Could a bad boss actually supercharge your career rather than stymie it? According to Michelle Obama, a stint working with a rubbish leader in an underwhelming job might actually be good for you in the long run.
Speaking at a live podcast recording in London this week, the former first lady cautioned young people heading into the workforce with expectations of a perfect experience might be doing them a disservice, as even the bad times might pay dividends in the long run.
“That’s what I want young people to understand: that every experience, the bad boss, the boring assistant job, the job [in which] you thought that you weren’t appreciated, the one that didn’t give you the assignment you wanted when you wanted it – all of that is learning to be resilient,” the 62-year-old told the audience, noting that it is “important” to “learn how to do something you don’t like and be good at it”.
Young people, Obama added, might want to immediately do “what they are good at” in their career, but she says that “you have got to earn that, carrying some bags and having some tough times and having people treat you unfairly”. Even the boss who doesn’t give you a pay rise “when you think you deserve it” might be “character building” and prepare you “before being your own manager, being your own leader”, she suggested.
open image in galleryObama’s advice might feel a bit like the career equivalent of telling kids to eat their vegetables (you see this thing you really hate, it’ll be good for you in the long run, honest kids!). And it will likely be framed in generation-clash terms, as a boomer telling fragile youngsters to suck it up and get on with it. But if you listen to her carefully, the ex-Flotus’s words are much more than Gen Z bashing and bad boss championing.
Instead, they’re a reminder that seeking to totally eliminate less-than-ideal experiences just isn’t realistic – no one walks straight into their perfect job. But learning to deal with the foibles of a strange boss or to navigate some tricky office politics will stand you in good stead for when things get tough later in your career (often when the stakes are higher too).
As someone who has weathered more than their fair share of bosses who could be described as… ahem, unique, I’m with Michelle on this one – their idiosyncrasies and, in some cases, sub-par behaviour have made me more capable (even if they’ve simply shown me what not to do).
In one completely bonkers PR internship, I was dispatched to the media houses of London clutching display stands teeming with nail varnish branded in the agency’s colours, expected to somehow sweet-talk my way into securing a spot for this plastic abomination on the front desk. In shocking news, major media conglomerates did not wish for some random unsolicited tat from a PR company to block up their chic reception spaces, and their reception staff let this be known in no uncertain terms (as was entirely reasonable).
I was in a constant state of ‘what the hell is going to happen next?’ for the duration of my time with [my former boss] – but it did make me far less precious about over-preparing and perfectionism
As someone who hates causing any kind of scene, and who is prone to reliving cringe-inducing interactions over and over again in my mind in full Technicolour, this was a real low. At one point, I contemplated chucking the whole lot into the Thames (consideration of the local marine life stopped me – they didn’t need this rubbish either).
But I now see that it was also a sort of exposure therapy, forcing me to try to feign some confidence and worry a bit less about what others thought of me. After I’d faced the sheer embarrassment of this, the rest of my intern tasks seemed pretty easy.
And there was another boss who was, quite simply, never there, which created a whole load of problems for me to sort out in her (extended) absences. I would have to pick up the pieces on tasks that were well above my pay grade and was summoned to speak in meetings that I’d had no idea about 30 seconds earlier.
It wasn’t great for my fight-or-flight response – I was in a constant state of “what the hell is going to happen next?” for the duration of my time with her – but it did make me far less precious about over-preparing and perfectionism. Sometimes, I learned, good enough is actually pretty great.
For Charlotte Leigh, who now owns a fine jewellery business, one early bad boss had a “profound impact” on how she would later lead her own company. “She was extraordinarily unprofessional,” Leigh recalls. “During an office move, I found myself painting the staff toilet because, as a keen and eager junior desperate to impress, I simply did what I was asked. On another occasion, after an anonymous email was sent to one of her clients criticising her conduct, she systematically accused every member of staff of being responsible. The atmosphere became one of suspicion rather than trust.”
open image in galleryThis boss, Leigh says, would often rock up late “carrying shopping bags”, while the team worked long hours, creating a “disconnect between leadership and example”. But while this was frustrating at the time, she now sees these experiences as “invaluable”.
“When I started my first company at 21, I was determined to create a culture built on trust, respect, accountability and leading by example,” she says. “Some of the most important lessons in business come not from great mentors, but from witnessing poor leadership first-hand. Those early experiences shaped the way I treat employees, clients and suppliers to this day.”
Career coach Hannah Salton also believes that “having bosses I didn’t click with earlier in my career helped me develop my resilience”. At the time, she says, it was difficult to see the positives, “but afterwards I really understood how much it taught me about working with different people, and managing different personalities”. Now, when her clients clash with their managers, she encourages them to “list the things they are learning from them, even if it is just how not to lead”.
If you feel frustrated but still able to cope, a demanding boss might actually end up making you more resilient in the long run
Hannah Salton, career coach
But it is also important to draw a line between character-building experiences and those that step into outright mistreatment or bullying. I’m sure Michelle Obama would not advocate for young workers to put up with a toxic environment, and neither would I. A controlling, aggressive boss can destroy self-confidence in ways that can be hard to bounce back from, and just as it isn’t feasible to expect every work experience to be perfect, we shouldn’t have to try and scrape nuggets of positivity from jobs or bosses that are truly toxic.
So, how to tell the difference? Salton recommends considering how someone’s behaviour is making you feel. “If you feel frustrated but still able to cope, a demanding boss might actually end up making you more resilient in the long run,” she says. “But if you genuinely feel it’s eroding your confidence and self-esteem, that’s the signal it’s gone beyond character-building and is worth addressing.”
Chartered counselling psychologist Dr Kirstie Fleetwood-Meade adds that a “challenging but healthy manager” might prompt you to feel “stretched, frustrated or occasionally stressed, but ultimately more capable and confident”. A toxic manager, meanwhile, “leaves you feeling increasingly anxious, depleted or questioning your own judgement”. In that instance, she explains, focus at work will shift from developing your own skills in response to “feeling like you have to survive”. She adds: “If you are constantly on edge, doubting yourself or dreading work, it may be a sign that something more concerning is happening”.
Resilience, Fleetwood-Meade notes, “is built through navigating challenges and setbacks while still feeling supported and capable” – it is not “about tolerating intimidation or behaviour that undermines your wellbeing”.
Being able to spot the difference between these situations with confidence is probably one of the most important lessons that you can learn.