Non-Negotiables in Life & Revisiting Utopias

Inspired by the re-digging from Tim Urban’s Wait But Why article on “How to Pick a Career” once again.

In the light of reviewing Q1 of 2020, I stumbled upon the above mentioned article while clearing out my 50+ open tabs on my phone. After spending some ~4 hours reading and pondering, I thought I’d try to cohesively put to works my “want”. 

Tim Urban describes his career as: 

"My current job description is: “Writer of 8,000-to-40,000-word articles about a bunch of different topics, with cursing and stick figures, on a remarkably sporadic schedule.” Think conventional wisdom has any job openings for me with that description?"

For me, it’s a career where: I write about my interests. I speak to people I’m inspired by and want to learn from. I work with leaders to help them design systems to invest in human potential within their organization. I invest in leaders who invest in human potential. I invest as a manner of challenging conventions. Where I’m not bound by location. Where I am complete control of my time. Where I run a small and lean operation. Building a media engine that can fund my investments in the long term. To earn a living working with and investing in entrepreneurs and intelligent fanatics. 

Digging into Assumptions.
As Tim recommends, I dug into my assumptions. This brought me to another bend in the road where I tried to pull away from the rational arguments I had made before to the new insights that developed from continuously embarking on my journey. 

The location, time and directional independence is work I’d done prior to in this essay: Three Freedoms That Come Before Financial Freedom

But I thought about digging further into why it’s so important to invest in people. Why it’s so exciting for me to find leaders who invest in people and as a result… have unconventional organizations. 

There is the rational view of how I came upon the idea of Utopian Organizations. Yes, the company one works for impacts their every day livelihood in so many ways. One’s career becomes a major part of one’s life in # of hours invested in a day and all the overflow effects into one’s psychology and social web (i.e. friends, family). 

The rational view is that leaders who build these organizations are the system architects because the culture of the organization, inevitably, takes on the form of the leader. 

Beyond Rational Reasoning. 
This can have a flywheel effect for society. Thinking about careers that are particularly “fulfilling”… this is not the case for many people. It was not the case for my parents. When I was starting out in my career, I was informed that no one liked their job and that should be accepted. I was told the path I selected would be the one I would die doing. 

When I started out in my accounting career, my parents told me I shouldn’t be honest because that’s going to hurt me. I was told I should do everything I was told to do, don’t question and always be grateful I have a job. 

Only as my parents got older and my father got deeper into his years as an entrepreneur did they start telling me to find something that would make me happy. Maybe the fact that I had switched careers more time in 3-4 years than my parents did combined.. in their lifetime.. made them think their past advice wasn’t going to work with me. 

But this is the cycle that I think needs to be broken. I still have family members and friends who continuously believe fulfillment at work is a joke. The number of times I’ve been scoffed at for wanting to do what I do… I think it’s a result of the organizations they’d worked for that limited their perspective on what a career should be about. 

The way I see it… if an organization actually build an organization where its people were looked after… where its people were taken care of… where its people were incentivized for long-term development… then that can build a foundation that changes their future beliefs of what life could be about. This will then alter how they raise children and what values they impose on future generations. 

I’m still learning to accept that things of the past were required to lead to the person I am today. However, I very much do hope for others in the future to not have to go through so much pain to realize work is not something dreadful but something to further enhance one’s time on Earth. 

It’s such reasons that form the basis of why I’m actually obsessed with trying to work with and invest in leaders… specifically entrepreneurs… to build organizations that invest in human potential. 

Leading to the Non-Negotiable.
In the essay, Tim refers to what the non-negotiable element of the career is.. 

Though he separated out lifestyle and personal into different segments of one’s life.. for me, I do not see it being separated as the career I want to build is one where I have the freedom to do the work I’m passionate in. To do the work that fulfills me, excites me and allows me to utilize my strengths. 

What is non-negotiable is the independence and freedom of time and location I need to have in what I do. That’s something I’ve learned in the last 2 years of building my own platform. 

Given such non-negotiable… it changes what meets with the options present in ‘reality’.

This has been a great way to think about updating the “Now” page as I go about selecting the monthly projects for the present and future. 

My Interpretation to Great vs. Good
The key in separating the ‘Great’ vs. ‘Good’ projects has been to think about how much ‘pace’ and ‘persistence’ I believe I can deploy with each project. This makes me look at “low hanging fruits” in a different context as what may appear obvious and easy might actually be a fruitless endeavour if I lack the persistence to follow it and the pace for it as I procrastinate because of how much I hate doing the activity. Simply put, it doesn’t align with my non-negotiable focus. 

Conversely, the project/option that everyone says is impossible and hard might be the low hanging fruit for me if I believe I can deploy a greater sense of pace and persistence. It’s such a way of refining what “reality” is for me that’s brought about a shift in selecting which projects to pursue each quarter and monthly sprint. 


Disclaimer - I’m writing this for myself. For my past, present and future self. Much of what I write is my opinion. If it somehow ignites agreement in you then great, I’d love to hear about it. If it sparks disagreement in you, don’t reach out because I don’t care for it. There always are obvious exceptions and the flawed person in me hasn’t considered them all.