‍Apr 14 · 2 min read
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About six years ago, I started a tradition of hand-writing letters
to my five-year future self. A decidedly analog version of futureme.org,
take stock of where I’ve been and where I might be going.

At the end of each academic term, in the final meeting time of my writing classes,
I’d invite my students to join me. "Take out a piece of paper, and a pen"
And write themselves a snapshot of the big questions: where am I?
where do I think I’m going? What do I care about? What do I hope for?
What are the defining characteristic of my daily life and mindset? Will that change?

I remind my students that audience is everything —
and to write something that they would enjoy reading.

I’ve kept my letters in a little bundle.  I've just read the letter I wrote to myself five years ago, in May of 2015, when I would have just turned 33.

photo by @seanwaters_ on Instagram

“You should be feel happy for what you’ve done and what you continue to do…
and you should remember: remember the love of your mother —
how she loved you and how her love lives on and pays dividends…

you’ve been thinking about investing this year —
the first year you’ve had some actual money to play with —
thanks to the actualization of your careers in teaching and music —

and I encourage you to think about your love as a kind of investment in your self:
when you love — and when you love yourself, you expand your ability to be more of what you are —
to share that love outwards, and nourish the whole creation with it … this love will keep you whole and healthy.”

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You can invest in condos, careers, and relationships,

But the greatest investment you’ll ever make is in loving yourself.

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Hope this helps. Have you ever written letters to yourself? Want to join me this May 2020? What will we have to say to our 2025 selves?!?!?!