Navigating a Lucrative but Unfulfilling Role – When to Jump Ship?

Greetings HN,

I find myself in a very peculiar career conundrum. I currently work as a Staff Software Engineer at a unicorn that successfully went public a few years ago. My compensation is excellent (nearly $500k/year) and I have a healthy retirement account from the IPO. As thankful as I am for my current position, I am also fully aware about the disparities in pay across different geographies and how luck played a big part in landing this role. I just want to make sure I'm not coming off as bragging or unaware of my luck for this.

But here's the problem: The job is making me miserable. The upper management, including my director and C-level executives, seem to lack the necessary competence in their roles. The organization continuously fails to achieve the main Key Results (KR) which leads to a lot of mental gymnastics by the management to redefine success.

My superiors, who are not technical, often give unrealistic directions. Metaphorically speaking, they would come in a building project and look around and say "we should be using red bricks here" but the building is completely made of concrete and we're installing the windows... The lack of connection with reality is frustrating but pushing back feels intimidating.

My major concern, however, lies in my personal and professional growth. I hardly do any coding in this role. Last quarter, we installed a new npm package and wrote a few tests, that's it! It seems the org's inefficiencies are not coming to light because we're not in the main line of business.

So, my question to the HN community is: How long should I endure this situation? The pay is good and the workload is light, but at what point will this start hurting my career? It's clear that this inefficient system will not last.

Would you, in my position, consider sacrificing $200-300k a year of your income to join a smaller startup? One that could provide an atmosphere of inspiration, learning, and teaching about the proper management of an engineering organization?

Thanks for your insights and advice!