Riding Different Waves of Mastery & Slow Productivity

How a new vision of work helped me reimagine my life

May 23rd, 2024: Hello! Currently writing in from Greece while on vacation. Looking back at my time in New York, the last few months have been a lot less hectic than the first one. I feel like I’m beginning to find my groove in the city, going to the same coffee shops and co-working spaces and gaining some regularity in seeing the same folks at these places. As I mentioned in a previous post, Total Football, my hope after the sabbatical was to transition from exploring new places and cultures to exploring new interests such as Progress Studies Research and Screenwriting. I finally feel like I’ve been able to do this, starting my screenwriting class and writing my first few movie scenes as well as reproducing the methodology of a simple research paper. While it has been mostly calm in NYC, I do feel an undercurrent of unrest following the police crackdown on student protests at Columbia.

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Growing up, I was ambitious. The more I worked, the better I got at it, and the more I enjoyed doing it. It was the primary source of meaning in my life, how I was going to make my dent in the universe. Since it felt so noble, any personal sacrifice in relationships or hobbies felt justified. More was always better, and yet still never enough. This generational shift in meaning towards work is something I cover more in my last post.

After a few years of work and a quarter-life crisis that resulted in a sabbatical, I learned to need less and do what I enjoyed more, like writing, and it felt meaningful in a way different than work did before. Before it was all about the impact being made on the extrinsic world, and with my new passions most of the rewards were intrinsic (while I was still hopeful that what would be most impactful to others would align with what felt most meaningful to me).

Therefore, I had come to see the paths forward for my relationship with work as two-fold. In the first path, I dedicate my life to work in order to give myself the best chance at building something that might make a meaningful difference in the world. In the second path, I minimize my needs and strive to find fulfillment outside of work. The only third option that I had come across was to pursue the F.I.R.E, or Financially Independent Retire Early path which, while in principle was the opposite of the first path and viewed work as a necessary evil as opposed to as salvation, had very similar working day at first. I wasn’t sure which path, if any, was the right one for me.

Finding a New Path

For the last few months, I’ve spent a lot of time trying to get better at new things, like research and screenwriting. While I’ve been pleasantly surprised at how much I’ve enjoyed each of these new fields that I’ve never tried before, what has been even more delightful is the feeling of being able to hop between the worlds of these fields as a tourist and see how different each world is. This experience has led me to the first big idea I want to cover in this post:

1. Why I’ve really come to resonate with this advice from Sam Altman: Almost everyone I’ve met would be well-served thinking more about what to focus on.

This has also made me more curious about the process of how to get good at things, or mastery as some call it, and I’ve been hoping to learn everything I can from the stories of how others achieved mastery. From these stories, I have come across incredible new ideas about work, particularly ideas from Cal Newport in his new book Slow Productivity, that have revealed a path for work I had never considered before:

In this new path, I can give my all to something I really enjoy without having to sacrifice the other pillars of life that have become non-negotiable for me. This is the second big idea I want to discuss in this post:

2. Instead of being exploitative and draining, work can be fulfilling and life affirming if approached from the lens of Slow Productivity.

The first idea has helped me feel a lot more comfortable taking a leap in faith in new fields and the second has helped rekindle the joy of putting it all on the table for these new pursuits. So, without further delay, let’s dive deeper into each idea.

Almost everyone I’ve met would be well-served thinking more about what to focus on

Metro Man from Megamind finding his true calling in music, not being a superhero

Mastery as a Lifestyle

The single biggest thing I’ve learned exploring new fields of interest is how consequential choosing what field to pursue can be for your life. This is one of the reasons why I believe that so many people can be better served by spending more time exploring multiple fields before choosing one. For me, as I grew to better understand what kind of work I wanted to do, I increasingly felt like what I wanted from work was incompatible with being dedicated to work or fully pursuing mastery in a field. For example, I’ve come to learn that when it comes to work:

• I like obsessing over quality. 

• I prefer working in small teams as opposed to big ones. 

• I don’t enjoy managing a lot of people. I’d rather be engaged in doing the deep work myself. 

• I want to give my all into something and get as good as I can at it.

• I don’t want to work on one project forever. I really enjoy starting over and trying new things.

• I want the freedom to take long breaks and sudden left turns.

• I want to do something that I truly feel is important and makes a difference, but I’d rather make a big difference in a few people’s lives than a little difference in a lot of people’s lives.

