How To Fail Successfully!

Winning all the time isn't as great as you think
How To Fail Successfully!
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CosmoBy Cosmo -

The bragging résumé is dead, with CEOs and founders the world over now writing “failure CVs” instead. Here three leading women divulge their least enviable moments.

June Sarpong.
The 41-year-old is a TV presenter, author and panellist on Sky News’s The Pledge. Her first book, Diversify, is out now (HarperCollins, Dhs89).

1997 - Messes up dream interview

I’d always wanted to be a TV presenter, but I didn’t start out as one. When I was 19 years old, I was working in music at BMG & Arista Records, and got the chance to audition to host a new MTV show. I got home late the night before, so decided to wake up early to read the script they’d sent me.

But I overslept. I woke up half an hour before I had to leave. I nearly bottled it, but a friend changed my mind. I even signed a different name in the visitors’ book – if I was bad, I didn’t want anyone to know. I felt as if I’d failed as I hadn’t prepared for the opportunity of a lifetime.

Then I got the call: I was invited back for the next round. I was so glad I didn’t bail. Sometimes you have to step into a problem – it might just work out.

2008 - Personal project collapses

I left T4 in 2007. The year after, I set up a website for women called Politics And The City, mixing topical issues with fashion and beauty. At first, it did really well: it got lots of press and advertisers were calling. I had a really cool editorial team including Ronnie Wood’s wife, Sally. Then, after six months, we began to lose readers. Our user numbers depleted so much we couldn’t get anyone to place ads. I tried to keep it running by putting my own money into it and ended up losing a lot. The hardest thing was the shame. It paralysed me for a long time. I felt as though I’d disappointed the people working for me, as I’d had to let all five of them go. I was really hard on myself.

2017 - Writes a book no one wants

Diversify [a manifesto about race and inequality] was turned down by five literary agents and a couple of publishers. One agent didn’t come back to me for six months – and then said my book was absolute rubbish. Someone else didn’t think I should be rocking the boat as I was “likeable”. Another said it should focus on gender as that was safer. The rejections were hard, but I listened to them and modified the idea, and then, suddenly, everyone wanted to publish it. 

Payal Kadakia
The former consultant, 36, is CEO of workout-booking app ClassPass and artistic director of The Sa Dance Company.

2005 - Misses a big work meeting

I used to work full-time as a consultant and danced in my free time – it’s been my passion since I was three years old. I rehearsed every evening and every weekend. But one show I was in clashed with a client meeting. I didn’t know what to do and was really torn, but I chose to perform instead of going to the meeting. I was pretty scared about the consequences – would I be fired? My boss was disappointed and angry that I had put my private life before work. I wanted to have a career, but I didn’t want to give up my passion. In that moment, I knew that to succeed in the company, I would have to give up dancing. I didn’t want to do that, so I quit. It was actually a really hard moment for me. My priorities were out of sync with work’s expectations, which felt like a failure, because I was used to people saying “great job”.

2010 - Creates a dud product

My team and I built Classtivity, a search engine for classes, over the course of a year. Lots of gyms signed up, and people really liked the idea. We had false signals of success and ended up getting quite a lot of press. But once we launched, it wasn’t right: people browsed, but few booked. We experimented for several months: we even offered people a free class, but no one took up the offer. I had to let go of half my team. I then went in a totally different direction, building a new product and trying to figure out what people wanted. That product was ClassPass.

2013 - Fails to raise investment

It took three years to get ClassPass off the ground. Every June, I would go to Silicon Valley to raise money. For two years, no one was interested – everyone said no. I remember my advisor telling me that when someone wants to invest in you, you’ll get an email an hour after the meeting. My inbox stayed empty. Then, suddenly, my phone wouldn’t stop ringing. I declined a lot of offers – I didn’t want people to invest just because it was the hot new start-up. I wanted people who believed in me and the product. You can’t chase greed and power, only purpose and passion.

Jess Phillips
The 37-year-old has been the Labour MP for Birmingham Yardley since 2015. She campaigned for women’s welfare, before becoming a local councillor.

1998 - Fails to get key qualification

At A level, I really wanted to study politics, but I went to an all-girls’ grammar school and the subject was only offered at the boys’ school. My mum asked if I could study it there, but the school said no. I was really annoyed, so I did economics instead. I had no intention of becoming a politician – I just liked the subject. When it came to university, I chose politics and history at Leeds, but I hated the course. After my first year, I switched to social and economic policy, something I wouldn’t have been able to do without an economics qualification.

2004 - Misses out on dream job

I’d always wanted to be a civil servant. My A levels, degree and experience in the voluntary sector were all in preparation for that job. After university, I applied to the Home Office, doing the first set of tests on my home computer. The internet kept cutting out, so I had to redo them – but I passed. For the next stage, I went to a test centre. Following that, there was another round, which I couldn’t make because I was pregnant and having a scan. They didn’t allow me to take it at another time. I was still shocked to be pregnant, so I didn’t fight back on the grounds of equality. Yet I wish I had. My acceptance of the situation felt like a failure. I had always wanted this job, yet I resigned myself to doing something else. I felt as if I had failed to pursue my dream after all.

2012 - Wavers just before an election

While I was standing for election in Longbridge, Birmingham, I almost backed out. My brother, Luke, is a recovering heroin addict, and had a psychotic episode in the street. I wrestled him into a car, in front of prospective constituents, to get him to mental-health services. It made me question everything. I thought it wasn’t fair on my family that their lives had become public. I felt so low, but my family and friends were able to convince me that I could get through it. I decided to always be upfront and honest, and so far, it’s worked.

Epic Fails

These celebrities have all dusted themselves off after a crash.

1. Vivien Westwood

She lost confidence in herself, dropped out of art college and became a primary school teacher. Then she slowly discovered her signature style selling her own jewellery designs in London.

2. Jennifer Lopez

Way back in 2002, JLo tried to expand into the restaurant business, with a Latin-focused menu of the food she enjoyed growing up. There was a star studded opening and then a slew of bad reviews. It closed six years later.

3. Bill Gates

After dropping out of Harvard, his first business idea, Traf-O-Data (catchy), was entirely unsuccessful, leaving him with no degree and a failed business on his CV.

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