Tax Planning
Adair & Associates | Wealth Management
Tax Planning Services
Most people think about taxes once the year is already over. We look at them earlier, while there is still time to change what your income, your investments, and your retirement accounts will cost you in tax.
A 15 to 20 minute conversation. No cost, no obligation.
- Hunter Adair, CFP®
- Financial planning since 2002
- Securities and advisory services through LPL Financial
The short answer
What is tax planning?
Tax planning is the ongoing work of structuring your income, investments, retirement account withdrawals, and charitable giving so that your tax bill is managed across many years at once.
Tax preparation reports what already happened. Tax planning happens earlier, while there is still room to change the outcome. For most households the real opportunities show up in the years leading up to a return: which account you draw from first, whether to convert part of an IRA to a Roth, when to realize a gain or a loss, and how one year's income affects the next year's Medicare premium.
Two different jobs
Tax planning vs. tax preparation
Both matter. They answer different questions at different points in the year, and they are usually handled by different professionals working together.
| Tax Preparation | Tax Planning | |
|---|---|---|
| Timing | After the calendar year closes | Before and throughout the year |
| Core question | What do I owe for last year? | What can I still influence going forward? |
| Time horizon | A single filing year | Multiple years, often a full retirement |
| Typically handled by | A CPA, enrolled agent, or tax preparer | A financial advisor, coordinating with your tax professional |
| The deliverable | A completed, filed return | Decisions: withdrawal order, conversion amounts, timing of gains, giving strategy |
| What Adair & Associates does | We do not prepare or file returns | This is our role, alongside the professional who files for you |
What we look at
Tax planning services we provide
Tax questions come up in almost every part of a financial plan. These are the areas we review most often.
Roth conversion analysis
Modeling partial Roth conversions during lower-income years. That window often falls between the day you stop working and the day Social Security or required distributions begin. We weigh the effect on your bracket, your Medicare premiums, and the withdrawals you will be required to take later.
Tax-efficient withdrawal sequencing
Deciding which accounts to draw from, and in what order, across taxable, tax-deferred, and tax-free savings. The same dollar of spending can carry a very different tax cost depending on where it comes from.
Required minimum distributions
Planning for required minimum distributions well before they start: how large your tax-deferred balance is likely to grow by then, and whether qualified charitable distributions make sense if you give to charity.
Tax-loss harvesting & cost basis review
Reviewing realized and unrealized positions through the year, harvesting losses where it is appropriate, and confirming that cost basis is recorded and reported correctly. Bad basis records are a common source of overstated gains.
Asset location
Placing each investment in the account type that suits how it is taxed. Asset allocation sets your risk. Asset location affects what you keep after tax.
Social Security & Medicare timing
How provisional income determines the taxable portion of your Social Security benefit, and how modified adjusted gross income from two years earlier drives Medicare IRMAA surcharges on Part B and Part D.
Charitable giving strategy
Gifting appreciated securities instead of cash, donor-advised funds, qualified charitable distributions from an IRA, and grouping several years of giving into one year where it makes sense.
Withholding & estimated payments
Reviewing paycheck, pension, and distribution withholding so the year ends without a surprise in either direction. A very large refund is its own kind of planning problem.
Legacy & beneficiary coordination
How assets are titled and who is named on each account, step-up in cost basis, and the rules that apply to beneficiaries who inherit retirement accounts. We coordinate this with your estate attorney.
Who this is for
When tax planning tends to matter most
You are five to ten years from retiring
This is often the most useful window you will get. Once your paycheck stops and before required distributions begin, you may have several years of unusually low taxable income. Those years are easy to let slip by, and you do not get them back.
You have a large 401(k), IRA, or TSP balance
A tax-deferred balance is a bill that has not come due yet. The larger it grows, the larger your eventual required withdrawals, and the less say you have over the bracket they land in.
You are already retired and drawing income
Each year brings a new set of choices: what to withdraw, what to convert, what to give, and what to sell. Small adjustments add up when you make them every year.
Your income is uneven year to year
Business owners, people with equity compensation or a concentrated stock position, and anyone facing a one-time event like a sale, a severance package, or an inheritance usually have more flexibility on timing than they realize.
How we work
Our process
Four steps, built to work alongside the tax professional you already use.
Introductory call
Fifteen to twenty minutes on the phone to hear your situation and decide together whether it makes sense to keep going. No cost, no obligation.
Review
We look at your recent returns, account statements, and plan documents to understand how your income is actually taxed today.
Strategy
We model the options for conversion amounts, withdrawal order, and timing, then walk you through the trade-offs in plain language.
Implement & revisit
We put the plan in motion, coordinate with your CPA or attorney, and come back to it every year. Your life changes and so does the tax code.
Experience
Why clients bring us their tax questions
Adair & Associates is a wealth management practice in Marriottsville, Maryland. Our team brings more than 45 years of combined industry experience, and securities and advisory services are offered through LPL Financial.

Hunter Adair, CFP®
Wealth Management Advisor, Partner
A CERTIFIED FINANCIAL PLANNER™ professional who has worked in financial planning since 2002, Hunter leads the firm's planning work and meets personally with every prospective client.

Pat Gibbons
Wealth Management Advisor, Partner
More than 30 years in financial services, including time as a partner in a CPA firm and as a business owner. That background shapes how the practice thinks about tax.
We work with your tax professional
How we fit in
We do not prepare or file returns, and we do not replace your CPA or enrolled agent. We handle the planning side, which they often have no time for during filing season, and we make sure everyone is working from the same information.
