Jumpstart Your Minimalism Take the 17-Day Handwritten Letter Challenge

My challenge to you is simple. Over the next 17 days (starting whenever you want), write and mail 17 handwritten letters.

The letters can be any length and can be addressed to anybody you want; friends, family members, your favorite companies; it doesn’t matter. The only rule is that you can’t write to the same person twice.

If you accept my challenge, tweet me to hold yourself accountable.

Imagine the look on your one friend’s face when she opens up the envelope and sees your handwritten letter. Yeah, she might make fun of you for the next five years, but deep down she’ll appreciate it.


“Minimalism” is a pretty hip term these days. We all talk about minimizing possessions and distractions and stress levels; we talk about spending less time watching TV and less time on Facebook and less time working for the man.

Okay, great. We’ve talked about getting rid of all of the time-sucks in our lives. But what now? What are we supposed to do to fill that void?

This 17-day challenge is an easy way to start. I know first hand that life can get a little empty at the start of a minimalist journey, especially when you’re brand new to it. Which is a bit unexpected, because the whole point of minimalism is to maximize your life. This little exercise will help you kickstart a minimalist lifestyle and fill the unintentional void with a supremely intentional activity.

And filling the minimalism void isn’t the only reason. Here are just a handful of additional reasons.

1. Be silly.

It’s weird. Nobody does this anymore. Your friends will likely think you’ve gone a little coo-coo. They might text you and say “hey man, is everything okay?” And when you explain to them that you’re perfectly fine and are just sending them notes because you appreciate them, they’ll simultaneously laugh at you and love you.

2. Strengthen connections and increase happiness.

There’s a fairly famous article that outlines five simple emails you should send to have a better life. There’s no need to cover all five here, but arguably the simplest and most important is the first one: “Every morning send a friend, family member or co-worker an email to say thanks for something.” These daily thank-yous are proven to increase happiness and life satisfaction, and decrease depressive symptoms.

If a thank-you email can have that much impact, imagine how much impact a handwritten thank-you letter to a friend could have. And imagine how much stronger your relationship with that friend might be after reading your letter.

3. Learn to write better.

Typing on a computer means “fixing” every sentence halfway through. Writing by hand means giving more weight to your original thought. And it means continuing on to the next sentence instead of focusing on the previous one.

But when I write longhand, the experience is different. I think it is because that critical part of my brain is busy picking apart my handwriting (which truly is horrible) instead of my prose. It tells me that my handwriting is atrocious. And it gets the satisfaction of being right. But who cares? While it’s busy the words are just rushing out. And they’re not henpecked or second-guessed before they’ve had time to cool. They exist in a flawed, but pure state. This kind of prose has a feral power that seems to be lacking from the things I type. Maybe that’s not it, maybe it’s just harder to get my head in that effortless writing space when I use a keyboard. But whatever the case is, writing longhand makes it easier for me to reach a writer’s high.

A Defense of Writing Longhand by Patrick E McLean

4. Scare yourself.

This challenge is going to feel awkward. At points, you’ll be scared. You might have doubts like:

  1. “What if my friends don’t like it and they isolate me?”
  2. “What if nobody responds?”
  3. “Are we good enough friends that I can get away with this?”

But from that fear you will feel alive.

5. It’s less commitment than a journal.

Want to start a handwritten journal but afraid you’ll abandon it? This challenge has a finite end time so the commitment is infinitely less. Try the challenge first, and if you fall in love with writing, maybe go ahead and give that journal a shot.


Anybody you want. But if you’re looking for ideas, here are my addressees.

letter to triple aught design

My first letter. I felt like a 4th grader while writing this letter. So simultaneously fun and awkward.
- 8 friends.

  • 3 influencers in the blogosphere. Who said this challenge can’t be a little selfish? There are three bloggers in particular that I’d absolutely love to make a connection with, but my odds of doing that with an email or a tweet are minuscule. At least this way I give myself a fighting chance to be noticed.
  • 5 companies that have produced amazing products which have brought a lot of joy and utility to my life. Those companies are Vivobarefoot, Latitude 64, Outlier, Triple Aught Design and Wool&Prince.
  • 1 author of a book that I met at book-signing six years ago. I don’t know that it was meant to, but the book had a big impact on my life, and I still think back on it six years later.

If you’re struggling to find a 17th you’re more than welcome to write me a letter! But the only way to get my address is to subscribe to get email updates (address is at the bottom of those updates).

A special thanks goes to Nathan Atkinson. His recent post on journaling was my inspiration for creating this challenge.