Apologies in advance. this is long, this is personal, and this is probably going to annoy some of you. If you’re the type of person who doesn’t like long and personal on someone’s personal blog, go and read the lolcats site for a while, Thanks.

When it Changed…..

Five years ago today I sent out the email to my team announcing I was leaving Apple after 17 and a half years. I posted a copy of it here. I left slowly, working with my bosses to make the transition smooth, so it was two months before I actually handed in my badge and became a free agent.

It was an interesting time in my life. At that time, I said this:

So I’ve made the tough decision that it’s time to make a clean break of it, take a little time off, and then find a new position where I can make a fresh start in a situation where the stress levels are easier for me to cope with.

I’m not really happy with this decision; the word I’d use for my feeling is that I’m comfortable that it’s the right one. I’m not leaving for a new position; I’ve just started exploring what I might want to do, and what might make sense.

With the passing of time and the sharp focus of hindsight, I have to say it was definitely the right decision; in all honesty, I was tired of Apple, and Apple was tired of me, and we both needed to make the break. You can see from Apple’s stock price since then just how badly they missed me.

Two events precipitated this decision, although it was honestly a long time coming. The first one was when a really neat lady I liked and respected asked me an unfortunate question when I was having a bad day, and I went off on her. It was mean — it was abusive — she didn’t deserve any of it, and 30 seconds after I did it, i was mortally embarrassed at what I’d done. It was also something that you can’t undo with apologies, although i definitely tried. It was at that moment that I realized if I was that stressed out that I was losing it that badly, I had to make changes before I did something seriously dangerous or the stress killed me. (to her great credit, she eventually stopped being freaked at the thought of being in a room with me, but it is one of those moments in my life I will never forgive myself for).

Then a few weeks later, I was in a planning meetings when the alarms went off because the system was down. It turned out the database machine threw a drive, the primary data drive. On the primary master server, which was two weeks from being made a fully redundant, multi-machine server with automatic failover. We were that close from avoiding this disaster — and that drive was basically the one piece of the system that wasn’t redundant or easily replaced on failure; of course, it was the piece that fried. We knew about the risk, we were working to resolve it, and we missed it by THAT much.

It took us 13 hours to bring the system back live, swapping in one of the redundant slaves in the mysql pod and turning it into a master. There was no data loss (thank god), but still, that was one of the most stress-filled, panic-inducing times I’ve had in my life. At the end, I wandered into my director’s office, slumped to the floor, looked at him, and told him I couldn’t do that again. I was done. He sent me home, told me we’d talk later, and I went home and slept for 15 hours.

We agreed on two months as an offramp, plenty of time to bring up the new team and train them. That gave me, I thought, time to find a new project and home at Apple; in reality, I had no clue what I wanted to do — only that it was time to stop doing what I was doing — and didn’t try very hard. So I handed in my badge, got in the car, and drove off the face of the earth for a couple of weeks, my first “no phone no modem” vacation in years.

That project started out as a skunkworks with myself and one other programmer to see if it made sense to bring Apple’s marketing email inhouse. It turned into a behemoth that when I left was conservatively driving $50m a year in revenue and we were showing at least $10m a year in cost reductions within the company with a team of about seven. It was recognized as having the best ROI of any project in Apple IT — ever. We extended it for use globally, localized to something like 20 languages. It was the first Apple IT project to make significant use of open source technologies and be hosted 100% on xserves, so we blazed a few trails I’m rather proud of. it was (and still is) one hell of a hack; the team that took it over has done an awesome job and done some nice things to it I wish I’d thought of. If there’s one thing I’m really proud of, it’s that the transition went off about as smoothly as you could hope for, which is what I wanted. The whole open source thing was a fascinating experiment in itself (by design), and both a blessing and a curse, and deserves some discussion on its own; maybe later I will get to it.

What I didn’t know then, wouldn’t know for another six months, was that 95% of the problem I was having was sleep apnea. I’ve talked about that before, so I won’t go into detail, but in the 18 months before I left Apple I gained 90 pounds; in the 5 years since I’ve gained 15, ten of that in the last 9 months while we’ve been driving to get the TouchPad launched (and now I’m working to change that and pull that back). What I do know is when I got the apnea treated, my blood pressure dropped more than 25 points and a whole lot of problems in my life went away.

