Companies take your unemployment length as a negative signal

"He's been unemployed for 13 months? Why doesn't anyone want to hire him? Must be something wrong with him"

It's typically easiest to find a job when you have a job.

Maybe. Probably? But I also sense a fallacy here. I could get a new job tomorrow. Maybe it took me 8 years to find that job and I didn’t realize that because I was employed the whole time.

Does that make sense?

People wonder why something was picked over before committing to it, that's all it comes down to

Focus on what you can control, and you can control the perception of that. If you are interested in money, professional validation, and corporate structure, go that way.

You can try to alter the cultural fundamental assumptions when you're done.

I didn't come up with that idea, it has been passed down through generations of workers, and by multitudes of co-workers.