“What matters to you and why?” – my journey so far with this loaded question

Isfandiyar Shaheen
Sep 24, 2016 · 9 min read
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Challenges faced [15 mins]

In my life so far I have started multiple efforts, given up on too many and completed very few. I have often thought about what is it that makes me “show up” each day for the fulfilment of certain objectives but not others? Why do some objectives matter more than others? What is the best way to figure out what matters to me and why? I’ve written quite a bit about ideas of “Chul” and the benefits of understanding the reception conviction of your colleagues.

In 2014 for the first time I sat down to write what mattered to me and why? I found that introspection was very challenging, eventually after much struggle I concluded back then that “aligning incentives of driven and capable people with positive character traits (specifically the traits include: zest, grit, curiosity, optimism, self control, gratitude and social intelligence) matters to me because I want to live an incredible life but I don’t want my work to become a source of stress for my family, my colleagues, my customers or my partners.”

Living an incredible life meant dedicating all my energies to solving a really big problem that I care about and creating an a**-hole proof environment in the process.

2015 turned out to be an incredible year of self discovery. I came across the work of Ken Robinson who describes ways through which anyone can “find their element”. For Ken, our element is where talent meets passion. But is passion static? are talents static? I don’t think so. If talent and passion keeps evolving then so does our element. Considering our element keeps evolving, the same must be true for other human beings who collaborate with us to help achieve certain objectives.

For me, the answer of what mattered to me and why evolved as well. What I wrote in 2014 is still true, but it still is a means to an end. I have spent the past 2.5 years continuing to write down iterations of the same question and as of today I think levelling the playing field for all consciousness matters to me, but specifically what that’s now boiled down to is the following:

  • I want to dedicate my time and energy to join efforts through which I can significantly accelerate the following outcomes: a) make internet access free, b) make electricity access abundant / free and c) make financial capital abundant.
  • I believe the above 3 outcomes will happen irrespective of my efforts, I simply want to join conversations where the above 3 goals are a core focus. My hypothesis is that I will find beautiful minds across the globe if I join such conversations. After all, we are the “average of 5 people we spend most of our time with” and so the likelihood of me pushing up my average by talking to people who intend solving audacious goals is quite high

My journey has taught me that passions are not static. They evolve and that’s a problem to some extent for leaders and founders in particular because passions only get tested when the going gets tough. Often what separates success stories from failures is grit and persistence.

I believe that as entrepreneurs when we declare a commitment to a vision, we are making a statement about our passions and our convictions. It is the quality of our introspection that ensures authenticity of our stated purpose, and in my view determines the likelihood of our success.

As such, I turned to technology and research to improve the quality of my introspection

Pathways explored [25 mins]

What gets measured gets done, what gets rewarded gets done repeatedly

When I genuinely started introspecting, I found the process of introspection to be quite flawed and prevailing academic literature seemed to suggest the same. So about 2 years I decided to measure my daily activity by installing a highly invasive application on my computer and smartphone, called Desktime

Measuring exactly how I was spending my time in 2014 helped me get a better sense of the delta between my actions and stated beliefs. So in 2015, I started pushing for change and initiated a process through which I could extract myself from my commitments in order to focus on what was really important. I found that measurement solidified my conviction and helped me follow through on actions which some of my friends thought were a bit “outrageous”. They felt this simply because I had a rather “stable / well paying job”.

As preparation for this talk, I decided to do a literature review and found an excellent paper that was published on HBR which captures my thought process in a much better way.

Do Your Commitments Match Your Convictions?

This paper needs to be read at a leisurely pace, it had one very potent exercise though:

“The first step in managing your commitments is to take a quick inventory of what matters to you. (For a helpful work sheet, see the exhibit “Taking Stock.”) You probably have at least a vague sense of what you value most, but it’s important to clarify those themes from time to time. This exercise lets you check whether you are putting your money (and your time and energy) where your mouth is. A systematic inventory of where your money, time, and energy are going often reveals surprising gaps.”

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In addition to Desktime, I think your credit card statement or a tool like Expenify can help fill the money column most accurately. Energy is subjective, but a good rule of thumb: energy is maximum 90 minutes after waking up and then declines through out the day. So give more weightage to activities done 90 minutes after waking up. Clearly answering e mails shouldn’t be the first order of business!

Some gems from this paper:

Group Exercise: Write-down 25 goals, circle the 5 most important, and no matter what, don’t do the rest!

List of additional pathways explored:

One very cool exercise is auto-writing: write for 2–3 minutes anything that comes to your mind 5 minutes after waking up!

  • Learned Optimism, by Martin Seligman

Consider taking the Learned Optimism test

The general view being that being in a state of flow allows for much better quality introspection. Mindfulness exercises through apps like Calm and Headpsace are highly recommended.

Lessons Learned [20 mins]

To get a better sense of why introspection is often flawed, becoming more aware about how our mind is wired and how our brain makes decisions, it’s critical to understand the unconscious, something Leonard Mlodinow explains very well in this talk

  • Talk starts with an exercise to explain anchoring on the likely cost of a stay in a hotel(here’s a super cognitive bias cheat sheet)
  • Incredible examples are used to show case how the brain confuses itself in terms of identifying actual colour AND the brain’s inability to tell what the actual expression is when the face is upside down
  • Bottomline: the path to identifying what matters to you and why starts with awareness, it helps to understand our brain’s natural limitations and biases, and finally, without being completely honest to oneself, all introspective exercises are futility

Perhaps the biggest challenge remains the ability to find alignment between what we actually believe deep deep inside and the statements we make to the external world about our source of motivation

We can all figure out what really matters to us, all we really need to get there is a growth mindset, a term and a very powerful idea coined by Carol Dweck.

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A lot of my learning related to my inner world has happened because of my wife, she has pretty much introduced me to most sources mentioned here. My wife’s latest discovery in her pursuit of her own self discovery is Angela Duckworth who has written an amazing book called Grit which pretty much brings together a whole lot of lessons I have sort of observed, but never had the ability to accurately articulate

Grit is doing what you love, but not just falling in lovestaying in love

In Chapter 4 of Angela Duckworth’s book — Grit, she dives into something she calls the Grit Scale, and the big message delivered is that grit does not mean dogged intensity. Grit means finding consistency with investing 10,000 hours of practise while continuing to push towards one common higher order goal or life philosophy.

…[D]ogged perseverance toward a top-level goal requires, paradoxically perhaps, some flexibility at lower levels in the goal hierarchy. It’s as if the highest-level goal gets written in ink, once you’ve done enough living and reflecting to know what that goal is, and the lower-level goals get written in pencil, so you can revise them and sometimes erase them altogether, and then figure out new ones to take their place.”

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Excerpts from chapter

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My own worked example

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