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Retirement Timing: How to Know When You're Actually Ready

| May 07, 2026

For many University of Maine faculty and staff, the question isn’t “Can I retire?”; it’s “Why don’t I quite feel ready to retire yet?”

You might have:

  • Reached the age and years of service that technically qualify you to retire
  • Built a healthy retirement account balance
  • Considered health care options and associated costs
  • Dreamt of how you’d spend your day-to-day in retirement

And yet something still feels uncertain. 

That uncertainty is normal, and it does not necessarily mean the timing is wrong. It usually means you have not yet mapped out all the pieces. And truth be told, there are so many moving pieces to consider before taking the retirement plunge. Your finances are only part of the picture!

This post walks through the specific guardrails you can use to determine retirement readiness, both financial and personal, that indicate you may be genuinely ready to make the transition. Think of it as a practical framework, not a pass-fail checklist.

The Financial Checklist: What the Numbers Need to Show

No single number tells you whether you are ready to retire. Instead, your retirement decision should be a zoomed-out view of several different factors that impact your finances in the near and long term. Let’s take a look at a few items we review with clients before they decide to make the transition to retirement:

Sustainable withdrawal rate. A widely referenced starting point is whether your portfolio is large enough to support a 4% annual withdrawal without depleting your savings prematurely over a 25-to-30-year retirement.. If you cannot fund your projected annual expenses at that rate, it may indicate you need more runway. If you work for the University, you might consider a partial retirement or delaying your retirement by a few more years.

Income gap analysis. Map your guaranteed income sources against your projected monthly expenses. Guaranteed sources might include Social Security benefits, income from a TIAA annuity, or any other fixed income stream. If those sources cover your essential expenses, your portfolio is available to fund the rest, which is a much more comfortable position than relying solely on portfolio withdrawals.

Healthcare bridge. Do you have a funded plan to cover insurance premiums and out-of-pocket healthcare costs from your retirement date through Medicare eligibility at 65? 

For many early retirees, healthcare costs in this during this window can run into the tens of thousands of dollars per year. You will want to explore options, including COBRA continuation coverage, marketplace plans under the Affordable Care Act (ACA), and spousal coverage, if applicable. For more on this, see our post on healthcare coverage options during the transition to Medicare. 

Debt and liquidity. Are high-interest obligations resolved, or at least well-managed? Do you have a cash reserve covering 12 to 24 months of living expenses? A liquidity buffer matters because it protects you from being forced to sell investments during a market downturn in the early years of retirement, which is one of the most damaging things that can happen to a long-term financial plan.

Retirement Timing: A Real-World Example

Margaret is a 63-year-old associate professor at the University of Maine in Orono. She has done almost everything right. She has consistently contributed to her 403(b); her TIAA balance is strong, and she feels ready to step away within the next year or two.

Her assumption was that since the numbers look good, the timing should work, and she could make an appointment with her Dean to make retirement arrangements.

When she sat down to map it out more carefully, one key piece changed her retirement roadmap:

Healthcare.

Margaret had planned to retire at 62. What she had not fully accounted for was the cost of covering her own insurance until age 65. Based on her income level and coverage needs, that gap came out to roughly $24,000 to $30,000 per year.

Once that cost was factored in, the question was no longer "Can I retire?" It became "Hold on, can I afford to cover these costs for 3 years until my university insurance kicks in, and still enjoy my retirement lifestyle?”

After working through the full sequence of income, benefits, and expenses, Margaret adjusted her plan. Instead of retiring at 62, she chose to retire at 64 with a clear, funded strategy for the remaining gap year.

Different timing. Much higher confidence.

The goal is not to delay retirement unnecessarily. It’s to make sure the decision holds up once all the moving pieces are accounted for.

The Benefit Timing Piece: What University of Maine Employees Need to Confirm

Beyond the portfolio math, there are university-specific and federal benefit details worth confirming before you finalize a retirement date.

Years of service and age thresholds. Verify the specific age and service requirements for any university retirement benefit eligibility. These thresholds affect when you qualify for certain benefits, and missing a threshold by a few months can have lasting consequences.

TIAA distribution options. Your 403(b) retirement plan gives you several ways to take income: 

  • Lump sum withdrawals
  • Annuity payments that provide a guaranteed income stream
  • Systematic withdrawals that let you control the pace (like fixed-period payouts)
  • A combination of the above

Each approach has different tax implications and longevity considerations. Understanding your options before you retire, rather than deciding under pressure afterward, puts you in a much stronger position. 

Social Security timing. Pull your Social Security earnings record at SSA.gov and run the claiming scenarios. Claiming at 62 permanently reduces your benefit. Waiting until your full retirement age (67 for those born after 1960) or delaying to 70 increases it meaningfully. For University of Maine faculty and staff, who pay into Social Security through FICA taxes, this is a significant lifetime income decision. 

The Non-Financial Questions That Matter, Too

Beyond the numbers, consider your sense of purpose and structure post-retirement, alignment with your spouse or partner, and whether you’re retiring towards something meaningful. For faculty who value academic community, phased retirement options may offer a smoother transition.

Questions Worth Asking Before You Decide

  • Can I cover 12 months of living expenses without touching my investment accounts?
  • Do I have a concrete, funded plan for healthcare coverage through age 65?
  • Have I modeled what my finances look like if I live to age 90?
  • Do I know my Social Security break-even age, and have I compared claiming scenarios?
  • Have I sat down with a financial advisor who understands University of Maine benefits to review the full picture?

If most of those answers are clear, you are likely in a strong position. If they feel murky, take more time to map out the details. 

Putting It Together

Retirement readiness comes from working through interconnected questions: your financial runway, healthcare bridge, benefit timing, and personal readiness. For University of Maine faculty and staff, the benefit-specific details make it worth working through carefully with someone who understands these systems. 

Ready to Work Through the Details?

A retirement readiness review is not a one-size-fits-all process. It is a conversation about your specific benefits, your timeline, and what you want retirement to actually look like. If you are within five years of a potential retirement date, now is the right time to start. Reach out to schedule a consultation with our team here! We can’t wait to hear from you.