BookWatch: Reassess your life and career every 7 years by asking these 3 questions

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We can’t plan our lives and careers forensically and rationally, but we can make the time and space to check in with ourselves. If we periodically stop to ask the right searching questions, we can reset our paths for a better future.

But how?

Avivah Wittenberg-Cox, a gender and future of work expert, recommends breaking our lives down into seven-year blocks. Just as the body replaces itself with a largely new set of cells every seven years, we should take time out at the end of each block to contemplate, assess and plan.

Some of this is getting to grips with how to leave behind what is no longer right, useful or relevant. Like a snake shedding the skin that no longer fits, we need to identify and shed the skills, practices and opinions that no longer serve us. And some of this is deciding what to do next and how to adapt to new circumstances.

We don’t have to be obsessive about the timeframe — check in with yourself whenever feels right to you — but seven years is a good rule of thumb. It’s long enough to have transitioned from education to the workplace, to have weathered some sort of a crisis — life-changing or merely disappointing — or to have moved from one relationship to another. Yet it’s short enough to feel manageable, a period where it’s genuinely possible to analyze how you’ve changed.

So here are the three key questions we need to ask ourselves to recalibrate our ambitions and make sure our careers (and our lives) are mirroring our inner life compass.

What should I leave behind?

Working out what you don’t want is as important as working out what you do want; it allows you to define your red flags and non-negotiables. It steers us toward businesses and cultures that align with our own needs and views.

Wittenberg-Cox believes we need to get better at giving ourselves permission to move on: “We’ll need to get more skilled at letting go of what was — our old identity, relationship, competencies — to embrace what’s next — as yet unknown, undefined, and ambiguous.”

In order to work out what to leave behind, here are some areas to explore: Is the culture I have been working within holding me back or bringing out the worst in me? Have I experienced micro-aggressions that chip away at me? Does my workplace encourage a culture of overwork and presenteeism? What does that mean for me and my own boundaries; does work leak into evenings? Am I feeling burned out? And outside of work, do I have relationships with certain people that make me feel bad, sad, lacking or depleted?

This is where the biggest question of all comes in: does this still work for me?

What has changed in my life?

Ambition doesn’t follow a set trajectory; there are ebbs and flows as life throws us curveballs. What has changed since the last time I checked in with myself? It could be anything: an elderly parent has had a fall or a partner’s new commute creates havoc for school drop-offs. It may be that you are moving back home to live with parents, are having health problems or are going through a relationship breakup.   

All of these things dictate the way we want our careers to intersect with the rest of our lives. At certain points, life is purely about coping rather than taking on expansive or ambitious projects.

So we need to ask ourselves what has changed. What can I take on? The tug of home life can be intense at times; at others it can be imperceptible. Permission to define success in the way we want to —whether it is raising a family or raising hell at work— is liberating.

What drives me?

We are all driven by different things. We might be motivated by more money, prestige, a job title. We might see success as Instagram likes or just more autonomy. But the things that drive us change over time. We need to ask ourselves: are my values still the same? Do I still define success in the same way?

Changing priorities might happen at any point in our lives. They might be as small as new interests or as big as a changing view on the world. They may spur you to look for something different in your career — the time to pursue a hobby, or even to quit to find a job that better reflects your new purpose.

Jonathan Rauch, the author of “The Happiness Curve,” identifies one such change as happening inmidlife: “Normally it is not — contrary to stereotype — a crisis. Rather, it is a transition.  During this period, our values, our priorities, even our brains tend to shift away from competition and social striving and toward connecting and giving to others”.

This may drive us to pivot to a new industry; former Financial Times journalist Lucy Kellaway retrained to become a teacher. She explained: “For me, this had been a long time coming. When my mum died, I thought I’d had it with journalism because it was too shallow . . . I sat around with all these journalists fussing over what the headline was, and I thought: ‘No, I don’t want to do this anymore. I want to do something useful.’ ”


Regularly tackling these big questions can help us work out what we want to leave behind, what we really value in our lives and what we want to prioritize going forward.

This shouldn’t feel like something to tick off the to-do list. It is an ongoing process that you might want to document in a journal or discuss with trusted confidants. Allow yourself time to mull, and don’t worry if the answers don’t come quickly.

We need to stop holding ourselves hostage to the people we were, and allow ourselves and our ambitions to evolve. The ability to flex to change will be a superpower. As futurist and philosopher Alvin Toffler said, “The illiterate of the 21st century will not be those who cannot read and write, but those who cannot learn, unlearn, and relearn.”

Also read: Your midlife malaise is totally normal — and this simple strategy can keep it from turning into a crisis

Annie Auerbach is the author of “FLEX: Reinventing work for a smarter, happier life”.