<prompt> Human: Posting from a throwaway of course, and I am likely going to ramble, so thanks for reading this.They say money isnt everything. They say the last thing you want to do is have a bunch of regrets on your death bed - I shouldnt have done this, I wish I had done this, I should have taken this chance or that chance, I wish I didnt spend my entire working career doing something I hate,. If you love what you do youll never work a day in your life. And so on.I am in a really bad, dark, place right now, and have been for a while. Insomnia, clinical depression, major anxiety, major worrying. All the time. I am consumed by it. Some of it is due to personalfamily reasons which I will not go into here but the majority of it is due to my job. At this rate, my job is literally going to kill me before I am 50 - heart attack, stroke, etc. That is, it will kill me if theres even a job to have. There is a complete political shift coming in two months, resulting in yet another management change, not even a year after the last one. And from what I can tell, major financial problems are on the horizon within the next 12-24 months. I literally am a department of one doing what other places of similar size have at least a staff of 4 doing. My responsibilities have increased to the point where I am so overwhelmed Im starting to make mistakes. Plus, it is dead-end - there is one place to move up and it would be even more stressful in that position - I have no aspiration to strive for it.I always worry about things. I always take everything personally. I always think the worst is going to happen, and a lot of the time it does. I do these things to a fault, but I cant seem to change my way of thinking while still there. I am in therapy and have been for a few years. I recently saw a psychiatrist to try and find me an anti-depressant that doesnt nail me with side-effects - we will see if that helps as well.I despise my job. I hate it. I barely get myself out of bed to go. Even on good days where I try to be positive, more and more is unloaded onto my plate. Things go on the plate at twice the rate they come off. I am very concerned with my health if I continue as I am. I have lost 27 pounds in the last 9 months despite not exercising or changing my eating habits at all. All physicals and blood tests have returned normal, yet the weight continues to come off. I have no energy due to depression, stress, and lack of sleep - even with Lunesta I am up in 3 hours and tossing and turning and worrying the rest of each night. I have dropped most of my interests and hobbies. I dont have the drive, desire, or anything to pursue them. I am everything but suicidal.Some further backstory - I landed into this job close to 20 years ago and figured Id take a chance and see if I liked it. Soon thereafter my spouse was diagnosed with malignant cancer, which came back several times over the next decade plus. From that point on I basically did everything I could to keep that job for the insurance. It wasnt really a bad or stressful job the first many years, but I didnt ever have the opportunity to decide what I wanted to do when I grew up. My spouse passed away a few years ago. We were fortunate to have life insurance in place before they were uninsurable, plus there were a few group policies through work. But now here I am in my 40s, absolutely miserable at work, and fully aware first-hand at how short life can be - as I said at the beginning - I dont want to to regret wasting away at this job and dying early from the depressionstresshopelessness that it brings. The job market in this field is all but dried up, and the jobs available either require advanced degrees I do not have, or are for much less pay. As you can see above and below, the less pay wouldnt be a deal killer if the stress levels were lower and future looked better, but accepting a lower paying job would mean I would have to find a job making what I do now or get out of government in approximately 5 years. The pension amount is based on the highest 48 consecutive months earnings in the last 10 years. Too big of a paycut for longer than 5-6 years screwing my lifelong pension.So heres some details-Thankfully I have transitioned to a lifestyle that is not obsessed with stuff. I dont need the latest and greatest anything. Everything I spend money on is a consumable now - very little in terms of anything else. I have been saving nearly half of my income the past two years. 44 years oldsingle but in a relationship - we are happy together, but neither of us want to marry anytime soon. We live separately, but we spend a lot of time together ... weekends, and a few nights a week. Although she says otherwise, my state as of late has her deeply concerned. only degree is an AA in MarketingHouse - no mortgage. Its currently worth approximately 200K, about 40K less than purchase price.2013 Car - 50K miles, 40mpg, no loanNo credit card, student loan, or any other type of debt 50K in Emergency funds General savings taxable fundsApproximately 60K- half in online savings accts, half in a brokerage accountRetirementOther457 deferred comp account no penalty to withdraw under age 59- just income taxes - 40KRoth IRA - 25K 21K in contributionsI am fully vested in a municipal pension plan. If I never worked there another day, the monthly pension at age 55 will be 1450 increasing about 50 per year thereafter, for life. If I wait until 62 it is about 2700 per month increasing about 70 per year for life.I receive an annuity for life from my spouses pension. It will not increase so eventually inflation will eat away at it. After tax withholding it is 510 per month. It is currently funding my Roth IRA.So heres what I have figured out so far:Property taxes, house, car, umbrella, and dental insurance expenses are pretty much exactly what the annuity is.Other expenses - utilities, cell phone, internet, netflix, estimated fuel costs for 1,000 miles a month which is likely overkill, foodgroceries, and 200 misc come to about 1,200 per month.A big missing factor above is healthcare. COBRA would be approx. 