Why you should ask "why" to things you don't like

South Africa Summer 2014 Blog

Written by: Bryan Hernandez

July 2, 2014

Yesterday, one of the founders mentioned to me that he was struggling with the program.  He came to me and explained that he didn't feel like he was grasping the methods well enough to see much success nor inherent positive feeback.  I was surprised to hear this because I would rank him in the top 5% of intelligence and work ethic in the program. 

Was it because I had him well outside of his wheelhouse—far from engineering?  Running around talking to prospective customers; making calls until he was blue in the face and his Airtime account had run dry? 


People generally don't like being held to high expectations in work for which they do not feel competent.  And when you throw a person with an ego that identifies with being a smart, competent, and hard working person into a game for which a 10-15% success ratio is considered 'killing it', it's not hard to imagine what valence of emotions are sure to emerge from this.

When I probed a bit deeper about what specifically was troubling him, I discovered a couple important things.

1) He was focusing on an end goal and not on the process.  With every attempt he makes, he feels like he comes back empty-handed.  And this might be true.  It's not an easy thing to know when it's OK to be outcome oriented and when we should be process oriented.  In this case, I believe he was too outcome oriented to the degree that he could feel no positive feedback for his efforts.  What's remarkable about this individual is how long he was OK keeping his head down, grinding away, while allowing himself no feeling of accomplishment.  I believe the duration one can continue working hard without any sense of positive feedback is a good way of characterizing people with a large amount of grit. That trait that is very difficult to teach.  And as admirable as it is to see it exercised in someone, I have to offer a warning:

We all have our breaking points. 

We all have a day when we decide to give up because the implausibility of what we're doing outweighs our belief in ourself to make it happen.  When you catch this happening, you need to first: get help to make sure your method is appropriate for the goal; and second: refocus your attention on the process you're going through so that you can celebrate and feel good about the small wins—the fact that you've been hitting this problem hard for the last 10 days straight, have made over 100 calls, and know a lot about which markets are not viable right now (at the very least.).

2) He had some distracting beliefs about business, entrepreneurship, and economics in general.  For myself, I have always considered myself a philosopher and scientist.  It's not uncommon for engineers to have similar ways of looking at the world, and what often comes with this perspective early in life is a slight disdain for business activities, in general.  This isn't a universal. But it's definitely common. 

In my earlier years, I maintained somewhat superficial understandings of what business was.  And although they were accurate, they were not the end of the story.  What I never quite understood was the purpose and context under which these human activities emerged and what that actually meant for people who choose to engage in them, as well as those who choose to ignore them or actively fight against them.  As I am writing this during a single pomodoro session, I do not have time to satisfactorally explain how business activities can actually be understood from a more philosophical or scientific framework that is not disagreeable, and so I will only claim that it is possible.  The thought work that I've put in to achieve this level of understanding has made all the difference for me.  At the highest level, it has allowed me to accept the world as it is, to learn to play more "games" than I ever thought possible, and to generally accomplish my goals with less friction than before I had an understanding and appreciation for how things work and why they have developed into the structures we see today.  As a teaser about what can lead to asking the right questions in order to develop in yourself a similar depth of understanding, consider the types of problems you will need to solve if you were going to run your own community, society, or even city state.  This has been the fodder for thought for many great thinkers, and the tools with which to deal with the problems that emerge are as diverse as all human endeavors since the beginning of our evolution.

But to wrap my point—if you know you have some deep conceptual or philosophical problems with the game you're playing, it's wise to spend some thought cycles (preferably at the beginning of the day) to rooting out the incompatibilities.  You might find you are in fact playing the wrong game.  Or you might just solve a nagging conceptual uncertainty for yourself once and for all.

Remember what it was like to be young, naive, and idealistic—but most of all, remember what it was like to enjoy asking "Why?".