TRICARE for Life Planning for Women Military Retirees and Business Owners
When women military retirees hear about TRICARE For Life (TFL), it’s often described as a healthcare benefit that “starts at age 65.” While this is technically true, focusing only on age 65 misses the most important part of the conversation.
For women military retirees—especially those who also own businesses or continue working—TRICARE For Life is one of the most valuable benefits earned through service. However, protecting this benefit requires planning years in advance. Understanding how healthcare decisions intersect with income, taxes, and employment choices is critical when planning for your future healthcare access.
In my work with military-connected women, I see the same story again and again: smart, capable retirees make reasonable decisions in their late 50s and early 60s—without realizing how those decisions can unintentionally increase Medicare costs, create coverage gaps, or limit flexibility later. With the right planning, TRICARE For Life can be a cornerstone of long-term financial security rather than a last-minute scramble.
What is TRICARE for Life?
TRICARE For Life is wraparound coverage for TRICARE-eligible beneficiaries who are entitled to Medicare Part A and enrolled in Medicare Part B. Once in place, Medicare pays first and TRICARE pays second, significantly reducing out-of-pocket healthcare costs.
TRICARE For Life has no separate premium, but it is not automatic. Enrollment in Medicare Part B—on time—is required for TFL eligibility.
Why TRICARE For Life Planning Starts Long Before Age 65
Medicare Part B Is Required—Even If You’re Still Working
This is one of the most common and costly misunderstandings I see among military retirees.
In the civilian world, individuals who are still working at age 65 and covered by an employer health plan can often delay Medicare Part B without penalty. It is important to understand that this rule generally does not apply to military retirees who want to keep TRICARE.
If you want to retain TRICARE coverage after age 65, you must enroll in Medicare Part B when first eligible—even if you are still working and covered by an employer plan that is considered creditable coverage for Medicare.
What This Means For Most Military Retirees:
TRICARE Prime and TRICARE Select end at age 65
TRICARE For Life replaces them only if Medicare Part A and Part B are in place
Employer-sponsored health insurance does not replace the Medicare requirement
Choosing to delay Medicare Part B at 65—even if you’re working—will result in suspended TRICARE coverage and loss of access to TRICARE For Life. Late enrollment penalties may also apply and can last for life. There is a narrow exception for those on active duty at age 65, but these exceptions do not apply to retired service members or individuals in civilian employment.
Medicare Part B Premiums Are an Income Planning Issue
One of the main issues when planning for TRICARE For Life, is navigating premiums. While TRICARE For Life itself has no premium, Medicare Part B does—and that premium is income-based. Higher-income retirees pay more due to Income-Related Monthly Adjustment Amounts (IRMAA).
For women military retirees and business owners in particular, income often comes from multiple sources:
Military Pension
Business or Consulting Income
Investment Income
Asset Sales or Roth Conversions
A single high-income year in your early 60s can trigger higher Medicare premiums after age 65. That’s why income management before Medicare eligibility matters so much.
Business Income Can Quietly Increase Medicare Costs
Many women military retirees continue working by choice—often through business ownership. While Business income may be uneven, with strong years followed by quieter ones, Medicare does not smooth income over time.
One profitable year driven by business growth, a buyout, poorly timed compensation, or large Roth conversions can increase Medicare premiums for multiple years. Strategic income planning—adjusting compensation, timing income, and coordinating retirement plan contributions—can help manage these costs without limiting opportunity.
TRICARE For Life Changes How You Think About Work
When women understand that TRICARE For Life can provide stable, comprehensive healthcare after 65, it often changes how they approach work and business decisions.
Healthcare planning should not be the deciding factor in whether you continue working, scale back a business, or shift into consulting or part-time roles. With TFL in place, many women find they can make decisions based on purpose, flexibility, and lifestyle—not out of fear of losing health insurance.
Healthcare Stability Enables Smarter Tax Strategies
Healthcare uncertainty is one of the biggest barriers to executing good tax planning. TRICARE For Life reduces that uncertainty.
When healthcare coverage is secure, women military retirees are often better positioned to execute Roth conversions before Required Minimum Distributions begin, draw down taxable accounts strategically, coordinate withdrawals across accounts, and avoid holding excessive cash “just in case.” In this way, TFL supports long-term tax and income planning rather than constraining it.
Women Retirees Face Unique Longevity and Caregiving Considerations
Women live longer on average and are more likely to serve as caregivers for spouses, parents, or adult children. These realities make long-term healthcare planning especially important.
TRICARE For Life can help reduce long-term healthcare cost uncertainty, survivor healthcare risk, and budget pressure during later-life transitions. When paired with thoughtful tax and income planning, TFL supports independence and flexibility over decades.
Action Steps for Women Military Retirees Approaching Age 60
If you are nearing age 60, now is the time to shift TRICARE For Life from an abstract future benefit to an intentional planning focus.
Your First Steps:
Review your income sources and tax projections for the next 5–7 years, paying close attention to years that may trigger IRMAA surcharges.
Evaluate business income and compensation strategies, especially if you expect uneven or increasing income.
Coordinate Roth conversions and asset sales with future Medicare costs in mind.
Confirm your TRICARE eligibility status and understand how your coverage will change at age 65.
Work with an advisor who understands military benefits, Medicare rules, and the realities women retirees face around caregiving, longevity, and work transitions.
The Bottom Line
For women military retirees—especially those who also own businesses—TRICARE For Life is one of the most powerful benefits earned through service. But its value depends on early, informed planning.
Understanding how Medicare enrollment rules, employer coverage, business income, and tax strategy interact well before age 65 helps ensure this benefit works for you, not against you.
Your service has already given you access to an extraordinary healthcare benefits. Thoughtful planning ensures it supports the life you’re building today and the future you’re preparing for tomorrow.