Rob’s Winding Path

In two-three sentences how would you describe what you do most days/weeks?

I have developed a transformative routine I follow daily called “2-2-2” – two hours of meditation/working out in the morning; two hours of reading; and two hours of writing – which allows me to accomplish most of my goals in terms of self-education, publishing, personal and professional development, and the like. If I have teaching, administrative, or executive duties – or meetings – I try to work them around my 2-2-2 which is my secret sauce.

What did you want to be when you were eight?

 I wanted to be a professional basketball player, but I didn’t have the height or the skills 😉

What did you learn about work that you learned from your family?

My sister – who is a Yale, Harvard, and Oxford educated medical doctor – taught me the value of the most important aspect of educational or professional success: focus.

What professional experiences/employers had the greatest impact on you?

Honestly, reading a (voracious and) wide variety of things across disciplines and genres – both nonfiction and fiction – has had the greatest impact on my thinking, how I relate to the world, how I take on professional challenges and opportunities, and beyond. Because I am able to see the world from many perspectives – and not just one – it helps me navigate across a diverse array of professional experiences. While I realize we exist in the “age of the specialist” where we do not see many examples of this, I think there is a lot of room for the “generalist who has a handful of ‘specialties’” because they seek to be a little more broad minded about how they show up in the universe.

For example, I move at the intersections of positive psychology, public policy, entertainment, and education so that I can change minds, hearts, and possibly political outcomes through creative storytelling AND positive psychology (I see all of these things as interconnected in a way other specialists who are more siloed might not because human beings are simultaneously influenced by a variety or combination of things even if our current workplaces refuse to understand this basic reality). And here’s a good example of this. In Brazil, the average woman used to have around 6 children and policymakers tried a variety of things to change this to no success. But when a few filmmakers decided to subtly introduce family planning into popular soap operas there – by creatively and psychologically making having less children a personal and social good in these television shows- the average woman’s birth rate dropped to 2 children per woman. So, in this case it took a different and multifaceted understanding of how to address the birth rate and overpopulation challenge beyond simply trying to change laws or politicians debating why laws should change in the first place. Instead, it took understanding the psychology of Brazilian women, the mediums that influence them, and the policy goal to craft a creative solution that frankly never factored into the thinking of politicians or their staffs because they were not trained to see the world beyond legislative politics.

What is something about your career journey that people might not expect?

Each time I switched industries – from politics to startups, for example, or from startups to entertainment, or from entertainment to higher education – I have often had to start from zero and climb my way (rapidly) up. Because we live in a society that has a strong bias against people making lateral moves between sectors (i.e., if you are a tech CEO it is assumed that you can’t be a producer even though it is the same exact job in terms of executive and administrative responsibilities), this meant I had to prove myself over and over again by starting at the bottom of the different industries I pivoted to. In other words, I wasn’t given a handout or free lunch when I decided to venture out beyond the things I had previously done. Furthermore, I don’t necessarily pivot “away from” old spaces. Even though I still flow back and forth between spaces, my pivoting process was still the same in terms of having to learn new things and prove myself in whatever sector I found myself in. Moreover, when I pivot into spaces, I still work in some (but not all) of the old siloed ones simultaneously (i.e., I’m still heavily engaged in entertainment even though I’m teaching and writing fiction and non-fiction books).

Why did you pivot?

I pivoted to be able to capture more day-to-day meaning in life because I realized that it is more important to enjoy the journey than it is to enjoy the destination. In some of the roles that I had, for example, I only wanted them because of what I felt the destination could bring me – in terms of fulfillment or success – and hadn’t thought much about who I was becoming during the journey (or if I actually liked the journey I was on). I pivoted to find out who I was supposed to be, to find out how I could best grow into that person. When I was in tech, for example, I was so myopically focused on getting my venture-backed company acquired (which was seen as the ultimate success – along with an IPO) I was blinded by the false idea that my personal and professional growth could only (or mostly) come as a result of that success. As a consequence, I was too results-oriented (and not process-oriented enough) which did not allow me to fully enjoy (or benefit from) the team or tech I built, the meetings I had with partners, or the customer relationships I developed. It was all a means-to-an-end which over time I realized is a suboptimal way to (think and) live. In other words, I didn’t want to continue living for some abstract concept of success or some supposed future fulfillment because I felt I would be missing most of the true meaning life has to offer, that life is about finding inward success, not just outward accomplishment.

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