What to Bring to a Tax Strategy Session

You booked a tax strategy session. Now you are staring at a folder of 1099s and a vague memory of what you paid in estimated taxes. That is a normal place to start.

Forty-five minutes goes fast. If you spend twenty of them hunting for last year's return, you have less time for the questions that matter.

This guide covers what to bring, what to ask and how long to keep your records. Rough numbers are fine. You do not need a perfect spreadsheet to have a useful conversation.

Key takeaways

• Bring income, expense and asset records, plus your most recent tax return. Rough numbers beat no numbers.
• Arrive with specific questions. "Do I need to change my estimated payments?" is easier to answer in 45 minutes than "Help me with my taxes."
• Your records matter beyond this session. IRS retention periods run from 3 years to indefinitely, depending on your situation.

What a 45-minute tax strategy session can and cannot cover

Think of the session as a strategy conversation. The goal is focused discussion of the questions you bring. It is not enough time to review a year of receipts line by line.

CCA's Tax pillar includes a one-time complimentary 45-minute tax strategy session with a tax professional, then a discounted rate for later sessions. If your questions do not fit into 45 minutes, later sessions are available at a discounted rate.

The core documents to bring

The IRS describes records that show the amounts and sources of your income and what you spent. Group your paperwork into four piles.

Income records show the amounts and sources of your income.

• Forms 1099, such as 1099-NEC or 1099-MISC, from each group, facility or payer
• Invoices you sent
• Deposit records or bank statements showing payments received

Expense records. The IRS says good records show the payee, the amount, proof of payment, the date and what you bought.

• Receipts and invoices
• Credit card records and account statements
• Canceled checks or bank transfer records

Asset records. An asset is something you bought for your practice that lasts more than a year, such as equipment. The IRS says to keep records showing:

• When and how you acquired it
• What it cost, and any improvements
• Depreciation and Section 179 deductions you took (Section 179 lets you deduct the cost of certain equipment in the year you start using it)
• How much of its use is for business
• Sale details, if you sold it

Last year's return and this year's payments. Bring your 2025 return and a list of the estimated tax payments you have made in 2026. Your 2025 tax and adjusted gross income (AGI) feed into the safe harbor rules covered below.

For more on quarterly payments, see our guide to quarterly estimated taxes for 1099 clinicians.

Items specific to clinicians

Your work has its own paper trail. These are planning prompts, not an IRS-required list, so bring what applies to you.

• 1099s from every group or facility. If you work at several sites, gather one from each.
• Health insurance premiums. The IRS uses Form 7206 for the self-employed health insurance deduction, so bring a record of premiums paid. Insurance coverage, eligibility and terms are controlled by current membership, plan and policy documents.
• Retirement and HSA contributions so far. A health savings account (HSA) is a tax-advantaged account paired with a qualifying high-deductible health plan. Bring year-to-date totals and ask about limits and deadlines.
• Home office details. If you use a space exclusively and regularly for business, the IRS simplified method allows $5 per square foot, up to 300 square feet. Bring your square footage.
• A mileage log. The 2026 IRS standard business mileage rate is 72.5 cents per mile. A log with dates, places and purposes beats a guess.
• Equipment purchases. Note what you bought, what it cost and the date you started using it. That date can matter for Section 179 and bonus depreciation.
• CME and license costs. Continuing medical education, licenses and dues are commonly deducted if they are ordinary and necessary for your current business. Confirm with your tax professional.
• Malpractice premiums. The IRS lists business insurance among small-business expenses.

Our article on common tax deductions for 1099 clinicians covers these categories in more detail.

Entity paperwork and questions about entity choice

If you already have an LLC or an S corporation, bring your formation documents and any tax election you filed. That means Form 8832 (an LLC electing corporate tax treatment) or Form 2553 (an S corporation election).

If you run payroll through an S corporation, bring payroll records too. The IRS says to keep employment records for at least four years.

If you have no entity, you can still ask about one. A single-member LLC is generally taxed by default like a sole proprietorship, so it does not change your self-employment tax on its own. An S corporation works differently, with payroll and a separate tax return.

