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Does anyone know how important it is to look for a job immediately if you don't think your job will exist for much longer?

I have the funds to last about a year unemployed + I wanted to work on my own software projects for a few months. However, I'm concerned that if I don't hop back in the job market quickly enough, the decent paying jobs might dry up.

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If you only want a two month break start looking now. It will take about a month to two months to get a job and then you can push back your start date for another month. You can also go slower in the job process which will let you be picky and negotiate better.

I've considered this myself-- investing my time in my own projects while trying to lower expenses to the absolute minimum.

It makes sense, in a way. If the market is valuing your labor less than it was yesterday, your opportunity cost is lower and it might make more sense to invest in yourself.

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