Failing in Public

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.

Confident Incompetence

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")

The Best Question to Overcome Rejection

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.

A Million Miles or a Millimeter?

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.

When Helping Hurts

"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?

The Things I Want To Share

I've been struggling with a massive amount of writers' block this past week. No, it's not for lack of things to share. At present, I have over 200 article titles stubbed out as ideas. They just sit there waiting for me. Waiting for me to take the time, to prioritize them, and to birth them into the world.

The "Hit By a Bus" Rule

Buying a life insurance policy is a sobering experience. You get to answer uncomfortable questions like "How many years would you like them to live at your current lifestyle without you?" Of course, we'd love the answer to be forever, but that is hardly a realistic response. So you do your best to try and not feel ashamed or like an asshole asking whether or not five years would be enough. Thankfully, current average life expectancies are more than double my current age. I also lead a reasonably active lifestyle, so I pray the policy is never needed.

How Writing Led Me To My Wife

I flew 2,000 miles from Boston to Denver to meet my wife for the first time. I was excited as hell. I was also nervous as hell for many reasons. First, I would be staying at her parents' house. Making a positive first impression is already hard enough. Just imagine the pressure of knowing I didn't have the money to get a hotel if I messed that up! Second, we didn't know what each other looked like. We met in 2008, which was many years before it was customary to Facebook-stalk someone to confirm they were not a hot mess or a mass murderer.

The Three Reels

I had a powerful conversation with a mentor yesterday, and it got me thinking about the paradox human connection in the era of the internet and social media. Specifically, technology provides us with endless opportunities to connect with anyone worldwide, yet we're seeing epidemics of isolation and disconnection. Why are so many people lacking strong friendships or communities to be a part of? This led to a thought exercise about the types of people we feel comfortable with reaching out to and what kinds of people we felt were unapproachable (thereby leading to more disconnection).