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Careers involve choices. And with each choice comes risk, sometimes large, sometimes small.

Sukhinder Singh Cassidy has identified 23 choices she made over a career spanning three decades, taking her from her hometown of St. Catharines, Ont., to her perch in Silicon Valley, where she is president of the ticket exchange service StarHub. Some of those choices worked out while others didn’t. But her career flourished. “I managed to achieve many more of my dreams than I would have with more limited risk-taking,” she writes in her book, Choose Possibility.

Too often, she feels, we fear career risk-taking. We buy into what she calls “the myth of the single choice” – career success depends on a single leap that has the power to make us or ruin us. We need to free ourselves from this all-or-nothing perception of career risk-taking, in which we need to come up with the perfect plan and perfect timing. We need to reduce our fear of each single choice while giving more weight to our ability to keep choosing and ultimately getting ahead. We keep in mind that the riskiest career choice might be the one that seems safest and instead choose possibility.

“Risk-taking is not the single, epic brush with peril that we imagine. It’s a continuous process that we humbly but hopefully embrace, knowing that individual chances we take may be likely to fail but that our probability of overall success will increase as we iterate,” she writes.

The two main reasons for not taking risk are to avoid loss or shame. But holding back can mean losing out on learning and growth. She urges you to build your risk-taking muscles, taking advantage of opportunities that arise every day to take chances, big and small, to further your goals. As you take more risks, it becomes progressively easier to take others.

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In your career, she suggests pursuing multiple opportunities in parallel. Don’t just stick with one possibility in a job search; try several. If you have a good job, keep looking around for better. She calls it pipelining in parallel, maximizing the opportunities available to you – placing multiple bets, mostly small but perhaps some big that could pay off. It worked for her, notably after taking a job after university with TD Bank but still pursuing her dream of a global banking career and ending up not long afterward with Merrill Lynch.

Fear of missing out has been mocked these days as foolishly leading us to take on too many activities in our life. But she feels fear of missing out – fear of missing career opportunities – is advantageous for our careers. If fear of failure is greater than fear of missing out, you’ll stagnate. But if fear of missing out is greater than your fear of failure, you’ll gain.

Put “who” before “what” in taking a career risk. “Who” is the person or people you will align yourself and work with. The “what” is the type of work you might do. “Don’t be so sure that falling in love with a given field, job type or industry will take you most quickly to the mountaintop. Pay much more attention to the individuals who will accompany you on the journey,” she says. If possible, find the kind of person Dartmouth College management professor Sydney Finkelstein calls a superboss, who is a talent magnet, bringing superb people together, inspiring them, and helping them to move to even better positions.

When bigger risks come, she suggests rating the choice on four factors: Your goals, your passions, the associated tailwinds and headwinds, and your fit with the people you would be working with. Against that, consider your fears – financial, reputation, ego and other personal issues. She suggests rating each of the four factors on a one to five scorecard – five high – and then assigning an overall score also out of five to your fears. Subtract the fear score from the total of the other four factors and you’ll have a good guide to the decision.

So don’t ignore risk. But don’t be blocked by it either. Choose possibility.

Quick hits

  • When failure is reversible, act quickly advises Atomic Habits author James Clear. When failure is irreversible, think carefully.
  • A mistake in delegation is thinking it is successful when done exactly how you would have done it yourself. Serial entrepreneur Robert Glazer argues that sets the bar too high. Effective delegation is when something is done 85 per cent of how you would have done it yourself, without you having to be involved.
  • Mental toughness coach LaRae Quy recommends sorting through the areas of life causing anxiety and lumping them into two piles: Those you can control and those you can’t. Claim ownership of the issues you can control and deal with them, thus eliminating stress and anxiety in the areas you have power over.
  • Treating a client to a two-hour lunch on a Friday doesn’t earn their loyalty, observes sales consultant Colleen Francis. What does nudge them in the right direction is when you can say: “I have something to offer you that will make your operation more efficient.”
  • If your keyboard unexpectedly changes languages on you – from Canadian English, say, to French – be sure you aren’t hitting the alt + shift combination, which will trigger a language change (and if repeated, return you to the norm). Microsoft Word expert Allen Wyatt adds that you can also select Language on the Review tab; from the drop-down menu pick Set Proofing Language; and clear the Detect Language Automatically check box.

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