Anna Hart | Contributing Writer | 1,204 day ago

Ask An Adult: How To Learn From Your Mistakes At Work, Not Be Crushed By Them

The Debrief: Because newsflash: your boss isn’t always right

Illustration by Beth Hoeckel

Gutsy new anthology Mistakes I Made At Work: 25 Influential Women Reflect On What They Got Out of Getting It Wrong by Jessica Bacal, features interviews from 25 high-achievers across different fields who have all, at some time, made a mistake at work. It includes Anna Holmes, founding editor of feminist website Jezebel, who is brilliantly and brutally honest about mean bosses, burnout, and knowing when to move on.

Here Anna shares her five rules for not being crushed by an apparent failure. And you know what? We really, really trust her.

1. Don’t allow yourself to be timelined

'I’ve always been very suspicious of having a timeline; setting arbitrary goals like "I must write a book before I’m 30" or "I want to be a CEO by 40." Of course believe in having goals – but don’t be rigid about them. Sure, work towards being a CEO at 40, but if it doesn’t happen until you’re 48, or if it doesn’t happen at all because you end up doing something completely different, this obviously doesn’t mean you’re a failure, or that you’ve made a huge mistake with your life. As it happens I did do a book before I was 30, but I didn’t do this because I felt like I "should" do a book before I’m 30. I did it purely because the project was exciting. It would never have worked if I was doing it simply because it was something I "should" do according to a prescribed timeline. Beware of "shoulds" in your career path; when you hear them, think long and hard about it. Don’t feel like you have to follow the timeline of people around you, or achieve things within certain parameters that society deems right and true.'

 2. Your boss might not actually be right

'I didn’t have a great experience with my first boss (the editor of a popular entertainment magazine) and it’s only now I’m older that I can see that the problem was probably mainly my boss’s, not mine. I’m not saying that I was the perfect employee – I’m sure that many of her issues with me were entirely valid – but aged 21 I let her contempt for my enthusiasm and work seriously get to me. Since I had no other workplace experience to go on, I assumed that all bosses were like this boss, that all workplaces were like this office, and that there was some chip I was missing, a "how to win at office politics" gene that I just didn’t have. I honestly thought there must be something wrong with me, and felt incredibly disheartened and frightened, wondering how I’d ever succeed in any work environment.

Now I’m older, I can see that my boss didn’t necessarily have it all together herself. She was in her early 30s (which seemed old to me at the time but I now realise is pretty young to be in management) and perhaps she didn’t know how to mentor or develop someone. OK, she was neglectful and at times downright hostile, but she was in a stressful position, one of the few female editors in a male-dominated publication within a male-dominated industry. She had a lot of stuff going on, I guess. It takes time to gain this sort of perspective, but I wish I could say to my 21-year-old self: it gets better. What you’re going through now is not necessarily how things are going to be for you forever.'

 3. Some good decisions don’t feel good right away

'In 2006 I was presented with a choice: to stay at InStyle magazine, where I’d been for about a year, and run their website. Or take a gamble on a new launch, a female-oriented spin-off of Gawker. I thought hard about it, and ultimately, my fear of inertia outweighed my fear of failure at something new. I really felt like I couldn’t carry on doing what I’d been doing for years, ie editing copy about Hollywood stars' lives and captioning pictures of female celebrities in dresses.

I wish I could say that this decision felt great right away, but no, it was terrifying. It was completely destabilising and threatening, to know that a) I couldn’t hack my old career any more and b) I was giving it all up for something new that might not work. In retrospect I can call my decision to leave InStyle and launch Jezebel an empowering decision, but at the time, it didn’t feel empowering at all – just scary. So don’t expect big decisions to feel great right away, to immediately feel 100 per cent convinced you’ve done the right thing. In the real world, unfortunately, there’s a lot of work to be done before you get to this stage.'

 4. Don’t let yourself be manipulated into thinking you’ve made a mistake

'Women are socialised to be amenable and agreeable and to take care of other people’s needs, and this makes it really, really hard for us to say no to things. And the reverberations afterwards are just as challenging. But try not to ruminate about how you’ve let your boss down by taking another job, or left colleagues in the lurch by taking on a new project. As women we’re conditioned to take care of other people's needs, often so much that we find it hard to recognise what our own needs are.

'I think the world would be a better place if young girls were taught and strongly encouraged to say 'no'. 'Thanks, I’m flattered, but I don’t think this is right for me.' 'Wish I could, but I’m just too busy right now.' One awesome thing about getting older is that you get far better at weighing up who to say yes to, and who to say no to – and a lot more comfortable with the word itself.’

 5. Experience is never a waste

'Some people seem to be blessed with certainty from a young age about what they’re meant to be doing, and they never waver; or at least they never admit to wavering. If you’re not sure you’re in the right field, you don’t need to interpret this is something to be concerned about. This is not a definitive indication that you’re somehow lacking something, that you’re on the wrong path. A lot of very successful people I know still fantasise about doing something completely different. It’s completely normal to have doubts about what you’re doing, and the truth is, this doesn’t really change as you get older.

But here’s the thing: your experiences lead you to other experiences that you can never predict. In my 20s I felt acutely frustrated within the women’s media, stuck producing stuff I thought wasn’t smart enough or diverse enough or inspiring enough for young women. But if it hadn’t been for these years of frustration, Jezebel would never have turned out the way it did.'

Follow Anna Holmes on Twitter @AnnaHolmes and Anna Hart @AnnaDotHart


Tags: Ask An Adult, Work it