The “Workaholic” Trap and the Joy of the Grind

“You are too much of a workaholic.”

An executive coach told me that during a session years ago. It stuck with me because, for most of my career, that drive was my greatest strength. But over time, it had curdled. The “strength” had become a shadow.

The evidence was everywhere. I was commuting weekly to an office (SF) a thousand miles away, or I was in Tel Aviv, Tokyo, or one of the many international offices and customers even further away. I was an executive in motion, but a father and husband in absentia.

Recently, I was catching up with two friends over happy hour, and I realized we represented three distinct stages of a tech career:

• Friend A is “Living the Hobby Dream.” He’s fallen down the rabbit hole of track car racing—spending hours in a professional virtual harness to gain 1/10th of a second. He has the high-paying job that requires three hours of his day, leaving the rest for fishing boats and the shooting range.
• Friend B is in the “Retirement Chicken” phase. He’s grinding it out, waiting for a layoff or a pension. He’s exhausted by the corporate “lazy and stupid” tax. He and his wife are basically waiting to see who gives up first.
• Then there’s me. I told them I haven’t had time to watch a movie in my home theater for weeks. But ironically, I’ve never been more energized. Every hour is spent with people I love, solving problems that matter.

Looking back at 30 years in tech—from the cloud at Microsoft to marketing at Salesforce—I can finally see the “arcs” of what makes this career either a dream or a nightmare.

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The Internal Arc: Chaos vs. Safety

I remember being assigned an “impossible” task: fixing one of the world’s largest Azure services to prevent our leadership from being fired by Satya Nadella. I went from a big-org leader to an Individual Contributor. People offered me condolences, assuming I was on my way out.

Instead, it was magic. A team of two, navigating chaos, building a world-class system from scratch.

Conversely, I’ve worked for this one leader who destroyed psychological safety. He triggered a visceral, physical reaction in me—the kind they warn you about in HR training. I once spotted him at a conference while I was preparing to speak to hundreds. I had to walk the other way, literally hiding, just to ensure I wasn’t “broken” before I took the stage.

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The Upward Arc: Strategic Courage vs. Simple Bullets

In the corporate world, you are always “managing up”—navigating the thin line between being a “yes man” and pushing for truth.

I remember the moment I realized our five-year strategy was failing. I pushed—harder than I ever had—first with my manager, then his. I ended up in Malaysia, jet-lagged and wired, writing a new product vision for the CEO. It was deemed business-critical and changed our direction.

Contrast that with a GM who, after a technical deep dive, simply told me to “just do the right thing.” He didn’t want the technical “framing memo”; he wanted simple slides. In the end, he decided I wasn’t a team player and put me on a layoff list—only to be fired himself shortly after.

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The Full Circle

I’ve realized that my current flexibility—the ability to build my own ventures—is a direct result of the heavy lifting I did in those corporate trenches.

I don’t want to “retire” in the traditional sense. I love to work. It keeps my brain sharp and my network vibrant. The difference now is the alignment.

I no longer choose between a global commute and my family. I spend my mornings at breakfast with my son and my evenings on our nightly reading challenges. My “4K home theater” might be gathering a little dust, but for the first time, I’m enjoying the satisfaction of a life where work and home aren’t at war.

It turns out I wasn’t a workaholic. I was just looking for work worth doing, with people worth doing it with.

For #ELF#