Ask HN: How to Break Career Stagnation?

5 years in and I never expected the job search to get more miserable as I gained more experience. Everyone says the market is great right now and so I’ve begun looking again, but man the jobscape is depressing. I want to increase my pay (I have certain targets of mine), break out of stagnation, and by the grace of gods work on something I find interesting, but it’s just looking so grim. I’m seeing a lot of “senior” level roles mostly in areas I have no experience in. This might mean technologies / languages / working on software of scales that I just couldn’t get at my current company or past companies. This isn’t a matter of “I don’t fit all of the qualifications” more so “the only qualification I meet is general YoE”. To be blunt, I have little experience with modern technologies and what I do have is a little old to be relevant. I’ve never had direct interaction with any clouds/cloud technologies and I’ve never had to do significant system design or work on any softwa