Jennifer Romolini has made a name for herself by embracing her weirdness.
In her book, “Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures,” she offers relatable advice for facing down fears, finding the perfect job and keeping it. In this excerpt, she lays out the right way to send a work-related email “and not seem unhinged.”
Let’s get right to it: you are writing bad e-mails. You overthink them or underthink them. You agonize over each word, padding your e-mails with too much information, a sundae of cover-all-bases requests and hedge-your-bets recaps with an overwrought cherry of pleasantries on top. You take too much time crafting the perfect message when the recipient is only going to skim your soliloquy for action verbs, sort out whether they need to respond, and discard it like a flyer for Live Comedy in Times Square. Or you underthink, reacting to each group e-mail upon arrival, rapidly crafting a response, your finger hovering over the reply-all button so you can join the group conversation and get your name on the board, clogging everyone’s in-box in the process. First rule of thumb with e-mails: Say less. Second rule of thumb: Chill. Here are the other rules on the other thumbs.
➣ Don’t write an e-mail when you are feeling angry or anxious or sad or ashamed. Don’t speed-read an e-mail that includes critical feedback, get riled up, perhaps misread the message, puff up your chest, respond with something defensive, and subsequently come across as a demented ass. If you are experiencing an extreme level of emotion, write a draft of the e-mail you want to send and wait at least two hours to send it, after reading it over first. Don’t pop off and send something you may later regret. It’s in writing forever.
➣ Read your most important e-mails aloud before you hit send. If they sound testy or rude, and you do not want to sound testy or rude, soften the language. Kindness is a choice, and it’s an easy one, once you let down your guard and realize that no one can actually hurt you over this e-mail chain. Equally, read your correspondence aloud and listen for overly timid language and excessive apologies. You are allowed to be direct and ask for what you want. Just do it with correct grammar and a few niceties, like “Thanks.”
➣ When in doubt, go slightly more formal. (Unless you’re writing to someone you know well, and a formal tone would seem spiteful or passive-aggressive.) Use all of the manners you have learned in this world as a civilized human. Be friendly, but polite.
➣ Keep in mind that the person you’re writing to is probably receiving dozens of e-mails a day. Be considerate of their time; ask them to do the fewest things possible, and identify the point of your e-mail or what you want help with in the first few sentences.
➣ Consider whether you want this message in writing. Would you rather not have a permanent record of this conversation? Can you achieve what you desire by picking up the phone or walking a few steps to an adjacent cubicle? Would this actually make things less complicated?
➣ Have a goal. Whenever possible, an e-mail should be about one topic and about how the other person can take action on this topic.
➣ Keep it concise, direct, and to the point. Don’t include feelings or extraneous information. This is a business e-mail, not a love sonnet or a Dear John letter. You should become the Raymond Carver of e-mail, conveying your message in the most specific and sparest of prose. Before you send, see if there are words, thoughts, or paragraphs you can completely delete and still effectively make yourself heard.
For context, let’s apply these rules to an actual e-mail. Imagine you are trying to get paid for something you’ve written, your payment is late, and you are following up. Here is your first draft of the e-mail.
Hi so and so who has not paid me!
How are you? I hope you are well! I’m so sorry to bother you about this because I know you must be super busy and I hate sounding like a nag. (Please tell me I’m not one of those annoying people who e-mail all the time? This is my worst fear.) Anyhoo: I’m writing today because I wanted to check in about my payment for that story I wrote way back in April. I know we talked about the payment a few weeks ago, and when last we spoke you said I’d have it by June 15th, but now June 15th has come and gone and I still haven’t received a check.
Maybe it’s lost in the mail? My apartment building is weird right now and it totally could have been lost or taken from the community mail table but I just wanted to see if I should be worried about this or if the check actually hasn’t gone out.
Totally fine either way!
Hope everything is great—I really loved working with you guys and would love to pitch something else and write for you again. Let me know when would be a good time to send pitches or what you guys are looking for.
I mean after this check business is all sorted out. Is there someone else I can call/bother about this?
Just want to get to the bottom of it.
Thanks so much for your time.
Best, Person who has not gotten paid.
Here is what you should say:
Hi so and so who has not paid me!
How are you? I hope you are well! I’m so sorry to bother you about this because I know you must be super busy and I hate sounding like a nag. (Please tell me I’m not one of those annoying people who e-mail all the time? This is my worst fear.) Anyhoo: I’m writing today because I wanted to check in about my payment for that story I wrote way back in April. I know we talked about the payment a few weeks ago, and When we last spoke you said I’d have it by June 15th, but now June 15th has come and gone and I still haven’t received a check.
Maybe it’s lost in the mail? My apartment building is weird right now and it totally could have gotten taken in the community mail table but I just wanted to see if I should be worried about this or if the check actually hasn’t gone out.
Fine either way!
Hope everything is great—I really loved working with you guys and would love to pitch something else and write for you again.
I mean after this check business is all sorted out.
I know you’re busy—is there someone else I can call/bother about this?
Just want to get to the bottom of it.
Thanks so much for your time. Person who has not gotten paid.
There is one occasion when you should abandon all of the above e-mail rules. This is when you are intentionally sending a passive-aggressive fuck-you e-mail, a covering-my-ass e-mail, or an I’m-documenting-this-for-posterity e-mail, the contents of which you want a permanent record of with a date and time, basically when you are formally, covertly being a dick for a greater cause. These e-mails are annoying and should not be used frequently, but they’re often necessary for recapping live conversations and protecting yourself or your job down the road, or when you are trying to fire someone and are creating a paper trail of how much they suck. You should use these e-mails when an unreliable boss makes you a promise you’re afraid she won’t keep, a client agrees to something verbally and you want him to acknowledge the terms in a more official way, or you are reporting on problematic events in the office that need to be documented and addressed. Mastering the tone of these e-mails is delicate. You should report the facts while using the least emotional language possible.
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