I don’t know how many hours I spent ripping, downloading, organizing, and checking MP3 files in high school.

My favorite tracks to find were more obscure acoustic performances from bands I was into.

I’d have to listen to every track for the blips that could come from a scratched disc or whatever electronic hiccup got encoded into an audio defect.

I would find cover art and edit ID3 tags to make sure every album and track had the right title. I burned CDs to take in the car and share with friends.

I loved finding Winamp skins, and the eventual iTunes skin would be dark foreshadowing.

In college, we had an incredible network where downloading music and entire movies was instantaneous.

Out-of-town friends visited and stayed in my cramped dorm room, plundering the network like unsupervised kids in a candy store. I fell asleep to them downloading movies and woke up to them playing console games on an emulator like smiling zombies.

My collection was vast and meticulous.

I don’t have a single file of it anymore.

Not even the CDs and DVDs I collected for so long. At some point I got tired of lugging them around and we didn’t have anything to play them with.

This is fine, except when I have to dig through my fuzzy memory to remember the music I loved most. I have an Apple Music subscription now but I’ve never been all in on any streaming platform, so I don’t have any long-running lists or compilations. Good for the sense of freedom, bad for remembering music.

I went on to collect and curate other things.

Less interestingly, I got my first document scanner in October 2009. I’ve scanned just about every receipt and piece of paper I’ve come across since then.

I’m pretty good at taxes and home inventory, and I’m not sure if that’s a brag or a confession.

More than that, receipts offer little clues about where I was and what I was doing when my journal and memory are blank. I know that there are uncomfortable capitalist overtones to a life viewed through transaction receipts, but here we are.

I started journaling with Day One in 2011, and at this moment have 857 entries. I don’t go back through them much, but more often than the physical notebooks I used to keep for notes and doodling and drawing shapes when I’d have to think through math.

It can be shocking to find recurring patterns of struggle in those entries, and heartening to see evidence of change.

I refer back less to physical notebooks, but I take more time going through them because they’re more richly-detailed and surprising. I can tell from my handwriting what headspace I was in, and notice seasons of playfulness and stress that come and go. That visceral dimension is absent from writing on a computer, even though I write more at a keyboard, feel less constrained, and refer to that writing more often.

Photos are a different mess.

My oldest photos are scans from family albums, and negatives I sent away to have scanned in bulk just before I got my first digital camera. The photo count increased with that digital camera, then hockeysticked once the iPhone was part of my life. That’s also when I started snapping things and put less effort into seeing them. It’s when photographs became pics, the latter being a word that grinds against my soul.

Photographs are about seeing. Pics are content.

I get a lot of inspiration from people taking photographs and sharing them. You remind me I’m taking pics and that there’s a joy to paying attention and making images.

I used to keep my pile of photos in Adobe Lightroom, then Apple Aperture which was perfect. Ever since Apple retired Aperture and I’ve been post Adobe Creative Suite, I’ve wandered around with frustratingly clunky photo storage. I insist on storing them locally on a NAS to avoid recurring fees for something so personal and basic. I used Luminar until that got weird, and now ON1 which is okay. Can’t decide whether the NAS is too slow, the software isn’t right, or I’ve made overall poor life choices.

I kept bookmarks with Delicious for a long time before Pinboard, and made an awkward turn to DEVONthink before just recently trying and loving Raindrop. Raindrop is great.

I collect and even sometimes read RSS feeds with Reeder.

Recipes moved from Paprika to Mela, another stylish app from Reeder’s developer.

Where I’m most excited for the future is Obsidian. I’ve written about how I use it regularly, and it’s the first time I’m building something like a digital brain in a way I feel good about.

I loved Notion, but couldn’t get comfortable keeping personal information in a service locked behind a subscription.

I previously used nvALT and iA Writer to sling Markdown files, but Obsidian’s great trick is getting me to structure, link, and grow a body of information that I previously treated like pages in a notebook. (Without the fancy index you more diligent creatures may hand-write.)

So instead of notes that are useful for a day or a week, I’m starting to develop actual references and writing that looks like carefully-arranged documentation. The more time I take to detail how I try something—set up a new tool, for example—the better reference I have for myself or a blog post. The more structure I give to my notes, the more I see opportunities to think and write and expand. I can recall all of it quickly and zoom out to visualize patterns. Best of all, it’s mostly Markdown that would be intact and useful without Obsidian.

There’s still a lot of crap in there, but it’s growing into something more interesting.

My information is not me, but it enhances what I can remember and think about. Managing, balancing, and finding relationships between all this information has a direct relationship to how I think. Which is pretty neat.

This becomes especially powerful if I can find ways to share whatever I think is interesting or useful. I don’t do much of this yet, and I’m really interested in how others do. There’s something very special about finding a likeminded stranger on the internet and getting to explore their stories, ideas, and things they’ve learned. For me, that’s the antidote to carefully-curated LinkedIn profiles and algorithm-optimized content.

People sharing their own thoughts and ideas outside of giant platforms give me hope for wherever all this is headed.

So I hope that I can be a patient and careful gardener, helping things grow and paying attention to patterns and opportunities.

I think I’ll know it’s working when the systems get smaller and more ideas blossom into new shapes.