How do I choose what to work on?

You ought to be more intentional when deciding what to work on.

Think about how often when you ask a friend “how’s life?” the topic of work is completely left out. Sure, it could be because work isn’t too closely tied to their identity or (which I think is more likely), they aren’t too big a fan of what they are doing on a daily basis and prefer to not interrupt their real life with their, well, mandatory responsibilities. I’ve found this to be especially true for those who rather than treating work as a buffet, sat down and behaved as though their career was being served to them as a set menu. 

In 2014, Democratic Presidential candidate, Andrew Yang, published the book “Smart People Should Build Things.” His company Venture For America had found that well over 50% of graduates from universities like Harvard and Penn funnelled themselves into a few default paths: Financial Services, Law, Management Consulting, Teaching, Government and Medical School. The surveyed students mentioned prestige, money and experience as reasons for their choice of career path. Yang had begun his career as a corporate lawyer in New York City, where he described the job as “a pie-eating contest, and if you won, your prize was more pie”. After five months he left the law firm, which he has called “the five worst months of my life”. He went on to establish Venture for America to show students an alternative path because building a career isn’t as predictable as it once was. The talent density of companies is skewing further away from junior-level, so whilst the odds of you wanting to become a consultant, finance, lawyer are very high — the chances of you doing so aren’t so. Venture for America is now tackling the problem statement: What if the same proportion of talent that is currently flowing to professional services were instead going to start-ups around the US? How long would this take to impact job growth and innovation nationwide?

You might be thinking, this piece isn’t for me — I have no interest in working at a startup. Good, because I will not be convincing you to do so. Other than the fact startups require long hours, stress over payroll and much more— I am here with another message and a process for you to execute. The message is this: If you work a traditional 9–5, you will spend around a third of your life in the office. So it pays to be doing something that moves you. What I am going to show you is how to make your work and passion the same.

The Big Choice

“Dream your work and then work your dream” — Emory Jones

In July of 2023, Paul Graham published an article on his famous blog titled “How to Do Great Work”. The article assessed different techniques for doing great work across a lot of different fields. He then summarised these findings into a guide, specifically for those with ambition to follow.

Whilst I personally recommend taking some time to go through the essay itself, a particular part of the essay stuck out to me which would be the first key step in doing great work — answering the question: What do I work on?

Before I share the framework, here’s why we should care about Paul’s advice. Paul is a Philosophy graduate turned Computer Programmer and Investor. So for a start, he has had a broad career. In 1995, he started Viaweb, the first software as a service company which was acquired by Yahoo in 1998 for somewhere the region of $49 million. So, secondly, he has experienced creating and selling a product. Finally (maybe most importantly), he is the founder of the globally renowned startup incubator Y Combinator. Y Combinator has funded over 3000 startups, including Airbnb, Dropbox, Stripe, and Reddit. This means that Paul has an eye for spotting whether you are sufficiently suited to the work you are doing to be commercially successful.

“The first step is to decide what to work on. The work you choose needs to have three qualities: it has to be something you have a natural aptitude for, that you have a deep interest in, and that offers scope to do great work.” Assuming you are already ambitious, let’s forget the third bit and focus on the first two: Finding something you have a natural aptitude for and something you have a deep interest in. 

A simple way of looking at something you have a natural aptitude for, is asking the question “what I am naturally good at?” Well, a few things you can do to help you here is ask your friends. Friends are around a fair bit so will have some insight for you. You naturally have blindspots, so what is oblivious to you about your nature may be obvious to others. Second, take personality tests and quizzes — try the myers-briggs test and see what job titles your personality type is associated with. Lastly, write down what you do regularly. Here, look for the things you can do in almost auto-pilot mode that others might struggle with. This is very much a discovery phase, you are a detective searching for patterns. Let’s say like me you record a podcast once a week that 100 people listen to — the chances are you are good at verbal communication. Something like this is what you are looking for. 

