It strikes me that one of the biggest challenges we face is reconciling our desire to be successful by societal definitions while not giving up on being successful by our definition.
The challenge lies in the fact that extrinsic measures tend to be breadth focused (e.g. number of customers/successful exits/employees) while the stuff that make us feel intrinsically successful tend to be depth focused (e.g. deep relationships, immersive experiences).
Anyone who has built products or services has faced this in their work. It is much easier to move vanity metrics than it to create meaningful impact.
The answer, in work and in life, isn’t to shun extrinsic measures and breadth. We need some of it to ensure it doesn’t get in the way of us getting to the intrinsic stuff.
The challenge, however, is not being so sucked in by the allure of breadth and scale that we forget that its main purpose is to enable the depth we really seek.
Put differently, the optimal strategy tends to be to do things that scale easily so we can then spend more of our time doing things that don’t scale.