH POTENTIAL CLIENTS
"If we had talked last November, you would have saved $50,000. But here we are in February..."
It's brutal because the money is gone. The deadline passed. The opportunities expired on December 31st.
Everyone thinks tax planning happens in December, but the smart moves need to start NOW, in early November, while there's still time to execute.
Here are the five year-end strategies that separate the people who pay what they owe from the people who overpay by tens of thousands.
1. Entity Structure
This is the foundation of everything else, and fixing it creates permanent savings.
I just met with a solo consultant making $400,000 a year who had no entity and no planning, just writing checks to the IRS every quarter.
We restructured him and he's saving $32,000 annually. FOREVER.
But here's the catch: you can't retroactively change your entity structure. If you're in the wrong setup now, you're stuck with it for 2025. We can only fix it going forward.
2. Salary Optimization
An S-Corp isn't magic, but it creates massive opportunities if you pay yourself correctly.
Without planning, you could overpay self-employment tax, miss out on maximizing the Qualified Business Income deduction, and leave retirement contribution opportunities on the table.
The problem? Your salary has to be set and paid by December 31st. Get it wrong now, and we can adjust for next year, but 2025's savings opportunity is lost forever.
Calculate your potential S-Corp savings here to see what's at stake.
3. Retirement Planning
Everyone talks about asset diversification. Nobody talks about asset location.
The right mix of taxable accounts, tax-free accounts like Roth IRAs, and deferred accounts like 401(k)s can make or cost you millions over your lifetime.
Rule of thumb: save in a Roth at 24% effective rate. Think about deferring at 32% and above.
Getting this right lets you control your tax rate in the future and save a bundle while you work. Your heirs will thank you too — SECURE 2.0 killed the stretch IRA, so they'll pay tax on your full deferred balance within 10 years of inheritance.
4. Quarterly Estimates
Most folks don't realize that W-2 income takes taxes out every check, but 1099 and business income means YOU handle the taxes.
The IRS wants their money quarterly. They charge 8% interest plus penalties when you don't pay.
I see this all the time, business owners having a great year, paying zero estimates, then getting hit with a massive tax bill plus penalties in April. Sometimes we're talking $200,000+ owed with over $10,000 in penalties on top.
The fix is simple: monthly financial review and reserving 25-35% of profit. Stay ahead instead of scrambling in April.
5. Better Bookkeeping
I know. Bookkeeping doesn't sound like a tax strategy.
But your bad books are costing you more than you think.
I can't tell you how many times people say, "I have so many deductions, but they're all over the place. I'll just avoid taking them so I don't get audited."
This is a terrible idea and a foolish way to waste your money.
When I reviewed one client's DIY books, I found personal expenses mixed in, missing vehicle deductions, ignored home office deductions, and no tracking of business travel.
We found $34,000 in missed deductions.
Clean books let you keep score and push all the tax levers to dial in real savings. It's not about perfection. It's about keeping money in your pocket.
November Is Your Last Realistic Shot
Tax planning isn't a December sport. It's year-round discipline that pays off big.
But if you haven't been thinking about it all year, November is your last chance to get ahead of it. December is too chaotic. January means it's too late.
The difference between acting now and waiting until February is thousands of dollars. Sometimes tens of thousands.
Book a call with Better Bookkeeping and let's make sure you're not the person I'm having that painful conversation with in February.
We'll review your situation, identify what you can still do before December 31st, and make sure you're paying exactly what you need to, not a dollar more, not a dollar less.