women on the biggest career “mistake” they’ve ever made – and how they overcame it

8 women on the biggest career “mistake” they’ve ever made – and how they overcame it

When it comes to career mistakes, it’s important not to let them define you. Two experts share the best ways to bounce back after a slip-up at work.

We’ve all had one – some of us, more than one – of those awful head-in-hand moments when we realise we’ve made a mistake.

And while a slip up of any kind is painful to navigate, there seems to be a special kind of torture reserved for when we commit a faux pas in our career, the thing we spend so much of our time and energy building.

Whether it’s taking a leap of faith that doesn’t work out or a fallout with a colleague coming back to haunt you, that sinking feeling deep in the pit of your stomach will be a familiar one.

While it’s important to hold our hands up when we’re at fault, these situations can often come down to a matter of perspective. Errors we think are catastrophic at the time can end up propelling us in a different and unexpected, but ultimately positive, direction.

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“Making mistakes is something everybody does and they can be a powerful learning tool,” explains Luciana Andreoni of agency True & North.

“But when it comes to career mistakes, we are less quick to brush them off – and it stands to reason. Career mistakes feel very much of our own doing. And it does lead you to question how successful you are or will be in your job or career, which can have a direct impact on your confidence and sense of worth.

“But career mistakes are inevitable and, in a similar way to mistakes in any other aspect of life, provide an opportunity to grow and develop. For example, messing up an interview will make you sharper when the next one comes up. Plus, very few people start their careers knowing exactly what they want to do or what their strengths and weaknesses are. It’s only by taking a job you turn out to hate (or that you suck at) that you find out what your path should be.”

“I’ve come to realise over time that experience is everything, both good and bad,” agrees Vicki Maguire of advertising agency Havas London. “So it’s not just OK to make career mistakes, it actually makes you a better candidate. The secret is to own them. If I was interviewing a candidate who’d had a varied career path and could tell me stories of how she messed up but learned from her mistakes, I’d hire her on the spot.”

Stylist asked eight women about their biggest career “mistake” and how they overcame it. This is what they said.

“I assumed I had to do everything myself to get things done”

“The greatest mistake I made as an entrepreneur was assuming I had to do everything by myself to get things done. When I realised the true measure of a leader is not how much they can bear, but how well they can delegate, my life changed! There is strength in numbers and you are your greatest asset. Do not allow your mental health or peace to be weakened by trying to carry the world on your back. There are people who are ready and willing to support you.”

JoAnn, founder of Maskee

“I was too scared to ask for more flexibility”

“I wish I had explored hybrid working when I was in the corporate fashion industry. While I was worked there I got married and had kids. I couldn’t see any mums doing what I’d want to do so I decided I had to leave. Looking back I wish I’d had the confidence to have these tricky conversations and, knowing what I know now, ask for more flexibility. I’m not sure how it would have been received – but I wish I’d tried – I adored the company and the team.”

Louise, founder of Daisy Chain

“I went back to office work and resigned four months later”

“After 15 years of being self-employed, last September, I decided it was time to step back into the corporate world. My sons were both at senior school and I was looking for a challenge. Fast forward to Christmas and I was in the fast lane to burnout and misery.

“I didn’t realise just how much of a free spirit I was. Being my own boss allowed me to pursue different opportunities using my wide skill set, while still being able to get out for a dog walk on the beach and collect my kids from school – something I missed and today enjoy as it’s a time to catch up and chat with my boys. While most of my team were fun, the overall feeling was one of toxicity, being undermined and chained to Teams and timekeeping software.

“On 4 January 2022, after a snotty crying session with my husband in a coffee shop on New Year’s Eve, I resigned. While I felt like a failure for not seeing this role out, the relief of being set free was enormous and five months on I have rebuilt my PR business, focusing on mental health brands and experts, and am building my own team with a culture of trust and support.

“What I learned most was the grass isn’t greener, but you just need to spend more time looking after your own lawn.”

