Choose Possibility


Sukhinder Singh Cassidy is the former CEO of StubHub who has stubbed her toe many times while climbing various corporate ladders, and learned valuable lessons along the way. She distills this wisdom in her new book, which begins with this eye-catching vignette in the opening chapter:

Have you ever reached an inflection point in your life or career only to feel terrible pressure to make a choice? My older sister Nicky can identify. In 2010, she was running her own Optometry practice in a suburban mall. Caring and giving by nature, she loved to serve patients and took immense pride in her office and small staff, whom she treated like family. For a decade, her business prospered, but more recently it had struggled due to macro conditions … Serendipity stepped in to help: a friend told her of a new medical clinic opening up much closer to her home, part of a larger venture-backed medical company opening locations throughout the region. Each location offered combined medical and optometry services, and the company was seeking optometrists to build out these practice … Nicky’s success didn’t happen overnight. Rather, she pieced together smaller and then bigger choices over several years to unlock an entirely new career possibility, one that leveraged her experience as an entrepreneur and optometrist in a whole new way.”

I had hoped that there would be more detailed discussion in the book about Nicky’s experiences, as eyecare private equity acquisitions is something that has been considerably on the rise over the past few years. Perhaps there hasn’t been enough time to objectively evaluate how her ostensibly sweet deal has worked out in actuality. In September of this year, The Wall Street Journal reported that Keplr Vision, a private-equity-owned business that provides operational support to 300 optometry practices across 35 states in the U.S., was exploring a sale. One wonders how sustainable these business models are.

Ms. Cassidy is a graduate of the Ivey Business School at Western University, which bills itself as Canada’s leading provider of real-world, case-based business education, and the 2019 recipient of its Alumni Achievement Award.

If you look carefully at the cover of Ms. Cassidy’s book, you’ll notice that the ladder of choice has a ghost image that leans in another direction. Her principal message in the book is that choices always carry an element of risk, which is why it is good to have irons in multiple fires simultaneously though not to excess.

She calls this concept of juggling multiple pursuits at once, rather than pursuing opportunities in a linear or sequential manner, as “parallel pipelining”. Her message is part of a larger genre of business thinking in which one must be willing to fail, and in many instances fail repeatedly, in order to take calculated risks that lead to cycles or spirals of success.

Among the many pearls of wisdom that Sukhinder offers is the tactic of having brainstorming buddies in your career. These are people who understand your ambitions, are adept at generating possibilities, and who can help you stay optimistic. She writes: “We all have wisdom to glean from different people at different stages of our journey. Seek out a tribe of people who enhance rather than diminish your ability to generate ideas in any particular phase. Make sure they’re open to listening to your list of opportunities in an unbiased and nonjudgmental way, and to contributing to that list as well.” As she progressed in her career, a professional coach played a pivotal role in her development.

For me, personally, Toni Bristol was the right professional coach at a pivotal time. Yet I would not have encountered Toni were it not the group of brainstorming buddies I was privileged to network with around 30 years ago. Originally dubbed PMS (Practice Management Seminar) and then PMG (Practice Management Group), two of the members (Drs. Birnbaum and Getz) sang her praises to me and I enjoyed the tune. The practitioners involved, all of whom specialized in vision therapy and rehabilitation, ultimately morphed into the present day VHG or VisionHelp Group. In that regard, reading Sukhinder has been a validation of some of the principles that have served us well.

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