The Art of Reaching Out: Why I Email Strangers

I remember the first time I attempted to email someone I didn't know. I spent what felt like an eternity—maybe five minutes—with my cursor trembling over the Send button.

I was plagued by a swarm of anxieties: I'm interrupting them. I'm being a nuisance. My question is probably stupid.

Ultimately, these were just masks for a deeper, more pervasive feeling: “I am not enough.” This is the tragedy of low self-esteem; you reject yourself before the other person even has a chance to.

However, I have managed to push through that suffocating anxiety.

A Legacy of Connection

Email is a veteran of the digital age, predating the smartphone, the hyperlink, and the World Wide Web itself. While Tim Berners-Lee was still conceptualizing the Web, developers were already communicating via electronic mail.

In 1971, Ray Tomlinson pioneered the first computer-to-computer email, famously selecting the @ symbol to distinguish the user from the host machine.

This longevity makes email a perfect case study for Lindy’s Law, which suggests that the future life expectancy of a non-perishable thing is proportional to its current age. Mathematically, we can view it as:

$E(t) \propto \text{Age}_{\text{current}}$

While social media platforms flare up and vanish like accelerated empires, email persists.

Email vs. Social Media

Feature	Email	Social Media
Longevity	Decades (Lindy Law)	Ephemeral/Cyclical
Pace	"Human Time"	Perpetual Now
Discovery	Intentional/Deliberate	Algorithmic
Privacy	Private correspondence	Public/Semi-public feed

The Beauty of "Human Time"

What I cherish most about email is its capacity for intentionality. It doesn't have to obey the frantic pace of the modern era. You can engage with it on a human schedule: write when you have a genuine thought, and reply when you have the mental space to reflect.

This creates a rare environment for conversations that deepen rather than scatter. Unlike the anxiety-inducing "typing..." bubbles or read receipts of instant messaging, email allows a thought to linger.

Overcoming the "Void"

Over the last year, I've reached out to a diverse array of people: artists, thinkers, bloggers, and developers. While I've avoided the soul-crushing experience of a corporate inbox, I've found that I no longer dread my personal one.

There is an inherent vulnerability in sending a message into the void. We are often taught that unsolicited contact is "spam," but there is a vast difference between automated junk and genuine effort.

Guidelines for Meaningful Outreach

If you want to reach out to someone, consider this checklist:

• Friendship Potential: Only contact people you would actually want as a friend.
• Research: Understand what drives them and find common ground.
• Active Listening: Be a "fascinating" conversationalist by asking thoughtful questions and noticing small details.
• Brevity: Avoid the trap of long-windedness.

"I have made this longer than usual because I have not had time to make it shorter." — Blaise Pascal (17th Century)

Avoid being like Pascal. Furthermore, avoid professional or commercial requests unless the person has explicitly invited them. If you lead with patience and grace, people will appreciate the gesture, even if they are too busy to respond.

Where to Start

If you are looking for people to connect with, here are a few suggestions:

1. My own inbox: You can reach me at hi@zacharykai.net for a low-stakes first try.
2. Derek Sivers: A fascinating individual who keeps an open inbox for introductions.
3. The Indieweb & 32-Bit Café: Hubs filled with creators who love being contacted.
4. People Blogs: An interview series by Manu Moreale featuring independent writers.
5. Deliberate Wandering: Simply explore the web and see who resonates with you.

Unlearning the Algorithm

Moving from the whirlwind of social media to the "poetic web" requires a shift in mindset. As Ava of Ava’s Blog noted in her piece on things to (un)learn, the norms are different here.

function connectionType(source) {
  if (source === 'algorithm') {
    return 'Suggested/Passive';
  } else if (source === 'intention') {
    return 'Chosen/Active';
  }
}
console.log(connectionType('intention')); // Output: Chosen/Active

Ava points out that in these circles, email isn't viewed as "too formal" or "outdated." Instead, it's a space where you can write as naturally as a message, but with the depth that only a deliberate choice allows.