Natalie, author, coach and PR director

How to deal with career mistakes

“I held on to a job out of fear”

“In 2018, I clung to a job that wasn’t working out. I was an overworked new mum; so many things had gone wrong, but I was terrified to go as I was afraid of the unknown of working somewhere else.

“I ended up being made redundant, which helped teach me that sometimes it is OK to quit. Quitting isn’t always a bad thing, nor is ‘failure’.”

Caroline, founder of Upsource

“I took advice from the wrong people”

“I would say that one of the biggest mistakes I have made so far was letting myself be too influenced by someone who had more experience than me. We were offered a deal that sounded a little too good to be true, and I felt in my gut that it wasn’t right for us, but I was talked into it by someone who was a so-called expert. Lo and behold, it didn’t work out; some money was lost, but mostly, I lost a lot of time working on something I knew was off from the start. Now don’t get me wrong, speaking to people who have more experience than you can be extremely valuable, and there is a lot to learn, but there are also instances where you need to listen to yourself, your own experience and that indefinable ‘gut-instinct’ that we all have.”

Anneke, co-founder of The Camden Watch Company

“I thought I knew it all”

“I was running my own business at 21 years old, and in the first year I had everything: the car, the profits, Asos wanting to stock our clothes. I thought I had it sussed. I did not. In year two, I lost everything. My home, my car, my business and my relationship. Everything crumbled. I had to re-enter the workforce with a failed business and not much else experience and work my way from the bottom up – certainly a humbling experience.

“But that failure is what allowed me to work for someone else for 10 years; that failure is what gave me the time and the skills to launch my new business, Klowt. That failure is why I now succeed. We all see failure as the opposite of success, it’s not. It’s part of it. Because there is no such thing as win or lose – there is only win or learn.”

Amelia, founder of Klowt

How to handle making career mistakes
How to handle making career mistakes

“I underestimated myself”

“When you come to a new country as a single woman with a foreign accent, you are sometimes judged by factors unrelated to your actual professional abilities. I knew I already had the knowledge, experience and drive to build a successful company even in a new country. I had a fortunate career for many years in Montreal, where people spoke my native language. Why couldn’t I do it again in another country?

“Initially, I would go after big potential clients who would be deterred from giving me bigger orders for reasons unrelated to my company’s capabilities: I didn’t have a big enough office at first, have enough employees, or drive a nice enough car. These were things completed unrelated to my ability to give them the best product and customer service.

“When you believe in yourself, don’t let other people tell you otherwise. By nature, I am a people pleaser, and I had to tune down this habit. I also had to follow my own rules, commit to my own goals, be consistent in business management, be persistent and not let anyone defeat me with some cliché stereotypes.”

Zee, production manager and CEO

“I wasn’t cautious enough”

“Over time, I have learned to take a first impression with a grain of salt and do a lot of research before hiring and trusting people. I have previously hired a few people based on my gut feeling and/or recommendations from friends who didn’t really have my best interest at heart. I still wear my heart on my sleeve and chose to believe that people are generally good… but I am much more cautious now.”

Chriztina, owner of Eagle Rock Werkshop

How to manage a career mistake

“The most important thing is to never hide your career mistakes away in that dark part of your mind that tells you you’re not good enough. Quite the opposite – the best thing you can do is to talk about them openly. It helps you to reflect and learn from your experience and get some perspective, as well as get the advice you need in planning your next move,” suggests Andreoni.

“The more you fail, the less worried you are about failing and the more fearless you become,” agrees Maguire. “If you do make a career mistake, move on quickly. Work out how and why things happened like they did, draw a line and get on with the next thing. Don’t worry about what might have been.”

“My long and successful career of mistakes have actually made me better at my current job. I don’t fear failure and that frees you up to take leaps you wouldn’t have otherwise made. No one likes to admit they’ve failed or made a mistake and that’s crippling. But the more we share our bad experiences, the less hold they have over us. Trust me, I’ve learned through experience that the world doesn’t end. The sun still rises, so just put it behind you and move on.”

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