Rethinking Risk To Accelerate Your Career Growth
We recently hosted a Fireside Chat with Sukhinder Singh Cassidy, an incredibly successful Canadian tech executive and entrepreneur who now resides in Silicon Valley. Sukhinder is currently the Founder & Chairman of theBoardlist and Venture Partner at Acrew Capital.
We chatted about her soon to be released book Choose Possibility, taking calculated risks by preparing for ‘coconut events’ and leaning on your network of ‘professional priests’ to help you make better decisions.
Here’s what we learned!
Risk is not one ambitious, monumental decision that gets you there
Living in a place like Silicon Valley, you are surrounded with stories of monumental epic glory about Elon Musk and Jeff Bezos and while those are all great stories, they tend to make one believe that risk is for the risky, and that in order to have success you need to take this gigantic, step off a cliff.
This kind of risk taking leaves most people not wanting to take risks at all! Rather my advice is to learn how to take a little risk, and treat risk like a process just like any other type of process. And if you do, you can achieve the returns.
Prepare for ‘coconut events’
Coconut events can never be predicted and they have this massive potential impact, but there's nothing we can do to prepare for them.
So what happens when you encounter a coconut? People learn a lot about themselves and their ability to be agile. For example, I watched the StubHub team be more agile in the 30 days of having to restructure the business when we lost 95% of our revenues in a single week! Truly it was like falling off a cliff!
So be more agile. Coconuts also make us rethink what we really want to do. It helps us re-examine our goals. So I would argue that coming out of this pandemic, people have learned a lot about themselves and their ability to be agile and resilient at the same time. I think there has never been a better time to think about what risks we are willing to take than we have right now. The pandemic has helped put everything in perspective. It has taught people that there's probably a continuum of risk and many things we previously thought were big risks, may not be as big as you first thought.
Planning for what goes wrong vs what goes right
When people take risks, it's typically because of FOMO (fear of missing out) or on the other side, it is fear of failure.
People tend to increase their FOMO by planning for things to go right and don’t take into account that there's also fear of failure. So instead of always planning for everything to go right, spend time planning for the downside as well. One of the better ways to take action is reducing our fear of failure by planning for what goes wrong. This is the “central risk taking equation”.
Start by writing down 4-5 things on a whiteboard that needs to get done. Then create a rough guide, and learn to maneuver and navigate while being true to your Northstar as opposed to spending all your time in detailed planning.
Save your energy by planning for a variety of outcomes while still being very attached to the goal, whether that be a career change or leaving your job to jump into entrepreneurship.
Build a network of professional priests
Simply put, these are people who know you well in your professional circles. They understand what makes you tick, your strengths, your weaknesses, your superpowers, but they are also objective enough to be able to give you advice and tolerate listening to all your stresses!
Professional priests can run the gamut from ex-bosses to Board members to women who are similarly situated and have been through similar dilemmas as you.
Your reward is often not one choice away but can be multiple choices away
A reward is often the result of multiple iterative cycles and we're very used to seeing this in companies such as Uber who has pivoted five times to become what it is today, or Apple who released the iPhone which was pretty buggy until they kept improving through iterations.
In our own careers, expect to go through cycles of failure and cycles of success that create compounding returns. You have to expect that the relationship between risk and reward is a fairly nonlinear one, though it has its own predictability if you're willing to iterate -- which is the core thesis of my book.
Thank you Sukhinder for this insightful and inspiring talk. We can’t wait to learn more and read your book! And for those of you who want to build your own risk-taking muscles further, you can follow up directly by:
Learning your natural risk-taking style with this simple, fun and brief risk-taking quiz from Sukhinder and the Choose Possibility Team. Figure out what kind of a risk-taker you are today!
Get a copy of Choose Possibility now, that is available for pre-order. Any book purchasers pre launch will receive an invite to an exclusive, interactive and off the record book club session with Sukhinder to tackle risk-taking in real life work situations.
Missed this Fireside Chat? You can request a recording here.
