Tax Season Timeline: Key Investing Moves Doctors Should Make Each Quarter

You’re in late January. Clinic’s already slammed, your inbox is a mess, and a 1099 just popped up in your email while you were between consults. You know tax season is coming, you know you “should be doing more” with investing and deductions, but everything feels last‑minute and reactive.

This is where you stop playing defense.

You get one tax year. Twelve months. The IRS doesn’t care that you’re Q4 busy, post‑call, or in the OR. The only way to stop overpaying in taxes and underfunding your future is to treat the year like four deliberate quarters, with specific moves in each one.

I’ll walk you through it chronologically: Q1 through Q4, with “at this point in the year, you should…” style checkpoints. Assume you’re a typical attending or senior resident: W‑2 income, maybe some 1099 side work, a retirement plan at work, student loans lurking in the background.

---

Big Picture: Your Year At a Glance

Here’s the skeleton of what your tax/investing year should look like. We’ll fill this in with specifics in each quarter.

Doctor Annual Tax and Investing Timeline

Period	Event
Q1 - Jan	Gather prior year tax docs
Q1 - Feb	Adjust withholdings and contributions
Q1 - Mar	Finalize last year return and IRA contributions
Q2 - Apr	Review new tax year goals
Q2 - May	Check withholding and estimated taxes
Q2 - Jun	Midyear investing and entity check
Q3 - Jul	Rebalance portfolio and tax-loss review
Q3 - Aug	Plan for big expenses and retirement boosts
Q3 - Sep	Pre-plan Q4 tax moves
Q4 - Oct	Final tax projections
Q4 - Nov	Execute tax-loss harvesting and gifting
Q4 - Dec	Deadline moves for retirement, gifting, and donations

---

Q1 (Jan–Mar): Clean Up Last Year, Lock In This Year’s Structure

In Q1, you’re doing double duty: closing the books on last year’s taxes while setting the framework for this year’s investing and tax strategy.

January: Get Your House in Order

At this point in the year, you should:

1. Create a single “Tax & Investing” hub

   • One folder (physical or digital) for:
     • W‑2s, 1099s, 1098‑E (student loan interest), 1099‑INT/DIV/B forms
     • Brokerage statements and year‑end summaries
     • HSA, FSA, 401(k)/403(b)/457(b) contribution statements
     • Records of charitable giving
   • If you own a practice or side LLC, add:
     • Profit and loss statement
     • Mileage log, CME and license receipts, equipment costs

2. Run a quick damage check on last year’s taxes

   • Pull last year’s return and glance at:
     • Effective tax rate (total tax / taxable income)
     • Refund vs. amount owed
   • If you owed >$5k or got a huge refund, your withholdings/estimates were off. Q1 is when you fix that.

3. List every investment account you actually have

   • Employer plans, IRAs, Roth IRAs, brokerage, HSA, 529s.
   • For each: who owns it (you/spouse), pre‑tax vs Roth vs taxable.

Account Type	Tax Status	Priority Rank*
401(k)/403(b)	Pre-tax/Roth	1
457(b)	Pre-tax	2
HSA	Triple tax	1
Backdoor Roth	Tax-free	2
Brokerage	Taxable	3

*Priority will vary, but that 1/2/3 structure is the general order I’d hit.

February: Adjust Withholding and Contribution Rates

By mid‑February, most W‑2s are out. This is your first lever‑pull month.

At this point in the year, you should:

1. Dial in your paycheck settings

   • Update your W‑4 at HR if you:
     • Married/divorced
     • Started/stopped 1099 work
     • Got hammered by underpayment penalties last year
   • Goal: avoid penalties and huge surprises, not to hit a perfect $0 refund.

2. Set retirement contributions on autopilot

   • Decide your target savings rate for this year (e.g., 20% of gross income).
   • From that, decide:
     • 401(k)/403(b) % per paycheck
     • 457(b) % if you have one
   • Then actually log into your benefits portal and bump the numbers. Not later. Now.

