A whole new world

Hi, I’m Dave.

A year and a half ago, I had a “moment of clarity.”

I still remember when it hit me. It was 530am, and I was sitting at my desk at my great job in a Fortune-50 technology company, one of Silicon Valley’s founding alumni. No, that’s not right. Maybe it was 245am and I was trying to sleep a little on SFO-TPE. No, not right again. I guess it must have been 7pm and I was eating from a to-go box on the couch in the Springhill Suites that I called home for 2/5ths of my week. Wait… none of these are right. Well, I may not remember exactly where I was when I had my “moment of clarity,” but I sure remember where I wasn’t. I wasn’t at home. I wasn’t with my family.

I missed my family. I wanted more free time.

I decided to leave.

I asked for, and was granted, a year-long leave of absence.

For that year, I traveled around the United States and Canada in a 30ft RV with my wife, our 13 year old daughter, and our 9 year old son. For a year, I didn’t work. For a year, I didn’t think about work. I just drank in the time with my family, soaked in it, tried to be present for every moment. I tried not to think about what “work” might be when our year came to an end – and I (mostly) succeeded.

As part of our walkabout, we spent almost two months in Florida, seeing out 2018 and welcoming in 2019 while enjoying their fantastic “winter” weather. My wife’s side of the family calls Central Florida home, and it was while we were there that my brother-in-law asked me to come work with him as Chief Technology Officer at the independent insurance agency he owns.

“Chief Technology Officer.” Mmm… nice ring to that. But, at an insurance agency?

And, moving my family across the country? (Not that, in our then present nomadic state, we had much for roots anyway.) I was scared, and I had become quite comfortable at the job I intended to go back to. I had industry relationships and good credibility. I could go back, I told myself. I could engineer a better work/life balance than when I decided to leave. I just needed to be sure that I intentionally shaped my new role to meet the “environmental criteria” I’d spent my time on the road defining:

1. 1. No longer “on call:” No standing expectation to be available (email, text, cell) outside working hours
   2. Less hectic calendar: Fewer meetings & more time for doing, innovating, giving back
   3. Healthier work/life balance: Respect for sanctity & prioritization of family time

Even though the CTO offer clearly met these criteria, after a lot of deliberation and marital discussion I called my brother-in-law and said, “Thanks, but no.” Like I said: I was scared, I was comfortable.

Thing is, I had already committed to attending a “technology in insurance” conference with him and the agency CFO. I mean, let’s analyze it: They were paying, it was a free trip to New Orleans, time with people I liked, and I couldn’t really claim I was busy given I was literally living in an RV and unemployed. So, off to the insurance technology conference I went.

SMACK!

That was the sound of my hand hitting my head as I sat through the day-one keynotes. “I know this stuff!,” I told my brother-in-law, excitedly. Turns out, the insurance industry’s “technology transformation” looks a lot like transformations I’d partnered with other industries through. Challenges facing the industry echoed challenges I’d helped guide other, earlier adopters, through. It was an important realization: There is technology in insurance, and I have something to offer (more on that in blogs to come).

I changed my mind. I said “yes.” I took the job.

After 12mos on the road our family made one last cross-country trip, only this time it was a one-way trip from California to Florida. A whole new world.

So here I am. An ex Silicon Valley tech guy trying to figure out the insurance industry. And, as I work through “learning mode,” I figured it might be fun to write about it. Hope you’ll follow along.

Until later.