• I want to be able to see and understand the people impacted by what I do.

What I’ve realized from exploring different fields is that the constraints of your lifestyle in one field can be very different than the constraints in a different field. For example, I prefer working in a small team, but I used to equate success with working with a growing number of people. When I began learning more about research, however, I realized that even breakthrough research can result from the efforts of small teams. 

Another example of this diversity of constraints across fields is along the time horizon of working on a project. Within research, it took Marie Curie a decade to do the groundbreaking work on radioactivity that won her a Nobel Peace Prize. Mastery in being a freelancer, on the other hand, can involve making the most of ebbs and flows of projects as current ones wind down and new ones come up. In film, it took Quentin Tarantino just two years to create Pulp Fiction and he was able to work on almost a dozen blockbuster films with different genres, casts, and storylines throughout his career. Therefore, these fields may better match my preferences of wanting to be free to take long breaks and continuously work on new things than research would.

Mastery is not just what you do, but it becomes who you are

This insight is perhaps the most obvious and yet the most profound. What you do reinforces who you are and how you see things. We may choose certain professions because we think it matches who we are: if we enjoy spending time alone and breaking down problems we may become engineers, and if we like working with others and acting, we may become actors. But what we may not realize is that this then also reinforces that side of ourselves.

The more I employed an empirical problem-solving mindset as a Product Manager, the more I felt that I was just naturally a more logical and rationally minded person. But while screenwriting, I am more often trying to solve story problems through looking inward and investigating what sparks different emotions within me. Since I began screenwriting I have felt more empathetic and, in all honesty, less numb to emotion. It has made me question if I am naturally just a logical person or whether it was just what was reinforced by my work.

In the words of Aristotle, you become what you practice. Just as a healthy diet consists of a balance of food groups, and a healthy exercise routine a balance of working out different muscles, I have come to believe that you need to practice a balance of everything that adds up to being a complete human being. I do not know if I have any natural affinity for screenwriting or any kind of art, but I want to practice looking inward and self-expression, not to become an artist, but to become a full person. This holistic perspective is also embodied by how, in Greece, The Lyceum, Aristotle’s school of philosophy, included a gymnasium, and how in the Olympics, athletes had a personal philosopher along with a personal trainer, emphasizing the importance of needing a healthy mind and body.

So, when considering what field to work in, or even just how to spend your day, it may be worth it to ask, is what you are practicing making you more numb or more joyful, more cynical or more hopeful? What is being left out of your daily practice that could be important? If success in what you are currently working on scares you more than failure, then it may be time to change your work. This is why taking the time to explore all the practices that make you whole, understanding the subtle constraints of the work you are in, and being able to hop between worlds of different ways of thinking can be an ultimate superpower that is worth getting off the road you are on now to see what else is out there.

A New Vision of Work: Slow Productivity

Two Visions of Mastery: Fletcher, from Whiplash, and Big Z, from Surf’s Up

As a society, it seems that we are plagued by burnout and work anxiety, beaten to the point of being ready for AI to deliver us to the promised land of a post-work society. But there are thinkers that provide a perspective that may be able to redeem work and through this redefine how we see our own lives.

So, what is this new perspective? This new perspective is one that does not see extreme hard work, pain, and sacrifice as necessary ingredients of excellence, but in fact as obstinate deterrents of it. In the words of thinkers who have professed this philosophy:

Mediocre man is one who learns to trust the journey because he is fully aware that one cannot quite know what will result from any specific effort. Society tells him he is lazy and that he is a fool and that he should have goals, big goals! But he has stumbled upon a secret: mediocre effort beats extreme effort for most people, most of the time. A little bit of effort into something you like doing can have shockingly good results over a long period of time.

— Paul Millerd, The Way of Mediocre Man

This philosophy rejects busyness, seeing overload as an obstacle to producing results that matter, not a badge of pride. It also posits that professional efforts should unfold at a more varied and humane pace, with hard periods counterbalanced by relaxation at many different timescales, and that a focus on impressive quality, not performative activity, should underpin everything.

— Cal Newport, Slow Productivity 

The prevalent idea of genius of the likes of Elon Musk, who famously works 100 hours a week and compares entrepreneurship to eating glass, and Mark Zuckerberg, who compared it to being punched in the gut, may be a deceptively harmful one. True genius can stem from a natural pace, a curious mind, and a ton of long breaks in between and most of all, it can be fun, life-affirming, and give us a healthier sense of purpose without having to sacrifice the other sorely needed pillars of health, family, and connection. 

