Should I quit? Here's my story:
I used to have a job where, among other things, I was a liaison between the programmers and users of a computer system. I worked in a central office with the programmers and did training and trouble-shooting for people in 14 different offices (aka "my chickadees"). When my workload doubled, that was rough, but when I got a new boss who tried hard but actually increased my workload and frustration levels more while simultaneously pushing all my buttons, I stuck it out until I had acquired one more year of service toward my pension and then I quit. I would have been eligible for a pension in three years, but quitting meant it could take up to six (depending how much state employment I got in the next three years).
I wanted a break, but one of my chickadees asked me fairly shortly thereafter to work part-time for them temporarily. Other chickadees have since jumped on the band wagon, and I ended up with full-time work for most of the next year, earning another year toward my pension. My plan is to continue working with my chickadees so long as they want me (or for the next two years, whichever comes first). I've got one half-time job ending mid April, one more at the end of May, and another chickadee who's asked me to contact him when I am next available (no guarantee, of course).
I only have to deal with my old boss once a week, but the program is in transition (they're re-building a new version from the bottom up and pressuring people to switch to it before they're even done). The programmers are good, but the new liaisons are ignorant (as expected for new people) and quite possibly don't have the brain power to ever be able to properly understand either the big picture or the details. So even my new little jobs are often quite frustrating. (Instead of just speaking plain English, we have to use special phrases to get any respect such as "data integrity issue" and a new one I just learned, "I don't feel comfortable going live without that feature.") On the other hand, I love that I am able to stick around and help push to make the new system better from the outside, which will help all my chickadees not to mention the thousands of end users. My longer-term goal is to never have to work for money again.
As a person in a (previously) stable job (the latest recession brought layoffs) with a pension that would cover my post-retirement expenses, I've been not too worried about having funds to cover unemployment or early retirement. (Yes, punch-worthy.) But I did buy a small house and pay it off. (Not quite as exciting as it sounds--I live in a state with high property taxes.) I've been maxing out a Roth IRA ever since they were invented. (That money is in index funds). A couple of years ago, I also started buying growth dividend stocks. And a few months before I quit, I finally started saving toward an early retirement fund to cover the years before I can collect my pension.
So now I have 5.5 months of expenses saved. I'll have a couple more months worth saved at the end of May, not nearly enough to cover the remaining 3.5 pre-pension years. My dividends are up to an average of $18.78/month; that's not helping much. And 4% of my IRA is $350. Better, but, well, my expenses are $1663/month, though I'm cutting out the ballroom dance classes ($70 every five weeks) and dance club membership ($100/year), so that should help slightly, depending on what I do instead.
Here's the interesting part. With a Roth IRA, you're allowed to withdraw the amount you deposited (not the extra value that has been gained) at any time, even if you're not yet old. That 57K amounts to 34 months of expenses. I could be done working forever. (Assuming nothing crazy happens like my country gets so berserk that if I'm lucky, I escape with my life and start over with nothing.)
So, option A is to quit when the chickadees stop offering me jobs and never work again. This idea makes me very happy.
Option B is to look for just over 1.5 more years of work for the state, which would mean I could keep adding to my IRA instead of draining it, increase the pay of my pension (by at least $190/month forever), and, if the work is full-time, keep making the big contributions to charity I like to make and maybe increase my renovation fund a bit more (I'd really like a dishwasher and covered parking and a separate laundry room so I can move the washer out of my kitchen and the drying rack out of my bedroom).
The other work would probably be some kind of clerical thing. And I would take classes to be able to do bookkeeping which is in pretty high demand at my current employer (because the pay is so low).
So is it stupider to drag out my unhappiness just for piles of money, or is it stupider to risk my future financial security by cutting things so close? As is, my pension should pay $2088 gross (plus free health insurance). My guess is that would leave $1896 after taxes. And an article I read implies that, because pensions don't keep up well with inflation, this is the equivalent of getting $1340 in today's dollars indefinitely. Subtracting my current $199/mo insurance brings my expenses to $1463. Subtracting dividends = $1443, subtracting 4% of my remaining IRA ($171) would be $1272. So that's less than $1340. But health expenses cost more when you get old, plus at age 65 I have to start buying some Medicare thing and my pension insurance becomes just supplemental, so that's more even if I don't have health problems. And pension rules can change.
I'm extremely risk averse (love having a nice cushion) and really, seriously think I might never work for pay again. sure, it's possible that the math book I'm planning to write will be publishable. And it's possible that the math tutoring I want to do at the local middle school will lead to creating some kind of saleable materials, but I really can't imagine anything else coming up. So it's quite possible that the inflation hedges MMM talks about won't apply.
I'm pretty sure I want to just quit. Draining my IRA sounds bad, but that's what it's for, right? (Another weird thing is that being ready to quit improves my negotiating skills. Because I really do want to walk away in some cases, no matter how loveable the chickadee.)