January-August – 2017 Challenges – A Series of Unprecedented Failures

Let’s Start with Game Theory

During a 2016 Live2Lead presentation, Simon Sinek (consultant, motivational speaker and author)1 shares his experiences speaking at leadership summits for Microsoft and Apple. At Microsoft he observed that about 70% of the executives spent roughly 70% of their presentations addressing ways to beat Apple. At Apple, 100% of the executives spent 100% of their time discussing ways to improve education in schools for teachers and students2.

Furthermore, at Microsoft Mr.  Sinek was gifted a new product, the Zune. Being the pot-stirrer that he is and hoping for a reaction, Mr. Sinek spoke with a very senior Apple executive and told him that the Zune was far and away better than the iPod Touch, competing products. The executive’s response: “I have no doubt.”2

Microsoft was focused on beating their competition in the moment, or winning. The executives at Apple were looking into the future… into infinity… and looking for opportunities to make better products with a positive societal impact. Apple understood that they may not be the best in the world every single day, and perhaps more importantly, that that was OK. They would charge forward and frustrate their competition along the way.

Now… game theory consists of two different types of games: finite games and infinite games. They have the following characteristics2:

Finite Games

Infinite Games

·         Has known players

·         Has fixed rules

·         Has agreed upon objective (to win)

·         Example: chess / baseball

·         Has known and unknown players

·         The rules are changeable

·         The objective to keep the game going

·         Example: business / evolution

Finite games are great. Chess provides me and others with a creative, competitive and enjoyable outlet where we know where we stand after each game… win, lose or draw. Baseball provides a community where we can root alongside fans of our favorite teams… win or lose.

Life, however, is by no means a finite game. There are no fixed rules. Everybody seems to have their own objectives, if they have any at all. No one could predict the people (players) who might influence us over a lifetime. On top of that, life can be tough. Unexpected surprises, emergencies or disasters can drain us of resources, and in more extreme cases, even the will to carry on.

What Kind of Game Am I Playing?

With about a 67% success rate over the first two years I was doing OK, but not spectacularly. Then came 2017 and the beginnings of an unprecedented series of failures in these challenges which I will humbly illustrate shortly.

I used to think of my monthly challenges as rotating, finite games. Each month Jen and I would choose challenges for each other with established rules and objectives. For a long time I wanted to win each challenge. You could call it my competitive nature I suppose. Jen might call it stubbornness (lol). Either way, I was looking at these challenges with a somewhat limited scope by focusing on the short term winning or losing.

Now I am coming to see these challenges in a different way. Their spirit is not about winning or losing each and every month or beating each other (although that would be nice); rather, it is a shared experience between two friends to grow and become “better” people over the long term. We would probably have little personal challenges for ourselves if these challenges had not been formalized over three years ago. It is an infinite game and, so long as we have the resources and the will to keep playing, we will more than likely succeed in becoming better versions of ourselves over time.

And now, without further ado, my failures and minor successes:

January – March – 2017: Three Month Exercise Challenge

Coming off of the December holiday season and much work, an extended fitness re-set seemed like a good idea… and it was. While I have lost the data, the first 1.5 months were quite successful. I made time away from work to go to the gym, swim, and eat well. I was losing weight and feeling good. Then, it all fell apart (haha).

I was finishing my work agreement at the end of March, I wanted to end as strongly as possible. Unfortunately, this coincided with a particularly stressful time for the organization and I compensated by doubling-down on my efforts at the expense of my own personal health. By the end of March I was a mess. I weighed over 108kg (roughly 238lbs.) compared to when I’m at my best I hover between 89kg-93kg (195lbs-205lbs). Exercise had all but disappeared and diet had converted to whatever was most convenient. I wasn´t sleeping enough and it showed. I was stressed and it showed. While I might have done my best professionally, there was no balance, and I can firmly declare this three month challenge a FAIL.

April – 2017: Professional Advancement Challenge

The benefit of all that work was that I had positioned myself to take a mini-retirement… yay! I was free to do whatever I wanted and indulge in my favorite activities… exercising, hiking, exploring, reading, etc… I did that quite well. Perhaps seeing the potential dangers of this lifestyle, I was challenged to update my resume, LinkedIn profile, to network and begin looking for future opportunities. Little did Jen know, I had already updated my resume and LinkedIn page in March, so no effort was dedicated to that in April. In fact, no effort was dedicated to any of this challenge (sorry, Jen!). I was so pleased to be pursing my other neglected interests that nothing else mattered. I can’t say that I regret my choice. I had been so looking forward to this freedom and I did enjoy every minute of it. In retrospect, I appreciate the forward-thinking on Jen’s part, and it’s always good to keep your eyes and ears open to opportunities at all times. Nevertheless… chalk this one up to a FAIL.

