Our “One More Year” Syndrome Turned Into Five: How to Actually Pull The Trigger on RE

The FIRE community has a name for the invisible force that keeps people tethered to their desks long after the math says they’re free. We call it “One More Year” (OMY) syndrome.

It starts innocently enough. You hit your FIRE number—that magical figure where your investments should theoretically support your lifestyle forever. But instead of celebrating, you hear a whisper: “One more year wouldn’t hurt. Just to be safe.”

That whisper is seductive. One more year adds a buffer. One more year lets you upgrade your lifestyle projections. One more year buys peace of mind.

For us, one more year turned into five.

We reached our “minimum FIRE number” in 2021. We had the spreadsheets, the withdrawal strategy, the portfolio allocation. Everything was ready. But we kept finding reasons to stay. The market was volatile. Inflation was surging. Healthcare was uncertain. Just one more year.

Five years later, we finally pulled the trigger in early 2026. Looking back, we realize that OMY syndrome wasn’t about the money at all. It was about fear, identity, and the terrifying leap into the unknown.

Here’s what we learned about why we stayed—and how we finally broke free.

Part 1: What One More Year Syndrome Actually Feels Like

If you’ve never experienced OMY syndrome, you might imagine it as a rational calculation: you run the numbers, realize another year of income would increase your margin of safety, and make a logical decision to delay.

That’s not how it feels.

In reality, OMY syndrome is a fog. It’s the feeling of reaching your goal and feeling… nothing. No fireworks. No celebration. Just the quiet hum of “okay, what’s next?”

One early retiree on the Early Retirement forum described it perfectly: “I’ve basically reached the minimum number I was aiming for… and I’m not particularly excited. No fireworks. No big emotional payoff. Just… okay.”

That’s the trap. When the goal you’ve been chasing for a decade finally arrives, it doesn’t feel like a finish line. It feels like a plateau. And when you’re standing on a plateau, the easiest thing to do is keep walking toward the next hill.

The mental math of OMY works like this:

At your current FIRE number, you have a 95% success rate in retirement calculators.
One more year of work adds a significant cushion to your portfolio.
With that cushion, your success rate climbs to 99%.
Why wouldn’t you work one more year to eliminate that remaining 5% of risk?

But here’s the problem: the goalpost moves. Next year, that 99% success rate will feel insufficient, and you’ll convince yourself that one more year can get you to 100%.

This is what forum user Fru-Gal identified as the core illusion: “Money is potentially infinite but our time is not. The nice thing about pulling the plug for FIRE is you gradually erase that illusion that you have an infinite supply of money available to you if you keep your job. Eventually, pretending that life is infinite becomes completely unpalatable. At that point, you are free.”

Part 2: Why We Stayed—The Five Hidden Reasons

For us, OMY syndrome wasn’t a single decision. It was a series of justifications that accreted over five years. Looking back, we can identify five distinct forces that kept us working.

1. The Safety Margin Mirage

Every year we worked, our portfolio grew. Every year, we told ourselves we were just adding “a little more safety.”

But what is “safe enough”? The forum user GuitarStv captured this perfectly: “I think the problem is that the appropriate safety margin is always going to be a bit of a guess. So once you achieve a given safety margin, it’s easy to question if that was really an appropriate safety margin that covers enough potential negatives.”

In 2026, Morningstar’s research suggests that even a 3.9% withdrawal rate carries a 10% failure rate over 30 years. That 10% failure rate becomes the hook. If there’s any chance of failure, why not eliminate it?

But here’s what we didn’t understand: there’s no such thing as 100% certainty. The market could always do something unprecedented. A health crisis could always emerge. The question isn’t whether you can eliminate all risk—it’s whether you have enough to live a good life while managing the risks that remain.

2. The Identity Trap

We spent two decades as “successful professionals.” Our identities were wrapped up in our titles, our accomplishments, and the respect of our peers.

The thought of giving that up was terrifying. Who would we be without our jobs? What would we say when someone asked “What do you do?”

One early retiree, Gwendolyn Merz, discovered this after leaving her job: she felt unmoored without the structure and identity her career provided. She returned to work nine months later—not because she needed the money, but because she needed the anchor.

We realized that OMY syndrome was, for us, a way to postpone answering the question: Who am I when I’m not what I do?

3. The “Just One More Thing” Mentality

Each year brought a new “one more thing” we wanted to accomplish before leaving.

Year 1: Let’s wait until the youngest finishes college.
Year 2: Let’s pay off the mortgage completely.
Year 3: Let’s build up a cash cushion for a major renovation.
Year 4: Let’s wait for the market to stabilize.
Year 5: Let’s see how the new administration’s policies affect healthcare.

These were all real considerations, not excuses. But they were also endless. There’s always one more financial milestone, one more home project, one more market uncertainty. The list never ends unless you decide it does.

