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Alan Gertner, founder of Tokyo Smoke, has quit his job as chief retail officer at Canopy Growth and is re-evaluating his life once again.The Canadian Press

Why is it that people in seemingly great places – good careers or relationships – leave to pursue more?

Growing up, Alan Gertner was the type of kid who preferred computer camp to sports camp. And in 2015, he was working his dream job at Google, having spent six years rising through the ranks. He started in Mountainview as a senior associate and ended up in his most recent role, based in Singapore, leading the Asia Pacific Online Travel team – at only 30 years old.

Alan had everything that he’d ever hoped for: A job with prestige, earning more than he thought he’d ever earn, leading a great team at a top-tier technology company. And it wasn’t enough.

He’d dedicated his 20s to winning at work, and for the first time in his career, he questioned whether he was authoring his own story, or living someone else’s.

And so, he left. He quit his dream job at Google with no clear plan for what he was going to do next.

He spent the following year on his own self-directed, meticulously documented journey of self-discovery, and came out on the other side with clarity on what was next. He went on to start a company in the cannabis industry, Tokyo Smoke, which he eventually sold to Canopy Growth Corporation for a reported $250-million.

The new normal

For millennials, leaving a good or great opportunity to pursue another one is the new normal. A recent Gallup report reveals that 21 per cent of millennials have changed jobs within the past year, and Career Builder found that by age 35, nearly 25 per cent of young employees have worked at least five jobs.

What this means is that this generation will be starting and stopping, switching and moving much more frequently. This constant urge to evaluate new opportunities is forcing us to do more frequent gut-checks and self-assessments to determine what it is we really want to do.

Career coach Lauren Malach works through these issues with her clients every day. She finds that the most common reason people leave seemingly great opportunities to pursue better ones is the desire for self-determination: the feeling of being in control of your own life.

But that doesn’t have to mean leaving your current opportunity. In her coaching, Malach has worked with clients who love their jobs, as well as those who stay in careers that they don’t necessarily love in order to support the people or the life that they love.

Given how much we give up for our work, we often expect work to offer everything back to us: meaning, happiness and engagement. We sacrifice our leisure time, hobbies, and even relationships, so we expect work to make up for it somehow. We layer on countless professional goals so we can work on the goals and not ourselves.

The passion myth

Finding work that you truly love to do is an iterative process, and sometimes a love for the work emerges from first becoming really good at it. We may end up developing a passion for our work by first identifying an opportunity that we can be uniquely good at, hone our skill, and then find a way to love it.

Safety nets

It’s rare to have the unique privilege of putting a career on hold for dedicated introspection. Those who have the ability to do it often have a safety net of sorts: a supportive (and income earning) spouse, accumulated savings, or in the case of Prince Harry and Meghan, pre-existing wealth.

Millennials have the confidence to make direction-changing choices because it’s less risky to start over at 35 than it is at 50. Those who make the leap have developed enough confidence, or mitigated the risk, to know they’ll be fine. They have a track record of some professional successes, or a new opportunity in the works before leaving their current position – like Harry and Meghan’s trademark application for the name “Sussex Royal,” which leverages their personal brand.

Self work

Gertner used an excel spreadsheet to literally score each and every day: what conversations did he have; what gave him, and drained him of, energy; and what patterns emerged on his best days? This tracking led him to some significant insights that changed the course of his life. Six months after the acquisition closed, Gertner left his job as the chief retail officer of the world’s largest cannabis company to re-evaluate his life once again.

Starting, stopping and switching is the new normal – a reality that employers and employees are going to have to face head-on in the new era of work.

This column is part of Globe Careers’ Leadership Lab series, where executives and experts share their views and advice about leadership and management. Follow us at @Globe_Careers. Find all Leadership Lab stories at

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