I’m Arun Venkatesan, and this is the arun.is newsletter, where I share my current obsessions, inspiration from around the web, behind-the-scenes content, and more. 

In this week’s issue:

  • Healthy and unhealthy ambiguity
  • Updates on my upcoming essay: Japan redux
  • Recommendations: Words & music

Healthy and unhealthy ambiguity 

I’ve worked in startups for my entire professional life of more than ten years. In that time, I’ve learned that the name of the game in business is ambiguity. Ambiguity is what opens up opportunities for startups. While incumbents may see fog in an area, startups see an opportunity.

Over the years, I’ve had to deal with so many different forms of ambiguity that I’d safely say that it is one of my strengths. During that time, I’ve learned through experience that there are healthy and unhealthy forms of ambiguity, and each can be dealt with differently.

For example, it’s okay for startups to have not yet found the different components of product-market fit. Startups often don’t know the ideal UX for their product or haven’t identified the core value proposition. This is a healthy form of ambiguity. Entrepreneurs need to live with the feeling that they haven’t yet found the correct balance of parameters.

At the same time, it’s unhealthy to have ambiguity around what the current experiments are. In the past, the teams I’ve worked on, and I have followed our intuition without fully forming a hypothesis. In these cases, since we didn’t have a prediction and a framework for analyzing feedback, once we build something and feedback starts to roll in, we don’t know what conclusions to make.

Another example involves careers and jobs. I think it’s okay for those in a startup or small organization not to know what position they could have in the company in a few years. The process of wearing different hats and growing the company usually clarifies which direction each teammate should go. We find our path through doing. 

On the other hand, it’s not okay to have ambiguity around roles and responsibilities. Even though people may be pitching in wherever they can, there should always be clarity around who is accountable for critical decisions and tasks. I’ve experienced situations that felt like a baseball falling in the middle between two outfielders. Each teammate assumes that the other will catch the ball, and as a result, the ball falls to the ground. Worse, the teammates may proverbially run into and hurt each other, and the ball still falls to the ground.

To me, dealing with ambiguity requires first identifying the type of ambiguity.

If it’s of the healthy type, then it is worth acknowledging it and living with it.

If it’s of the unhealthy type, then we need to take action to remove it. I often turn to structured workshops like anonymous retrospectives and silent brainstorms. Ambiguity, by its nature, can often lead to emotional, unproductive conversations. By adding structure to the conversation, I find it’s easier to focus on the problem at hand and address it systematically.

Have you noticed examples of healthy and unhealthy ambiguity in your work?

Upcoming essay: Japan redux

My upcoming photo essay will focus on a month-long trip to Japan in 2015 — a journey that transformed my life. While organizing my thoughts and photos, I’ve found too much material for one essay. Therefore, I plan to split it into three. 

Among other things, the first issue will focus on my photographic gear and style, the experience of attending a massive convention in Tokyo, and some shots from the street. Please keep a lookout for it next week.

Recommendations: Words & music

I’ve been recommending quite a bit of audio content in this newsletter. Audio has become my preferred medium while doing household chores and taking walks around the neighborhood. This week, I have a few recommendations that are part book, part music.

The first is Yo-Yo Ma’s Beginner’s Mind. In a past life, I was a cellist — more serious and better than most, but never diligent or talented enough to rise to the absolute top. Even though I rarely play today, I often find myself listening to music played on the Cello. The timbre, tonality, and pitch of the Cello produce music close to the human voice.

Beginner’s Mind is a memoir woven together with music. Between stories of his past and contemplations on the many lessons from his life so far, Yo-Yo plays some of the music he holds dear. Unfortunately, it is an Audible exclusive, but you can download it for free if you have an active subscription. 

The second is more of a cross between a biography and an interview. In Miracle and Wonder, Malcolm Gladwell and Bruce Headlam try to understand what makes Paul Simon tick. The prolific artist, now in his 80s, has continuously explored and made music since he was in his teens. The depth and breadth of his repertoire, alongside his critical acclaim and reach among the masses, puts him at the top of the top of musicians.

Miracle and Wonder has opened my eyes to a genius that I previously overlooked. I’m sure it will inspire you as it has me. 

That's it for this issue. As always, this is my personal email, so feel free to respond directly.

Stay curious,
Arun Venkatesan

Copyright © 2021 arun.is, All rights reserved.


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