🌠 Reflections on Sharpening Your Mind

Obsidian is a bootstrapped company with a new(ish, at this point) slogan that I love.

According to Substack, the most popular newsletter with subscribers of Obsidian Iceberg is The Pragmatic Engineer by Gergely Orosz. So when my husband sent me one of Orosz’s articles, I clicked through — and came to the conclusion that my subscribers have good taste. The article in question was lessons from bootstrapped companies — here’s the accompanying HackerNews discussion.

I’ve always said that I care more about a company being bootstrapped than open source. That’s one reason of many that I’ve gravitated to Obsidian over Logseq. The preference is partly because I’m not a programmer and have seen way too many abandoned software projects in my life, and partly because I think ‘sustainable profitability’ is more likely to result in a product that will stick around in a form that’s useful for me. Dan Doyon (founder of the bootstrapped company I work for these days, Readwise) had a great write-up about a year ago about how niche apps have smaller carrying capacities that frankly can’t support big investment returns, and realistically, I mostly use weird niche apps.

But Orosz’s article also covered some things that make intuitive sense but hadn’t explicitly occurred to me. For example, one of my big takeaways was that that bootstrapped companies tend to fly under the radar because they don’t have big media budgets, which based on my experiences with Obsidian is definitely true — this newsletter wouldn’t exist in its current form if the Obsidian developers had spent venture capitalist provided money on a community manager or media relations team, heh.

That said, Obsidian’s got a CEO now, and the team has expanded a lot since the early days. There’s been a bunch of media coverage lately — FastCompany, the Verge — and Kepano and the rest of the team have been a lot more active on social media sites like Twitter and Reddit than Licat and Silver ever were. It’s one of the things I’ve noticed as I continue to ramp up my online presence since having my baby — hope you’ve been enjoying the articles!

In addition to finishing up the articles I had in the queue before I got incapacitated (I’ve been meaning to finish that article about why human sacrifice is a thing that happens for months) I’ve been reacquainting myself with my note-taking software, trying to figure out what’s changed (LLMs are magic, apparently), figuring out who’s doing what, and all that fun stuff.

One of the neat things that happened while I was out of commission was Obsidian’s rebranding. Personally, I love the new slogan — I’ve written before about how I never liked the “second brain” framing. “Sharpen your thinking” is so much better, particularly because it doesn’t claim to “make you smarter.” Casey Newton is totally right to say note-taking apps can’t do that. They’re a useful tool; I don’t suffer from the information overload Casey mentions (reading very fast helps a lot, as does aggressively triaging my priorities list) and I don’t particularly expect AI to do more for my workflows than Obsidian itself did. Which is to say that yes, tools help speed things up on the margins (it’s amazing at turning a voice to text transcript into a workable first draft!), but they can’t really turn a sow’s ear into a silk purse.

Casey’s article focuses on the promises of AI, but I worry that people are getting too excited about what is, from a workflow perspective, fundamentally improved search and proofreading. Once I manage to get the QuickAdd AI assistant set up, I expect it to be an extremely useful tool — Christian builds great plugins and QuickAdd has been incredibly helpful for me so far (here’s how!). But it’s not magic. It’s not going to make us smarter. As exciting as revolutionary workflows and tools are, people are hopefully going to keep on being people. One of the reasons I value reading history so much is because I think it’s really important to keep perspective: no matter how fast or fancy my computer is, at the end of the day, my problems are not that different from those faced by any given Babylonian priestess you care to name.

Yours might be — if so, let me know!