29 APRIL 2022

A Reason To

Working for oneself, what it takes to be the boss and how to be productive while binging Netflix

One of the trickier things that came up during this transitory journey of being on sabbatical was not in rumbling with the question of ‘why are you doing this?’, but instead the ‘how are you not working?’ question.

In some ways, it was a completely valid question to ask. I have been at this for awhile now, having left my previous role in November 2021. But it is not like I had closed that previous chapter on a whim and dropped everything to aimlessly ‘chase my passion’; it was actually a painful and fully-conscious decision to enter a transitory phase where I would have enough time and space to consider what I would really want to dig into next.

As a result of being deliberate in making this choice, I had been preparing for some time in advance of November 2021 to ensure that this current phase would be financially feasible.

It was a choice to exchange short term income in favour of taking all the time that was necessary to make the right longer term choices for the next chapter. This, obviously, has been an extremely privileged position to be in.

In gratitude of this, I have been sprinting since crossing the start line back in November and doing everything within my control to figure things out.

As clear as this sense of intensity and urgency has been to me internally, it turns out to be more opaque to others around me.

Maybe it was not so much the question of, ‘how are you not working?’ that was most provoking. That would have been an easy, tactical financial question to answer.

Perhaps it was the more implicit question of, ‘how are you not working for someone else?

It was a funny question to grapple with. Most of my days have been lively and full of activity. Every waking hour spent on trying to figure things out — with chunks of time invested into networking, research into companies, publishing blogs weekly, self-reflection, coding projects, learning through podcasts and by reading books, staying active and eating well, being present with the family. Even though I was not strictly working for someone else, I was definitely still working — if anything, at an even greater intensity than it would have been otherwise.

Why is that? There was nobody I could blame or delegate responsibility to for coercing me into doing the things I had to do. Whether I would succeed or fail was purely up to me. The situation, then, was such that I had no choice but to lean in and try to make it work as best as I could—fuelled purely on intrinsic motivation and not much else.

This makes me think about how common it is, within the trenches of everyday life, to dream of being free of the constraints that external factors place on our shoulders. I deeply understand what this longing can feel like, and I got to see the complete opposite end of the spectrum over these recent months. What is counterintuitive, and perhaps surprising, is how quickly things can fall apart when there is a lack of imposed constraints.

There appears to be a direct relationship between freedom and personal responsibility, as explored previously in ‘Effortless’. Greater degrees of freedom comes at the price of taking up the burden of personal responsibility for deciding what the constraints shall be.

The escape from tyranny is often followed not by Paradise, but by a sojourn in the desert, aimless, confused and deprived.

- Jordan Peterson

Another example is in this: if there is no longer someone above you to tell you what to do with your time, that responsibility cascades down to your own individual self.

The boss of an employee is her employer.

The boss of a small business owner is his customer.

The boss of an entrepreneur is herself.

The impossible dream is to have all the privileges of being the boss, but without any of the responsibility that such a position demands.

A reason to

A few weeks ago, I received the news that a close friend would be flying into Perth for a visit of the city and would be around for about a week.

A very unusual occurrence, and one that I was not going to take for granted. This gave me a reason to take a brief break from the day-to-day activities I had been running — to show my friend around the town I had grew up in, share some food and see the sights.

There was nothing crazy extravagant during the whole week but perhaps, especially in the times we live in today, to be able to share time with the people we care about in-person could very well be an extravagance in and of itself.

It was really fun to take on the open and curious mindset of being a tourist in one’s own city. A simple shift that can be just what is needed to refresh one’s perspective on things.

This might sound strange to you, but for a long time I have found it difficult to ‘switch off’ from the internal pressure of having to do things. Most of the time, I am insatiably curious and do my best work when I am learning about the world.

There is often a strong sense of guilt that comes with the idea of ‘taking time off’ and doing what could be classically labelled like ‘unproductive’ — such as wondering around a city with no agenda.

An insight that a friend  recently shared has helped me reframe this perspective. The core idea came from Nir Eyal’s interview on the Australian Investors Podcast, where he elaborated on what it means to be ‘productive’.

Productive means could look like any of the following:

So you’re telling me that spending hours on Netflix can be productive??

Yes, it can be, but only if the activity helps you achieve the end that you have in mind. If your intention behind watching all those episodes is to wind down and relax, go all in with zero hesitation.

As Eyal explained, productivity takes place when we consciously choose to do things and are immersed enough within those means to reach particular ends in mind.

You can be productive by watching videos on the internet, if your true desire is to be entertained.

The problem that arises is when we intend to wind down but do not immerse ourselves enough in the thing that we put ourselves up to. What this results in is hours poured down the drain, a persistent unrelaxed mental state and the painful after-the-fact guilt that comes from having wasted all that time. This context is what is at the core of ‘unproductivity’.

An explicit example of this is within ‘doomscrolling’. Mindless, unconscious, and physical movements by our fingers, deployed to the task of scrolling through bottomless (and negative) information feeds on the internet.

Is having information at our fingertips a ‘bad’ thing? No.

Is the internet ‘bad’? No.

The act becomes unproductive when the time we invest does not return to us the end that we have in mind — whatever end this might look like.

And if there was no specific end in mind in the first place, then whatever we put ourselves up to is guaranteed to be unproductive and serve as a provocative agent of guilt and regret.

Knowing this, it then turns out that my original conception of sensing an internal pressure of ‘having to do things’ was not so much about constantly being engaged in doing and immersed within activity.

Instead, it was more about a perpetual desire to spend time well, and this could very well look like laying down on grass and looking up at the sky on a warm sunny day, or running iterations on a computer through code.

I have, let’s say, sixty years to live. Most of that time will be spent working. I’ve chosen the work I want to do. If I find no joy in it, then I’m only condemning myself to sixty years of torture. And I can find the joy only if I do my work in the best way possible to me. But the best is a matter of standards — and I set my own standards. I inherit nothing. I stand at the end of no tradition. I may, perhaps, stand at the beginning of one.

— Howard Roark