When I was planning my ER in 2007-08, I was trying to figure out the best time of year to retire. There were several things I took into consideration.
(1) My annual bonus was in early April, so leaving in January, February, or March, for example, seemed silly because I would be forgoing that nice lump sum.
(2) My annual company stock allocation was in early January, so leaving in November or December seemed silly because I would be forgoing that nice lump sum although the number of new shares I received had declined quite a bit when I reduced my hours and cut my pay.
(3) Similar to (2), my company revised its stock value every 3 months, so I did not want to annouce my resignation just before a quarterly update in case they told me to leave before the update (which was almost upwards; the 3rd quarter 2008 update was down slightly, not a lot). BUT....when I reduced my hours to 12 per week, I became ineligible for any more annual share allocations, so this reason went away.
(4) Outside of work, my volunteer activities began late in the year, so I preferred to not have to revise my schedule even if I ended up with more days available to do those things.
(5) And, the thought of commuting on the trains to New Jersey in the winter, even 2 days a week, was more depressing than commuting any other time of year. So I wanted to leave before the cold weather began. Similarly, having to run around to do some legwork relating to the distribution of my retirement plan assets was more easily done in moderate weather.
Based on all of these factors, I chose October 31st to be my last day once the last pieces of my ER plan fell into place. This best captured all my needs and wants listed above, both financial and otherwise.
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