In this post, I’m going to focus on what I’ve learned about how we can implement the ideas of Slow Productivity into our own lives. So, let’s dive in.

Do Less

Doing less enables us to achieve more

Charles Darwin worked only about four hours a day on his scientific theories. He spent the rest of his time walking, reading, and spending time with his family. Einstein often spent time sailing, playing the violin, and engaging in philosophical discussions. Charles Dickens often spent just a few hours each morning writing and the rest going on long walks and living his life. 

Well, that attitude may be fine for geniuses like Einstein, but for the rest of us hard work and long hours is the only way to catch up, right? What if all of these prodigious thinkers did not do world-changing work in spite of their seemingly lackadaisical attitude towards work, but because of it? Well that is the first principle of Cal Newport’s philosophy of Slow Productivity. In his words:

PRINCIPLE #1 - DO FEWER THINGS: Strive to reduce your obligations to the point where you can easily imagine accomplishing them with time to spare. Leverage this reduced load to more fully embrace and advance the small number of projects that matter most.

For me, this was the idea that was the hardest to internalize. How can doing less possibly help us achieve more? That was until I started comparing how I was learning today to when I was in school. In school I was often taking 5 classes and balancing this work load with multiple extracurriculars and social obligations. Every time I started an assignment it was in a panic to get it done as the deadline was fast approaching and several other things required my attention. If I came across a problem I didn’t immediately understand how to tackle, I would seek help to finish it as quickly as I could and move on. I always felt incredibly productive as whenever I was asked what I was working on I could list a lot of things and people seemed to be impressed. 

However, now that I am only taking one or two classes at a time, the pace is a lot slower and not at all impressive. Now, when I run into a problem, like a scene that doesn’t feel like it’s quite working, I’ll take my time trying to figure it out on my own. I’ll watch other movies with similar scenes and note why they worked or didn’t. I’ll rewrite the scene a few times, doing multiple different versions of the homework, seeing what emotions, if any, different rewrites bring out. 

As a Product Manager or Founder. I never felt I had the luxury of being unhurried. But now, since taking on less, I have gained confidence in what I’ve learned a lot faster, I have a lot more ideas, and, most importantly, it has just been a lot more fun. Even topics I had found boring before, I find fascinating when employing this slower, less ambitious method of learning.

How to Do Less?

Once you are in the hustle mindset, it can become difficult to do less. So how do you actually do less? Henrik Karlsson from LessWrong suggests you want to limit the projects you do to just two or, at most, three big projects. This keeps what Newport calls the overhead tax of just determining priorities and what projects to do manageable. Newport explains further, “This feedback loop can quickly spiral out of control, pushing your workload higher and higher until you find yourself losing your entire day to overhead activities: meeting after meeting conducted against a background hum of unceasing email and chat. Eventually the only solution becomes to push actual work into ad hoc sessions added after hours—in the evenings and early mornings, or over the weekend—”. I saw this happen often during my time as a Product Manager.

You also want to limit distractions and set aside big chunks of time for deep work. Creating the kind of culture that embodied this philosophy was a key goal for Jason and David, the founders of the bootstrapped company Basecamp. In their book, It Doesn’t Have to Be Crazy at Work, the founders describe how they created a policy of replacing sending ad-hoc messages through email or Slack with discussing ideas in set office hours and replacing weekly sync meetings with written updates. This way if a colleague needs something from you, they can either read the latest update from your team or wait for your office hours. This greatly reduces the amount of distracting pings or meetings that interrupt your deep work time during the day. 

Paul Millerd in his blog post also offers a philosophical shift in mindset that can help you do less, which is to resist the urge of setting overly ambitious goals. He describes how, “It took me 14 months to write my book, and the entire process felt leisurely, light, and enjoyable. [...] It delighted me. I decided I wanted to share it with the world immediately. I skipped any sort of book launch and started selling it. I sold a couple of hundred books in the first month and declared it a success. To someone aiming at great results, this would have been a disaster.”

Instead of setting unrealistic external goals, like selling a million copies of a book within one year, Paul simply set internally focused goals, like continuing to enjoy the process of writing. Research has often found that tying external goals to things that you are intrinsically motivated to do reduces your motivation. He likely couldn’t predict how long it would take to write his book or what the reception of it would be. However, since he followed the other principles of Slow Productivity, he knew that he was doing his best work every day and therefore was creating the best book he was capable of as fast as possible. 

