Choose Possibility is a new book by Sukhinder Singh Cassidy. It is part personal story, and part career guide for ambitious professionals.
I first learned of Sukhinder in 2012 while watching videos at Stanford’s Entrepreneur corner, where she was interviewed as the founder of Joyus.
Sukhinder has had a remarkable career with stints that include being part of the founding team at Junglee (acquired by Amazon for $280 million), one of the top executives at Google, President of StubHub, and even launching her own SPAC.
But she has also freely talks about her setbacks, out of which she shares crucial lessons. Yodlee and Joyus (two companies she co-founded) were not financial successes, despite the former going public and the latter being acquired.
She grew up in Canada as the child of two Indian doctors who emigrated from Zanzibar, to allow their children to have better opportunities in life. Below are some of my key takeaways from listening to the Audible version of the book:
Have the courage to embrace who you truly are: Sukhinder is naturally intense and this rubs some people the wrong way. When she took a job at Open TV she was told she was scaring the secretaries and she felt less free to speak up. She quit shortly after and in her words “found my tribe at Junglee”, where her drive and ability to get things done were highly valued. Junglee sold a year after she joined the company earning her, her first $1 million! And when, as a relatively junior employee at Sky, she spoke up confidently and persuasively in a meeting, the CEO noticed her and promoted her the next day.
Invest time in cultivating a high quality network & there is no substitute for hard work/getting results: Great opportunities are attached to influential people and the more people you know and who respect your work, the more opportunities that will come your way. Most of her best career moves (like Yodlee and Google) were the result of former colleagues reaching out to introduce her to opportunities.
When considering a risky move, clearly spell out and face the worst case scenario: By doing this, you will be more comfortable taking risks. For example, When Sukhinder quit her job in London and moved to SiliconValley with no plans, she figured out exactly how long she could live without an income and also knew her parents could help. She recommends using the formula FOMO > FOF = Action i.e. When your Fear Of Missing Out is greater than your Fear of Failure, you take action. Facing the worst case scenario reduces Fear of Failure
Pursue things in parallel and Take Lots of Little Risks. If you do things sequentially, waiting for everything to align perfectly before taking the next step in your career, you will likely miss out on great opportunities. Yes, focus one main thing is essential to success, but have feelers out on multiple possible next steps, and also take lots of little risks (versus waiting to succeed in one big fell swoop. Outside of the lottery this never happens)
Meticulous planning is overrated: Sukhinder didn’t have a grand career masterplan and was even unsure what she wanted to do after completing university (that’s what they call it in Canada :)) Unlike her peers, she struggled to find a first job but the big break came when she decided to throw caution to the wind and apply for a job that required an MBA and work experience, at a prestigious Canadian private equity firm. While she didn’t get the job, just being invited for a round of in-person interviews and nearly making it boosted her confidence a lot. Soon after, she landed her first job with Merrill Lynch in New York. Her career strategy might be summarized as ‘figure out your current skills and strengths then go after big opportunities that excite you’. In other words, choose possibility!
In addition to her own story, Sukhinder shares the career trajectories of various people in her network. Each is interesting. Buy the book to also learn about: