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I can give you my anecdote of a similar situation. I was pigeonholed into a job using legacy tech a couple years ago. I quit because it was a dead end. I found a company willing to let me learn modern tools on-the-job, which I did. That ended up not panning out in the long run because of work/life balance. But that is when the story gets interesting:

My next job was the old job. I got hired back into the job I quit, but instead of being stuck on the old tech, I'm working on modernizing multiple old products, including my own legacy products, into new tech.

It wasn't the original plan, but it ended up being a 12 month sabbatical to modernize myself.




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