Advice you hear often is to find work that you would do even if you weren’t paid to do it. I would argue it’s also worth asking yourself what work you would do even if it was completely abstracted away from any external impact it may have, even a positive impact like changing the world. In essence, this is what the philosophy of Doing Less is all about. It’s about getting rid of the feeling of hurry and distractions as well as the concern about the external impact of the work so that you can more deeply connect with what you are doing and relearn how to love doing it. This frees us from thinking we have to choose between living a good life and doing good work. We can set up a great life that enables great work instead of getting in its way.

Take the Long View

The Myth of the Born Genius

In a world where billion dollar companies are started seemingly overnight and 30 under 30 awards promote stories of those who succeed exceedingly young, it can be tempting to think people are born geniuses who achieve success effortlessly. This can happen, but the basis of this whole philosophy around Slow Productivity and Feel Good Productivity is to do what you truly love to do, and what you want to do for a long time (or at least would be ok doing for a while). It can be worthwhile to question the myth of the born genius, even in the exceptionally rare cases when it occurs. 

The famous organizational psychologist Adam Grant in his book Originals, highlights how many who are considered to be born geniuses, such as Beethoven, Edison, and Picasso, actually didn’t seem very remarkable in the beginning of their life and actually just outproduced many of their peers through years of dedication. Da Vinci, for example, created his most famous masterpiece, the Mona Lisa, not out of a spur of genius, but out of a torturous 16-year process in which he went back and forth working on the piece of art (Brittanica). 

Patrick Collison, the founder of Stripe and The Arc Institute, also advises that we expand our modern stories of success to include the likes of Bob Swanson and Herb Boyer, the founders of Genentech. Bob and Herb spent decades slowly accumulating the expertise needed to figure out how to produce cheap insulin using recombinant DNA. While so many modern ideas of genius look something like Young Sheldon, Patrick jokes that Herb Boyer couldn’t have achieved what he did at 23. It required an immense amount of time to gather all the knowledge and insight to tackle a problem at that level.

Why does Taking the Long View work?

Paul Millerd also further elaborates why taking the slow & long approach may get you to great results faster than the sprint approach: “Over long enough time horizons, you can actually become one of the best in the world at your craft because of a simple truth: most people quit.” Those who run the fastest out the gate usually quit first. Start-ups usually don’t work, books don’t usually sell, acting gigs don’t usually turn into big breaks. Success is a long-term game. Expecting success quickly is a recipe for disappointment that will take all the fun out of that long game and, as Ali Abdaal details in the premise for his entire book Feel Good Productivity, if you aren’t enjoying the process, you aren’t going to last long. If you do take the long view, it can help you follow Newport’s third principle of Slow Productivity:

PRINCIPLE #3: Obsess over the quality of what you produce, even if this means missing opportunities in the short term. Leverage the value of these results to gain more and more freedom in your efforts over the long term.

A common objection to taking it slow and having a long time horizon is that this will cause us to lose the First Mover’s Advantage. However, this is another idea that Adam argues is just a myth in his TED Talk, the surprising habits of original thinkers. In this talk he shares the results of a study that shows that the failure rate of First Movers across 50 product categories was 48%, while it was only 8% for Improvers, who came later and improved upon the existing work. This research supports the hypothesis that taking the time to obsess over quality and bringing the right solution to the market often trumps getting there first. 

When we look at what separates us from geniuses it may not be their speed we want to pay attention to, but the quality of work they were eventually able to produce by settling in for the long run. So, what is the kind of work you like to do? Is it work you could enjoy in the long run, even if there was no external reward for it. If we slow down and take the long view, we might not all become geniuses, but we may be able to do our best work and enjoy doing it so much that it doesn’t matter what comes from it.

Take Breaks

Small Breaks, Big Gains

Another critical principle of this philosophy is to take breaks. While we often valorize being able to work non-stop and a capacity to endure pain, it can often be counter-productive. Gloria Marks in her book, Attention Span, compares the mind to a rubber band that can snap if stretched too far for too long. Even a short well controlled social media break can restore your energy and mind, along with whatever else you may find enjoyable such as taking a walk or talking to a friend. 

