On October 25, 2021 during my 1:1 with my boss, I told him I was “starting” to think about retirement and asked him how long does he need to know by.
Of course, I already have a date in my head but he, of course, turned my question around and asked me something to the effect of “so, when are you thinking? Is this a 1-2 year thing or a 3-5 year thing”. “It’s not 3-5”, I said.
My retirement date has been moved many times. I’ll talk about those cases in future blogs. Suffice it to say, it’s been one of the hardest decisions of my life. There’s something about the finality of it that scares the hell out of me. More on this later.
I had originally planned to have it prior to my review which, at Apple, is generally early October. October starts our new comp cycle. But, as I started to think about it, I figured I should wait until after my review just in case my mind changed and I screwed myself out of money going into my review. So, I decided to wait until my review.
My review came and went and I still didn’t broach the subject. Of course, I call it a “review” loosely because the fact is, I haven’t had an officially formal “review” of my performance written down since 2013. Most would think this as a good thing and, I suspect it is. I’m my biggest critic and most of the times, I’m already well aware of what I need to work on without being told and often times, have a lot higher bar than others. However, there is a downside in that it can be misconstrued as coming off as your manager isn’t really “investing in you” and that he/she is merely interested in having you do the great job you already do…I tended to look at it this way, whether it was true or false, I don’t know.
Anyways, my new compensation and particularly my RSUs were so strong, I just couldn’t bring it up. I think mostly because, in the back of my head, I was saying to myself: “Are you fucking crazy, why would you give this up?”
Apple has been so incredibly good to me and my family. Don’t get me wrong. They expect a lot and it’s nothing like the country club Google, I had heard rumors it to be. Without a doubt, it’s a pressure cooker. The culture is so self-fed that high performing, highly talented folks naturally feed the competitiveness of other high performing, highly talented folks. You either sink or drown and ultimately leave the company.
Of course, I couldn’t stop planning and thinking about my retirement. Our boat is coming in December. We’re starting to talk to Real Estate agents about buying a new place near the boat. I’ve shipped one of my cars to Florida. I’m starting to pack up the house, putting things in piles of “garage sale” versus “store.” I keep telling myself this is happening as well as everybody else in my life.
So, when my boss scheduled our 1:1 a few weeks out, I decided that would be they day. Following, I felt pretty normal. No new anxieties. Started to think about who my successor would be. There was one individual I worked with who had been on the short list (of one) a while ago. “When was our next 1:1?”, I asked myself.
On October 27 we had the conversation. I confided in this person my timeframe and told him that nobody else knew so to keep it confidential. This morning, BTW, I started to keep a running list of folks I’ve told whom and what to…there’s too much at stake for folks telling my story and me not controlling the narrative. He seemed pleased for me. I gave him a loose timeline of pre-Thanksgiving for feedback on interest. I encouraged him to speak to my boss.
This conversation hit me a bit harder. I kept asking myself “why?” I’m still not sure I have the answer but for some reason this seemed to be a much bigger step towards my retirement than even telling my boss. I’ve either quit or left Apple 3 times now (I’ll talk about those in future blogs because there’s a lot of good info there!). I’m not new to this. However, this felt a lot more like the ball started rolling down the hill and couldn’t be stopped…and, I guess, it really can’t. There’s no coming back to that individual to say “I changed my mind.” You just can’t do that to people. For your boss, you can…he/she will most likely be delighted.
Anyway, I had a gig with my band, Identity Problem, as San Pedro Market that night. This subject was in my mind the entire time. So much so that when I woke up this morning I decided I needed to write this.
To be continued…