If retirement is on the horizon (or already underway), Social Security will likely play an important role in your income plan. Yet one of the most common frustrations retirees face is realizing that what seems like a simple claiming decision can quietly affect monthly income, taxes, and long-term financial stability for decades.
In 2026, the average Social Security benefit is about $2,071 per month, but what you personally receive depends heavily on your earnings history and, just as importantly, when you choose to claim. Many retirees unintentionally leave money on the table or encounter unexpected tax consequences simply because they didn’t fully understand how the timing decision fits into their broader financial picture.
At Tapparo Capital Management, we help clients evaluate Social Security as part of a larger retirement strategy, not as a standalone choice. Below are several common pitfalls we see, along with practical considerations to help you make a more informed and confident decision.
Mistake #1: Claiming Benefits Too Early
You can begin collecting Social Security as early as age 62, but doing so comes with a tradeoff: your benefit is reduced, and that reduced amount typically stays in place for the rest of your life.
For many people, delaying benefits can increase the amount you receive each month. In fact, every year you delay claiming between ages 62 and 70, the Social Security Administration increases your monthly benefit by 8%. For retirees who have other resources to rely on in the early years (like retirement accounts, savings, or part-time income), waiting can be a smart move.
That said, claiming early isn’t always a “mistake,” but it is a decision that should be made intentionally. The key is making sure you understand what you’re giving up in exchange for starting sooner.
Mistake #2: Not Factoring in Life Expectancy and Health
Some retirees delay claiming because they’ve heard it always pays to wait. But the truth is, this decision needs to be personal.
If you have health concerns or a family history that suggests a shorter life expectancy, claiming earlier may allow you to receive more value from benefits over your lifetime. On the other hand, if longevity runs in your family, delaying benefits may provide stronger long-term stability, especially later in retirement when the risk of outliving other assets becomes more real.
Social Security decisions shouldn’t be based on what your neighbor did or what your coworker recommends. Your health, lifestyle, and financial situation should guide the timing.
Mistake #3: Forgetting Social Security May Be Taxable
One of the most overlooked issues is taxes. Depending on your total income, up to 85% of your Social Security benefits may be taxable.
That’s why it’s important to coordinate your claiming strategy with the rest of your retirement income plan. For example, if you’re pulling from a traditional IRA or 401(k), generating capital gains from investments, or receiving pension or rental income, those sources may raise your taxable income and cause more of your Social Security to be taxed.
Many retirees are surprised when they realize Social Security isn’t “tax-free” the way they assumed it would be.
This is where a tax-aware plan matters. At Tapparo Capital Management, we help clients evaluate how their Social Security benefits interact with:
- Retirement account withdrawals
- Investment income
- Part-time or consulting income
- Rental income
- Required minimum distributions (RMDs)
A small shift in when and how you draw income can sometimes make a meaningful difference in your overall tax picture.
Mistake #4: Not Coordinating Benefits As a Married Couple
If you’re married, it’s important to avoid treating Social Security as a purely individual decision. Your claiming strategy may affect not only your benefit, but also your spouse’s options.
Depending on your ages and earnings history, one spouse may qualify for a spousal benefit, which can be worth up to 50% of the other spouse’s full retirement benefit. In some cases, coordinating correctly can result in thousands of additional dollars over time.
There are also survivor benefit considerations that can become important later in life. This is one reason couples benefit from reviewing their options together, rather than making two separate decisions in isolation.
Mistake #5: Not Taking Advantage of Ex-Spouse’s Social Security Benefits
If you’re divorced, you may be eligible to claim Social Security benefits based on your ex-spouse’s work record. To qualify, your marriage must have lasted at least 10 years, you must be divorced for at least two years, and you must still be single. Additionally, you need to be at least 62 years old and not eligible for a higher benefit based on your own work history.
Unlike spousal benefits for married couples, your ex-spouse does not need to have filed for benefits for you to claim them. This is a potential source of additional income that many overlook, especially if they haven’t considered how much more they could receive by tapping into their ex-spouse’s earnings history.
Let’s Simplify Your 2026 Social Security Claiming Strategy
With so much discussion and mixed messaging around Social Security in 2026, it’s easy to feel unsure about what decisions make the most sense. The key is to focus less on headlines and more on how and when claiming benefits fits into your overall financial picture, supporting your lifestyle, shielding long-term income, and working alongside your tax strategy.
If you’re wondering which approach is right for you, the team at Tapparo Capital Management can help you explore your options. We view Social Security as one important piece of a broader financial plan built around your goals and priorities.
Would you like to talk through your situation and create a strategy you feel comfortable moving forward with? We’re here to help. To schedule a “Get Acquainted Call” to see if we are a good fit for each other, call 978-887-1121 or email andrew@tapparocapital.com.
About Andy
Andrew Tapparo is a fee-only financial advisor at Tapparo Capital Management, a financial planning firm in Topsfield, MA, helping clients turn their savings into a retirement income that lasts. Inspired by the quote “Choose a job you love, and you will never work a day in your life,” Andy founded Tapparo Capital Management in 1997 with a passion for helping clients enjoy a truly worry-free and fulfilling retirement and experience financial freedom. As a Retirement Income Certified Professional (RICP®), he designs retirement strategies along with sound money management to help clients retire with confidence.
Andy holds a Bachelor of Science in Industrial Engineering from Rochester Institute of Technology in Rochester, New York, and a Master of Science in Finance from Bentley University in Waltham, Massachusetts. Specializing in retirement income planning, Andy completed a comprehensive financial industry education program at The American College of Financial Services and was awarded the Retirement Income Certified Professional® designation. He is frequently quoted in the media as a financial expert.
Andy and his wife, Susan, live in Topsfield, Massachusetts, and have two beautiful daughters. Outside of work, he is an automobile enthusiast, enjoys taking road trips, and loves the Outer Banks of North Carolina. In his spare time, he volunteers with the local high school varsity girl’s basketball team as the team statistician and runs the team’s website. He is passionate about supporting charities that serve our veterans and their families. To learn more about Andy, connect with him on LinkedIn.
