I think I've been in a similar situation. I'm not a fan of building simple I/O apps, and I'm actually not very good at it either (even though it has been done a

I think I've been in a similar situation. I'm not a fan of building simple I/O apps, and I'm actually not very good at it either (even though it has been done a million times by others). I do much better when people give me challenging problems, so I think we may be similar in that regard. First I'd ask how long you feel you've been bored for? It could be that you're just in a lull of interesting things. Do you have any of your own projects? Do you contribute to open-source? Have you considered work outside the 'regular' IT space? I almost always have a project on the go, and often find some interesting challenges in there. What worries me most is when I don't have any side projects, but a new idea always eventually pops up. When you talk about 'product-market-fit' being the big issue with most startups, that is what makes me think you're not looking at the start-ups that are doing the challenging work. It often isn't in web or typical software/service companies. IoT security is something that constantly comes up as an area still in need of being addressed. Or have you played with BlockChain and distributed contracts. There are lots of problems to be solved, maybe it's just finding the ones that interest you. I think meetups can be a good source too, just don't go to the 'language' meetups, but maybe pick an industry meetup or two where you might be interested but wouldn't normally be in scope of what you're familiar with. Worse comes to worse, you can always leave. Those are my thoughts, but I don't think you're alone.