5 Things to Consider if You’re At a Career Crossroads


A former Google career coach weighs in.

Whether it’s the threat of redundancy, the need for flexibility, or just a general feeling of unrest, facing a career crossroads is becoming increasingly common for many of us. However, while you might feel paralysed by indecision now, it’s important to recognise that this period of uncertainty can bring with it great opportunity. But where to begin? Answering these five questions may help establish what direction you want your career trajectory to take.

1. If everything remained the same, would that be OK?

If someone told you that in 12 months’ time you would still be holding the exact same position as you are now, how would that make you feel? If that prospect disappoints you, it could be a pretty clear indication that while you want to move on, something is holding you back. You certainly wouldn’t be alone; it’s estimated that less than half of all working Australians are happy in their jobs, yet only a small percentage are actively looking for a new position.

2. What do you fear most about moving on?

Business and career coach Jenny Blake understands the predicament of facing a career crossroad more than most. In 2011, Jenny made the controversial decision to leave her coveted position as a career strategist at Google in order to venture out on her own. “I was at a fork in the road,” Jenny, now a career and business strategist, recalls. “I’ve got to pick one, and I knew that not ever trying to do my own thing, that’s what I would regret more than leaving, even if I failed.” Now, when her clients tell her their own fears, the Pivot; The Only Move That Matters Is Your Next One author tells them, “Yep. Those things might happen. But will that stop you?”

“Investing in a side hustle will allow you to dip your toe in a new industry without the added pressure of trying to make it the main source of your income.”

3. Is it really your career you need to change?

It’s easy to pin feelings of discontent on your career – but is that really the issue here? A toxic workplace, a micro-managing boss, or even symptoms of a rapidly approaching burnout can easily be misconstrued as dissatisfaction in your career. Perhaps look for a similar role in a different environment, either by changing teams or joining a new company altogether. Once you’ve taken the factors that were negatively impacting you away, you might find a new appreciation for your current career.

4. Are you willing to put in the effort?

Just because you’ve decided that you want to forge a completely new career as, say, a graphic designer, that doesn’t necessarily mean you have all the qualifications or experience required to jump ship straight away. Whether it’s through retraining or picking up occasional freelance work, investing in a side hustle will allow you to dip your toe in a new industry without the added pressure of trying to make it the main source of your income. “You essentially have two jobs,” notes Jenny, who wrote her first book – Life After College – while still working at Google. If the idea of giving up your evenings or occasional weekend doesn’t appeal, it could indicate that this isn’t the vocation for you after all.

5. What is your primary motivator?

Finally, ask yourself what it is that really makes you tick. Is financial security your driving force or are you more focused on the opportunity to continually learn and grow or perhaps make a difference? On the topic of her book Pivot, Jenny notes that the most successful career moves come from “a strong base of who you already are, what works, and how you define success for this next phase of your life.” Once you’ve established what you want, take a series of small actions in order to get there. “Some pivots take one month, while others can take years,” concludes Jenny. “And sometimes it takes several smaller pivots to reach your destination.”

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