Congratulations to Victoria Winkler for Winning the April 2025 Barefoot Writing Challenge! (Your $100 prize is on its way!)
The challenge was to write an essay that answered this prompt:
What is your earliest memory of sending or receiving an email, or learning for the first time what an email was?
Victoria shared a relatable story with loads of throwbacks to early tech. Enjoy her winning submission:
Is this Thing On?
by Victoria Winkler
I am of the last generation that reached high school without email. Yes, I un-ironically remember the simpler times of floppy disks, dial-up internet, and shared family computers. In short, a Gen Xer.
My mother was weirdly ahead of the tech curve. She had Hotmail before anyone else I knew, and she’d check her inbox often, hoping something new had appeared. Maybe there would be a forwarded chain letter or something with 37 blinking GIFs and a Comic Sans signature. She had made a family account and a professional one for her real estate business.
One day, she showed me how to log in to the family email and instructed me to send her a message to try it out. I typed, “Is this thing on?” and hit “send.” Mostly as a joke, but also genuinely wondering if the message would beam through the internet tubes to wherever my mom was sitting with her AOL account and massive laptop. I heard a bing in the other room.
I shrugged and went back to my pizza rolls and my game of Where in the World Is Carmen Sandiego?
While I may have been oblivious, it did work — I got a reply. Even if it was just my mom excitedly typing back to me, asking what I wanted for dinner. She had to come into the room to remind me to check for the reply, which sort of defeated the purpose, but her joy at the back-and-forth success was evident, even to my heightened level of teen blasé.
I didn’t use email myself until I went to college. One day, I was free-range and analog — making mix CDs, recording funny outgoing answering machine messages with my roommates — and the next, I was told to check my inbox daily, “or you’ll miss important information.” Suddenly, email was how professors, administrators, and that one weird guy in your group project communicated. Email became infrastructure.
It wasn’t until I found myself obsessively checking my own email that I realized this wasn’t just special nerd magic. It was actual communication. Faster than a letter, more mysterious than a phone call, and less commitment than showing up in person.
Honestly, kind of perfect.
Email allows us to maintain our distance while still staying connected. It allows us to be witty and brief. But you can’t fully trust it, can you? You can’t read tone or inference. I can think of many times as an adult that an email has been misinterpreted because what one line meant as humor was read as serious.
My first email wasn’t exactly profound, but it was a moment. A turning point. A sarcastic, slightly skeptical entry into the digital age. As the world has progressed into texting, there is now almost a sentimentality toward the humble email, which you can read without expecting an instant reply. Somehow, email is now considered the slow form of communication, and maybe that’s okay.
Because, as it turns out, this thing was on.