May – 2017: ???

Wow… I tried so little with this challenge that I don’t even remember what it was!!! Neither does Jen. I was still caught up in hiking, visits from friends, and my personal pursuits. Again I am happy with how May unfolded in other areas, yet I learned some lessons from this humiliating negation to the monthly challenges:

  • Try!
  • Write things down so I do not forget.
  • Update my blog regularly to better reflect on my life experiences.

In no uncertain terms, this month was an EPIC FAIL.

June – 2017: Daily Meditation

I will admit that I had previously viewed myself as a person who “just couldn´t meditate”. I have on-and-off practiced yoga over the years and even participated in some meditation classes. Still, I “couldn’t” do it. What bullshit! I’ve come to see this attitude for what it was: my falling into a fixed mindset as opposed to a growth mindset. To learn more about this you can look into the work of the Stanford psychologist of Carol Dweck. I will quickly and superficially summarize it here3:

  • Fixed mindset: believing that we cannot change who we are. It’s the “I’m good at math or I am not” attitude. We are who we are and no amount of work or effort can change that.
  • Growth mindset: believing that we can change through hard work and learning from failures. It’s the “I can learn to dance with practice” attitude.3

For whatever reason (perhaps 5 months of challenge failures) I really took to this challenge. I practiced a number of different meditation techniques throughout the months. I reached out to more experienced friends and watched some helpful YouTube videos. I meditated at home, in nature, and tried to mix it up as much as possible. I’m happy to say that I did enjoy the experience and I still meditate to this day! While I will admit that I missed a day or two during the month, I would say that this challenge was by-and-large a SUCCESS.

July – 2017: Daily Haiku

I LOVE haikus… this challenge should have been a walk in the park. All I had to do was write one haiku based on my day and send it to Jen. That was it. I started the month off strong; however, I did not keep a record of my haikus and definitely did not send them to Jen. By roughly midmonth I had pretty much entirely abandoned the challenge. Another pity, as I remember feeling quite proud of some of the haikus I wrote. Sadly, they are lost forever. The lesson here is to, again, write down all of these wonderful creative moments… and to listen to Jen’s instructions ; ) So… another FAIL.

August – 2017: Update Blog

It should be obvious to everyone, but I am a little over a full month behind on beginning this challenge, haha, and about 5-6 months removed from updating my blog on a regular basis. Better late than never, I suppose. Extensive travel and some challenges in my personal life left me blatantly unmotivated to tackle this challenge in August. A shame, really, as these blog posts are for me more than anybody else who happens to be reading it right now (it’s for you, too!), and the sooner I update the blog the better my reflections are for Future Jack to read. But what’s done is done. No excuses. I’m just grateful to have the opportunity to work on it now. As a formality… this challenge was a FAIL.

Reflection and Moving Forward

Clearly, not the best 7 month stretch I have had when it comes to my monthly challenges… and that’s OK! : ) I can forgive myself for letting things slip for a while. And while this area of my life took a hit, as well as other areas, I also had many great successes, which I will write about in future blog posts coming soon (pinkie promise). The principles of growth mindset and a better understanding of the infinite game will no doubt be on my mind as I set out to crush the rest of 2017 and beyond. I look forward to the many wondrous adventures to come, and hopefully sharing some of them with all of y’all!




  1. “Simon Sinek.” Wikipedia, Wikimedia Foundation, 29 Aug. 2017, en.wikipedia.org/wiki/Simon_Sinek. Accessed 6 Sept. 2017.
  2. “Most Leaders Don’t Even Know the Game They Are in – Simon Sinek at Live2Lead 2016.” YouTube, YouTube, 2 Nov. 2016, www.youtube.com/watch?v=RyTQ5-SQYTo&t=710s.
  3. Popova, Maria. “Fixed vs. Growth: The Two Basic Mindsets That Shape Our Lives.” Brain Pickings, 29 Jan. 2014, www.brainpickings.org/2014/01/29/carol-dweck-mindset/. Accessed 5 Sept. 2017.

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