3. Plan for backdoor Roth IRA if your income is high

   • If you’re over the Roth income limit (most attendings are), Q1 is when you:
     • Confirm you have no pre‑tax money in traditional, SEP, or SIMPLE IRAs, or you’ll trigger the pro‑rata mess.
     • If you do have old pre‑tax IRAs, consider rolling them into your employer 401(k)/403(b) this year so you can start clean next year.
   • Set a reminder to do the non‑deductible contribution and Roth conversion by year end (you can do it any time, but Q1 is easy).

March: Finish Last Year’s Return and Max Retro Contributions

By late March, you should be in “finalizing last year” mode.

At this point in the year, you should:

1. Finalize last year’s tax return

   • Review with your CPA (or software) with three questions:
     • Where did most of my tax liability come from? (W‑2, 1099, capital gains?)
     • Did I leave any obvious deductions or credits on the table?
     • What should I change this year to fix that?
   • Get them to translate into actions: “Increase 403(b) to X%,” “start tracking CME,” “switch to S‑Corp if 1099 hits $X.”

2. Make prior‑year IRA and HSA contributions (if eligible)

   • You can still contribute for last year up to the tax deadline:
     • Traditional IRA / Roth IRA (if eligible)
     • HSA contributions
   • If cash flow allows, this is a clean way to retroactively reduce last year’s taxable income (traditional IRA, HSA).

3. Set Q2 estimated tax reminders if you have 1099 income

   • If you’re doing locums, moonlighting, telemed, or consulting:
     • Use last year’s 1099 totals to estimate quarterly payments.
     • Block the four dates in your calendar now:
       • April 15
       • June 15
       • September 15
       • January 15 (of the following year)

---

Q2 (Apr–Jun): Midyear Reality Check and Course Correction

Tax season hype dies in April, which is exactly when most doctors mentally check out. Bad move. Q2 is where quiet, boring changes save you five figures over the next decade.

April: Post‑Tax Season Debrief

At this point in the year, you should:

1. Debrief your return like a morbidity and mortality conference

   • Go line by line on the summary with your CPA:
     • Marginal tax bracket
     • Capital gains
     • Deductible vs non‑deductible expenses
   • Ask bluntly: “If I want my tax bill lower next year, what 3 things should I change?”
     Then actually write those on a Q2 checklist.

2. Reconfirm your savings hierarchy

   • Based on cash flow after Q1:
     1. Get employer match in 401(k)/403(b)
     2. Max HSA if you have one
     3. Max 401(k)/403(b) and 457(b)
     4. Backdoor Roth IRA
     5. Taxable brokerage
   • You don’t need perfection. You need a consistent order.

May: Withholding & Estimated Tax Tune‑Up

By mid‑May, you’ve seen a few paychecks under the new year’s comp structure.

At this point in the year, you should:

1. Run a midyear tax projection

   • Rough back‑of‑envelope:
     • Last year tax ± expected changes (raise, less/more moonlighting)
   • Are you on track to owe a ton again? Fix it now:
     • Increase W‑2 withholding
     • Increase quarterly estimates

2. Adjust retirement contributions if you mis‑aimed

   • If you’re behind pace to max your 401(k)/403(b):
     • Figure out the remaining pay periods.
     • Divide the remaining max contribution by that number.
     • Update the percentage on your benefits portal.

3. Check you’re not accidentally generating dumb taxes in taxable accounts

   • Common Q2 mistakes:
     • Active mutual funds spewing capital gains every year
     • Constant trading (or your advisor doing it) creating short‑term gains
   • Prefer broad, low‑turnover index funds/ETFs in taxable.

June: Midyear Investing and Entity Check

Late Q2 is a good “deep breath” moment.

At this point in the year, you should:

1. Review your portfolio allocation

   • Stocks vs bonds vs cash.
   • US vs international.
   • Compare across all accounts, not just one.
   • You’re not rebalancing yet (that’s Q3), just checking if your overall strategy still matches your risk tolerance.

