Further Confessions of a Semi-retired Silicon Valley Executive

La Digue. Seychelles. Source: https://benfa.smugmug.com.

“I only need you to work half days… The other twelve hours you can do whatever you want.” — Anonymous.

We’re coming up on two years of self-imposed semi-retirement for yours truly, so I figured it was time for an update. I blogged on the topic when I first announced it in October 2016 (not so coincidentally also my 52nd birthday), then offered an update a year later as the reality of retirement actually started sinking in, and followed up with even more thoughts after 18 months.

It seemed only fair that I should write this blog post now as we get close to the second anniversary of my semi-retirement. So much has changed that it feels more like a dozen years than just two, as you’ll see. After a 35-year career, the changes were dramatic and the impact immediate.

In my case, thankfully, retirement has meant significantly less stress and a massively healthier lifestyle. It’s meant a slower pace of life, days devoted to cycling and reading, traveling and spending time with the family. I still work a bit, advising some startups, but as I told a young CEO recently, I’m happy to report that I spend more hours on the bike these days than behind a desk.

First and foremost, I stopped doing a lot of things that I’d been doing for decades. I stopped managing teams of people responsible for writing system software — what I’d done for much of my career. I stopped working sixteen hour days. I stopped commuting to San Francisco on the train for three hours a day to work at a startup. I stopped sleeping an average of four hours a night, tossing and turning at 3:00 AM, worried about a project or an employee or a bug. I stopped taking calls in the middle of the night from the operations team that ran our cloud services.

I stopped reading and responding to several hundred pieces of email a day. I stopped going to release planning meetings and war room meetings. I stopped arguing about budgets, people reviews, raises, diversity, employee morale, recruiting, attrition, office space, stock grants, leadership development programs, layoffs, office politics, and a dozen other topics.

I stopped looking at incoming bug reports. I stopped listening to customer complaints about quality issues. I stopped arguing with product managers about feature priorities and with project managers about deadlines. I stopped talking to salespeople about what features I absolutely had to implement in the next release because they’d already promised it to a “strategic” customer and next quarter’s numbers depend on it. I stopped talking to marketing people about why our products are the coolest on the planet and which audiences they should target. I stopped talking to industry analysts and reporters.

I stopped going on insane international business trips where I’d spend more hours in the air than on the ground. I stopped taking Ambien just so I could sleep on trans-Atlantic flights so I could be awake for the 8:00 AM meetings in London or Bangalore or Beijing after landing there at 3:00 AM. I stopped dialing into conference calls while sitting in a hotel room half a world away. I stopped presenting slides to audiences in large auditoriums written by someone else and scripted by yet a third person.

I stopped spending every waking minute (and some of the sleeping minutes, too) thinking about and stressing about work… something I’d done non-stop for 35 years.

Instead, very soon after I walked out the door from my last full-time job almost two years ago, I started sleeping an average of eight hours a day — instead of tossing and turning in bed all night thinking about that last email, that heated exchange in the meeting earlier in the day, instead of replaying conversations in my head (“what exactly did he mean by that?!?”), instead of grabbing my phone from the bedside table to send just one more email at 3:00 AM (why was it always 3:00 AM?), instead of waking up more tired than when I went to bed, instead of trying to recover from last week’s jet lag before jumping on the next plane.

Even the smallest of corporate jobs entail hundreds, if not thousands, of narratives that you have to keep straight in your head at any given moment. Hundreds of story lines you have to follow, hundreds of details you have to keep track of, hundreds of action items; maybe not on a piece of paper but definitely in your head.

Let them all go one day, let all the plates spinning on top of the poles crash to the floor, let the stories go on without you as a cast member, and you’ll find out very soon that you no longer have trouble sleeping at night. It won’t be overnight. It might take weeks or, more likely, months. Your brain will thank you for the peace of mind. I promise. And your body will thank you for the time you give it… so it can finally heal.

I’ve been sleeping like a baby ever since I retired. And, by that, I don’t mean waking up every hour and screaming my head off. I mean sleeping blissfully, like I don’t have a care in the world. Amazing how well you can sleep when your mind is at peace.

Meanwhile, I had to do something with all that time I had on my hands. So I started biking up the mountain an average of three hours a day. I biked 6000 miles and climbed 500,000 feet last year and am well on my way to exceed those numbers this year. Did I mention that I was barely walking right before I retired, hunched over with severe back pain and taking pain killers just to get through the day? These days, I’m beating 20-year-olds up the mountain with a grin on my face. All it took was time and reduced stress. I dare say my body healed itself.

Given that I had a lot more time on my hands, I also stopped stress-eating. I stopped grabbing a donut on the way to work and a sandwich on the way to the noon meeting. My weight dropped by almost forty pounds within a couple of months and I’ve had no trouble keeping it there. My diet still consists mostly of pizza, beer, and hamburgers but my body doesn’t seem to mind! As long as I don’t stress-eat, they seem to contain sufficient nutrients to allow me to bike three hours a day and not feel tired at all! If I actually start eating healthy food… nah, that’s just crazy talk.

I’ve continued to read books obsessively but now, instead of doing so at 3:00 AM as I think/obsess/stress about work, I do it in the late afternoon with a glass of wine in hand. Since my brain is not occupied with a dozen random topics, I actually even understand what I’m reading the first time around.

Did I mention I also started blogging? It’s surprising to look back and realize I’ve published almost a hundred blog posts in the past couple of years. Who would’ve thought I had so much to say or that so many tens of thousands of people would want to read what I write? It’s amazing how much you can accomplish if you don’t “fritter away the hours” sitting in meetings or glued to a screen.

Did I mention that I also became a grandpa for the first time six months ago? I absolutely adore the little one and have already blogged about him twice!

Two years into semi-retirement, I have to say: “Life is not just good; life is great!”

I’m now healthier in every measurable way than I was two years ago. A dozen or so co-workers from my last job were in attendance at a talk I gave recently and reminded me that I’d been hunched over with severe back pain in the days right before retiring. How did I go from looking and feeling twenty years older than my age to feeling and acting twenty years younger in a span of just two years?

Ultimately, only two things: more time, less stress. Our most precious resource is time. And that’s exactly what you get back when you stop working, yours to use in any way you wish.

You and only you control the knobs for how much you want to achieve in life and what price you’re willing to pay for it, what your priorities are. The biggest mistake we make, one which I’m definitely guilty of, is that we don’t understand this simple fact and blame others for our problems instead.

I look back now and that world seems so far away, so strange, so artificial, so focused yet so confused in so many ways. Our industries are so wasteful in how they go about doing things… and I happen to have worked in one of the most advanced and efficient industries out there!

The key realization, though, was that, despite adamant protestations to the contrary from my ego, *I* (the proverbial I) am the one who felt all those feelings: stressed, tired, exhausted, yet running faster and faster on a treadmill just to keep up. *I* was the one who signed up for more and more deliverables, larger and larger teams, bigger and bigger responsibilities. “It’s my own damn fault!”, as Jimmy Buffet so wisely diagnosed.

And it’s that understanding, ultimately, that allows you to realize that *you* (the proverbial you) are the only one who can change those dynamics. What is enough and when is enough enough? You are the only one who can answer those questions.

Don’t get me wrong. I may still go back to work. Everyone tells me I’m too young to retire. But, this time around, I’d do it based on a whole new set of rules.

Former CTO of VMware, former VP at Microsoft, recovering long distance runner, avid cyclist, newly minted grandpa.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store