I've been meaning to write this article for several years, but kept stopping for two reasons:

Everyone knows the difference between right and wrong, right? Wrong. And this includes me. I have a certain level of paranoia that things I believe with 100% conviction will turn out to be utterly wrong in a decade. Only hindsight will confirm whether my sure bets were not delusional gambles. Until then, I try and live by the philosophy of Marc Andreessen of "strong opinions, weakly held." However, I'm human, and I have my blind spots. Maybe my belief systems have already been invalidated, yet I'm still unknowingly and unwittingly living on the wrong side of history.

10,000 hours. This is the number made famous by Malcolm Gladwell in his book Outliers. The claim is that it's the (minimum) time necessary to achieve mastery in a subject matter. The bad news: it's not a guarantee. Without proper knowledge, strategy, and natural talent, it can be a lot of effort with minimal results.

Leaving a tribe is painful.

No, I'm not speaking in hand-wavy metaphors. Literally, loneliness is a biological feedback loop to urge us back into a tribe. The reason being is that evolutionary wise, reliance on a tribe was a survival mechanism that we still benefit from this day. Only the most extreme introverts (and this is exceedingly rare) can truly live the lifestyle of a hermit apart from a family, a community, a tribe, or even strangers.

I know this pain. I've left or lost my tribe multiple times.

A friend of mine recently asked if I had any experience with all-or-none-thinking. I wanted to respond, "Always! Never!" in my typical #dadjoke fashion. However, when "the stakes are high and the moment is brief" (to quote Joel Roberts), this subject matter warrants a serious, nuanced conversation.

Nobody wants their mistakes to be on public display. This is why the default strategy is to practice in private before performing in public.

However, not everything works this way.

Comedians can rehearse a joke a hundred times in front of a mirror, but it only comes to exposed to a live audience.

An executive can read a dozen books on leadership, but the real test is making a bold and difficult decision in a meeting or in the media.

Most people are familiar with the 4 stages of mastery:

1. Unconscious incompetence (e.g., "I don't know what I don't know.")
2. Conscious incompetence (e.g., "I know what I don't know.")
3. Conscious competence: (e.g., "I can succeed with conscious focus")
4. Unconscious competence: (e.g., "I can succeed automatically")

In a past business, my co-founders and I had the perfect product for The Bob Dylan Archives. With Kairos, they would get an iTunes like interface to search, sort, modify and export any one of the thousands of assets they managed. Before Kairos, this was a tedious process that involved a lot of manual searching and digging through analog tapes. Making the switch would not only reduce their operational costs but open up new opportunities to make money licensing content.

Sadly, they said no.

One of the most frustrating parts about goals is the paradox: the feeling of being so close, yet so far apart and vice versa.

We may feel like we're on the verge of a breakthrough! Yet, we are getting further apart as we sprint in the wrong direction.

We may feel like we're a million miles from the finish line! Yet the answer can be hiding in plain sight a millimeter from our face.

Close, yet far.

Far, yet close.

"Open a chrysalis, and you kill the butterfly." I still remember the first time someone told me that because it seems counter-intuitive from the vantage point of how humans approach problems. If I could avoid a roadblock entirely, why wouldn't I? If I could take a shortcut to get through it faster, why wouldn't I? Of course, the butterfly wants to get on with its life, so why help them?