By Brent Matthew
If you’re like many people, you don’t look forward to paying your taxes each year. And when you’re retired, tax planning looks a lot different than it did when you were working.
I’ve helped countless retirees plan and prepare to file their taxes. Having one-on-one assistance is an important part of the process, but before you start, this tax planning checklist can help you get ready.
Gather Key Income-Related Tax Planning Documents
Before you file your taxes, take some time to gather the documents you need. Do this well in advance of the deadline! If you have trouble retrieving a particular document, you don’t want it to stop you from filing on time.
Depending on your tax planning situation, you might need to gather one or more of these documents:
- SSA-1099: Shows the amount of Social Security benefits you received
- Form 1099-R: Documents distributions from retirement accounts, annuities, and benefit plans
- Form 1099-INT: Reports interest income from financial accounts
- Form 1099-DIV: Reports dividend income
- Form 1099-MISC or 1099-NEC: Reports income from freelance or contract work
- Form W-2: Reports employee income (if you worked part-time)
- Form 1099-B or 1099-S: Reports income from the sale of property or stock
You often receive these forms in the mail, electronically, or both. To reduce stress around tax time, store them in a safe place as soon as they arrive.
Gather Documentation for Your Deductions
If you itemize deductions (or if you think there’s a possibility that you may itemize this year), you should also assemble documentation of deductible expenses. You may need to gather these forms when tax planning:
- Form 1098: Reports the mortgage interest you paid
- Form 1098-T: Reports any tuition you paid. Deduction only if the student is a dependent. If not a dependent, the student’s parents may be able to claim an education credit.
- Form 1095-A (or Health Insurance Payment Records): Documents how much you paid for health insurance
- Records of Medical Expenses: If your medical expenses exceed a certain percentage of your AGI, you might be able to deduct them.
- Property Tax Records: Show how much you paid throughout the year in state and local property taxes
- Records of Charitable Contributions: Document cash, stocks, or other contributions you made to qualifying charities
If you miss a potential tax deduction, you could also be missing out on thousands of dollars in savings. When you let our team handle your tax planning, we’ll take a careful look at your finances to verify you aren’t leaving any potential savings on the table.
Review New Tax Changes
Part of retirement planning is monitoring for changes in tax law and determining how those changes impact you. In 2025, the passage of the One Big Beautiful Bill Act (OBBBA) introduced sweeping tax law changes that impact virtually everyone, retired or not.
One of the changes that may impact retirees is the temporary “bonus” senior deduction. From tax years 2025 to 2028, taxpayers 65 and older may deduct an additional $6,000 ($12,000 for married couples filing jointly).
You’re eligible for this deduction whether you itemize or not. However, the deduction starts phasing out for taxpayers with a modified adjusted gross income of $75,000 ($150,000 for married filing jointly).
Navigating tax law changes can be challenging, but we’re here to help you understand the OBBBA provisions and how to adjust your tax planning accordingly.
Need Help With Tax Planning?
At Scottsdale Wealth Advisory, we’re dedicated to helping our clients find financial confidence and clarity. If you want to learn more about our team and how we can help you with tax planning, contact us online today.
To schedule your complimentary financial coaching session, call (480) 247-9090, email info@SWAFirm.com, or book directly at calendly.com/BrentMatthew.
Frequently Asked Questions
Why is tax planning different in retirement?
Tax planning in retirement is different because income often comes from multiple sources, such as Social Security, retirement account distributions, investments, and part-time work. These income streams are taxed differently and can affect deductions, Medicare premiums, and overall tax liability. Without proactive tax planning, retirees may pay more in taxes than necessary or miss opportunities to reduce their taxable income.
What documents should retirees gather for effective tax planning?
Successful tax planning starts with gathering the right documents before filing. Retirees should collect income forms such as SSA-1099s, 1099-Rs, and 1099-DIVs, along with records for deductions like medical expenses, charitable contributions, property taxes, and health insurance premiums. At Scottsdale Wealth Advisory, we help retirees review these documents carefully so nothing is overlooked and potential tax-saving opportunities aren’t missed.
How can working with a financial advisor improve tax planning for retirees?
Working with a financial advisor can make tax planning more strategic and less stressful. A professional can help retirees understand new tax laws, coordinate deductions, and align tax decisions with broader retirement goals. At Scottsdale Wealth Advisory, we guide clients through changing tax rules, identify opportunities such as senior deductions, and help retirees feel confident that their tax planning supports both their short-term needs and long-term financial plan.
About Brent
Brent Matthew is the founder and CEO of Scottsdale Wealth Advisory, a full-service fiduciary retirement planning firm serving pre-retirees and retirees across Arizona and multiple states. With a strong commitment to always putting clients first, Brent leads the firm in developing comprehensive, tax-efficient financial plans tailored to each family’s unique goals. He is responsible for researching investment, annuity, and life insurance strategies and building smart asset allocations that reflect both long-term growth and risk management.
Brent is driven by a core belief: “The success of this firm will be measured by the success of the families it represents.” That client-first approach has guided his work since the beginning. He is currently enrolled at the College for Financial Planning and is on track to earn his CERTIFIED FINANCIAL PLANNER® designation. He also holds his Series 65 license and Arizona Life and Health Insurance Producers License.
Outside the office, Brent embraces the Arizona outdoors with “lil B” and their two pomskies, Heimo and Kota. Whether he’s hiking, fishing, dirt biking, skiing, golfing, kayaking, or skeet shooting, Brent finds balance and joy in staying active. He’s also a fan of CrossFit, brunching, and cruising the Phoenix canal system on his beach cruiser—usually with classic tunes from the Marshall Tucker Band, Gordon Lightfoot, or Crosby, Stills & Nash playing in the background. To learn more about Brent, connect with him on LinkedIn.
Advisory services are offered by Scottsdale Wealth Advisory, LLC, an Investment Advisor in the State of Arizona. Insurance products and services are offered through Scottsdale Wealth Advisory, LLC. Scottsdale Wealth Advisory, LLC is not affiliated with or endorsed by the Social Security Administration or any government agency, and is not engaged in the practice of law. Be sure to consult with a licensed financial professional to confirm the accuracy of the insurance product you are considering.