2205 Warwick Way, Suite 300, Marriottsville, MD 21104 · (443) 609-7727 · hunter.adair@adairadvisory.com
Before we meet
What to bring to a tax planning conversation
Nothing is required for an introductory call. If you want to get further in the first conversation, these help:
- Your two most recent tax returns. They tell us more in five minutes than an hour of questions would.
- Current statements for retirement accounts: 401(k), 403(b), IRA, Roth IRA, TSP, or a pension summary.
- Taxable investment account statements, including cost basis if it is shown.
- Your Social Security statement, or an estimate of your expected benefit.
- A rough sense of your annual spending, and when you expect to stop working.
- Any upcoming one-time events, such as a home sale, a business sale, an inheritance, or a severance package.
Common questions
Tax planning FAQs
Do you prepare or file my tax return?
No. Adair & Associates does not prepare or file tax returns, and we do not provide tax advice. We do tax planning, which means looking ahead at how the decisions in your financial plan are likely to be taxed and coordinating with the CPA, enrolled agent, or tax preparer who files for you. If you do not have one, we are glad to help you find one.
What is the difference between tax planning and tax preparation?
Tax preparation looks backward. It reports and files what already happened during a calendar year. Tax planning looks forward, shaping decisions while the year is still in progress and the outcome can still change. Preparation answers the question "what do I owe?" Planning answers "what can I still do about it?" Most households want both.
When is the best time to consider a Roth conversion?
Usually in a year when your taxable income is unusually low compared with what you expect later. For most people that falls after they stop working but before Social Security and required minimum distributions begin. A conversion is taxable in the year you make it, so the real question is whether paying at today's known rate beats paying at some future rate you cannot know yet. The answer depends on your bracket, your other income, your Medicare premium exposure, and how long the money is likely to stay invested. It is worth modeling before you act.
At what age do required minimum distributions start?
Under the SECURE 2.0 Act, required minimum distributions from traditional IRAs and most employer retirement plans currently begin at age 73. That age is scheduled to increase to 75 in 2033 for people born in 1960 or later. Roth IRAs are not subject to required distributions during the original owner's lifetime. These rules have changed several times in recent years, so it is worth confirming your own start date with your tax professional.
What is tax-loss harvesting?
Tax-loss harvesting is the practice of selling an investment held at a loss in a taxable account, using that realized loss to offset realized gains elsewhere, and reinvesting in a way that keeps your overall strategy intact. Losses beyond your gains can generally offset a limited amount of ordinary income each year, with the remainder carried forward. Wash-sale rules restrict repurchasing a substantially identical security within a set window, so how you reinvest needs as much thought as what you sell.
How does my income affect my Medicare premiums?
Medicare Part B and Part D premiums are income-related. The surcharge, known as IRMAA, is based on your modified adjusted gross income from two years prior, so a large Roth conversion, capital gain, or one-time distribution today can raise your premiums two years from now. The brackets work as cliffs, so going over a threshold by even a small amount can cost you real money. That is one of the main reasons we model conversion amounts carefully.
Is my Social Security benefit taxable?
It can be. At the federal level, up to 85% of your benefit may be included in taxable income depending on your "provisional income," a figure that combines your adjusted gross income, tax-exempt interest, and half of your Social Security benefit. Other withdrawals feed that calculation, so the order in which you draw from your accounts can change how much of your benefit is taxed. Maryland does not tax Social Security benefits and offers a pension exclusion for eligible retirees. State rules and amounts change, so check current figures with your tax professional.
Do I need to change financial advisors to get tax planning help?
Not necessarily. Many people start with an introductory call just to get a second look at one specific question, like a conversion, a pending stock sale, or a withdrawal strategy. If it turns into a longer relationship, that is a decision for later. The first conversation commits you to nothing.
How much money do I need to work with Adair & Associates?
We start with a conversation. The introductory call is where we learn what you are trying to solve and tell you honestly whether we are a good fit. If we are not, we will say so.
How often should a tax plan be revisited?
At least once a year, and again whenever something significant changes: retiring, selling a business or property, an inheritance, a death in the family, a move to another state, or a major change in tax law. Many of the most useful moves, including conversions and qualified charitable distributions, have to be completed before December 31, which makes a fall review particularly worthwhile.
Related
Tax planning connects to everything else. See also Retirement Planning, our full range of wealth management services, and the tax resource center for articles, calculators, and videos.
Let's look at your situation
Schedule a short introductory call with Hunter Adair. Bring a question, bring last year's return, or bring nothing at all. We will start wherever you are.
Adair & Associates · 2205 Warwick Way, Suite 300, Marriottsville, MD 21104
Important disclosures
Content last reviewed September 2026.
Adair & Associates and LPL Financial do not provide tax or legal advice or services. This material is for general informational purposes only and is not intended to provide specific advice or recommendations for any individual, nor is it a substitute for specific individualized tax or legal advice. Please consult your qualified tax or legal professional regarding your particular situation.
Traditional IRA account owners should consider the tax implications, age and income restrictions in regard to executing a conversion from a Traditional IRA to a Roth IRA. The converted amount is generally subject to income taxation in the year of conversion.
All investing involves risk, including possible loss of principal. No strategy assures success or protects against loss. Tax laws and regulations are complex and subject to change, which can materially affect investment results.
Securities and advisory services offered through LPL Financial, a registered investment advisor. Member FINRA & SIPC.
The LPL Financial representative associated with this website may discuss and/or transact securities business only with residents of the following states: CA, CO, CT, DC, DE, FL, GA, IL, MA, MD, NC, NH, NY, PA, TN, TX, VA, WA, WV.