Do the Hardest Thing

A simple piece of career advice — pick the hardest worthwhile problem and stick with it — somehow turned into a full-blown comment-section philosophy brawl. Justin Jackson’s article praises founders like Bento and Transistor for choosing difficult, valuable ideas instead of chasing smaller, easier wins. His big flex? Working yourself to death on the wrong idea, like his old snowboard shop, is very different from taking on a truly difficult challenge that few people even dare to try.

And the crowd? Very into it — mostly. One reader called the post “refreshing” in a world obsessed with speed, basically cheering for the radical idea that good things might actually take time. Another loved not just the message but the vibe, applauding the site for having a real personality instead of looking like “just another Medium article,” which is the kind of oddly specific online shade commenters live for. Then came the inspirational life-story energy: one commenter said they learned this lesson “by accident,” turning the thread into a mini support group for people who stumbled into harder paths and somehow made them work.

But not everyone was ready to tattoo Do the hardest thing on their forearm. One skeptic pushed back hard, saying the opposite often feels true: choose something easier, execute better, and maybe you’ll actually win. That’s the real drama here — is this bold wisdom, or startup-brain romanticism? Meanwhile, another commenter dropped artist Tom Sachs’s rule, “Do the easy/hard thing first,” like a cryptic mic drop. The result: part pep talk, part reality check, part internet book club with knives out.