The last three jobs I've held in the last 5 years have all felt like someone just handing me the keys to a sinking boat before they jump off. Every job is sold as having at least some greenfield development where you can "own" the domain and "lead" the direction of the project, but once you accept the offer and get on-boarded, you realize that the system is so brittle that any change will completely break and cause incidents, and there is a year's worth of backlog issues to address with duck-tape and glue before you could even consider fixing the fundamental problems.

Often the teams that built these systems are long gone, so there is nobody to ask for help when you're learning the rough edges, you're just on your own. The technology decisions are all completely set in stone because we could never justify the risk of making changes. There is so much tech debt and maintenance work, we don't really have time to do any new development with the current staffing levels. The job then becomes dominated by on-call responsibilities and fire-fighting. It's 90% toil, and almost zero actual system design and development work.

Being responsible for a whole system that you didn't build, that you know is brittle and broken, but which you cannot fix, is incredibly stressful. It's almost a hopeless situation.

While there were undoubtedly people who came in for the food, worked 3 hours a day, and enjoyed their early retirements, all the people I met were earnest, hard-working, and wanted to do great work. What beat them down were the gauntlet of reviews, the frequent re-orgs, the institutional scar tissue from past failures, and the complexity of doing even simple things on the world stage. Startups can afford to ignore many concerns, Googlers rarely can. What also got in the way were the people themselves - all the smart people who could argue against anything but not for something, all the leaders who lacked the courage to speak the uncomfortable truth, and all the people that were hired without a clear project to work on, but must still be retained through promotion-worthy made-up work.

Another blocker to progress that I saw up close was the imbalance of a top heavy team. A team with multiple successful co-founders and 10-20 year Google veterans might sound like a recipe for great things, but it’s also a recipe for gridlock. This structure might work if there are multiple areas to explore, clear goals, and strong autonomy to pursue those paths.

Good teams regularly pay down debt by cleaning things up on quieter days. Just as real is process debt. A review added because of a launch gone wrong. A new legal check to guard against possible litigation. A section added to a document template. Layers accumulate over the years until you end up unable to release a new feature for months after it's ready because it's stuck between reviews, with an unclear path out.