Would Working One More Year Materially Change Retirement?

Ross Marino |

You may be close enough to retirement that another year of work feels measurable. There is one more bonus, one more year of employer health coverage, or one more round of retirement-plan contributions. The year also has a personal cost. It postpones the ordinary days, relationships, and plans that retirement is meant to make possible.

Working one more year can materially change retirement for some households. For others, the improvement is modest or depends on one specific benefit. The useful comparison identifies what the year changes, by how much, and whether that difference is worth the time being exchanged.

Why can one year change more than the account balance?

A working year can add employee contributions and an employer match. Existing savings may remain invested, and the portfolio may avoid funding a year of spending. Research on working longer finds that those effects can combine to improve retirement income, although the size of the improvement varies by household.[1] Other retirement research identifies delayed withdrawals and delayed Social Security claiming as two important financial effects of continuing to work.[2]

The headline result can hide the real driver. The difference may come mainly from postponing withdrawals. It may depend on a pension milestone, bonus, or equity award. Someone who already saves little from each paycheck may see a different result from someone receiving a large match. Separating the parts shows what the year actually buys.

How should the two retirement dates be compared?

Put the current retirement date and the one-year-later date through the same assumptions. The shared criteria keep a large change in one area from making every other difference look equally important.

What Does the Year Change on Each Path?

Compare both dates on the same six lines. Then circle the two or three differences that drive the decision.

Same question

Retire on the current date

Work one more year

Savings

Contributions end and existing savings begin their retirement job.

Employee and employer contributions may continue.

Withdrawals

The portfolio may begin supporting spending sooner.

A paycheck may cover another year of spending.

Health coverage

Marketplace, COBRA, Medicare, or a spouse's plan may take over.

Employer coverage may continue for the household.

Benefits

Social Security or a pension may begin on the earlier schedule.

Another earnings year or milestone may change future benefits.

Taxes

A lower-income planning period may begin sooner.

Wages and contributions continue for another tax year.

Life timing

The next season of life begins on the preferred date.

Work keeps its place for another year.

Materiality comes from the differences that meaningfully change the household's choices. It does not come from the number of rows that move.

When can health coverage become the deciding difference?

Before Medicare eligibility, leaving work may move the household from employer coverage to a Marketplace plan, COBRA, or a spouse's plan. Losing job-based coverage can create a Marketplace special enrollment opportunity.[3] Near age 65, the employer's size and the source of active coverage can affect how Medicare enrollment should be coordinated.[4]

Compare the plans that would actually be available. Start with premiums, deductibles, and expected out-of-pocket costs. Then compare prescriptions and provider access. If someone else depends on the employee plan, test that person's transition separately. A one-year coverage difference can be large, yet the plan details determine whether it is decisive.

Dovetail Principle: Measure the Year, Not the Slogan

One more year has value when its specific financial changes matter to the household. Its cost belongs in the same comparison: another year of time, energy, and plans placed on hold.

What can change in Social Security and tax planning?

Another earnings year can raise a Social Security benefit when it replaces a lower year in the worker's highest 35 years. A later claiming date is a separate decision. Delayed retirement credits may increase the monthly benefit after full retirement age and through age 70.[5]

Working longer may also delay the lower-income years between wages and later required distributions. Those years can provide room to evaluate Roth conversions or capital-gain realization, depending on the household's tax picture.[6] Compare the working year's after-tax income with the tax opportunities that move to a later calendar year.

Which differences are material enough to justify the year?

Use after-tax cash flow rather than salary alone. Show the account balances, healthcare costs, and benefit dates under both paths. Evaluate any pension or equity milestone separately. Then name the plans that each date would allow or postpone. The 2026 Retirement Confidence Survey reported different confidence levels among workers and retirees.[7] That difference is useful context, while household facts should carry this decision.

Test the assumptions that could reverse the answer. A bonus may be uncertain. Investment returns may differ. Health or job conditions may change before the year is complete. If a full additional year feels out of proportion to the benefit, compare a later retirement month, reduced hours, consulting, or a different claiming date. Dovetail's Work & Identity Transitions page explains how work can end, continue, or change while the financial and personal effects are considered together.

The final comparison should be explainable in a few sentences: what the year materially changes, which assumptions matter, and what the household would give up to receive those changes. That supports a choice between understandable paths.

Related Reading: Before You Pick a Retirement Date

About the author

Ross Marino, CFP®, CeFT®, is the Founder & CEO of Dovetail Financial and creator of Human-First Financial Guidance®. He helps people nearing or living in retirement connect their lives and wealth so that financial decisions become clearer, more personal, and easier to navigate.

Notes

  1. The Power of Working Longer, National Bureau of Economic Research, January 2018.
  2. “Unretiring”: Why recent retirees want to go back to work, T. Rowe Price, March 2025.
  3. Health Coverage for Retirees, HealthCare.gov.
  4. I'm Turning 65 Soon, but I Like My Current Insurance. Do I Have to Enroll in Medicare?, KFF, September 1, 2025.
  5. Working, Applying for Retirement Benefits, or Both, Social Security Administration.
  6. Why Pre-Tax Retirement Contributions Are Better Than Roth in Peak Earning Years, Kitces.com, September 25, 2024.
  7. 2026 EBRI/Greenwald Retirement Confidence Survey, Employee Benefit Research Institute, April 21, 2026.

Disclosure

This content is provided by Dovetail Financial Group LLC (“Dovetail Financial”) for informational and educational purposes only. It is not intended as, and should not be construed as, individualized investment, tax, legal, or accounting advice; a recommendation to buy or sell any security; or a recommendation to adopt any investment strategy. Because each person’s situation is unique, readers should consult their own financial, tax, and legal professionals before taking action based on this content. Information contained herein is believed to be reliable, but its accuracy or completeness is not guaranteed. Any opinions expressed are current as of the date of publication and are subject to change without notice. All investing involves risk, including the possible loss of principal. Asset allocation and diversification do not guarantee profits or protect against losses in declining markets. Past performance is not a guarantee of future results. Dovetail Financial Group LLC is a registered investment adviser. Registration does not imply a certain level of skill or training. Additional information about Dovetail Financial Group LLC, including Form ADV Part 2A and Form CRS, is available at adviserinfo.sec.gov. © 2026 Dovetail Financial Group LLC. All rights reserved.