When to Quit Your Job

Thanks for engaging with the piece, although reading some content you've put out into the world called "naive" isn't a great feeling. I wonder what other word might have been used to accomplish your point without being degrading. "Incomplete" perhaps?

To your points:

1. Stock options vesting and accomplishing something meaningful to show your value to your next employer are tactical considerations to make if you've decided to leave. So you're right that if you establish that your current place of employment won't allow you to satisfy your intrinsic motivations, isn't in a context you're interested in, or won't let you accomplish your lifestyle goals, you need a plan to quit. In creating that plan you'd need to consider the questions you asked, but those are more questions of when to quit, or how to quit, rather than if you should quit.

2. Money to fill you bank account is a shallow reason to work - working to support your family or send your kids to college isn't - those are intrinsic motivations - to feel like you're providing for your family - or to feel like you're being a good parent - working to get money in your bank account speaks to responding, like trying to get peer recognition, to an extrinsic motivator - earning more money. Many of my peers when I was in my 20's worked for the money, and the toys, but never finding satisfaction in that.

I would submit, and particularly in the case of my clients who are all software engineers, that they are able to fulfill most of their lifestyle/income goals, while still doing a MUCH better job of understanding what kind of work they want to be doing, and pursuing career opportunities that provide those to them.