Personally, my approach to this principle has been to cut down or push back my evening activities and expand my working hours. Whereas at my previous job, I would usually work non-stop, crash, then watch the clock till 5pm, I now will be working at 8pm or even 10pm regularly. But I’ll usually take big breaks in the middle, switching up locations, playing video games, or listening to a podcast. I’ll even switch back and forth between working on two very different projects, giving myself a break from working on one kind of problem for too long (akin to not doing all the exercises for a single muscle back-to-back, but breaking them down into a rotating series of reps of different muscle groups). 

Adam, in the same TED Talk referred to earlier, also discusses how taking breaks or waiting till the last minute may look like procrastination but can actually be a way to boost creativity. In his talk, he even shares the results of an experiment where participants randomly assigned to procrastinate after learning about a task were able to come up with ideas deemed more creative than those who were able to start right away.

Big Breaks, Huge Gains

Taking breaks isn’t just a principle that can be applied to your day to day. It can also be applied to taking long breaks in between projects. Lin Manuel Miranda famously came up with the Broadway musical Hamilton while reading Hamilton's biography on vacation. Steve Jobs recounts his forced break from Apple as necessary medicine for him to rediscover his purpose and work on incredible projects like growing Pixar. J.K. Rowling often credits her time abroad with helping her create the world of Harry Potter. 

The ideal of a worker who never takes any time off may be a false idol. That is why at Basecamp, Jason and David give their employees month long sabbaticals every 3 years. A growing amount of evidence backs up that sabbaticals help improve psychological well being as well as improve work performance. The research also shows that more than days or weeks, a month can be needed to truly see the positive effects. 

Even giving employees a structured break from their projects to try something new can yield great results. Jason and David at Basecamp let employees set aside 25% of their time for side projects, a strategy that led Google to some of its most successful creations such as Google Maps, AdSense, and Gmail (Inc). 

Taking breaks is another principle that can seem to be at odds with our current ideas of dedication to work and mastery, but this could not be further from the truth. Taking short breaks helps you get more from the working hours during the day. Delaying working on something can help you bring more creativity to the task. Long breaks can be even more beneficial, giving you the space to completely dissociate from your work and give you the distance to come up with completely new connections you may have never seen from just putting in more hours.

What if We Built Society Around this Idea?

These ideas have profound implications for us as an individual, but if taken seriously, even greater potential if embedded into how we run our companies, and even our societies. In this post, we’ve often referred to Basecamp as an example of a company built around this new philosophy of work. In Jason and David’s words:

For nearly 20 years we’ve been working at making Basecamp a calm company. One that isn’t fueled by stress, or ASAP, or rushing, or late nights, or all-nighter crunches, or impossible promises, or high turnover, or consistently missed deadlines, or projects that never seem to end. No growth-at-all-costs. No false busyness. No ego-driven goals. No keeping up with the Joneses Corporation. No hair on fire. And yet we’ve been profitable every year we’ve been in business.

— It Doesn't Have to Be Crazy at Work 

Jason and David demonstrate how these principles can enable a more humane working culture for employees without sacrificing on success.

Utopian thinkers such as Elle Griffin have also proposed radical new ways of thinking about topics such as retirement if we were to take this new philosophy of Slow Productivity seriously. She proposes that, instead of work being a mad sprint towards retirement where you finally get to rest completely, we allowed people to use their retirement savings for intermittent breaks in between work? What if we were able to do work that filled us instead of draining us? What if we were able to do this at a natural unhurried pace with plenty of well-deserved breaks instead of weaponizing this enjoyment as an excuse to do it for free or less.

This new perspective is so powerful because it isn’t about using hacks or short-cuts to make us more productive. It’s a more humane way of doing work that we can be proud of, without looking to it for our salvation or sacrificing the other fundamentally important pillars of our life. It is a different bedrock with which we can re-invent not only how we work, but how we run our organizations and society.

Rediscovering Life through Work

Choosing a path for work is choosing who is around you, what characteristics to reinforce within yourself, and what the constraints for your lifestyle are, so it can be worth spending more time deciding what to focus on. Employing the principles of Slow Productivity such as Doing Less, Taking the Long View, and Taking Breaks is all about leveraging joy and leisure to make slow sustainable progress towards your best work, just as several masters including Da Vinci, Charles Darwin, Charles Dickens, Bob Swanson, and Herb Boyer have done before us. In my life, I’m leveraging these learnings to gain confidence in continuing to explore different things as well as how I approach this learning and I hope within these ideas there is something that can spark a change for the better within you as well.