Tax Planning & Preparation

Tax Planning & Preparation Attorney

Tax planning is the year-round work of legally arranging your income, deductions, and business decisions to reduce what you owe; tax preparation is the annual filing that follows from it.

Milton Law Group handles both. By developing a deep understanding of your personal, professional, and financial life, the firm’s tax professionals provide clients with comprehensive year-round tax planning advice and year-end tax return preparation — led by Mark C. Milton, a former U.S. Department of Justice Tax Division trial attorney who holds a degree in accountancy and worked at two large public accounting firms before practicing law.

The combination of a tax attorney with a genuine accounting background is what lets the firm plan and prepare with an eye on the same rules the IRS uses to audit.

The firm prepares income tax returns for individuals, families, self-employed taxpayers, and small businesses, including W-2 wage earners, independent contractors with 1099 income, single-member LLCs, trusts, estates, partnerships, and S corporations.

Jump to Tax Return & Tax Planning FAQs ↓

Why Work With a Tax Attorney for Planning and Preparation

The main reason to have an attorney plan and prepare your taxes rather than a preparer alone, is the attorney-client privilege, which keeps your conversations confidential and protected.

When you discuss a sensitive question with a licensed tax attorney (an aggressive deduction, unreported income from prior years, a complicated business sale), that communication is shielded in a way conversations with a return preparer generally are not.

A limited confidentiality protection exists for some non-attorney practitioners, but it is far narrower: it does not apply in criminal cases, does not cover return preparation itself, and does not extend to many state matters.

There is also a practical advantage. Because the firm both plans and prepares — and has represented taxpayers in audits, collections, and litigation — it prepares returns with a clear view of what draws IRS scrutiny and how a position would hold up if questioned.

For clients who have fallen behind, that same team can help with unfiled returns and back taxes and, when a dispute has already started, with tax controversy matters.

“As a former DOJ Tax Division trial attorney with a background in public accounting, I’ve seen both sides. The most effective time to address a tax issue is before it becomes one — thoughtful planning during the year is far more powerful than scrambling at filing time.” — Mark C. Milton, Esq., Founder and Managing Attorney

Year-Round Tax Planning

Effective tax planning happens throughout the year, not in April, because most of the decisions that lower a tax bill have to be made before the year closes.

Milton Law Group works with clients to anticipate the tax consequences of their choices and to structure income, deductions, and transactions accordingly.

Planning is most valuable when your situation is changing or complex. Clients who benefit most include:

• Self-employed professionals and small business owners weighing entity choice (LLC, S corporation, partnership), reasonable compensation, and retirement plan options
• High-income individuals and families managing the timing of income, capital gains, and charitable giving
• People going through a major life change — a business sale, a divorce, an inheritance, a move between states, or a liquidity event
• Taxpayers with equity compensation such as stock options or restricted stock, where timing drives the tax result

For clients with significant assets, tax planning works hand in hand with estate planning by coordinating income tax, gift tax, and estate tax so the pieces work together rather than against one another.

Tax Return Preparation

Milton Law Group prepares federal and state income tax returns for a broad range of clients, from straightforward individual filings to returns involving multiple entities and states.

Preparation is handled in-house by the firm’s tax professionals or in coordination with a client’s existing preparer, and it is informed by the same standards the firm applies in audits: accurate reporting, defensible positions, and documentation that would stand up to review.

Because return preparation and planning happen under one roof, the return reflects the planning done during the year, and next year’s plan begins with what the return revealed.

Tax Return & Tax Planning FAQs

What is the difference between a tax attorney and a CPA for preparing my taxes?

The key difference is confidentiality and scope. A CPA or enrolled agent can prepare returns and handle many routine matters, but only a licensed attorney extends the full attorney-client privilege to your communications, and an attorney is trained to spot and address legal exposure, not just calculate the return. For sensitive or high-stakes situations, an attorney who also prepares returns offers both the filing service and the legal protection.

What is year-round tax planning, and how is it different from tax preparation?

Tax planning is the proactive work done during the year to legally reduce future tax; tax preparation is the annual filing of your return. Planning is where most tax is actually saved, because the decisions that move the needle, such as entity structure, timing of income and deductions, retirement contributions, and charitable strategy, generally must be made before the tax year ends. Preparation reports what already happened.

