Thank you all so much for the well-wishes last weekend. Follow-up: Monsieur Hurricane Henri was a grand burger de rien.
So now, back to our regularly scheduled programming. Entrepreneur, technologist, and all-around smart person--and friend-- Sukhinder Singh Cassidy, has written a terrific book. It's focused on how to decouple the fear of failure from risk taking and the fabulous idea of having "hustle," a cousin to both ambition and risk-taking.
We had a chance to chat about our approaches to career, life, in the form of a q&a. Here it is, edited for length, clarity, and as always, to make me look like I understood all the complexities and acronyms Sukhinder brought to the conversation. Choose Possibility is a fun read, to boot. Blending personal and professional tales and lessons learned, I got to know someone I've known for 20 years so much better. Thank you!:
LZ: You dedicate your new book, Choose Possibility, to your parents, for showing you love and the idea of possibility every day. What's an example of how they did that for you?
SSC: My parents gave me everything I needed to pursue possibility- a stable secure home environment, everyday of examples of risk-taking in small doses - from my father being an entrepreneur and small business owner, to being a voracious learner and experimenter (he made us take apart the dryer a few times with him to learn how it worked; he helped me build a working model of the human eye for my second grade science fair, the list goes on), and room to run, letting me pursue ambitions on my own and be myself.
My parents were also immigrants to Canada who uprooted a prosperous and stable life in Africa to start over in Canada and re-certify as doctors, start over financially and more to give their children an education. While people would not call two doctors who ran a modest practice in a small town in Canada risk-takers, I think they came to a new country by taking one big risk, and they also had the hustle of immigrants and desire to give their children more. I think hustle is a companion to risk-taking while not quite the same thing.
LZ: You have worked at Google, Amazon and other Silicon Valley behemoth companies. You have started and run (and sold!) your own companies. Is it possible to keep a truly entrepreneurial mindset in a huge company (even a tech-focused one)?
SSC: It is possible to be a large company that fosters an entrepreneurial spirit and risk-taking but that requires getting out of people's way and balancing structure and focus with room for people to author. For eg, a quarterly OKR process that itself takes four weeks of planning to create and cascade through an organization can signal the opposite of agility, as can pressing people for perfect plans and perfect forecasting rather than allowing your team's room to maneuver or even identify the ranges of volatility in any plan they are presenting. Conversely, when companies can create structures that allow people to move fast in smaller teams, to manage a portfolio of businesses from cash cows to new incubations in a way that people aren't tripping over each other to do their jobs, and a culture in which people all feel safe to speak up, truth tell, and present new ideas, it's possible to be large and entrepreneurial.
LZ: Articles about women in tech, female entrepreneurs are popular with my subscribers. Why do you think this resonates with so many readers who are not themselves "West Coast Entrepreneurs"?
SSC: I think that everyone dreams of creation, makership, and possibility in their own careers, and perhaps they look to the tech/startup economy as having something to offer in how to make something happen from nothing . More importantly, I think that people look for inspiration that it can be done by people who look/are like them, so perhaps its no surprise that women would rather see female role models, just as diverse individuals may appreciate the stories of other diverse leaders more.
LZ: "Failing" is now a right of passage for every entrepreneur, according to you and other business gurus and super-successful people. What should we think if, when we less successful people "fail," we feel terrible and don't see a bright side to failure. Are we failures at failing?
SSC: This is a great question, because in Silicon Valley, just ask risk-taking is glorified, so is failure. But as someone who has had a decent number of failures in my own life, I think that to be good at failing is requires two things: a) to be willing to be honest and vulnerable, about just how much it truly sucks in our bigger failures and have strategies to manage through these times of shame and pain and b) to be able to put failures in perspective, by taking small risks in our every day lives that work out or don't, but help build our muscles and agility and help actively shrink our fear of failure.
LZ: Of all the great advice you've ever received, what was one nugget that seemed totally off base at the time, that you've come back to and now embrace?
SSC: My father gave me room to run, and agency over my ambitions and choices, but also always told me that everything is not in our control (and to take it a step further, as a deeply religious person, to leave some things in "god's hands"). As someone who wants to drive to outcomes using all my own power and capacity, to "let go" of an outcome at the end of any journey can be challenging. But what I've seen to be true, time and again as a leader, is sometimes we can't simply force an issue through our sheer will and brute force. Sometimes the best outcomes happen when we let things unfold as they are meant to, rather than believing that we alone are omnipotent. We're not; now I put my full effort into something but accept that I don't control every outcome and situation, and it may not all unfold the way I want or desire, or even the way that is best, if I push too hard.
LZ: When I do interviews and I describe my first decade or so in the Business, building and running various production companies and making movies--each one itself a start-up unto itself (fundraising, staffing up, transacting) -- I usually say something like "back then I was called a 'freelancer;' today I'd be called a 'serial entrepreneur.' How exactly do you define entrepreneurship? Is it a mind set or a particular business structure?
SSC: I think of entrepreneurship as a mindset of makership and authorship, of trying to make something new happen or manifest by our efforts. For me it is a mindset.
LZ: Where should my readers go to find out more about what you do today?
SSC: You can always keep up with me at: https://www.linkedin.com/in/sukhinders/ or on twitter @sukhindersingh
Who's gonna win the 2024 Presidential Election?
I prefer not to comment on politics :) no good can come of it in our divided country :)
Are we near the end of the pandemic or are we going back down the non-vaxxed rabbithole?
Somewhere in between - delta variant will reimpose restrictions we thought we were done with, for a while, but is also stimulating the vaccination rate of the unvaxxed
On a lighter note...What are you watching/Streaming right now that we all have to see?
Ted Lasso Season 2. I LOVE that show- it will make anyone feel good :)
Cat person or Dog person?
Definitely dog. we have 2 goldens at home
Favorite restaurant in SF or NYC, past or present?
Slanted door in SF - an oldie but a goodie
What's your go-to 'comfort food' you turn to on a rainy/down day?
Ben and Jerrys in some overly sweet flavor which caters to my sweet tooth or super soft french bread with butter, and it may even be both :)
Is your very best friends in the world from childhood, college/school, or your working life?
From University my best friend Anh who I met on virtually our first day in the dorms and I've known and adored for 33 years!
I never had an explicit fear of failure when I was making career decisions, even risky ones. But I certainly had my share of professional failures and flops. It is interesting to note that things I worked on, everything from Zoolander to Project Runway were originally, well, flops. We turned it around and definitely learned a lot. And we changed the next step on the path to avoid another stumble. But I can't say I ever embraced the concept of failing as a trigger for thriving. Sukhinder's book made me think about how I could have done that differently or better.
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Final question I should have asked in my Q&A: how can I learn to thrive when I fail on the tennis court, losing a match well in hand in a tie-breaker, I wonder? This is the part that gets me. Sukhinder says above that you must "be willing to be honest and vulnerable, about just how much it truly sucks in our bigger failures and have strategies to manage through these times of shame and pain." I am 100% there with the TRULY SUCKS, but I have no strategies to manage through this time of shame and pain. How am I am doing on the honesty and vulnerability front?
Koaches' Korner: split-step on the volley, girl--every time! That's the honest truth.
See you in September, folks.
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