Next, we look at interests. The question here is: What I am interested in? It sounds bizarre to say out loud, but you would be surprised how often one’s tastes match the outside world’s far too closely. This question, I find easier to figure out than knowing what you are good at. To solve this one you can ask yourself, what am I excessively curious about? To the point where others might tell me to shut up. If I use this on myself, I’m excessively curious about technology businesses, self-development and the trajectory of societies. So let’s say Business, Psychology and Sociology. 

Combining the first and second question into an initial answer:  I record about Business, Psychology and Sociology.

Paul says a good sign that you’ve reached an intersection of what you are naturally good at and what you have a deep interest in is where you enjoy the parts of the work that others find tedious or frightening. 

The Excitingness Rule

Most men lead lives of quiet desperation and go to the grave with their song still in them — Henry David Thoreau

There is one rule you must stick to throughout this discovery phase of trying and testing out different types of work: The Excitingness Rule. Paul tells us not to worry if what you are interested in is different to most people, instead embrace what is odd. The stranger your tastes in interestingness, the better. A field should become increasingly interesting as you learn more about it. If it doesn’t, it’s probably not for you. Maintaining a strong interest and excitement for your work will also improve your productivity and give you a higher likelihood that you will go looking where few have looked before.

Discovering what to work on requires you to employ a mindset which may be counterintuitive to other areas of life. During this search, you should not plan excessively. This is a journey that you and you alone have to undertake. Paul speaks on the danger of over-planning what to work on saying: “The trouble with planning is that it only works for achievements that you can describe in advance. You can win a gold medal or get rich by deciding to as a child and then tenaciously pursuing that goal, but you can’t discover natural selection that way.” Finding your work is an opportunity to sample. You have to picture yourself as a bird, choosing which altitude you want to fly at. Maybe you’re an eagle that wants to soar at 15,000 feet or perhaps you’re more of a swan and prefer life at half that height. All too often, I see people treat fields the same way as they might relationships. Remember fields aren’t people, you don’t owe them loyalty — at each stage optimise for whatever seems most interesting and gives the best options for the future. Don’t be afraid to switch. Rather than planning, the aim is to try and preserve certain invariants like excitingness.

It might seem that The Excitingness Rule is quite passive, but by adhering to this you put yourself at risk of rejection and failure. Paul mentions when you follow your personal interests you are pushing against the forces of “pretentiousness, fashion, fear, money, politics, other people’s wishes and eminent frauds. But, if you stick to what you find interesting you will be proof against all those forces.”

Owning your work is a crucial ingredient in this recipe. Rather than the idea of work being something that your manager tells you to do, you will need to direct traffic. What this means is developing a habit of working on your own projects no matter how small. Even in the case of a project not being completely owned by you, which is common in big teams or organisations — try and make sure that you are driving a part of it. Owning your work will unveil your likes, dislikes and competencies quicker than being a passenger.  

Happy Hunting

The people who get on in this world are the people who get up and look for the circumstances they want and if they can’t find them, make them — George Bernard Shaw 

There is an indescribable feeling you experience when you find thing you could happily do for a very long time. For me, it’s probably building companies, writing and recording this podcast. 

Paul Graham mentions the importance of luck in this process: “When you read biographies of people who’ve done great work, it’s remarkable how much luck is involved. They discover what to work on as a result of a chance meeting, or by reading a book they happen to pick up. So you need to make yourself a big target for luck, and the way to do that is to be curious. Try lots of things, meet lots of people, read lots of books, ask lots of questions.” 

The worst case scenario is you will choose late based on very the incomplete information you have to begin with. But choosing late is far from a disaster, because you will at least you be choosing slightly more accurately. Personally, I don’t believe in adage of working hard or smart, I believe in a combination of the two which feels like play. (But that’s a topic for another day.)

For now, this is your four step process on how to choose what to work on:

Step 1: Understand what you have a natural aptitude for. What are you good at?

Step 2: Understand what you have a deep interest in. Explore what makes you go down rabbit holes.

Step 3: Combine the two. 

Step 4: Start a project or drive a significant part of a bigger project

(Maintain: Excitingness, interest and ownership)

Happy Hunting!