The last five years have been an interesting journey, in both the literal and chinese way. The executive summary of the last five years:

  • Sleep Apnea — once I was diagnosed and treated, my blood pressure dropped over 20 points. It’d progressed enough I was falling asleep in meetings. But the first night I put on the CPAP, my life changed radically, and I’ve never looked back. But I was very close to falling asleep at the wheel, or snoring myself into a stroke.
  • When I left Strongmail, it was with the intent of launching a site called Dare2Thrive, and try to break out onto my own. A secondary deal I thought I had with a friend blew up in my face, costing me a chunk of change, and then it became clear Dare2Thrive was dead on arrival (I really need to talk about that some day), so I took it out behind the barn and shot it. This, needless to say, did wonders both to my self-image and my pocketbook, but not as badly as if I’d launched the thing. I did, however, self-destruct in interviews for weeks, costing me a couple of really good jobs and probably guaranteeing I’d never work for Yahoo without a name change (not that, as it’s worked out, that this is a bad thing).
  • I got my exercise program up to about 1 1/2 miles three times a week, which was making nice progress on my weight, and then stepped in a gopher hole, tearing the meniscus in my right (good) knee. Which didn’t heal, which is how we discovered the arthritis in both knees. Neither of which is operable, until we decide it’s time for replacements. Fortunately, 500mg of Relafin twice a day keeps them mostly functional and it hasn’t seemed to progress much. But that indirectly caused a serious case of tendonits in one ankle, which took nine months to get rid of. That made life interesting (and exercise impossible) for most of 2008.
  • But 2008 was the year my dad got sick and died; it was a year of tests and hospitals and funerals and laywers, as I spent a big chunk of time in SoCal (or in transit: 12,000 miles on the subaru, just driving up and down the state) and helping mom get settled and things under control with the estate and her life. When I surfaced, it was October, and honestly, I remember almost none of it.
  • Somewhere along the way — my best guess is around March — I went diabetic, but we didn’t diagnose it until 2009 when the simptoms got significant enough (significant enough: blood sugar > 400, tryglicerides > 600, blood pressure way up…). Fortunately, it all responded well to treatment and is well controlled and stable without a lot of fuss.
  • And once I got that under control, I went and fired up the exercise program again — and fell down and went boom, going back on the shelf for about two months before I could even think of doing any significant exercise again (not that I wanted to; given recent history, it’s suprisingly hard to get up much enthusiasm to try again, although I’ve been starting slow and trying to build carefully…)

I mention all this not to whine or elicit sympathy, but to bring forward the thought. Sometimes life is good, sometimes it throws you challenges. It was Nietzsche who said that which does not kill us makes us stronger. It was in a hotel room on the road, with dad in the hospital and it increasingly seeming like he’d never get out, my ankle wrapped in ice so I’d have a chance of walking the next day (because i had no choice), Laurie hundreds of miles away, feeling very much alone and tired of it all.

And I had a moment that can only be described as howling at the moon. I found myself yelling at nobody in particular that if life would just leave me alone for a while, I could get this all under control and be happy again. That was the moment I realized that life didn’t owe me easy, that it was up to me to make it easy. And that I didn’t like who I was, and until I fixed that, nothing was going to change.  I had no idea what it meant at the time, but I knew it was important to find out. And that’s been the journey since.

Five years ago I was in dream gig with a great team, awesome bosses for a company that was changing the world — and I was absolutely miserable (and really had no idea why).

Today? Much different gig — but a great group of people I enjoy being around even more than my team at Apple, which is something I never thought I’d find. Great challenges, lots of fun, lots of work to do. It’s hard to believe five years have passed. I feel like I’m a much different person than I was.

And I’m happy. With what I do, with who I am.

And isn’t that what really matters?

Whenever I end up talking about Apple with folks, there is one question that always pops up, so I figure since I brought it up myself, I might as well answer it. That question  is “Would you go back?”

The answer is yes, with some qualifications. Apple is doing many good and interesting things, and in many ways, is changing the world (mostly for the better); there are lots of challenges there to take on in the right situation. but the implied question within that question is whether I miss Apple or feel some need to go back, and that answer is definitely no. I left at a time when it was the right thing to do, had a great run there, regret almost nothing, and enjoy what I’m doing now. I’ll admit that I’ve looked into a couple of positions there over time, but in each case, it was a position targeted at an internal candidate.

If the right situation came up, I’d do it. A lot of where my interest today is around photography imaging and how technology and people (i.e. this “social” stuff) come together. Apple still seems to me too afraid of losing control of its message to embrace social — just look at Ping (sorry, really qualified and talented folks who built that). That’s a social media for companies who are afraid to be social, and that’s just not that interesting to me, and not close to what I was encouraging people to consider even before I left.

But if you’re smart, you never say never.

I’m not sure what the five years have in store. Good times for sure, challenges just as surely. All I know is that I’m looking forward to seeing what they are…