I’ve talked to a lot of early-retired people. It’s basically my job, but also, there is a steady stream of early retirees coming through Longmont. And I’ve noticed a pattern that’s remarkably consistent. Ask a retiree what they’d change and nearly every single one says some version of the same sentence.
“I wish I would have left my job sooner.”
Some even add, “I can’t believe I ever had time to work.”
Not “I wish I’d bought more index funds.” Not “I wish I’d understood tax-loss harvesting.” Just: I stayed too long. I could have walked away earlier and I didn’t.
Now, I’ll grant you, we’ve had quite the tear in the stock market recently, and a rocky market has a way of making everyone nervous about their number. But here’s the thing. This pattern was showing up in what retirees told me long before the market got twitchy, and it’s still showing up now. The volatility doesn’t change the underlying truth. It just makes it a little harder to hear.
Wait, Nobody Regrets Retiring? Really?
Okay, fine, that’s not entirely true. A couple of people I know went back to work after retiring. So let’s not pretend this is some universal, no-exceptions law of the FI universe.
One person, off the top of my head, went back because they genuinely didn’t have enough money when they pulled the plug. They were significantly short of what they needed, and looking back, I think the honest label for what they did wasn’t “retirement,” it was “a “sabbatical.” A long, well-earned break that they eventually had to end because the math wasn’t there yet.
And that distinction matters more than it sounds like it does. Retirement implies permanence. A sabbatical is just a pause with a return date you might not have picked yet. If you leave your job and your numbers aren’t solid, you’re not failing at retirement, you’re just taking a sabbatical that might need a sequel. There’s no shame in that. Don’t pretend the math worked when it didn’t and then be blindsided when reality shows up with a bill.
So yes, some people leave too early. That’s real. But it’s the exception, not the rule. The overwhelming majority of the retired folks I talk to didn’t say “I left too soon.” They said the opposite.
This Is Time You Don’t Get Back
I want you to sit with that for a second, because it’s easy to read past it. Time is the one asset you cannot refinance, reinvest, or earn back with a side hustle. You can rebuild a portfolio. You cannot rebuild a Tuesday afternoon in your 50s that you spent sitting in a status meeting instead of doing literally anything else.
This is exactly why “one more year syndrome” is such a sneaky trap. It feels responsible. It feels prudent. Surely one more year of income, one more year of contributions, one more year of padding, can only help, right? And sure, mathematically, it usually does help, at least a little. But it’s not free. You’re trading a year of your finite, non-renewable life for a marginal improvement in a number that, if you ran your projections correctly in the first place, was probably already fine.
I’m talking directly to the people who hate their job right now. Not the people who mildly tolerate it, not the people who have a boss they occasionally want to strangle but otherwise don’t mind the work. I mean the people who feel that specific, low-grade dread on Sunday night. If that’s you, and the numbers are actually working, spending an extra year there “just in case” can be genuinely soul-crushing.
I’ve had that job. The one where you watch the clock, do about an hour of work, then glance up to see 5 minutes have passed. I get it. And I also know how easy it is to keep telling yourself “just one more year” because leaving feels scary and staying feels familiar, even when familiar is miserable.
How Do You Know If the Numbers Are Actually Working?
Before we go any further, let’s address the obvious question. I keep saying “if the numbers are actually working,” but how do you know that? This is where a lot of the anxiety creeps in, and honestly, a lot of it comes from vague math instead of real math.
If your entire retirement confidence is built on a single number you saw in a calculator once, three years ago, and you’ve been mentally rounding up ever since, that’s not a plan. A real check involves running your actual expenses, not your hoped-for expenses, against a withdrawal rate you can defend. It means stress-testing against a bad sequence of returns in your first few years, since that’s historically the scenario that sinks people, not the 30-year average. It means accounting for healthcare costs before Medicare kicks in, because that line item alone has talked plenty of people back into their cubicles.
If you’ve done that work and the numbers hold up even in a rough scenario, then the “just one more year” instinct is worth questioning hard. If you haven’t done that work, then honestly, do that first. Not because you necessarily need one more year of income, but because you need one more month of clarity. Those are different problems, and they call for different solutions.