600 per month. Ive begun looking at the ACA marketplace as well, which would have lower monthly premiums, but higher deductibles.Sooo...I am giving serious thought to resigning my position and focusing on getting me healthy again. To put myself first. I havent really had the opportunity to do that for the majority of my adult life. To really decompress from especially the last 2 years, where I lost my spouse, a pet, my mother, and a dear co-worker and friend. I do not have another job lined up. I would like to take some time to accomplish the following things: the house still needs to be purged for lack of a better term- of a lot of stuff that we accumulated over the years my spouse was sick. Not a hoard, and mostly contained to the garage and basement, but a stress-builder nonetheless. Our therapy, especially my spouse, was to buy buy buy stuff stuff stuff to feel better. Of course, that meant huge credit card bills, but we wisened up at the end and were credit card debt free at the time of death. But there is a lot of cleaning up I need to do. 20 years worth. In doing so I believe I would be removing a stress.Id like to do some traveling. Go see my father who has been across the country for 16 years and whom I have only seen a handful of times the last few months of my mothers life. Several months ago, my girlfriend and I booked and paid for a cruise for us and her children, which is in July. Id like to increase my volunteering. I rarely do any due to my mentalphysical state of exhaustion. I would like to increase my volunteering at an animal shelter and also at the Hospice Center that provided care for my wife. While I would do any volunteer work they ask, I would try to offer help in something I am experienced in - finance, HR, IT.Get back to the exercise. I know it is good for mental stability, but again I am so far down a hole I have no energy to do so.Id like to learn new skills or vastly improve on those I have and that interest me. I have about 6 Udemy courses I paid for ages ago and have never looked at. They range from Photoshop Lightroom, Photography, iphone app development, web development, etc. Id like to sit down with a career counselor either at my community college or elsewhere, and discuss a career change- perhaps take some networking and A certification classes, or pursue a degree in the IT field.I can freelance some of my skills - basic web design, computer repairs, etc. I have been the tech support for family and friends for years.I do not want to sit on the couch.The big question...Am I crazy for even thinking about this? I do not want to just apply for every job where I be qualified for the sake of having one, especially since that July cruise is something I have been highly highly looking forward to. Would my plans above volunteering, learningimproving skills, education be enough to cover a resume gap?I figure I am not getting any younger so if I were to do something like this there is no better time than the present. As you see from my financial situation, I am not going to be on the streets in a month or two, or even a year or two from now. I know my retirement fund building would be taking a major hit, but at this rate I would never reach an age to spend a dime of it. edited to add- would taking a part-time job of any sort just for some income hurt my resume worse than a gap??tl;dr - My job is killing me. I have enough financial cushion to resign before it does. I want to do something different with the remainder of my one and only life. Am I stupid?Thanks for reading, if you did - geez I have diarrhea of the fingers.  <response>: This hits REALLY close to home for me. I am in a eerily similar situation, just 5 years behind you. I am miserable, hate my job and am extremely depressed. However you are in a much better financial situation than I am. Reading your post I had one thought. Get out. If I had your financial situation I would gone from here so fast I would leave a puff of smoke behind me like Wiley Coyote. If your municipal retirement is like mine, you get credits for service years as well, and it transfers to other municipal jobs like working for the city as a street cleaner, etc. Can you make up for some of the pay decrease by finding a much lower stress municipal job, or would it cut your pension less to have your last 48 months be at your current pay rate? Either way, I really feel for you. If you dont already, check out MrMoneyMustache, he lives off his Vanguard investments. You may be able to work 6 more months, sock away a sizable cash hoard and increase your income through an investment plan. I found MMM and turned my financials around so that I could get out of hear debt free and ready to enjoy my life more. Internet stranger hug to you sir. 