On Olivia Reingold’s “A Cold Email Got Me My Job”

An idea worth drawing for.

This visual essay is a tribute to Olivia Reingold. It’s part of an ongoing series called Ideas Worth Drawing For, in which I make hand-drawn images to honor the excellence of essayists I admire.

She loves me… she loves me not. She loves me… she loves me not. She loves me…

Olivia Reingold

advises that, “A good cold email is not unlike a good love letter. It should make you feel vulnerable.” As I compose this tribute to Reingold’s essay about the art of writing to strangers, I’m distracted by the compulsion to refresh my email every few minutes. Earlier this afternoon, I asked a Pulitzer Prize winning journalist to grab a coffee with me. I know she won’t write back to me in mere hours, but I can’t help myself. Some junk mail jolted my heart in the milliseconds it took for me to register what the new email was about.¹

I have long been a devotee of the cold email, because this technique has helped me correspond with a number of famous scientists. (Not to brag, but one time Steven Pinker tweeted out an essay of mine that I sent him.) But compared to Reingold, who has been at it since the first grade, I feel like a newb. If you need a cold email guru, take heed.

Her tactics are bold:

If you treat your words like they’re powerful, you’ll usually get a response. 

Ask my enemies. Whenever corporate America has wronged me, I’ve gone straight to the top. 

In 2021, when my internet provider could not log me in to my online account, I wrote to the CEO.

I titled the email: “Re: Q3 Earnings Report.” 

And in the first line of the body of the text, I wrote: “Sorry, I made that subject line up just to get your attention. I’m actually emailing about a really frustrating customer service experience I had.” 

Forty-five minutes later, I got a call from corporate headquarters.

The problem was solved that day.                                                              

These days, everyone says networking is the route to success. But I’ve always been a strong believer that any door can open if you score the right invitation. My advice? Don’t ever ask to “pick” someone’s brain. The trick is to get inside their brain. Start by googling them, or rereading or relistening to their work. Why do you like it? Tell them that. Make them know they matter.

I’ll let you in on another trick of the trade. Sometimes the hardest part is finding the email address for the object of your heart’s desire. Academics are easy, because universities publicly list email addresses for even their most famous professors. Here’s a tip for tougher cases:

When you must resort to guessing someone’s email, Gmail will help confirm your speculation. Input your guesses into the “to” field of a new email, and if you are correct, Gmail may auto-fill that person’s profile picture next to the email address. Of course, for those who do not use a profile picture, this cannot clue you in. This trick works even when your target is not @gmail.com, perhaps because Gmail hosts so many other email domains.

A bit creepy? Perhaps. As in romance, when approaching a stranger you must toe the line between “dashing” and “boorish.”

And it was Reingold’s analogy to a love letter that really jived with me. Because like the leading man in a rom com, I want to make A Big Gesture to win the attention and affection of people I cold email. This impulse led to “Ideas worth drawing for,” because who can resist commemoration by a painstakingly hand-drawn image?

Dear reader, you may think that these essays are for your benefit, that I yearn to share compelling ideas to edify your soul. But that is mere byproduct. My ulterior motive is to befriend people I admire.

So if “hopeless romantic” is your style of intellectual engagement, too, then head over to

The Free Press

and study Reingold’s ways:

A Cold Email Got Me My Job—and an Afternoon with Gay Talese

1. Update: SHE SAID YES! Well, kind of. She’s feeling under the weather, so we’ll have to try to schedule something later. But still, she called my “Idea worth drawing for” essay about her Pulitzer Prize winning Atlantic feature “haunting”! You can read that “haunting” visual essay here: