Since ~2007, I’ve had a private Blogger site that marked the starting point of my sharing online and getting an appetite for writing in my free time. Between AIM, texts, and Blogger, I was in early training for life at Automattic without even realizing it. At one point, my dad sat me down and chewed me about sending 14,000 texts in a month. That same voraciousness for writing has served me well—2,477,583 words (and counting) across Automattic’s internal sites, not including slack or my work in the open source project.
I deleted all my posts in 2009 after a particularly hard year, thinking that restarting would help me move on. I still am not sure if that was a moment of awareness that I should listen to more or a sign of an immature teenager doing something cliche. Either way, I curse the day I did that as it erased some moments and years that I long to have insights from, including the first time I met my birthmom.
For many reasons, my Blogger has always been private. Just see this hilarious Blogger profile I wrote likely in 2007 that has remained untouched:
In fairness, 10 things I hate about you, Braveheart, and Gladiator are still some of my favorite movies and I do still listen to much of the same (non Christian) music although I am far more into electronic vibes these days. It’s fascinating to see what does and doesn’t change.
Over the years, I still write on this private site as there remains much that doesn’t belong in a public sphere. Having my private writing in Blogger helped me keep my work separate, gave me a taste of another CMS, and kept me in touch with a nostalgic interface that helped me return to a distinct headspace when writing (like visiting a favorite park). I deeply believe how a space feels matters, including online (which is likely why people rebel so much when interfaces change).
When Day One joined Automattic in 2021, my interest was piqued to switch. At some point, I looked into it but found myself unable to find a clean migration path. I moved on until recently I realized AI could likely quickly and easily solve this for me. In the span of about five minutes, I used Claude Cowork to take a downloaded backup of my blogger site (text only, no images) and convert it to a format that Day One could use (JSON Zip File) using a script it created. It then converted the backup and I was able to upload it easily to Day One.
To go from such a limited journaling environment to one with “On this day” functionality, an AI chat that can talk with you about your day and turn it into a post, a Strava integration to automatically pull my activity in as entries, end to end encryption, and more has been amazing. After importing the post, I immediately saw three posts from this same day, including one from 14 years ago that was incredible to have surfaced.
It’s going to be a fascinating experience to have the 772 Blogger entries from the last 17 years suddenly surfaced and more integrated into my life. I usually don’t go looking through Blogger unless I’m trying to deeply understand something about myself, check my memory, or am feeling nostalgic. To have teenage entries living alongside more normal, every day Strava adventures and journal entries will be a trip. I wonder if there will be any wild through lines like I noticed with my five year “one line a day” journal? I would love to see how my teenage and young adult self might still live on in my habits today. Writing has always been an outlet and the Blogger entries are my rawest form by far (always has been). For example, yesterday’s “on this day” surfaced a genuinely terrible yet heartfelt poem from 16 years ago where I talked about how hard the days were and worn out I felt. What a gift to come face to face with my teenage soul. Thanks, Day One.
If you too are wanting to switch over and relive parts of your soul, I shared the script Claude created with some instructions for how to use it.
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