September 25, 2019

New Year's Letters

Every year, at the end of September, I set a small challenge. Here's how it works:

Handwrite a letter to yourself that you will open on January 1st. The letter is due by the end of day on October 1st. Seal it in an envelope and keep it somewhere safe.

It's been a way to pause and recalibrate before the quickening pace of the fall and winter activities.

I just looked back at the letter I wrote last year. I wrote about the gratitude I have for my home, community, and work. I also wrote about the health issues I'd started to face. Little did I know things would get worse before they got better. But now, I can see just how much progress I've made.

That's the power in these letters, and in any sort of reflective writing. They become life's mile markers showing us where we've been and how far we've come.

And now…

I’m asking you to join me again — to pause long enough to check in with yourself.

A few guidelines:

  1. Schedule time to write the letter between now and Monday. 30–60 minutes should do.
  2. Handwrite the letter. Get off your computer/phone. Grab a pen and piece of paper. Handwritten letters are always more fun, especially when it’s your own handwriting.
  3. Place your letter in an envelope. On the front of the envelope, write Dear (insert your name). And the words “Do not open until January 1st, 2020.

What to write about

There are no limitations here. The audience is you. Here are a few questions to help you begin:

  • What do you want to remember about your year thus far?
  • What have you seen?
  • Who have you met?
  • How have you changed?
  • What do you wish were different?
  • What have you celebrated recently?
  • Where do you hope to be this time next year?

Compile all of those memories, thoughts, and bits of wisdom before the year speeds to an end. Use the sunlight of the summer and the freshness of the fall to capture important words before the cold takes over and the noise of “resolutions” rises. Then, as you start 2020, you’ll have your own words as clues and guides for your next step.

And if you choose to participate in this little tradition, can you leave your name/email address here: I’ll send a reminder to open your letter on January 1st. That’s all.

So go on, schedule those 30 minutes, turn everything off, and write that letter.

I’ll be doing this with you.

Happy Wednesday,


PS: Last week, our Kickstarter was fully funded! This week, we're going to start releasing new goals to make What's Worth Doing even better. Stop by the campaign to pre-order your deck.

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