Hearing about your envy of being an old man at his zenith reminds me of something one of my favorite thinkers, Viktor Frankl, says in Man's Search for Meaning. He would agree with you wholeheartedly.

He writes:
“There is no reason to pity old people. Instead, young people should envy them. It is true that the old have no opportunities, no possibilities in the future. But they have more than that. Instead of possibilities in the future, they have realities in the past — the potentialities they have actualized, the meanings they have fulfilled, the values they have realized–and nothing and nobody can ever remove these assets from the past.” (from Man's Search for Meaning, p.151 in the Touchstone 1984 edition)

That to me, is the true ideal – having the wisdom to appreciate where I am in my stage of life, not to get caught up in the rapacious hunger cycle you so described. This is especially for those that you described are “smarter, richer, luckier or more credentialed.” As I've noticed sometimes those people can be victims of their own success, at worst focusing so hard on the challenges that they let slip other important items in their life, family, friends, children, etc.

In Reflection, perhaps that's why I'm envious of old men, maybe when the need to challenge myself career wise has reached its zenith, I can just sit back… relax… and crap my pants. In the meantime, I remind myself of how many challenges I've already completed, content with where I am, and satisfied with farting in the elevator.

I think there's a lot of wisdom in what you write about putting measures to place to keep us from lying to ourselves. I talked a little about delusion in this interview I did recently, and about how I think it's the hidden startup killer. I'm curious to hear your thoughts and I'd like to write more about this eventually:

http://www.cooltownstudios.com/site/comments/so...

I think a lot of entrepreneurs, in particular, struggle with this. They are so glued to their ideas, business, etc. and they're so determined to succeed. They tell themselves, “Just a few more months, then I'll quit if x isn't accomplished.” They'll always end up convincing themselves to go another few months. Months turn into years, and very likely, years of true opportunity foregone.

One great takeaway I've received somewhere along the line from PSL (can't remember when or from who) is that it's important for us entrepreneurs to set strict and objective milestones and consequences (i.e. “Quit business”) for ourselves and our businesses far ahead of time – at least a year, and write them down. This way, when the deadline point comes and if we haven't hit that milestone, our consequence is purely objective and we can't argue with (lie to) ourselves any longer – we can at least be assured our decision/consequence (to quit, in this example) was not rash, rushed, subjective, etc.

I think your write-up seconds the merit of this, and can serve as assurance to those of us who may have to make these incredibly tough decisions in our business or personal lives. Thanks Blake.

I hear you about the risk of needlessly sowing doubt. I'm a believer in the idea that there's no real faith without doubt to test it and reinforce it. So I'd rather err on that side, especially when life's most important decisions are on the table.