Here's my story: I've had 3 "dream jobs." I only regret joining one of them and it basically followed the pattern you describe, and I think I just narrowly avo

Here's my story: I've had 3 "dream jobs." I only regret joining one of them and it basically followed the pattern you describe, and I think I just narrowly avoided entering into this cycle in my most recent job search. In the last year, I had multiple opportunities to continue the cycle and switch jobs to another local maxima, but I think I broke the cycle, but mostly by refusing to keep playing the game. I had weekly conversations with my friend who ended up hearing about all of my job complaints and this friend was able to see how my feelings about work changed over time. At times this friend was ready to hit me over the head because of how repetitive my complaints were. Every time I interviewed and got a job offer, I would convince myself that I wanted to switch companies because company Y was offering me more money and responsibilities than company X and I thought company Y would give me growth opportunities beyond what I would have at company X. I would rationalize the decision in a lot of ways and would be thorough in comparing the pros and cons of switching to company Y. And then I would talk to my friend. And my friend would say "okay, so company Y is offering you more money than company X. What do you want to do?" And I would say something like "I'm not 100% sure if I will be happy at company Y, but they're offering me more money and the company / team / product is cool. If I'm not happy in 1-2 years I can use that money to start my own company and be in a better position." It didn't seem like I wanted to work at company Y that badly if my answer to "what do you want to do" isn't "work at company Y!" I justified my decision to change jobs by finding the things I didn't like at company X and contrasted them with the things I liked at company Y. Leaving company X needs to be a separate decision from joining company Y in order to make the best decision. In the past I always considered them as the same decision. Even when I was interviewing at lots of companies which should have given me more choice, it always came down to making decisions about company Y based on company X instead of being about what I wanted to do for the long-term. I talked to a bunch of other friends and family about switching to company Y and everyone else except this one friend went along with whatever I said. Some people lightly questioned what I said but only to see that I had an answer for their questions, but the human mind can rationalize basically anything and I had already fooled myself into thinking I wanted to switch jobs when I was just unhappy with company X. I fooled everyone except my one friend, because my friend realized that my decision-making process was fundamentally flawed. That gave my friend the confidence to push-back on what I said. Having a contrary perspective gave me the space to reconsider my decisions. I quit my job at company X and am currently trying to start my own company since that's what I wanted to do all along.