A market drop, like the ups and downs we’ve recently had, is actually a great stress test in real time. If your plan still looks reasonable after a rough few months, that’s a good sign, not a reason to panic. If it doesn’t hold up, that’s useful information too, and it’s better to learn it now, while you still have a paycheck to fall back on, than three years into retirement.
But What If You’re Still Not Sure?
Let’s say you’ve read all of the above, nodded along, and you’re still not ready to hand in your resignation letter. Maybe the market drop rattled you. Maybe your FI number feels more like a suggestion than a guarantee. That’s completely fair. Nobody should walk away from a paycheck because a blog told them to.
If you want to pad your accounts for an adjusted, more conservative scenario, there’s an option a lot of people skip right past: getting a different job. Specifically, one that’s better suited to where you actually are in your journey.
Here’s the pitch. Go to your boss and propose keeping the parts of your job you actually like, going part-time, and handing off the parts you don’t like to someone else. You get to keep a paycheck, keep your benefits in many cases, keep some structure to your week, and cut loose the 60% of your job that makes you want to scream into a pillow.
This is not a wild idea. Plenty of companies are more flexible about this than you’d expect, especially for employees who’ve already proven they’re competent and reliable. And it’s worth remembering that this isn’t just a financial move, it’s a psychological one. Fully retiring cold turkey, especially from a career you’ve spent decades building an identity around, can be a bigger adjustment than people expect. Easing into it with a part-time arrangement gives you a chance to test-drive retirement while still having somewhere to be a couple days a week. Some people love that transition period. Others find out fast that they’re ready to be fully done, which is useful information too.
Don’t overlook the benefits question here either. Depending on your employer, part-time status might still come with access to health insurance, even if the premiums shift, and that alone can be worth a lot if you’re not yet eligible for Medicare. It’s worth asking directly rather than assuming the answer is no. Some companies have minimum hour thresholds for benefits eligibility that are lower than people expect, and you won’t know until you ask.
Read the Room on How You Ask
Here’s the part people mess up, though, and it’s worth slowing down on. A lot of employers hear “can I go part-time” and translate it in their heads to “this person will either work full-time for us, or they will work part-time for us, and either is fine.” That is not usually the message you’re sending, and it’s not usually the deal on the table either.
What you actually mean is closer to “I would strongly prefer part-time, and if that’s not an option, I’m probably walking away entirely.” But your boss doesn’t automatically know that. If you frame the request too casually, you risk it landing as a low-stakes scheduling tweak instead of the meaningful negotiation it actually is.
This is where being a good employee pays off, literally. If your boss respects your work and knows you’re valuable, the calculus can change fast the moment you make it clear what the real alternative is. Nothing clarifies an employer’s priorities quite like your two weeks’ notice sitting on their desk. Suddenly the “we don’t really do part-time” policy gets a lot more negotiable when the alternative is losing you entirely and starting a six-month search for your replacement.
So if you’re going to make this pitch, make it count.
Be specific about what you’d keep. Vague requests get vague answers. Walk in with a clear list of the responsibilities you want to keep and the ones you’re proposing to hand off, and to whom.
Know your leverage before you ask. Are you hard to replace? Do you hold institutional knowledge that would be expensive to lose? Use that. Not aggressively, just honestly.
Be willing to actually leave. This is the part that gives the request its teeth. If you ask for part-time and secretly know you’d never actually quit if they say no, that’s going to come through, and employers are pretty good at sniffing out bluffs.
Put a number on it. How many hours or days do you want? “Less” is not a proposal. “Three days a week, focused on client accounts, handing off internal reporting” is a proposal.
Time it well. Right after a big win you delivered is a much better moment than right after a rough quarter for the company.
The Bigger Point
None of this is a guarantee your boss says yes. Some won’t. Some jobs genuinely can’t flex that way, and some managers won’t want to set the precedent even if they could. That’s real, and it’s frustrating.
But the bigger point stands regardless of how any individual negotiation goes. If you hate your job, and your numbers are actually working, staying an extra year “just to be safe” is a real cost, not a free insurance policy. It might be the right call for your specific situation. It might not be. But it deserves to be weighed honestly, against the actual thing you’re giving up, instead of getting a free pass just because it feels cautious.
Ask the retired people you know. Ask them what they’d change. My guess is you already know what most of them are going to say.
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