[nonrandomstring]

How to turn a pit of misery and doom into an exciting challenge that makes you want to jump out of bed each morning?

Talk to your bosses.

Explain the situation (as above is perfect - keep it short and sweet)

Suggest that if you leave they won't find a better replacement because the problem is structural. And that if you stay you'll probably burn out soon and that won't help anyone.

Ergo: the project is doomed every which way.

Except for one hope:

Ask permission to rebuild it from the ground up using modern tools and software engineering. Ask for one or two additional helpers to build a small team to do:

Full system analysis of what it's supposed to be doing

Requirements finding to identify what needs removing or updating

Building a POC replacement alongside the legacy

Implement using all the fun things, including AI assisted code translation

From this system's POV you're probably the last hope. If they say no then;

You tried

You can quit with a clean conscience and escaped a slow miserable death

[robocat]

That is irresponsible advice.

What if it loses them their job and they struggle to get an equivalent job?

What if they have any financial responsibilities?

Great advice if you can change careers or easily slip into another position (which they've said they're worried they can't). Fine advice if you're a hippy hobo like me.

Hopefully they can find some other motivating force apart from the tech. Read https://www.kalzumeus.com/2011/10/28/dont-call-yourself-a-pr... Concentrate on other goals like learning how to influence the business, rather than technical goals.

[nonrandomstring]

> That is irresponsible advice.

"Well, son, a funny thing about regret is That it's better to regret something you have done Than to regret something you haven't done." "And by the way, if you see your mom this weekend,,,"

[robocat]

Regrets are hard to measure - the things you didn't do are usually hypothetical and often only occur due to perfect hindsight - using information you didn't have at the time you made your choice.

Optimising for immeasurables is not a good path to success in my opinion (and I have some external measures of success in my own life, plus some failures).

[al_borland]

Depending on the application, this can be easier said than done. My company has a lot of legacy apps. To de-risk and modernize they decided to write a replacement for one of the bigger ones. I first heard about it probably 12 years ago, after it got its first client and had already been in the works for quite some time. From what I can tell, they are still working on it, but the strong push behind it has faded, and the legacy app still exists and runs a vast majority of the workload. They put millions into it.

If the rebuild route doesn’t seem like it will work (OP might know this without the conversation), I think education is another viable path. When I don’t know much about a system, I don’t want to work on it. OP sounds the similar. Taking the time to learn about it and become the expert can make the tasks seem less daunting and can allow a person to find creative solutions or better ways to do things, working inside the existing systems.

For example, we had a legacy ITSM system everyone hated, so did I, until I spent time with it. I got a project working with the guy who had been running it for 10 years. I was able to learn from him, I got the white papers on it and read about the various ways things work, and was able to build things in there to solve problems I had, and our team had. In some places I went to the code to see how something worked, because the documentation wasn’t clear. In other cases, I ran a series of tests to better understand certain features. The fear and uncertainty around working within the platform went away, and I started to enjoy it. I became the go-to person in the company on some parts of it, because I took the time to get good at it.

9 times out of 10, when I hate something, it’s covering up for a lack of knowledge and fear around it. Then I have a choice, I can be depressed and miserable, run away, or take it on and learn/grow until the fear subsides and the depression linked to it fades.

[nonrandomstring]

> 9 times out of 10, when I hate something, it’s covering up for a lack of knowledge and fear around it.

Good point, I've experienced that. Equally I've experienced great frustration at things I can't understand, not from stupidity or lack of trying, but because the information is guarded or lost.

Interestingly we're getting back to the roots of why Stallman first set out on the Free Open Software mission.

The OP mentioned difficulty with opaque/obscure proprietary systems. I wonder if that's a factor at play?

[nashashmi]

Definitely a factor. He is working on something he does not work on because it is impossible to look online for help and resource. This is frustration.