BLUF: My proposed final date at work is August 18, but I’m considering resigning tomorrow.
I’ve accepted a new position and will be resigning from my managerial position of 8 years. The new position starts September 1. My proposed final date will be August 18. Today I looked at the calendar in detail and discovered that there are few “good” days for me to resign. My manager is traveling June 27-30, I’m out July 1 and July 6-11, and then he is on vacation from July 18-August 8.
That adds up to not very much time for us to work on transition together or for him to make a new hire, and it’s a small enough company that a new hire will be completely up to him (15 FTEs, he is the ED). I have three part time directs.
I could resign July 5, and then be out of office for a week, or July 12, when he will be going on vacation soon for 3 weeks. I'm concerned that either of those dates aren't very professional. I could potentially cancel what I have going on July 1, but I’m not normally in that day, so requesting a meeting would immediately be a red flag. July 6-11 is a very specialized, once-every-5-years conference that will be immensely helpful in my new job, so that’s pretty nonnegotiable for me.
I am not completely prepared to resign tomorrow—I’ve done some prep work, but I don’t have a full transition file prepared. I had been planning to complete that in the next week or two…
I am moving to a completely different industry. My boss and I have a very good relationship and I can’t imagine him asking me to leave same day—though no one has resigned in the past 8 years, so I suppose it’s remotely possible (i.e., I don’t have any past behavior to draw from).
What is the most professional choice—tomorrow, July 5, or July 12? Thanks in advance for any advice!