✍️

Become pen pals with another startup founder.

Send and receive a letter once a month. Via snail mail.

I love getting lovely letters from my friends. Just thinking about my wonderful pen pals makes me smile.
⎻ Anne Frank, The Diary of a Young Girl
In the past few years I have made friends with pen pals from around the world, enriching my life immensely.
⎻ Helen Keller, speech at American Foundation for the Blind Conference, 1925
I will be forever grateful for the dear pen friends who supported my spirit through difficult times.
⎻ Maya Angelou, interview in The New York Times, 1990
Never underestimate the power of a handwritten note. With pen pals, bridges are built.
⎻ Mahatma Gandhi, The Story of My Experiments with Truth (Gandhi's biography)
Reflection

Being a founder is like drinking from a firehose. There's always so much to do. This makes it difficult to sit down, take a deep breath, and reflect.

Reflection is incredibly important though. And as they say, if you fill your jar with pebbles, there will never be room for the stones. Having a pen pal that you write to once a month ensures that this "reflection stone" never gets deprioritized.

Vulnerability
As a founder, if you're being honest with yourself, who can you actually be vulnerable with about business things?
  • You want your investors to see you as a capable leader.
  • You want your team to feel optimistic about your company's future.
  • You don't want your friends, family or peers to think you're an imposter.
  • Your therapist is nice, but doesn't actually understand what you're going through.

Sometimes a stranger across the ocean is just what the doctor ordered.

Accountability

Do you shy away from spending time on things you don't like, such as marketing or sales? Do you do things you don't endorse, such as spending way too long before deciding to ship?

What if you knew you had to write to your pen pal every 30 days? Maybe that'd keep you accountable.

Connection
There's just something powerful about connecting with others. Especially when they're going through the same things as you.
Helping
From Mimi Silbert: the greatest hacker in the world:

Here's a problem for you: build an organization that transforms thousands of homeless people, ex-cons, and recovering drug addicts into productive members of society. OK, now do it with no money and no staff. And achieve a >90% success rate. While you're at it, make the organization double as a business that provides valuable services to the community. And make the whole thing self-sustaining.

Amazingly, Mimi Silbert accomplished this very feat. She's been at it for 35 years and her organization is called the Delancey Street Foundation.

Her secret? Helping.

Instead of having the members being passive recipients (welfare, treatment, punishment, analysis), have them actively help others who are in need.

Sounds cool. But why snail mail?

I dunno. I don't have strong feelings about it.

Maybe email is better. If you think so, please tell me. And if you don't think so, please tell me that too.

That said, I do have a good feeling about snail mail. Here are a few benefits that I see:

  • It forces you to slow down. Email is definitely faster, but maybe in this context of writing to a pen pal, speed is a bug, not a feature.
  • The pen pal you end up being matched with will be the type of person who wants to use snail mail. Maybe that points towards them being a cool and interesting person.
  • For reasons described in Cal Newport's book Digital Minimalism, spending time away from screens is healthy.