I had a 1:1 with my boss this past June, like we often have weekly. Besides status updates on a variety of project, he would often ask me on how sourcing my replacement were coming…and it wasn’t going well. Recognizing we were nearly 4 months or less from my previously given retirement date, he was keenly aware we needed a Plan B or even Plan C. There were a few questions he asked me:
- Was I still planning on retiring?
- What date was I planning on retiring?
- What flexibility, if any, did I have with that date in mind?
- Since Apple were heading into review season, he needed to know what to do about my annual stock grant.
He asked that I have a come-back to him by end of July. I started immediately preparing answers to these questions and had prepared an email ready to be sent out but I chose to sit on it a night. The next day I decided that it really didn’t serve me to send it out earlier than he asked. My boss had started to bring up the possibility of having me stay on until April (the next vest date) and I figured having that flexibility in my back pocket wasn’t a bad place to be in.
Late July I sent out my responses to these questions in email. Yes, I am still planning on retiring and, in fact, I have become more at peace with the decision and more excited.
I had done some research on what date I was going to leave. Initially I had figured early November would allow me not only to get October’s RSU vesting but it would also allow me to get the payout of the Director and above quarterly bonus. Further research on that seemed to suggest that the Fiscal Quarter were done September 24th and best that I could tell, I’d be eligible for that payout, should Apple hit its revenue targets. So, I figured a week after RSU vesting or October 22nd would be the earliest Friday. I was starting to get worried about the cross-country drive and having the time to visit all of the people and cities we wanted.
As for flexibility, I basically told him that my home was on sale and that I were leaving California. Further, I had a fixed, unmovable schedule of dropping While One back in the water to head down the coast to Fort Lauderdale for solar installation. I told him I expect to be in the Bahamas for Christmas…and I intend to do everything possible to keep this goal.
Regarding RSUs, I told him since I already had one foot out the door, it doesn’t seem fare to take part of his RSU budget from others on the team. I told him to withhold whatever he was going to give me.
Our next 1:1 we walked through my thoughts. First, let me acknowledge how fortunate I am to seemingly be as valued as I am. I’ve either left or quit Apple several times during my tenure and each time, I’ve been met with similar responses from management.
It became clear to my boss that it’s looking unlikely that my replacement will be found and all roles and responsibilities handed off to this person in the next 90 days or so. We talked about staying on till April with some extended Flexible Work Arrangement whereby I’d work remotely for 2 weeks with 1 week in Cupertino.
At first, this seems like a nightmare scenario. However, I’ve since come around to being agnostic or even slightly optimistic to this scenario. It would be extremely tiring but easing into retirement seems to have it’s benefits as well.
We talked about travel expenses and lodging when I were here to which I was told it was not to be paid for. I suspect I could push and play hardball a bit more. To be fair, Apple’s in a bind. It’s not that I’m not replaceable, it’s just that I’m not replaceable in 90 days. That said, I have an immense amount of gratitude for Apple and everything it’s done for me. Others, I suspect, might push this a bit harder…and maybe I should, but it’s just not me.