[qqqwerty]

And as a quick follow up to my last point. It might make sense to think about how taxes can work in your favor. If you take a year off, and you split the year across two calendar years (i.e. June 2021 to June 2022), you will get a nice refund from the IRS come tax day both years. Whereas you would get no refund if you do Jan 2022-Dec2022.

Alternatively, if you have a bunch of capital gains in stocks you could cash some of that out tax free if you have no income for the year (i.e. the Jan 2022-Dec2022 scenario).

Some other considerations in terms of timing are bonuses and PTO payouts. For example, I had a ton of PTO saved up (this was before everyone was doing unlimited PTO, which makes this issue irrelevant). My last day was in late December and they gave me a check for all of the unused PTO. Had I waited until January, that money would have been mostly tax free.

Probably not something you want to stress too much about. But if it works out you can put an extra $5-10k in your pocket which will take some of the sting off of losing the paycheck.