An S corporation does not always save tax, and many states charge annual fees or franchise taxes. Check your state's revenue or secretary of state website. For background, read LLC vs. S corp for clinicians.

Questions about payments and entity choice

Pick the two or three that matter most and write them down.

Estimated taxes and safe harbor

1. Based on my income so far, am I on track with my 2026 payments?
2. Does the safe harbor apply to me? The general rule is to pay at least the smaller of 90% of your 2026 tax or 100% of your 2025 tax. If your 2025 AGI was over $150,000 ($75,000 if married filing separately), the prior-year figure becomes 110%.
3. My income is uneven. Would the annualized income installment method help?
4. What is the next payment date? The next 2026 installment is due Jan. 15, 2027. You can skip it if you file your 2026 return by Feb. 1, 2027 and pay the full balance with it.

Entity choice and reasonable pay

1. Does an LLC or S corporation make sense for me, or would it just add cost and paperwork?
2. If I had an S corporation, how would reasonable pay be set? The IRS looks at factors such as training, experience, duties and what comparable businesses pay.

Questions about deductions and retirement

QBI and the SSTB threshold

1. Where does my taxable income sit relative to the QBI thresholds? The qualified business income (QBI) deduction can be up to 20% of qualified business income.

   Physicians, nurses, dentists and similar professionals fall into a category called a specified service trade or business (SSTB), which gets a reduced or no deduction at higher incomes. For 2026, the threshold starts at $201,750 for single and most other filers and $403,500 for married filing jointly.

Retirement contributions and deadlines

1. What are my contribution limits this year across retirement accounts and an HSA?
2. What are the deadlines for each, and do any need a plan set up first?

Deductions to document

1. Which of my expenses are most likely to be questioned, and what proof should I keep?
2. If I have both W-2 and 1099 income, how does the Additional Medicare Tax apply? It is 0.9% on wages and self-employment income above set thresholds ($200,000 single, $250,000 married filing jointly). The threshold is reduced by your W-2 Medicare wages.

Also bring a short list of changes this year, such as a new group, a move, a change in spouse income, a home purchase or a planned entity change. A rough year-to-date profit and loss and 2026 income projection help too.

How long to keep your records

IRS retention periods depend on your situation:

Ask your tax professional how long to keep records for equipment and other assets.

Keep digital copies, with one subfolder per year. Digital copies are fine for your own records.

How CCA helps

The Tax pillar, with its complimentary session, is one of six pillars: Insurance, Tax and Entity Formation, Wellness, Financial Planning, Mortgage Assistance and CME.

See how they fit together in our overview of the CCA membership benefit pillars, or browse the full list of CCA benefits.

FAQ

Do I need to bring everything on this list?

No. Bring what you have. Your 2025 return, your 1099s and a rough sense of expenses cover most of a first conversation.

What if my records are a mess?

That is a normal starting point. Rough numbers are fine for a strategy conversation.

Should I prepare questions in advance?

Yes. Two or three specific questions beat a general request. Put the most important one first.

How long should I keep the records I bring?

The IRS default is 3 years, but it can be 6 or 7 years, or indefinitely. Keep employment records at least 4 years. See the table above.

What if 45 minutes is not enough?

That can happen with an entity question or several income sources. CCA's Tax pillar includes a discounted rate for later sessions.

Is this article tax advice?

No. It is general education to help you prepare. Your tax professional can advise on your own facts.

Ready to see what CCA membership includes? Visit clinicianscareassociation.com/membership.

This article is general education, not tax, legal or financial advice. Talk to a qualified professional about your situation.

Insurance coverage, eligibility and terms are controlled by current membership, plan and policy documents.

Sources

• IRS: What kind of records should I keep
• IRS: How long should I keep records?
• IRS: 2026 Form 1040-ES
• IRS: Publication 334, Tax Guide for Small Business (2025)
• IRS: Qualified business income deduction
• IRS: Tax Topic 560, Additional Medicare Tax