I’ve lived a life that doesn’t fit neatly into any container. It’s been full of adventure, missteps, windfalls, and having to borrow money to keep the lights on. Looking back, I somehow lived my bucket list without trying to.

I share this because when people sit down with me — usually exhausted from trying to force their companies or their lives into a perfect straight line — they like to know they are talking to someone with a high capacity for reality, not someone who invented yet another sterile framework in a vacuum.

On paper, I spent the last 30 years managing complex tech projects, but my actual job was usually helping people navigate their own chaos. I’ve spent thousands of hours studying neuroscience, psychology, spirituality and the mechanics of the mind, mostly to figure out how to keep people sane when the building seems to be on fire.

The ability to hold a quiet, unbothered space for people doesn't come from a strategy. It comes from the things I survived, the moments of strange serendipity, and the times I had no choice but to drop the armor.

Here's a few of those interesting moments along the journey:

• I helped build the 3rd .com website in history, and the very first kraftfoods.com site, on which I hid an Easter egg just to see if I could, and nearly got fired for it.
• I started a software company at 23.
• I was mugged at gunpoint in a Detroit parking lot and negotiated to get my wallet back.
• I once came across a fatal car accident where the trained EMTs were so shaken they froze. Having never done it before, I ended up directing the firefighters and the jaws of life.
• I spent a week fearing arrest by the FBI after falling victim to a complicated con job in Goa.
• I sang Hava Nagila at a club in Bangalore with an 80-year-old, chain-smoking former Playboy bunny.
• I rode a bicycle from Seattle to San Francisco when I was 16.
• I have photographs archived in the Smithsonian.
• I got married in Israel, divorced 3 years later, moved into a rented room in New York City, and spent three months walking the streets at night taking photographs until my feet couldn't take it anymore.
• I once let a strange guy I met in a New York bar sleep on my couch in Boston. He introduced me to a woman who became one of my best friends and hired me for a multi-year contract that changed my life.