Thanks so much for sharing your experience. This scenario has so many parallels to mine. Financially, I'm in a good position as well, maybe not quite as flexible as I have a wife and a few pets - but also no kids. My wife and I live a very humble lifestyle that has us on track to pay off our house in just a few more years time, and we have zero debt outside of that. We also have a good sized nest egg that would allow me to go without income for at least half a year, maybe more (health insurance being the big variable). I'm a super risk-adverse person, so the idea of resigning and moving on without something else lined up definitely scares me. But I'm starting to think that might be what I should do. I know a few months off would do me really good mentally.
My dream would be able to work for myself or in a very small business after years of working in a huge corporation. Problem is I don't really have the connections to make that happen. Part of me wonders if just pulling the plug and putting my back against the wall is the best way to make that happen though.
Health insurance was a big one for me and although I'm relatively healthy, that public educator health insurance was sweeeeeeet. I did some research on the health insurance market place as a part of my decision making process, so I factored in that monthly cost to my living expenses. Definitely more money then I've ever paid for health insurance before, but not totally out of control.
"Risk" isn't really a word I dealt with prior to this. I typically get the same thing every time I go to restaurants because I don't want to risk not liking something, especially when I'm hungry. I talked to a lot of people before I made the jump mostly because I was waiting for anyone to talk me out of it. I got a lot of "You have to do it" and "I'm just pissed I can't do it". They made the risk less terrifying, but the "floor" I have is still a very nice spot and that is why I pulled the trigger.
The mental break I've had over the past three months has been great. I had a 90 hold on my contract once I put in my notice, but I ended up taking vacation for more than half of the days that I was supposed to be working. Today is the one week anniversary of my last "official day" as an employee, but it was also like my 20th vacation day in a row. Over that time I spread out my time working on setting up my business, making materials, and putting together my website, but also just sitting on the beach and reading. I knew I'd be bored eventually, but it is a change in mindset from "Accomplish task, next problem, accomplish task, next problem..." and I'm still working on that change.
As an educator at heart, I'm a big fan of helping people figure out their "why" and then helping them get to a spot that fulfills their "why". I think the perspective of "everyone has to go to college and get a degree to get a good job" is a bunch of garbage. I'd rather people find out what makes them happy and the "why" behind it, then figure out the skills and experiences necessary to fulfill that "why". Life is too short to spend it doing something you don't want to do every day.
There were many days where I'd be in my parking spot just sitting in my car because I didn't want to go in. Eventually my secretary would send me a text and be like "coming inside today?" and I'd regularly want to say no. Eventually, some people are going to get to the point where they do say no and I'm all for it.
I know you had asked in a post about approaching management with the "I don't really like this" issue. To me, good management is supposed to be getting the best out of their resources and people are their greatest resource. Some places of business are really only focused on the bottom line, which can make management not respond well to those types of conversations. If they see any move as a negative investment, they'd rather just let the person go. Luckily, in the world of education I didn't really "sell" a product and as long as my department didn't go over our set budget then I wasn't impacting a bottom line anywhere. That made my conversation a little bit easier.
"I can no longer mentally or physically do this position. I'd love to hear any ideas you have about how to make this work or if there are other directions we can go, but I'm not going to be able to stay here with the current circumstances."
I know that my Superintendent was a big fan of me and as he liked to say I was "value added" to any situation I was in. He told me to come up with some ideas that I would be okay with to stay. I gave him four plans the week after, including me staying in the current position I was in but hiring a specific Network/IT specific person down to going back to a teaching position. Two days after that we got shut down for Covid, which led to three of the most insane weeks of my life. After that, I said "Now there is only one plan. I don't want the title of Director anywhere near me. If someone else isn't in that position by August, I quit." They were incredibly supportive and basically gave me everything I asked for, which is crazy because I'd never imagined I'd be in a place to make demands. Almost made me feel bad leaving a year later anyways. Almost.
The conversation can be difficult, but I think when it is approached from the perspective of "I'm no longer able to be productive in this position" combined with "I'm looking for help", then it opens that door to work with them first to see if there is something that can be done there. If the conversation doesn't happen, then those paths can't be explored. I explored a path, still didn't work for me, so I packed it in. I was at "I'm either dealing with this stuff for the next 23 years of my life or I take the chance now.", so I typed my resignation letter and kept a copy with me that just needed to be signed and dated. Eventually the moment hits you when you just pull it out, sign it, and hand it in.
Good luck figuring out what works best for you. Not sure I'm a shining example or a paragon of making major life decisions, but I'll be here if you want to bounce anything off of me. I mean, what else am I going to be doing anyways?
