Rob’s Winding Path

I met Dr. Rob Carpenter almost a decade ago on a trip for global social entrepreneurs. Since then, I’ve been amazed by the breadth of what he has accomplished as founder, author, filmmaker and teacher. Rob, 37, is a resident of Los Angeles and teaches in the Department of Communications at UCLA.

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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.

What skills were portable from what you had been doing previously and what was brand new to you?

 In many ways, I’m inspired by President Kennedy’s Defense Secretary Robert McNamara. Before he was SecDef, he was head of the Ford Motor Company and after he was SecDef, he was head of the World Bank - all experiences which allowed him to serve in 3 entirely different fields (in automobiles, defense, and finance). From his experiences he learned that “90% of leadership roles” are similar across sectors and organizations (in terms of functions, responsibilities, and skill sets) and 10% are content differences. So, whenever he would get a new role, he felt comfortable that he could learn the 10% he didn’t know about whatever industry he was in relatively quickly.

In my own experience, I have found the lessons from his life to be true and applicable as well. Whether it comes to vision casting, recruiting, and motivating a team, mobilizing others toward a common objective, or constantly and empathetically communicating to make sure the trains run on time, the similarities between industries are astounding. More specific to my own life, I have found that the similarities between political campaigns, startups, and producing movies are profound. For example, they all have a product (whether it be a candidate or consumer/business product or movie); they all have a short-term orientation (campaigns end on election day, startups end upon acquisition or going public, and movies end upon wrap and distribution); and they all attract highly growth-oriented people who are often much more interesting to work with than the norm. So, because of these structural similarities to these things - and because of the similarities in executive leadership - skills can be very portable. That said, like McNamara, I have also had to learn new things in each industry (industry jargon, for example, who the players are, cultural etiquette, and the technical aspects specific to only those industries).

What was the hardest part about making a career pivot?

For me, the hardest part about making a pivot is how others perceive it and how, more often than not, they become dismissive of your background and experiences in your past career. For example, when I was raising money for a tech startup, I mentioned that I had learned a lot of valuable leadership lessons from political campaigns, but one investor said, “well, all that’s good for is cocktail party conversation.” Because he had never pivoted in his own career - and because he had not really seen others pivot - he had no ability to grasp the connections between the two fields. So, if I were to warn others about the challenges of the pivot it would be to be prepared for the complete lack of imagination many people have about being able to understand your transferable skill set (until you prove yourself in whatever new industry you’re entering).

What were the most important lessons you’ve picked up along the way?

 First, it is more important who you become as a person (defined as being loving, compassionate, and kind) than what you do (your job title, university degrees, the circles you hang out in, etc.). Second, it is essential to find intrinsic meaning in your work -and life - outside of notoriety, money, or success more generally (if you don’t find intrinsic meaning outside of these things you will, sooner or later, end up in an existential vacuum and encounter numerous “mid-life” crises causing you to question yourself and choices). Third, understand that if you focus on becoming an empathetic and emotionally intelligent person you will gain the greatest prize there is in life: learning how to be fully human.

What would you say to others who are doubting their ability to make a change in their career/vocation?

Information will kill most of your doubts. For example, if you focus on gaining as many practical specifics about how you will make your potential career change; the entry level steps you need to take; the online resources you need to consume; the low and mid-level people you need to connect to help get a foot in the door; and anything else that will allow you to take “baby steps” in the right direction, your fears about being able to pivot will greatly dissipate. So even if you still have some doubts, at least you are armed with knowledge - and an action plan - to stop thinking and start doing. 

Where did you get the confidence and support to make such a change? 

I am a very spiritual person, so my confidence is rooted in my meditation practices and connection to my Creator. But in terms of practical, daily confidence, I got it from 1) gaining specific knowledge about the career (or careers) I wanted to pivot into; 2) connecting with both entry level and mid-level people in that career (I have found that these two types have relevant information and advice for the moves you need to make as opposed to senior people who are more disconnected because they haven’t had to start out in a while so their experience or advice may not be as applicable to a newbie); and 3) making sure I was consuming the most positive and uplifting content possible (not just from books, videos, and podcasts, but also from surrounding myself with ambitious and positive people - and removing myself from unmotivated and negative people).

What was the hardest thing you had to overcome in your professional life? 

I don’t think this is specific to me, but I would say that generally speaking “uncertainty” has been the hardest thing to overcome. If I was on political campaigns, for example, it was uncertain if our candidate would win - and whether I would have a job afterward. If I was running a startup, it was uncertain if I could raise the money to keep the company afloat so we could prove our business and get it acquired. If I was running a movie set, it was uncertain if our end product would be any good (because of the myriad of complicated factors involving the making of “great art”) and whether I would get to make another movie as a result. So, all in all, uncertainty has been the most chronic challenge I - and I would think most people - have had to overcome. But what has really helped me grapple with this (and, many times, conquer it) has been meditation, reading about others' journeys, and surrounding myself with a multitude of counselors who could give me additional perspectives from which to view things that maybe I was incapable of seeing because I was too focused on my own thoughts and emotions in the moment and not focused enough on the objective reality of the situation.

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

I was once an NCAA basketball announcer, which was a very fun gig.

What, if anything, are you hoping happens next in your professional life?  

I’m hoping to point more people in the direction of finding true meaning in their lives - not just success. Because I’ve been around so many successful but unhappy and unfulfilled people, I think one of the most important things I can do is to be a guide for meaning - whether that be through teaching, books, movies, seminars, or beyond.

What social media links, if any, might you like to share in the piece?

LinkedIn -

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