Rebooting yourself so that you can reduce head but increase heart in decisions you make

Life is a constant search of finding your own game player fit.  

What is the game that I am the best player in ? 

What are games that can provide me money (safety), meaning (love), identity (belonging) and more ?  

Being the best hockey player in a country that is devoted to cricket may not serve you financially. At the same time winning the genetic lottery, piling investment returns not directly connected to your sweat and blood does not give you any meaning either. 

Terms such as FLOW or IKIGAI say the same thing. 

The generation before me had limited choice so had to be content with less. My generation and yours are awash with plenty of choice and that makes these choices hard. But even back then, it was well understood that there are two plays in every game. 

  Outer Game and an Inner Game. 

Popular chatter is always about the HOWTO of the Game outside. These are the discussions that become viral. However winning the Outer Game consistently requires dealing with your Inner Game. Sports makes you deal with the Inner Game explicitly. Another place where it is apparent is Entrepreneurship. 

i.e. Being a founder.

Kanwal Rekhi once said to me in a small group discussion

“ Entrepreneurship is a ‘Tapasya’

“It is the journey of self-purification, getting to know yourself “ 

Score is therefore always internal.

But yet as founders we boil ourselves seeking scores from the outside.

I have been following Jerry Colonna’s work (through for 14 years and finally had the chance last week to experience his transformation program to examine my Inner game. 

As the Buddhist saying goes 

”When the student is ready, the teacher will appear” 

These questions are designed to guide self inquiry. A radical self inquiry that helps align a person to her Inner core. In other words get to Game Player fit, Flow. 

Following five questions from Reboot shook me hard.


Beliefs formed when young may have served well growing up, may not help any more. These beliefs could be about anything, about money, independence or intimacy (or lack of ) in a relationship. These outdated beliefs are like the old maps that are no longer right. 

To add a Matrix movie spin these may be the Agent Smiths that have run rogue and are no longer serving you. 

Who are these Ghosts in the machine?  Can you name them? 

As Jerry would say 

“What are my beliefs that are no longer serving me ? “ 


Our beliefs shape our behavior. They are at times called mental models but we may have no name for those.  To rephrase Rene Descartes it is not “I think therefore I am”, it is “I mental model therefore I am” 

Do you know which mental model of yours are the ones that are silently driving you ? 

As Carl Jung said 

“Until you make the unconscious conscious, it will direct your life and you will call it fate”

When examining these mental models and looking to replace them you face the paradox of Ship of Theseus.  If you change each and every mental model that you held dear then are you even the same person that you once were ? Does it not change your identity? 

What is your unchanging core ?


We pick up peculiar phrase and words and abuse it without being aware of the abuse we mete out. 

You don’t ask someone how can I tango dance with you.  

Yet you say “How can I help ?” at the end of a meeting.  

If you have to ask then you can’t or don’t know how you can help

You and I learnt to mimic that phrase from others that we work with. Cabal of ‘fake it till you make it’ has encouraged us to use this for fewer even have the courage to challenge the fakeness of that question. 

What phrase are you going to stop using going forward ? 


A founder deals with a landmine of emotions.  Every founder goes through some or all of these emotions.

Anxiety - “I don’t have the skills for doing the task at hand but everyone else around has put faith in me.”

Burden  - “Too much advice and often conflicting, not clear which to pick” 

      “Of having to learn and perform at the field, on my own dime.” 

Confusion - “Should I put my hand in the profitability jar now or 10 years later ?” 

Disappointment - “Of others especially my employees not seeing the world the way I do”. 

Discriminated - “For not having popular skin color or the right Y chromosome.”  

Depression - “Due to envy or anxiety” 

Distrust -  “Of those whose incentive is not as aligned to mine, often times an co-founder, investor or advisor who sees me as a chess piece to be sacrificed in her larger game"

Envy - “Of the ‘Top 25’ or the ‘X under Y’ or some other ‘midas list’ that a fellow founder has been featured in.” 

Flying (albeit Blind) - “Others think I am flying blind, it is they are the ones that situationally un aware” 

Hero Complex - “I must save the world”

Lonely - “At the top of the mountain or the bottom of the pit” 

Panic - “How will make payroll and pay bills this month and the next one”

Yearning - “Be on the front of the TIME magazine cover” 

And several more

To suppress emotion in work is what is considered as a sign of strength. But as Rumi said hundreds of years ago, name them, invite them into the house of your soul for they are travelling guests.


All of this finally stops at a question like this . 

Am I a good man ? 

or a different version of it 

Am I a  good manager 

Am I a good father 

Am I a good brother 

Am I a good husband 

Am I a good leader 

Am I a good founder 

Am I a good investor 

All these questions can torture if asked through too much head. It can give a chance to heal if sieved through the heart.


Heart feels the right why


As the song goes ‘Mo Money, Mo Problems’ 

There are going to be several heartaches due to fake maps that are going to lead scores of founder astray. And even worser riches of gold worth hundreds of million of dollars will leave many Midas still feeling empty  

My takeaway from Reboot is that finding your game player fit flow is not an analytical exercise measured by some numbers through the head but what is it that feels right for me felt through the heart.

Jerry has gone through this journey over 3 decades and lived 3 different careers to help many global founders & investors deal with this. Undoubtedly it makes sense to learn from that experience. 

If you are India based founder or Investor consider going through a Reboot 

For some reason if you can’t make the leap across the sea to Colorado, I would encourage you to talk to a few of my friends in India who can help with these heart to heart conversations. Prasanna K, Shekar Nair (my current co-founders at Upekkha), Avinash R & Sharad Sharma (my prev org co-founder),  Manju Nanjiah and Shoaib Ahmed (old friends who have taken up mission of helping founders with self inquiry

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