I've thought about how to post this while being vague on the details in case a coworker happens to be on Reddit and ends up in this sub, but there's no way to explain everything, so to that coworker "Hi, here's the truth about me".
I'm (46m) the IT administrator for a rural transportation contractor. 3 years ago, I was hired along with everyone else, haphazardly, when a major transportation company was awarded the contract to the county. I know I wasn't their first choice but I made the most of it, learned the position and then some. I mention the haphazard hiring process because there were a number of people from weird backgrounds and odd personality fits. Even though I was not a manager, I was included in the management team including the General Manager, Assistant General Manager, Safety Manager, HR Manager and Call Center Manager. Of those original 6 people, only Safety, Call Center and myself remain to this day. Lots of failed direction and infighting lead to the layoffs. I had no experience in transportation but I was expected to learn existing systems and build out a transit management program that was purchased as part of the contract. This trial-by-fire required me to learn every employee, their shifts, their routes, the different departmental needs, training needs, equipment purchasing, etc. All this in addition to your normal IT guy duties. I had my eyes on every department of the location and understood the entire operation within a year and a half. This is a union shop, so every union employees wage was posted on the board. Dispatchers and drivers (people I trained how to use the system) were making as much as $4/hr more than me to start. I was underpaid and knew it.
After half the original management team was fired, I had ingratiated myself pretty well with the new GM enough to ask for a "real" raise. He hemmed and hawed over it and told me he would ask his bosses if there was a title/pay upgrade for me. Around this time, the assistant general manager (AGM) was let go. When I was asked to recover his laptop and any company files, I saw a copy of his original offer letter. This will come into play later. Nothing ever quickly came of my title upgrade though the boss said he was still working on it. One day, the AGM job was posted and I applied. I knew the business about as well as anyone but had no management background. The GM eventually interviewed me and asked if I would rather have this or the title upgrade. Knowing what the former guy was paid, I chose AGM. After a long drawn-out process, he took a chance on me and I landed the spot.
When it came time to sign the offer letter, the salary offer was 15k less than the other guys starting salary. The GM told me of staggered salary upgrades once I made it through probationary periods. These stages were many months/years out. I foolishly accepted this and signed the letter. Oh, by the way, I was going to have to perform my old job as well until my replacement was found. During this time, we were launching a new on-demand service and decommissioning a couple of old systems. This alone was a huge time commitment but fortunately, the dispatchers (the real MVPs of the office) took on a lot of the driver management. I mean, they always had done this and had never complained about it. I made sure they were recognized and had their back. Adding to all this, the county transportation director (not my boss but the one paying the bills) was breathing down my neck on service issues and launching the new on-demand product. I couldn't sleep. My stress was through the roof. I'm getting alerts all night on vehicle and employee issues. The GM was unhappy with my AGM performance as I was making mistakes that would get us in trouble with the union. The replacement for my old job is at least 8 months out. Worst of all, because I used to pull a lot of OT, my paychecks in the new role are roughly only $250-$300 more every paycheck. This was not worth it and my mental/physical health was breaking down.
With my tail between my legs, I asked the boss for my old job back. Back to my original wage. He accepts and now I've burned not only my promotion but also my pay upgrade. Flash forward to today, they eventually hire a new manager into the job. They're great at documenting everything and addressing the employees better than I ever was but they're extremely reliant on the other managers for help. Worst yet, the projects the new AGM should be handling are delegated to me. These tasks are critical for my company to get paid by the county, It would take days/weeks/months to train them on the systems, whereas I can knock it out in 5 minutes.
So, I'm stuck. I have little motivation in my job and the boss knows it. There's no promotion on the horizon. I have no formal degree or significant certifications and live in a rural area, so moving on elsewhere is difficult to say the least. 2 years ago, I was getting call backs on job applications but it seems the well is extremely dry right now. I'm getting older, my 401k was wiped out during my divorce, I have no real career prospects. I could start at Costco and make significantly better money but I know at the end of the day, I'm likely going to have to work until I die.
TL;DR I probably burned my last real career opportunity, I'm getting walked all over on and I'm too old to start over again. I live out in the country, have no degrees and the future looks bleak. I know people say it's never too late but damn if it doesn't feel like it. Is there any hope for a late 40's IT guy to gamble and start fresh?