4. The Sequence-of-Returns Fear

The 2022 bear market hit just as we were considering retirement. Watching our portfolio drop 20% in a single year was a gut punch. And it reinforced every fear we had about early retirement.

Morningstar’s research confirms that this fear is rational. Of the retirement plans that fail, nearly 70% fail because they experienced losses in the first five years. The sequence of returns—not the average return—is what determines success.

We used this research to justify staying. If the first five years are the most dangerous, we reasoned, we should work through the dangerous years and retire when the coast was clear.

But the market doesn’t cooperate with timelines. The “dangerous years” don’t come with warning labels. You can’t wait them out—you have to build a portfolio and withdrawal strategy that can survive them.

5. The “What If” Spiral

The final force was the most insidious: the endless loop of “what ifs.”

What if inflation stays at 4% for the next decade?
What if healthcare costs double?
What if one of us gets sick?
What if the market goes sideways for ten years?

Each “what if” demanded its own financial buffer. And each buffer required more years of work. We were trying to insulate ourselves against every possible downside, which is impossible—and a recipe for working forever.

Part 3: How We Finally Pulled the Trigger

The shift didn’t come from finding more money or running better simulations. It came from changing how we thought about retirement.

1. We Separated “Enough” from “More”

We had to confront the fact that “enough” was a moving target. Every year, we raised our FIRE number to match our growing anxiety.

The solution was to define “enough” concretely—not as a number, but as a set of conditions:

Our essential expenses covered by a 3.5% withdrawal rate
A separate healthcare buffer of $50,000
A paid-off mortgage
Two years of expenses in cash to buffer sequence-of-returns risk

Once those conditions were met, we agreed: enough is enough.

This approach aligns with the new FIRE philosophy emerging in 2026, where the focus shifts from “retire as early as possible” to achieving financial independence with flexibility and lifestyle balance.

2. We Faced the “What Ifs” with Specific Answers

Instead of letting “what ifs” spiral into vague anxiety, we forced ourselves to write specific answers.

What If	Our Answer
Market drops 30% in year one	We have two years of cash; we won’t sell stocks until the market recovers
Healthcare costs double	We built a 20% buffer into our healthcare budget and will use ACA subsidies strategically
Inflation stays high	Our portfolio includes TIPS and I-bonds; we’ll use a variable withdrawal strategy
One of us gets sick	We have long-term care insurance and family support

Writing these answers didn’t eliminate risk, but it made the risks manageable. As one forum user noted: “When you look at how people ‘fail’ at retirement in real life, it’s not running out of money that gets people. It’s all the non-numerical quality of life things like health, personal relationships, etc. Stuff that more zeroes in the investment account doesn’t solve.”

3. We Built a “Retirement On-Ramp” Instead of a Cliff

One of our biggest fears was the abrupt transition from full-time work to full-time nothing. So we built a ramp.

Year 1 (Transition): We dropped to 4 days a week. Used Fridays to explore hobbies and volunteer.
Year 2: Dropped to 3 days a week. Started consulting in our field to maintain identity and income.
Year 3: Stopped full-time work entirely, but maintained consulting and freelance projects.
Year 4: Wound down consulting to one day a week.
Year 5: Stopped all paid work.

This gradual transition is supported by retirement planning research. A survey by Sun Life found that 69% of workers who delay retirement do so for positive reasons: pursuing purpose, maintaining social connections, and staying mentally active. Building an on-ramp allows you to keep those benefits while stepping away from the pressure of full-time work.

4. We Tested Our Lifestyle Before Committing

We didn’t want to discover that retirement wasn’t what we expected after we’d already quit. So we tested it.

We took a six-month sabbatical in year 3 of our transition. We lived exactly as we planned to in retirement: no work, travel, hobbies, unstructured time.

The results were revealing:

We loved the freedom—but we also discovered we needed some structure.
We enjoyed travel—but we didn’t want to travel constantly.
We valued our social connections—but many friends were still working, so we needed to build new communities.

The sabbatical allowed us to refine our retirement plan before committing permanently. It also answered the question raised by forum user RedmondStash: “If you’re falling to OMY syndrome, maybe you’re just not ready to take the leap yet. There’s nothing wrong with taking your time to be sure it’s what you really want.”

5. We Calculated Regret, Not Just Risk

The final shift was moving from a “risk minimization” mindset to a “regret minimization” mindset.

We asked ourselves: What would we regret more?

Working five more years and having too much money, or retiring now and having to make modest adjustments if markets underperform?
Missing the chance to travel while we were healthy and mobile?
Losing years with aging parents and growing children?

When we framed the decision as regret minimization, the calculus changed. The forum user Fru-Gal captured this perfectly: “The 3 most helpful things in terms of me finally quitting were: 1) Regret minimization, 2) Stories of people who FIRE’d very long ago and weathered all sorts of supposedly catastrophic events and were perfectly fine, and 3) People who said they only wished they had FIRE’d earlier.”

