Embrace the Infinite Game

A Roadmap for Start-Up Founders to Enjoy the Process

I recently read a thoughtful essay written by Michael Ashcroft from the Every Substack. The essay is called: “Be Sincere - Not Serious - Why white-knuckling your way through life doesn’t work”.

This article really spoke to me. I think if more people operated from a place of sincerity rather than seriousness, our world would be a very different (better) place. Both in our personal and work lives, finding a balance between accomplishing short-term goals and enjoying the process over the long-term is indispensable to sustain a healthy life.

Startup founders would be wise to recognize this while building their ventures. While it’s important to take things seriously and work hard, it is equally important to maintain perspective. Having a positive, “loose” attitude will generally serve founders better than being uptight and serious all the time.

Founding a company is extremely difficult. At FFC, we recognize founders are the key to a startup success. We meet lots of founders who are driven, motivated, hard-working, intelligent, creative, conscientious, and talented….the list of positive attributes goes on and on. However, in order to spin these characteristics into success, it is essential for founders to be self-aware and sensitive to their situational approach. Ashcroft tees up the idea of situational approach nicely as he reflects on his own experience as a corporate manager:

“Back when I was a manager in a large corporation, I noticed myself alternating between two distinct states at work. Most of the time work was fun. Even when I clocked long hours on challenging projects, I enjoyed myself and looked forward to doing it again the next day.

Other times, I was a tightly wound ball of stress who sucked the joy out of a room like a Dementor from Harry Potter. Even when my workload was lighter, things just felt difficult. Eventually, I realized the work itself wasn’t to blame—it was my attitude that was triggering one state or the other.”

From time-to-time (more often for some than others), humans fall into the bad attitude trap, approaching a situation with negative energy. These moments have tremendous influence on our own health, as well as on the health of those around us. Startup founders are particularly susceptible to the ups and downs of daily interactions that come with the stresses involved with founding a company.

Michael Singer’s book Living Untethered has been instrumental for me in becoming more self-aware. I am learning to pay more attention to my situational approach. Singer argues that the first step to changing a negative thought is to recognize that those thoughts are occurring. He then suggests that we surrender to those thoughts, relax, breathe, and let go of them. Singer quotes the famous Indian scholar Yogananda who teaches, “every time you have a negative thought, replace it with a positive one.” Of course, this is easier said than done, but the concepts line up well with Ashcroft’s suggestion to prioritize short-term result (finite games) over the longer-term process (infinite game).

Ashcroft writes,

“This distinction between finite and infinite games maps well to the mindsets of seriousness and sincerity. A finite game, where the goal is to win, can easily become a serious, grave affair, devoid of fun and levity. An infinite game, where the goal is nothing more—or less—than continuing to play, lends itself to sincerity. Confusing an infinite game for a finite game can be a subtle source of suffering in life.”

Ashcroft provides a unique perspective on maintaining a balanced mind set. Comparing sincerity to seriousness, introducing the concept of finite vs infinite games, and suggesting some techniques for implementing a sincere posture, the essay is a good reminder for startup founders (or anyone) in the midst of an 80-hour work week.

This quote sums up Ashcroft’s article nicely:

“Seriousness can get in the way of the most constructive course of action. Think of a meeting at work toward the end of the day. People are tired, and there are some difficult decisions to make. As Jonny Miller tells us, the best thing to do might be to take some time to make sure everyone’s nervous systems are well regulated—perhaps taking a big physiological sigh, shaking your body, making some noise, or cracking some jokes. 

But in a lot of professional contexts, all of those things might be regarded as silly. This attitude of “we don’t do that sort of thing around here” can be seen another way: as excessive attachment to the supposed rules of the game. This perspective can interfere with easier and more effective ways of working and living. 

Adopting a posture of sincerity helps you navigate this problem. If you can regard yourself and your situation with a sense of humor, you can embrace what may feel silly and remember the rules you’re following aren’t set in stone. That allows you to more easily see through the limitations of the game you’re playing.  Playfulness makes it easier to adapt the rules of the game to meet everyone’s needs in the situation. You might decide to invent a new rule, change a rule—or play a new game altogether.” 

The bold section is my added emphasis. I strongly believe that having a sense of humor and recognizing flexibility of our situational approach is incredibly freeing. Approaching life with sincerity rather than seriousness liberates humans to solve problems in creative,  non-intuitive ways. Ultimately, this opens more doors to success.

Ashcroft’s essay inspired several takeaways that are useful for startup founders:

1. Be self-aware: Recognize the impact of your attitude with respect to your colleagues, friends, and family. Embracing a sincere and playful approach, rather than being tense and gloomy, will lead to better outcomes.

2. Embody the infinite game mindset: Focus on the long-term vision rather than getting overly fixated on short-term wins or losses.

3. Find joy in challenges: Rather than being overwhelmed by difficult decisions, try to enjoy the decision-making process and view challenges as opportunities for growth. Setbacks, failures, and obstacles, are useful to refine your technology and strategy.

4. Prioritize flexibility and adaptability: be open to adjusting strategies and rules. Be open minded to explore new possibilities and pivot when necessary. A rigid approach will limit your ability to adapt to emerging opportunities.

5. Invest in Continuous Learning: In rapidly evolving fields, staying updated with the latest advancements is crucial. Foster a culture of knowledge sharing and innovation.

I recommend that founders (and busy people everywhere) take a few minutes to read this essay. And the next time you are considering how to deal with a challenging situation, approach it with sincerity. Consider the big picture, the long-term, infinite game of life. Rather than getting stuck in a serious mind-set of solving for the short-term, finite goal of winning or losing.

Either way, make sure to ignore the confusion.