How Emptying Your Email Drafts Could Change Your Life

photographed by Anna Jay.
Women, please, take a moment. At some point today, go to your emails and open your drafts folder. I’m no psychic, but if you’re anything like me, I bet you a Trump blimp that it’s full of things you wanted to say but never sent.
Last weekend I got in touch with a bunch of women and posited my theory – that some of us, myself included, may be holding ourselves back because we’re not sending the emails we’re writing – and waited for confirmation to roll in.
Dani*, 29, is a teacher. She was shocked by how many emails she’d just forgotten to send. "I didn’t send an email complaining about a bad hotel so I never got a refund. I didn’t send an email to a distant friend saying I couldn’t come to her destination wedding so now I’m spending a fortune going to Germany in November. I just wish I’d had the courage to send these first time around."
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Sitting in the pub after work, you don’t have to wait long to overhear a conversation where someone is going apeshit because of what their colleague did. "He, like, ate all my cheese," she says. "So what did you do?" he says. "I wrote an angry email." "Awesome! Did you send it?" "Of course not." In this case that’s probably a good thing, but imagine how different our lives would be if we went into our draft folders and pressed send on all the emails we ever wrote.
I first became aware of the repercussions of having a crammed drafts folder when a Twitter contact got a freelance gig I'd gone for. A theatre producer had put a call out for writer-collaborators, and I wanted the job, hugely. I spent two hours crafting the perfect email, saying I'd be a good choice, but didn't send it because a moment of self-doubt made me question whether I could possibly be qualified enough. My contact is an enormously gifted writer and deserved the job, but I hadn't even given myself a fair shot at it. Now, I'm kicking myself.
I asked my partner how many emails he had in his draft folder: "zero". I asked my two male mates. Also zero. And a male colleague at work: "Just a few I started on my iPhone and rewrote in the office." A few female friends people always describe as 'lucky' also had much smaller drafts folders than me.
How many other opportunities had I missed out on because I never pressed send? A quick flick through my drafts folder (spanning 10, 20, 50, 65 pages) showed the start of at least 20 job applications and numerous emails inviting directors and other writers I admired out for a coffee.
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Suzy*, 28, from London is a project manager for an advertising agency. After working too much overtime, she wondered how to ask her boss a difficult question. "Project management is always busy, but when I missed three friends' birthdays in two weeks and was then late to a dinner I’d planned to celebrate my girlfriend’s promotion, I knew it was time to ask my boss if we could try to pull our meetings a bit earlier in the day. But, you know what… I never sent that email to ask. And guess what, I’m still staying late."
Unsurprisingly, career experts think this probably comes down to women lacking confidence in the office. Victoria McLean, managing director of City CV, says that "women are probably not putting themselves out there because they don’t want to be rejected." She adds that women can sometimes need more help than men in realising their worth. "There’s the story of a group of women and a group of men being shown their own job description, and only 60% of women thought they had the skills to do it, compared to 100% of the men. It’s the same thing when it comes to sending emails."
McLean explains that even really senior women can suffer from imposter syndrome and low self-esteem. "Even entrepreneurs and women who do well tend to brush off their success and say it’s down to luck. It’s not true – men detail exactly how they got to where they are now. Women need to take ownership of their journey."
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I glance over the draft emails from the past three weeks and consider which ones are still relevant enough to send. Maybe I should take ownership and send them.

With that in mind, I glance over the draft emails from the past three weeks and consider which ones are still relevant enough to send. Maybe I should take ownership and send them. One is an email to a playwright I’d met telling her how much I loved her most recent work. When I wrote it, I was worried it looked fawning and a bit stalkerish. This time around I think how much I’d like to receive an email like that, so I press send.
It’s possible men are immune to these thoughts. Joe is a theatre director. He spends a lot of time meeting new people and making connections. His success depends on it. "My drafts folder is pretty clear. I don’t fear sending emails because once they’re sent, it’s on the other person to do something, which does make me feel more relaxed."
Joe says he rarely stops to think before he sends an email. "If someone doesn’t want to email me back that’s fine, but I want to email them, and it’s a free country, right?"
So what’s holding women back? I spoke to several women across different professions, all of whom said roughly the same thing but in different words. "I don’t want to look silly" and "I don’t know if I have a right to email these successful people."
In whose eyes? McLean explains the concept of 'power distance'. This is when we perceive somebody is too senior to approach, so we don’t. Keeping the power distance is a "big thing" in the UK, and southeast Asia. In Malcolm Gladwell’s book Outliers he describes a situation in which a Korean Air pilot doesn’t challenge his captain because he’s too senior. He knows something’s wrong, and the black box records him trying to make a suggestion, but he’s unable to. Consequently the whole plane goes down and everyone dies.
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In New Zealand or Israel, there is much less of a power distance, says McLean, so people feel more at ease approaching one another. This makes work much easier, where there’s less umming and ahhing about who you’re 'allowed' to talk to.
Recently, I read an article which asked men to consider their interaction with women along the lines of: "If I was The Rock, would you treat me in the same way?" So maybe next time you think about sending an email, consider this. Would Michelle Obama ever pause before asking her friend to reschedule? Would Malala say, oh, maybe this email about not feeling respected at work can wait a few weeks while I do some admin? Would Beyoncé hold herself back before sending a demo tape to a new agent?

When you’re hovering over the send button, it may help to remind yourself of the possible outcomes.

Laura Holden at Reed recruitment suggests just not overthinking it. "When you’re hovering over the send button, it may help to remind yourself of the possible outcomes. That’s not to say you should have a blasé attitude when it comes to 'pushing the button' but in reality, you may just be overthinking it.
"What are the possible consequences of pressing send? Using the example of a job application, the worst case scenario is they don’t email back, or they email back with a 'thanks, but no thanks'. Best case scenario, they email back to say they’re interested. But if you never press send, you’ll never know."
Four days after pressing send on around 50% of the unsent emails in my drafts folder, no one has put a restraining order on me for bothering them. Two people I asked out for coffee agreed to meet me and I got a £10 refund from a burger company who served me bacon not brie. As a huge bonus, I also received a deeply apologetic email from an editor that just said, wildly: "Oh my God have we still not paid you? INVOICE ME AGAIN!"
Sending emails made me feel like I was more in control of my life. I was stepping on that niggly "don’t do it" thought and grinding it into the ground with my boot-heel. This felt great, and I got some free cash out of it. So, women, check your drafts, and press send.
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