2. Evaluate your 1099 structure (if you have side income)

   • If your 1099 is climbing:
     • Ask your CPA if it’s time to:
       • Move from sole proprietor to LLC (simple liability/organizational step)
       • Or from LLC to S‑Corp for potential self‑employment tax savings
   • These changes are cleaner if done midyear, not in a December panic.

3. Check student loan and PSLF tax implications

   • For those on income‑driven repayment or PSLF:
     • Your payments affect taxable income and vice versa.
   • Q2 is a good time to:
     • Verify annual recert date
     • Plan how retirement contributions may lower AGI and thus reduce payments (and long‑term taxable loan forgiveness exposure).

---

Q3 (Jul–Sep): Rebalance, Prepare for Q4, Avoid Sleepwalking

Q3 feels deceptively “calm” financially. Do not waste it. This is prep time for the heavy Q4 moves.

July: Midyear Scorecard

At this point in the year, you should:

1. Grade your progress like a resident evaluation

   • Savings rate so far vs target
   • Retirement accounts funded % vs plan
   • HSA funded or not
   • Brokerage contributions made or not
   • Any big one‑time expenses ahead (board exams, moving, fellowship transition)?

2. Fix autopay issues

   • Move recurring investments to:
     • The day after your paycheck clears
   • Eliminate “I forgot to invest” as a problem. Automate or it will not happen consistently, especially in Q4.

3. Check for lifestyle creep

   • Compare July take‑home vs January.
   • If your spending expanded as your income did:
     • Capture some of that creep back by pushing up retirement or brokerage contributions 1–3% now.

August: Rebalance and Early Tax‑Loss Scan

Markets have probably moved a bit since the start of the year.

At this point in the year, you should:

1. Rebalance across all accounts

   • If your target is, say, 70% stocks / 30% bonds and you’re now 80/20:
     • Sell in tax‑advantaged accounts (401(k), IRA) when possible to avoid realizing capital gains in taxable.
   • Stay disciplined. Rebalancing is risk control, not market timing.

2. Do a preliminary tax‑loss scan in taxable accounts

   • Look for:
     • Positions with significant unrealized losses.
   • You don’t have to harvest yet, but:
     • Make a list of “candidate” funds or ETFs.
   • This homework makes the Q4 harvesting way faster when time is tight.

3. Review your advisor situation (if you have one)

   • Are they:
     • Tax‑aware with asset location (what’s in taxable vs tax‑advantaged)?
     • Talking to you before Q4, not after April 15?
   • If their strategy is “we’ll see what happens at tax time,” that’s lazy.

September: Pre‑Plan Q4 Moves

Late Q3 is when you lay out your Q4 attack list.

At this point in the year, you should:

1. Schedule your Q4 tax projection meeting

   • Book your CPA for October or early November.
   • Send them:
     • Year‑to‑date pay stubs
     • 1099 income to date
     • YTD contribution amounts
   • You want a concrete estimate of:
     • Expected tax bill
     • Levers you can still pull before December 31.

2. Draft your Q4 to‑do list

   • Likely items:
     • Final retirement account contribution adjustments
     • Tax‑loss harvesting
     • Charitable giving (including donor‑advised fund contributions)
     • 529 contributions
     • Any gifting or estate moves

3. Confirm entity and payroll details if you have an S‑Corp

   • Make sure:
     • Reasonable salary vs distributions is on track.
     • You’re not underpaying payroll taxes.
   • Cleaning this up now beats getting an ugly letter later.

---

Q4 (Oct–Dec): Execution Season – All the Deadlines

Q4 is where you lock in the bulk of tax savings for the year. Most high‑earning physicians either win or lose their tax year here.

October: Final Tax Projection and Strategy Lock‑In

At this point in the year, you should:

1. Get a specific tax projection from your CPA

   • You want:
     • Estimated total tax
     • Expected refund / amount owed if you do nothing else
     • A short list of targeted moves (with dollar impacts) you can make before year‑end.

2. Decide on pre‑tax vs Roth for the rest of the year

   • If you’re in a very high tax bracket now and expect lower later:
     • Favor pre‑tax contributions (401(k)/403(b)).
   • If you’re early in your career or expect higher bracket later:
     • Roth may make more sense.
   • You can split. It doesn’t have to be all or nothing.