We never met anyone who said “I wish I’d worked five more years.” We met plenty who said “I wish I’d left sooner.”

Part 4: The 2026 Reality Check

Our final decision to pull the trigger in early 2026 was shaped by the current economic environment.

The Withdrawal Rate Reality

Morningstar’s 2025 research (released December 2025) found that for someone retiring in 2026, the highest safe withdrawal rate for a stable, inflation-adjusted paycheck over 30 years is 3.9%—and that still carries a 10% failure rate.

We built our plan around a 3.5% withdrawal rate, which provides a buffer below Morningstar’s base case. We also adopted a dynamic withdrawal strategy: in years when the market is down, we reduce spending; in years when it’s up, we allow ourselves more flexibility.

The Healthcare Plan

Healthcare was our biggest uncertainty. We’re retiring before Medicare eligibility, so we’re relying on the ACA marketplace. In 2026, we’re using a Silver plan with cost-sharing reductions, managing our MAGI to stay in the subsidy sweet spot.

We also set aside a separate $50,000 healthcare buffer—not part of our FIRE number—to cover unexpected medical expenses or premium spikes.

The Inflation Hedge

With inflation concerns persisting, we diversified our portfolio to include:

TIPS (Treasury Inflation-Protected Securities)
I-Bonds
International equities (which trade at lower valuations than US stocks)
A cash buffer of two years of expenses

This “all-weather” approach helps us sleep at night regardless of what inflation does.

Part 5: How to Know If You’re Ready

If you’re stuck in OMY syndrome, here’s the checklist we use to evaluate whether you’re ready to pull the trigger.

The Financial Checklist

Your withdrawal rate is 4% or lower (3.5% for conservative planners)
You’ve stress-tested your portfolio against 2008-style declines
You have a healthcare plan (ACA, spouse’s insurance, or private)
You have 1-2 years of expenses in cash to buffer sequence-of-returns risk
You’ve modeled your plan using a tool like ProjectionLab or Boldin (formerly NewRetirement)

The Lifestyle Checklist

You’ve taken a sabbatical or extended time off to test retirement life
You have a list of activities, hobbies, or projects you’re excited to pursue
You’ve built or identified a community of non-working friends
You’ve discussed the transition with your partner and aligned on expectations
You’re comfortable with the answer to “What do you do?”

The Psychological Checklist

You’ve defined “enough” concretely—and your portfolio meets it
You’ve moved from “risk minimization” to “regret minimization”
You’ve accepted that you can’t eliminate all uncertainty
You’ve read stories of people who FIRE’d earlier and wish they’d done it sooner
You’re more excited about what you’re retiring to than what you’re retiring from

Conclusion: The Leap Is Worth It

One more year syndrome kept us working for five years beyond our FIRE date. In hindsight, those years weren’t wasted—we saved more, we transitioned gradually, and we built confidence.

But they also cost us. Five years of waking up to an alarm. Five years of missed weekdays with family. Five years of deferred dreams.

If you’re stuck in OMY syndrome, here’s what we want you to know: the leap is terrifying. It will feel like jumping off a cliff. Your brain will generate a thousand reasons to wait one more year.

But on the other side of that leap is a life you designed, not one that was assigned to you. Time to pursue what matters. Freedom to say yes to opportunities you never had time for. And the quiet satisfaction of knowing you did what most people only dream about.

As one forum user put it: “The thing is, money is potentially infinite but our time is not. The nice thing about pulling the plug for FIRE is you gradually erase that illusion that you have an infinite supply of money available to you if you keep your job. Eventually, pretending that life is infinite becomes completely unpalatable. At that point, you are free.”

We’re finally free. And we wish we’d done it sooner.

Action Steps to Break Free from OMY Syndrome

Define your “enough” concretely. Write down the specific conditions that would make you comfortable retiring.
Take a sabbatical. Test retirement before committing permanently. Even 3-6 months can reveal what you love—and what you need to adjust.
Build your retirement on-ramp. Consider a gradual transition: reduced hours, consulting, or freelancing before full retirement.
Run a regret minimization exercise. Ask yourself: What will I regret more—leaving early or staying too long?
Find your community. Connect with others who have successfully FIRE’d. Their stories can give you the confidence to take the leap.

ProjectionLab and Boldin are excellent tools for modeling withdrawal strategies and stress-testing your FIRE number against sequence-of-returns risk.

If you’re struggling with the decision, a fee-only financial planner can provide an objective perspective. The XY Planning Network specializes in planners who work with FIRE clients.

Disclaimer:This article is for informational and educational purposes only. It does not constitute personalized investment, tax, or financial advice. Your personal circumstances, risk tolerance, and goals may require a different strategy. Past performance is not indicative of future results. Investing involves risk, including the potential loss of principal. Please consult with a qualified financial professional before making any investment decisions. We may receive compensation through affiliate links.