My wife and I had another couple over for drinks recently, Anu and Sunder. At some point during our conversations, the topic turned to business. Anu, a serial entrepreneur, remarked something to the effect that “a good business is one that survives.” This comment was made in reference to the natural ups and downs that a business endures, and how the real goal is often simply to keep playing.

The timing on this was interesting as it aligns with the central premise of a book I’m currently reading: The Infinite Game by Simon Sinek

In this book, Simon Sinek describes two unique types of games: finite and infinite. Finite games have achievable milestones and infinite games do not.

Business is a type of game and there are also a limitless number of mini games being played inside of business. Here are just a few:

  • Profit and Loss
  • Employee Retention and Employee Attrition
  • Net New Customers vs Customer Churn
  • Content Production
  • Website Conversion rate

Each of these games can be played with a mindset for winning, and a mindset for continued play. I believe that we all would do well to change our mindset to think further into the future, and to play with the goal of enjoying the game and continuing the game.

Keeping the Plates Spinning

Last week, I sat down to catch up with Geoffrey Klein, owner of Nine Dots Media and host of the Connect the Dots Podcast (which is part of my podcast network During the conversation we exchanged our relative struggles with our mutual tendency to take on too many projects. Geoffrey referred to this as keeping the plates spinning.

While I’m still learning how to manage my own expectations of myself and not take on too many projects, the analogy of plates spinning struck a different chord for me this time. I noticed how, relative to the concept of finite and infinite, the goal of (methaphorically) keeping the plates spinning is nothing more than to keep the plates spinning.

That’s it…to keep playing.


One of my goals is to regularly share my thoughts and ideas about business, life, the future of work, entrepreneurship, and personal growth. The specific goal I’d established for myself is to publish two blog posts per week on this blog; one on Monday and one on Thursday, both at 11:00AM EST.

Last week, one of my plates wobbled when I published my post on Thursday 40 minutes late.


Another one of my goals is to learn to speak conversational Mandarin. I do this by practicing Mandarin for 15 minutes every morning on Duolingo. For 47 days straight, I didn’t miss a day…and then I did.

Over the past 75 days, I’ve missed about 5 days total. That’s 93% of days practice…but it’s not 100%, which means plates have fallen to the ground. However, I’ve been able to pick them back up and keep spinning.


I set a goal to make a video every week for the Superhero Institute. I made a video every week from January 14 through March 22.

Then, my mother passed away on April 4th. I made one more video on April 22nd, and haven’t made one since.

The plate is on the floor broken, and even though I’m still planning to bring back those videos, I can’t pretend it’s currently spinning.


I first became acquainted with the concept of Kintsugi through the video by Nerdwriter1 on Youtube.

If you are unfamiliar with the term, Kintsugi is a Japanese art form whereby broken pottery is mended using a lacquer dusted with golden, silver, or platinum. Rather than attempting to repair the pottery to it’s original state and hide the prior damage, the cracks of the broken pottery are highlighted and beautiful.

As a philosophy, it treats breakage and repair as part of the history of an object, rather than something to disguise.

Why else would this technique exist except to convey the message that sometimes the damage and breaks we suffer in our past, can become something beautiful for our future?

Is it so bad to drop a plate every now and again?

What’s Beyond Winning and Losing

Earlier in my career, every setback was painful. Dropping the ball on even a single aspect of a project could cause a spiral of negative emotions from light to severe self-doubt to full blown anxiety and a desire to quit, hang up my cowl and cape and go get a 9-5.

While I can’t say I’m entirely beyond that mode of thinking, I have gotten far more patient. Perhaps it was turning 40, perhaps it was my daughter being born (which happened two days after I turned 40), but I suddenly see things on a longer time horizon. I have less ambition to accomplish things by certain dates but rather just to accomplish things at all. I’m more concerned with my aggregate and cumulative impact than fleeting metrics that fade away over time.

What’s really beyond winning and losing is sustainability and resiliency.

I’ll give you one more example to illustrate this point.

Back in 2013, I was feeling heavy and wanted to do something about it. My weight had gotten up to 175 lbs and it didn’t feel right. I made the goal of getting down to 160 lbs. I made some serious changes and over the next 6-8 months, I’d shed 20 lbs. I won. I felt great.

Today, I hover between 180-185 lbs. Who cares that I’d hit my goal in 2014?

I was thinking in finite terms. If I’d said that I want to develop and maintain a lifestyle that allows me to always maintain my weight between 160-165 lbs, I might’ve more easily noticed my carbs with cheese addiction creeping it’s way back in.

The Secret To Spinning Plates

Every big goal is comprised of multiple small events and lots of small events can add up to very big outcomes. Therefore, as I see it, the keys to success look like this.

  • Set a big goal out into the future that you can never complete but you can continually work toward
  • Create sustainable habits that support your big goals
  • Develop resiliency to keep moving forward on your habits when you have a setback.

In order to do these things, my advice would be…

  • Limit the number of things that you devote your time and attention to (i.e Don’t have too many plates spinning)
  • Pick projects and habits that do not require perfection. Make it achievable and try to build some flexibility into the process. (i.e Try not to use fragile plates)
  • Be patient and keep at it, you’ll find that it gets easier and easier to keep going the more experience you develop. (i.e Plate spinning is just a skill and like most other skills, it’s one that takes practice)
  • Be mindful of your pace. Going too fast can cause burnout, going too slow can make it difficult to achieve traction. (i.e There’s an ideal speed for spinning the plates)

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