Should You Take a Leave of Absence Before Deciding to Retire?

Ross Marino |

You may be financially ready to retire and still hesitate over making the exit permanent. Perhaps you want relief from the pace of work but do not yet know whether you will miss the role, the people, or the structure.

If your employer may allow a leave, time away can create useful evidence. But a leave is not automatically a protected trial retirement. Its value depends on what you are testing, what the pause costs, and what the documented terms allow you to do next.

What uncertainty would the leave test?

Start by naming the uncertainty. Are you tired enough that rest must come before a sound decision? Do you want to learn whether ordinary weekdays feel satisfying without work? Are you concerned about losing professional identity, regular contact, or a familiar reason to get moving?

Those are different questions. Research describes retirement adjustment as a process shaped by financial, physical, psychological, leisure, and social resources. Other research finds that leaving a work role can affect income, status, and social contact in different ways.[1][2] A difficult first week away does not prove retirement will fail. A useful test observes patterns over enough ordinary time to distinguish decompression from the life that follows.

What must be known before the leave begins?

“Leave of absence” can describe very different arrangements. Pay may continue, fall, or stop. Health coverage may continue only if you pay premiums. Retirement contributions, pension service, vesting credit, workplace-plan loans, disability coverage, and other benefits may follow separate rules. The employer, benefit administrators, plan documents, and any applicable agreement must supply the answers.[3][4]

Return rights also require precision. Certain qualifying leaves can carry specific job-restoration protections, but that does not make every personal leave protected.[5] A written right to return under defined terms is different from a manager’s friendly belief that a position should be available. Even a documented return may not preserve the identical schedule, compensation, responsibilities, or authority unless the controlling terms say so.

Make the leave produce evidence for the decision

Before leave

Protect the option

Fund the income gap. Confirm benefits, communication expectations, and documented return rights.

During leave

Test ordinary life

Notice daily structure, relationships, energy, purpose, and which parts of work you actually miss.

Decision date

Return, redesign, or retire

Use what you learned to choose the next step before the return window or other terms expire.

The leave earns its cost only when the final decision can use what the time away revealed.

How can an unstructured pause fail?

Without defined questions, a leave can become expensive waiting. You may give up income, employer contributions, service credit, or career momentum while filling the time with travel and projects that do not resemble ordinary retirement. When the return date arrives, the original uncertainty remains.

The household also absorbs the cost together. Map the paychecks that will not arrive, premiums and other benefit costs, expected spending, and any portfolio withdrawals needed during the leave. Then compare those costs with the value of preserving a credible return path. Retirement surveys repeatedly show that actual retirement timing can differ from workers’ plans, which is another reason to keep a backup path visible rather than assume the transition will unfold exactly as expected.[6]

Dovetail Principle: Important Decisions Need Room to Be Understood

Room is useful when it helps you understand the decision. A defined leave can separate temporary exhaustion from lasting readiness, while preserving a next step. An open-ended delay only pushes the uncertainty forward.

What makes the leave purposeful?

Give the leave a start date, an end date, and a decision date. Write down two or three questions you want the experience to answer. Build ordinary weeks that include household routines, relationships, community, health, and unclaimed time—not only a long vacation. Research on meaning in retirement points to meaningful engagement and identity reconstruction as real parts of the transition.[7]

Agree on how much contact with work is allowed. Frequent calls can prevent the leave from becoming a fair test; total silence may be inconsistent with the arrangement. Set the communication boundary with the employer rather than improvising it after the leave starts.

Use a leave only when it has documented terms, a funded time frame, specific questions to test, and a decision date. If the employer cannot offer a suitable return path, the cost is too high, or the pause will not answer a real uncertainty, a direct retirement decision may be clearer. The goal is not to postpone the ending. It is to reach a return, redesign, or retirement choice with better evidence.

Related Reading: Retire All at Once or in Stages? compares other ways work can change as retirement approaches.

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.

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Notes

  1. Barbosa and Monteiro, Retirement Adjustment Predictors—A Systematic Review, 2016.
  2. The Gerontologist, The Role of Life Histories in the Retirement Adjustment Process, 2015.
  3. Littler, A Guide to Employee Benefits Administration and Leaves of Absence, 2012.
  4. Electronic Code of Federal Regulations, Minimum Standards for Employee Pension Benefit Plans.
  5. U.S. Department of Labor, Fact Sheet #28I: Calculation of Leave Under the Family and Medical Leave Act.
  6. Employee Benefit Research Institute and Greenwald Research, Retirement Confidence Survey, 2026.
  7. Journal of Organizational Behavior, Retiring: Role Identity Processes in Retirement Transition, 2020.

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