I've had different kinds of interesting gigs. The first kind is what most would consider interesting, working at a small fast-paced startup with much freedom in

I've had different kinds of interesting gigs. The first kind is what most would consider interesting, working at a small fast-paced startup with much freedom in many of the choices of language, platform, frameworks/libraries. That's the case if you're early. Some of those same roles will end up becoming supporting a mishmash of varying one-off tech for different programs/services which can be challenging but far from interesting. Another kind of interesting that I'm starting to appreciate is using boring tech to solve or evolve standard platforms to grow with the sophistication of the customer base at a large company. Things move much slower, the tech, languages, tools can feel stagnant. At the same time, you're still solving the problems that need to be solved with good engineering producing pretty clean/clear implementations. Most wouldn't consider this very interesting. It only feels worthwhile when you take into account that you've now shipped improvements to 100,000s or millions of customers. It also helps greatly if you actually believe that what the company does is a largely net positive for society. As for my personal history of finding interesting jobs, I've found many of them randomly by being open to new experiences. Some were better than others but I don't regret taking any of them. Even the good small/fast ones were only good for about 1.5 - 2.5 years after which my learning opportunities slowed and I moved on.