3. Map your contribution finish line

   • For each account:
     • How much have you contributed YTD?
     • How much room is left until the annual max?
   • Adjust contributions for the last few pay periods:
     • Aim to hit the max as close to year‑end as possible without massively shrinking a single paycheck.

Typical Doctor Contribution Timing by Account

Category	Value
401k Maxed	70
HSA Maxed	60
Backdoor Roth Done	40
Taxable Funded	30

November: Tax‑Loss Harvesting and Charitable Planning

Now you’re getting tactical.

At this point in the year, you should:

1. Execute tax‑loss harvesting in taxable accounts

   • Sell losers to lock in losses you can use to:
     • Offset capital gains
     • Offset up to $3,000 in ordinary income per year
   • Immediately buy a similar but not substantially identical fund (to avoid wash sale rules) to maintain your market exposure.

2. Plan and execute charitable giving

   • Decide:
     • Cash donations vs appreciated stock
     • One‑off gifts vs donor‑advised fund (DAF)
   • If you’re in a high‑income, high‑tax year:
     • Front‑loading several years of giving into a DAF this year can create a big deduction while you’re in a top bracket.

3. Check FSA and other “use it or lose it” buckets

   • Health FSA
   • Dependent care FSA
   • CME funds at work
   • Schedule appointments, buy eligible expenses, or submit reimbursements before you lose the money.

December: Deadline Month – Last Chance Moves

This is where most doctors panic. You will not, because you’ve been staging this since Q1.

At this point in the year, you should:

1. Finalize all employer retirement contributions

   • 401(k)/403(b)/457(b) employee contributions: December 31 deadline.
   • Confirm with HR/payroll:
     • Your year‑to‑date contributions
     • That your final paychecks will hit your target without overcontributing (which is a paperwork mess).

2. Complete backdoor Roth IRA (if you do it by calendar year)

   • Many people:
     • Make the non‑deductible contribution in December.
     • Convert to Roth shortly after (to minimize growth in the traditional IRA).
   • Just keep clean records for Form 8606.

3. Finish tax‑loss harvesting and capital gain planning

   • If you’ve had big realized gains:
     • See if more losses are available to offset.
   • Or if you’re in a very low‑income year:
     • You may intentionally realize some gains at lower capital gains rates.

4. Execute any last‑minute gifts and 529 contributions

   • Gifts to family up to the annual exclusion amount per person.
   • 529 contributions (state deductions/credits may depend on calendar year).

5. Snapshot your entire financial year

   • On December 31, or first week of January:
     • Screenshot or save balances for:
       • All retirement accounts
       • Taxable accounts
       • Loan balances
     • This lets you compare year‑over‑year progress and simplifies next year’s planning.

Doctor Tax-Related Tasks Completion by Quarter

Category	Value
Q1	30
Q2	55
Q3	75
Q4	100

---

Putting It Together: A Simple Quarterly Checklist

If you want a bare‑bones version, here is what each quarter boils down to:

Quarter	Main Focus	Key Actions (Short)
Q1	Setup + Last Year Cleanup	File return, fix withholdings, set contributions
Q2	Midyear Reality Check	Tax projection, adjust investing, review entities
Q3	Rebalance + Q4 Prep	Rebalance, plan Q4 moves, book CPA
Q4	Execution and Deadlines	Harvest losses, max accounts, year-end giving

---

Your Next Step Today

Do one concrete thing now, not someday.

Open your last filed tax return and your most recent pay stub. On a single sheet of paper (or note app), write:

1. Your marginal tax bracket
2. Your year‑to‑date retirement contributions
3. Whether you owed or got a big refund last year

Then write one sentence: “In the next 7 days, I will ________.”

Fill that blank with something from this quarter’s list: increase your 401(k) percentage, email your CPA for a projection, or set up automatic monthly transfers to your brokerage.

That one written line is the start of your actual tax season timeline, not just another good intention.