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Why More Pinterest Employees Are Considering Social Security Early â€” And How Medicare Changes Play a Role

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'Pinterest employees weighing when to file for Social Security should consider both current health care costs and long-term income needs, so they can stay adaptable as retirement unfolds.' — Paul Bergeron, a representative of The Retirement Group, a division of Wealth Enhancement.

'Pinterest employees can benefit from thoughtfully coordinating Social Security timing with health care expenses so their retirement income stays aligned with their evolving needs over time.' — Tyson Mavar, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will discuss:

How Social Security filing age affects retirement income.
How Medicare expenses factor into when retirees claim benefits.
Why emotional concerns are shifting filing behavior for many Americans.

Written by Wealth Enhancement advisors Kevin Landis, CPA and Wesley Boudreaux

Advisors in the retirement-income space have long suggested that retirees consider delaying filing for Social Security benefits. For those with a full retirement age (FRA) of 67, waiting until age 70 can result in monthly payments that are around 24% higher. ¹ And for those with an FRA of 66, the increase if one waits until age 70 is closer to 32%. ¹ Pinterest employees nearing retirement often hear this same message.

However, new national data indicates a growing number of Americans plan to claim Social Security before age 70. Cost pressures and health care related issues are major influences in this trend.

The Retirees’ Reality

Today’s retirees face a very different environment than those in past decades, including less access to traditional pensions, rising health care costs, and mounting everyday living expenses. In the private sector, only about 15% of workers still have access to defined benefit pensions, ² affecting many households and Pinterest employees.

According to retirement consultant Wesley Boudreaux, 'most retirees are not choosing to claim early for the sake of it.” Instead, rising medical and living costs are driving earlier benefit decisions because of cash flow pressures.

One major factor? Health care. Nearly 39% of out-of-pocket health care spending by Medicare beneficiaries was equivalent to Social Security payments received, on average, in 2022. ³

Medicare Advantage: A Key Planning Factor

Additionally, shifts in Medicare Advantage plans have left many retirees unsure about upcoming costs. Benefit structures can vary significantly by year or by region, causing cost surprises that Pinterest workers and their families may need to plan for.

“We are already seeing clients paying more for health care than expected,” said Kevin Landis, CPA. “When medical expenses rise, Social Security often becomes the first lever people pull to handle that burden.”

This is why coordinating Social Security filing decisions with Medicare coverage choices remains important, particularly when plans change annually.

“This is the intersection of Social Security and health care planning,” Landis adds. “Changes in one can influence the other.”

Emotional Considerations Also Matter

Money matters aren’t the only reason retirees claim earlier. Concerns about the future of Social Security have caused many to look for the emotional comfort of taking benefits sooner, including some Pinterest workers preparing for retirement.

While benefits are expected to continue—even if trust fund reserves decline in the 2030s—worries about future payouts can play a role.

“It’s not just about math,” Boudreaux explains. “People want control and stability in retirement, even if that means receiving less over time.”

Finding the Right Approach for You

Whether filing early is a good fit depends a lot on health, cash flow needs, and longer-term retirement goals. Thoughtful planning helps maintain flexibility, rather than driving you to respond under pressure.

“The best approach balances today’s needs with what lies ahead,” Landis says. “And that begins with understanding how Medicare and Social Security interact.”

Need Help Reviewing Your Options?

The Retirement Group, a division of Wealth Enhancement, helps individuals evaluate Medicare electives, analyze Social Security filing alternatives, and design retirement income strategies based on personal goals—including guidance tailored to those employed by Pinterest.

ðŸ“ž Call (800) 900-5867 before your next enrollment period to schedule a Social Security & Health Care Review.

Work toward confidence in your long-term retirement income decisions.

About the Authors

Wesley Boudreaux and Kevin Landis, CPA, provide retirement income and tax planning guidance through Wealth Enhancement, helping people make informed choices about Social Security, Medicare, and financial well-being.