Annual Letters, and Why I Write Them

For the past several years, I’ve written an annual letter to family, friends, and colleagues. It’s both an update (since I don’t post much about myself on social media) and a reflection on the previous year. Shuffling between the U.S. and China during college, I started writing the once-a-year missives as a way to keep in touch with people I don’t see often. However, I never expected how transformational and therapeutic the practice would become.

A letter forces me to summarize my year. What am I proud of? What did I fail at? I find it easier to talk about both in writing more than in person. Getting rejected from beloved schools, then eventually being admitted. Failing miserably at dozens of job interviews, then eventually receiving an offer from Google. It’s an opportunity to be grateful for whatever I’ve learned and the times that I enjoyed throughout the year. Like when one week with Flora in Bali packed in more fun than the rest of a year. To write the thing, I have to consider what I did that actually matters to me. (Spoiler: I spend much more time doing things that don’t matter so much.)

Each letter is also a time capsule. What was I thinking and feeling at that stage of my life? Now that I have a several year history of letters, I can see patterns emerge. I see myself changing. From a flag-waving, nationalistic Fulbright Scholar in college to someone who’s wary of jingoism and big governments everywhere. From a wanna-be philosopher-king to a practical businessperson. From someone with a childlike interest in computers to a self-trained (and still quite incompetent) software developer. All of those Daniels are still within me. They’ve only evolved and intertwined as I’ve aged, like T.S. Eliot’s ‘old stones that cannot be deciphered’.

Most meaningful, is how every year about 5% of recipients reply with their own updates. The replies have rekindled dozens of old friendships, uncovered new shared interests, and inspired others to start their own annual bulletins. People even refer to the letters when we meet, saving many obligatory “so how have you been” monologues before real conversation. I feel deep pride when I receive updates from younger people I’ve coached, as I hope I’ve had some positive impact on their development. Likewise, I hope my letters serve the same purpose for the countless people who have mentored me through the ups and downs in my life. Even though it’s a bulk email, the letter at least opens the door to richer personal connection.

Friends still rib me for it. “Dan, when are you sending your Annual Letter to the Shareholders?” they quip. They’re amused by this absurd discipline and the gall I have to bore people with my trifling about year after year after year. It’s deserved. I take myself too seriously. After all, I am the first-born Tedesco grandchild and all that. I can laugh along and recognize the silliness of the endeavor.

But you know what, there’s always a glint of jealousy in my friends’ teasing eyes. It’s not that hard. You, too, can write an annual letter. Or at least something regular and with more depth than an Instagram post. If you do, I’d love to read it.

Until then, here’s a whirlwind tour of my annual letters so far:

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