Tax Planning Calendar for High Earners (What to Do and When)
Most high earners treat taxes like a yearly event.
They hand everything to a CPA in March, sign in April, and move on.
Thats tax preparation.
Tax strategy is different. Its a year-round operating systemespecially if your income is variable, your compensation includes equity, or youre building wealth across multiple accounts and entities.
This is a practical, client-education calendar you can use to stay aheadwithout turning your life into a spreadsheet.
The mindset shift: taxes are a subscription, not a surprise
If you earn a high income, your tax bill isn’t a one-time expense.
Its a recurring cost of doing business with the IRS.
The goal of planning isnt to avoid taxes. It’s to:
reduce avoidable mistakes,
improve timing,
coordinate decisions (equity, charitable giving, retirement plans, business income), and
avoid April panic.
Your year-round tax planning calendar
January: set the baseline (and stop guessing)
January is where good tax years start.
Gather last years W-2/1099/K-1 expectations (even rough)
Estimate your effective tax rate and expected total tax liability
Confirm your withholding strategy (W-2) and/or quarterly estimates (1099/business)
If you have equity comp: map vesting dates and expected income impact
Simple rule: if you can’t explain where your income is coming from this year, youre not planningyoure hoping.
February: coordinate your team before the year gets busy
High earners often have multiple professionalsCPA, advisor, attorneybut no quarterback.
Confirm who is responsible for projections
Confirm who is tracking equity comp and withholding
Confirm which accounts/entities matter (brokerage, trusts, business, donor-advised fund)
This is also the month to clean up admin:
update payroll settings (if you own a business)
confirm retirement plan contribution options
verify your prior-year tax return status and any carryforwards
March: run a real projection (not a vibe)
March is when you want a first-pass projection for the current year.
Update income assumptions (bonus expectations, commissions, RSUs, options, business profit)
Identify likely spikes (liquidity events, large vest, property sale)
Decide whether to adjust withholding or estimates now
Key idea: the earlier you identify a high-income year, the more levers you have.
April: filebut dont stop planning
Most people treat April 15 as the finish line.
It’s not. Its feedback.
Review the return for patterns: where did the tax bill really come from?
Confirm safe harbor rules and estimated tax requirements for this year
If you owe: fix the system (withholding/estimates) so it doesnt repeat
May: equity comp + concentration risk month
If youre a high earner with equity comp, May is a great time to get proactive.
Review RSU vest schedule and tax withholding assumptions
If you have options: revisit exercise strategy and AMT exposure
If youre concentrated in employer stock: coordinate tax planning with diversification planning
Common mistake: treating equity decisions as investing decisions only. They’re tax decisions too.
June: mid-year check-in (the highest ROI meeting youre not having)
Mid-year is where you can still change outcomes.
Re-run your projection with actual YTD income
Adjust W-2 withholding or quarterly estimates
Confirm retirement plan contributions are on track
Identify charitable giving opportunities (especially appreciated stock)
If you wait until November, your options shrink.
July: business ownerstighten the entity and payroll strategy
If you have pass-through income, July is a good time to pressure-test structure.
Review S-corp payroll vs distributions (if applicable)
Confirm bookkeeping quality (garbage in, garbage out)
Identify deductible business expenses and timing opportunities
This is also a good month to review state tax exposure if you travel or live in multiple states.
August: plan for big events (before they happen)
August is when you want to get ahead of the fall:
expected bonus / commission season
year-end equity vesting
potential liquidity events
large charitable gifts
If something big might happen in Q4, August is when you build the plan.
September: charitable strategy + capital gains planning
September is ideal for planning gifts and gains because you still have runway.
Decide whether you’re giving cash, appreciated stock, or using a donor-advised fund
Review capital gains exposure and tax-loss harvesting opportunities
If you have concentrated positions: coordinate sales with tax planning
October: benefits and retirement plan optimization
October is where high earners can optimize the boring stuff that adds up.
Maximize retirement plan contributions (401(k), cash balance plan if applicable)
Review HSA/FSA elections (if relevant)
Confirm any backdoor Roth / mega backdoor mechanics with your CPA/advisor
November: the last real month for tax moves
By November, you need to execute.
Harvest losses (if appropriate) and manage wash sale rules
Finalize charitable gifts (especially appreciated securities)
Review year-end bonuses/vesting and adjust withholding
If youre a business owner: finalize expense timing and retirement plan funding
December: close the loop and document decisions
December is about clean execution and clean records.
Confirm all gifts are completed and receipted
Confirm estimated taxes and withholding are accurate
Document equity decisions (exercises, sales, 83(b) filings if applicable)
Create a one-page summary of what changed this year (so next year is easier)
The 5 levers high earners actually control
Most tax planning comes down to five levers:
Timing of income (when you recognize it)
Timing of deductions (when you take them)
Character of income (ordinary vs capital gains)
Location (state residency and sourcing)
Coordination (equity, investing, giving, retirement, business structure)
You dont need 50 tactics.
You need a system that touches these levers consistently.
Bottom line
If youre a high earner, the biggest tax risk isn’t paying taxes.
It’s paying avoidable taxes because your planning is reactive.
Use this calendar as a simple operating system: one projection early, one mid-year check-in, and one Q4 execution window.
If you’d like, we can build a one-page tax planning dashboard that ties together your income sources (W-2, equity comp, business, investments), your estimated payments/withholding, and the 2-3 decisions that actually move the needleso tax season becomes routine instead of stressful.