How can I legally lower my tax bill?

Most legitimate tax savings come from timing, structure, and using the deductions and credits you qualify for. Common levers include choosing the right business entity, timing income and deductible expenses across tax years, funding retirement and health savings accounts, structuring charitable gifts efficiently, and claiming every credit you’re entitled to.

Which of these apply depends entirely on your facts, which is why planning is done individually rather than from a checklist.

What is the difference between a tax credit and a tax deduction?

A tax credit reduces the actual tax you owe dollar-for-dollar, while a deduction reduces the amount of income that is taxed. Because a credit comes off your tax bill directly, a dollar of credit is generally worth more than a dollar of deduction.

A tax attorney can help determine which credits and deductions you qualify for based on your circumstances.

Should I take the standard deduction or itemize?

You should take whichever is larger, the standard deduction or the total of your itemized deductions. Itemizing makes sense only when your deductible items (such as mortgage interest, state and local taxes up to the applicable cap, charitable contributions, and qualifying medical expenses) add up to more than the standard deduction for your filing status.

Because both the standard deduction and several of these limits change over time, it is worth confirming the current figures each year before deciding.

I’m a freelancer or self-employed with no tax withheld. What should I do?

You should make quarterly estimated tax payments to the IRS (and often your state) to avoid underpayment penalties and interest. Because no employer is withholding for you, the tax system expects you to pay as you earn across the year rather than in a lump sum at filing. Setting aside a percentage of each payment you receive and paying quarterly keeps you current and avoids a surprise bill.

How do I file an extension, and does it give me more time to pay?

Filing an extension gives you more time to file your return, not more time to pay. Individuals can request an automatic six-month filing extension (Form 4868) by the original deadline, which avoids the failure-to-file penalty.

But any tax owed is still due on the original date — interest and the failure-to-pay penalty continue to run on an unpaid balance regardless of the extension.

What are common IRS audit red flags?

High income, unreported income, and disproportionately large deductions are among the most common audit triggers. The IRS also pays attention to unreported 1099 or cryptocurrency income, cash-intensive businesses, and deductions that are unusually large relative to reported income.

The best protection is accurate reporting backed by records — and if you are audited, representation from a tax attorney can protect both your position and your rights. Learn more about audit defense and appeals.

How long should I keep my tax records?

Keep most tax records for at least three years, but longer in several situations. The three-year window matches the standard period the IRS has to audit a return.

Keep records for six years if you may have underreported income by more than 25%, and indefinitely if you filed a fraudulent return or did not file at all. Records tied to property (such as a home or investments) should be kept until the limitations period runs out for the year you sell the asset.

Is alimony taxable or deductible?

For divorce or separation agreements finalized after 2018, alimony is neither deductible by the person paying it nor taxable to the person receiving it. Older agreements finalized on or before December 31, 2018 generally follow the prior rule — deductible by the payer and taxable to the recipient — unless the agreement was later modified to adopt the current treatment.

About Mark C. Milton

Mark C. Milton is the Founder and Managing Attorney of Milton Law Group. A former U.S. Department of Justice Tax Division Trial Attorney recruited through the Attorney General’s Honors Program, Mark received the DOJ’s Outstanding Trial Attorney Award in 2014. He brings nearly two decades of combined experience in tax controversy, federal litigation, and accounting, having practiced at an AmLaw 100 firm in St. Louis and worked at two large public accounting firms in Chicago and St. Louis prior to law school. He earned his J.D., with Honors, from Saint Louis University School of Law and his B.S. in Accountancy, cum laude, from the University of Illinois at Urbana-Champaign, and is admitted to practice in Missouri, the District of Columbia, Illinois, and Florida.

Schedule a Consultation

Contact the IRS Problem Solvers at Milton Law Group to schedule a paid privileged consultation by calling 833-LAW-1040 or at miltonlawgroup.com/schedule-now.

This page is provided for general educational purposes and is not legal or tax advice. Tax laws and dollar limits change from year to year, and every situation turns on its specific facts; consult a licensed attorney or tax professional about your circumstances.