I was in a similar situation. I felt all the things you describe. Unlike the common advice you'll hear to "just take the leap", I didn't. After much soul-searc

I was in a similar situation. I felt all the things you describe. Unlike the common advice you'll hear to "just take the leap", I didn't. After much soul-searching I found I couldn't reasonably justify quitting from an economic perspective. So I stayed some more years, living quite comfortably but intentionally under my income level to bank more money. The timing turned out well for me because, during this period, the company's stock increased even more than the overall market (which was doing quite well). Bonuses were higher than expected too. Some projects were satisfying. Then some weren't. I got bored again and became "less happy" (because it's hard to even say "unhappy" given the circumstances). But now with several million banked in diversified long-term investments my perspective changed, though it was still hard to reasonably justify just quitting. I finally decided to intentionally increase my career risk-taking within the company. I sought out nascent projects which were more speculative and in business units that were considered less career "safe". The first couple projects luckily worked out well and I banked even more cash for a couple years while enjoying the challenges and feeling of "living on the edge". I kept scaling up the career risk-taking and eventually joined a cool new project that didn't work out. I actually had more fun than I'd had in years because the project concept was quite bold and different. But luck ran out mostly due to bad timing. Macro economic turbulence collided with a political shake-up at the SVP level. The executive appetite for funding explorations in unproven new markets dried up. The project was cancelled. And the next week the whole group was cancelled. As a now-senior person with a proven track-record, I was given the option of taking a few months to find a new project somewhere in the company. I looked around for something interesting but, frankly, I didn't look that hard and everything I did see wasn't very exciting. I finally decided it was time to leave. It had been almost a decade since my initial dissatisfaction. My diversified investments had done very well. The company's stock had done even better. So I decided to retire early. It's surprising how inexpensive a very comfortable, even luxurious, life can be in other states compared to astronomical bay area costs. It's been a couple of years and so far it's been working out very well. Loving time with family and especially the time for myself. Sure, sometimes I miss the go-go and challenge of the valley grind. But not very often.