> Makes me wonder whether we’re already setting up the next cycle 10 years from now, when everyone rediscovers why cloud was attractive in the first place and starts saying “on-prem is a bad idea” again.

My entire career I’ve encountered people passionately pushing for on-prem and railing against anything cloud. I can’t remember a time when Hacker News comments leaned pro-cloud because it’s always been about self-hosting.

The few times the on-prem people won out in my career never went exactly as they imagined. Buying a couple servers and setting them up at the colo is easy enough, but the slow and steady drag of maintaining your own infrastructure starts to work its way into every development cycle after that. In my experience, every team has significantly underestimated how all the little things add up to a drag on available time for other work.

The best case for on-prem that I saw was when a company was basically in maintenance mode. Engineers had a lot of extra time to optimize, update. maintain, and cost reduce without subtracting from feature development or bug fixes.

The worst cases for on-prem I’ve seen have been funded startups. In this situation it’s imperative that everyone focus on feature development and rapid iteration. Letting some of the engineers get sidetracked with setting up and maintaining their own hosting to save a dollar amount that barely hires 1-2 more engineers but sets the schedule back by many months was a huge mistake.

In my experience, most engineers become less enchanted with rolling their own on premises hosting as they get older. Their work becomes more about getting the job done quickly and to budget, not hyper-optimizing the hosting situation at the expense of inviting more complexity and miscellaneous tasks into their workload.