After 40 years as a CPA, I've reduced tax planning to three questions.
Answer these, and your tax strategy writes itself.
𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧 𝟏: 𝐇𝐨𝐰 𝐝𝐨 𝐲𝐨𝐮 𝐦𝐚𝐤𝐞 𝐲𝐨𝐮𝐫 𝐦𝐨𝐧𝐞𝐲?
→ W-2 income? Highest tax, fewest deductions.
→ Business income? High tax, lots of deductions.
→ Investment income? Lower rates, different strategies.
→ Real estate income? Depreciation shields, passive income treatment.
Your income source determines which strategies apply to you.
You can't use business deductions on W-2 income.
You can't use passive loss rules on business income.
Know your income type.
𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧 𝟐: 𝐖𝐡𝐚𝐭 𝐰𝐢𝐥𝐥 𝐲𝐨𝐮 𝐝𝐨 𝐰𝐢𝐭𝐡 𝐲𝐨𝐮𝐫 𝐦𝐨𝐧𝐞𝐲?
→ Save it? Use retirement accounts for tax deferral.
→ Invest it? Choose investments with tax incentives.
→ Spend it? At least get business deductions on spending.
→ Give it away? Use charitable strategies for maximum deduction.
The wealthy don't just make money. They deploy money strategically.
Deployment determines tax treatment.
𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧 𝟑: 𝐖𝐡𝐞𝐧 𝐰𝐢𝐥𝐥 𝐲𝐨𝐮 𝐮𝐬𝐞 𝐲𝐨𝐮𝐫 𝐦𝐨𝐧𝐞𝐲?
→ This year? Accelerate deductions, defer income.
→ Next year? Defer deductions, accelerate income (if rates are dropping).
→ Retirement? Use tax-deferred or tax-free accounts.
→ Never (leaving to kids)? Estate planning and basis step-up strategies.
Timing is everything in tax planning.
Real example:
𝐁𝐮𝐬𝐢𝐧𝐞𝐬𝐬 𝐨𝐰𝐧𝐞𝐫 𝐚𝐧𝐬𝐰𝐞𝐫𝐬...
👉 How: Business income ($500K/year)
👉 What: Invest in real estate
👉 When: Build wealth for 20 years, then transition to passive income
Strategy that follows automatically:
→ S-Corp election (reduce self-employment tax)
→ Cost segregation on properties (accelerate depreciation)
→ Real estate professional status (convert passive to active losses)
→ Defined benefit plan (defer income to retirement)
Same three questions, different answers...
𝐖-𝟐 𝐞𝐦𝐩𝐥𝐨𝐲𝐞𝐞 𝐚𝐧𝐬𝐰𝐞𝐫𝐬...
👉 How: W-2 income ($200K/year)
👉 What: Max out retirement, save for kids' college
👉 When: Retire in 15 years
Strategy that follows:
→ Max 401(k) and HSA (only available deductions)
→ 529 plans for kids (state tax deduction tax-free growth)
→ Tax-loss harvesting in taxable accounts (reduce cap gains)
→ Roth conversions in low-income years
Different questions. Different answers. Different strategies.
Most people fail at tax planning because they skip the questions.
They jump straight to tactics:
🤔 "Should I have an LLC?"
🤔 "Should I buy equipment?"
🤔 "Should I do a Roth conversion?"
Wrong approach.
Answer the three questions first.
Then the strategies become obvious.
Tax planning isn't complicated.
It's just systematic.
How do you make it?
What will you do with it?
When will you use it?
Answer those three questions, and I'll cut your tax bill in half.