I have been doing some thinking. I've only posted once in this thread since I joined after moving back from 2018 when my spouse decided to take a different career opportunity that altered our plans somewhat. I'm now targeting end of May 2019. But there may be some movement in that date depending on:
1. My project's contract is set to expire in 2019- this has been moved up a year, was originally set to expire in 2020. As a key player on this contract, and to help make sure my direct reports/co-workers continue to be employed, I may want to stay just long enough to ensure that we win the next round of contract. A new contract will come out sometime next spring, and its possible that our proposal/response will be completed by end of May, but if not, I'll stay long enough to help make sure we put out a good proposal and win the new contract. I don't want to bail and then cost everyone else in my local office their jobs as I know the company would probably look for a way shut the office down if we don't win the next contract.
2. Will keep my eyes open on markets/economy. Sequence of return risk is not a huge factor considering my spouse will stay employed, but I'd be hard pressed to not pad the stash a bit and load up on cheap stocks in the event of a big downturn. I couldn't imagine this would impact my date my more than a few months however, and if we're just floating along or down just modestly, screw it, I'm out. Right now, I'm having a hard time finding a lot of attractive ways to invest my money. That hasn't been the case much until recently.
3. Have two school aged kids. Really want to be done at least part (if not all) of the summer, so I can travel/take them on a long roadtrip. Waiting until school starts back up in August would be a downer (plus if I'm off we can save money by not having to put them in summer camp)
As my employer matches 401k each paycheck (rather than a lump sum), my plan is to shoot to fund say 85-90% of the max 401k contributions by end of May. In the event I end up working a few months longer I'll then have flexibility to continue to contribute and therefore continue to get the employer match until my end date is reached. If I decide to leave as proposed at end of May (will try to make final decision by late April) will just go ahead and raise 401k contributions for the last couple paychecks so I can max out the 401k right as I leave.
A couple of factors I am taking into consideration on the exact date of departure are 1. My company grants PTO for the month on the 18th of each month. So it would be silly to leave say between the 10th and 17th of the month. If I were to stay to the 18th, I'd earn another 2.5 days of pay. So I will likely make sure to leave sometime between the 19th and 31st of the month. 2. I enjoy being paid not to work on holidays. Ideally I will milk one last holiday or two. Memorial Day is May 28th. Would like to make it past that then quit. If I have to work beyond, then its a long way to July 4th, but I'd be somewhat annoyed to quit say on June 30th only to see a holiday roll around 7 days later that I could have been paid to play on! So that may be a factor (I'm looking at you July 17th as a plan B!).
I know the OMY is looked down upon around here, and the OLY is cheered, but for me this OMY I'm currently on (although I am totally ready now to not be sitting at a desk in an office), is a good thing as it has allowed me more time to get mentally prepared and work through some optimizations and give my spouse time to get established in a new position. I've made sure to take long lunches and walk to work whenever possible and use the time to daydream/solidify my thinking. I just put put my kids on the bus to start the new school year, and I'm planning this school year to be the last for me at my job! Future work, if I choose to pursue it, will not involve sitting on my butt in an air conditioned office.