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Um, not really. I'm "that guy" at work now and I can say it has only helped me.
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I think that if you aren't that guy from day 1 then people will judge you negatively for the change.
We have the type of environment that eschews Big Corporate because everyone here pretty much "fled" that environment, including myself.
Being "That Guy" can make you less likely to be included on valuable projects, less likely to get promoted, etc. Being visibly at odds with the work culture is rarely a good thing.
I think that if you aren't that guy from day 1 then people will judge you negatively for the change.
I love my new job and environment.
I finally feel like my work matters and directly contributes to our company's bottom line and the culture is fantastic. Hours are amazing and I'm getting paid more to do less work compared to my old gig.
And it's not like we go around ******** on Big Corporate for small talk and lunch. It's just that we all share a common "yeah I came from big corporate and I like this culture so much more" mentality.
I have a dental bill coming up that is going to take a really big chunk out of of my savings on account of my insurance isn't paying for it.