People usually think of "making it" as a single point in time that's binary. Granted, there's some truth to that: most people will feel fully comfortable with a few millions in their bank account.

But in reality, success can be savored a lot more pleasantly if you allow yourself to be conscientious of milestones and include having a great process of getting there as the definition of success.

I've met so many people (myself included) that burned themselves by thinking they will spend only a few years grinding to reach a certain milestone, and get frustrated when the narrow definition of success they've created for themselves isn't met.

I've also met a few others that have realized the above, usually with burnout then self-discovery, many which also "made it" by the standard definition, but have a strong sense of fulfillment.

Naturally the question is how. For myself, what worked is a mix of taking more risks (becoming a founder at 35+), experimentation and using various techniques (therapy, meditation, the usual suspects) to find what can drive me to work hard but with purpose or joy.