How to Break it to Your Friend That They’re in the Wrong Job


It’s not you… it’s your job.

Text message reading "how do I put this?"
We wonder, could it have been a trusted confidante that gave Oprah the confidence to call quits at the corner store and start reading news on her local radio station? Maybe it was a kindly chum who urged Martha Stewart to stop stockbroking and launch her own catering company, and, for all we know, Obama’s bestie convinced him to throw in the ice-cream scoop and move on from Baskin-Robbins. If your mate is treading water, or worse, undervalued in their job, as their friend you’re in prime position to deliver the well-intentioned boot up the butt they might need to make a change. So, in the spirit of stabbing your friend (gently) in the front, here’s how to tell them it’s time to get out.

First, ask yourself: Why?
Before you coax your friend into telling their boss where to stick it, take a moment to consider why you’re administering this push. Is it because you’ve listened to their relentless dissatisfaction and hand-on-heart believe they’re unhappy? Or might it be that you are the one who’s irked by their work? We all want the world for our beloveds, but your friend might be perfectly contented in accounting, snake wrangling – even stripping. And then there’s the question of what’s important. They might value the flexibility – or sizeable paycheck – over job love, choosing to get their kicks elsewhere. So be sure you’re basing your intervention on what’s best for them, not what you think is best for them.

Try face-to-face
Would you tell your friend they’re dating a douchebag via text? The same etiquette that applies to matters of the heart should be called on for qualms of the career. This is not an interaction that should take place in the same realm as emojis, nor is it one to be batted about in an email trail (and obviously, steer well clear of their work email address). Body language expert James Borg says that human communication consists of 93 per cent non-verbals (giving your actual words of advice a mere 7 per cent weighting), so set up a private time to chat, explain your concerns and listen carefully to their reaction. Also, keep in mind that, should this exchange not go so well, you mightn’t want it forever accessible with a click.

Go in with questions
The least offensive way to tell someone their job stinks is to get them to say it for you – for themselves – and the best way to probe a confession is with a little interrogation. It could be as innocent as asking them where they see themselves in five years (an apprentice beekeeper does not a diving instructor make) or how they envision success. Clearly identifying what they want to achieve will draw their current job – and its shortcomings – into sharper, harsher focus, and then you can get things rolling with some helpful follow-up questions, such as how someone they admire got to where they are, and what the first move they can make in this direction might be.

Arm yourself with solutions
Whatever the occasion, it’s just good practice to never bring up a problem without offering at least one solid solution. In this instance, it could be in the way of a mentor, contact, job site or specific listing or two (or 10) better suited to your friend’s passion. Or maybe it isn’t a matter of jumping ship. Are there other opportunities – or perhaps even entire departments – more likely to unlock you pal’s potential at their current place of work? Nut out a strategy to sidestep in this direction. But if a dead-end job is just that, and they’re not in a position to hastily hand in their notice, maybe returning to study or starting up a side-hustle is the way to go. At the very least, offer to help them dust off and brush up their CV.

Check in
Don’t drop the ‘bad job’ bomb and leave a brother hanging. You’re involved now, so let your buddy know as much and make yourself available to them as they take their next steps. A UK study showed that when people air their worries to others, it can really improve their situation (making the old adage ‘a problem shared is a problem halved’ ring true) so you’ve already given them a head start. Keep up the good work and hold your friend accountable by regularly seeing where they’re at and celebrating their progress – however small or stumbling – in the way of their dream gig.


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