Mastery

3 Questions to Help You Rise to the Level of Mastery

To rise to the level of mastery requires intense dedication. You have to really want it. What would make you have such commitment and dedication?
— Robert Greene

At the start of my career, I wondered what I was doing wrong. I wanted to dedicate myself to my career, but I didn’t trust myself to know which potential directions were worth going all in on. I was terrified of making the wrong decision. And my early 20s, ego gave me a false sense of confidence and deluded me into believing I could be anything I set my mind to. Rather than eliminating options and accepting that directions in life are mutually exclusive, I sat in indecision. 

But the truth is that you can’t be anything in this life. There are things you are uniquely suited to do based on your skill set, interests, and experiences. And the sooner you accept this reality and cross options off the list, the more time you give yourself to dedicate to the things you’re uniquely good at. But this demands reflection—you have to allow yourself to reflect on the skills you’ve excelled at, the subject areas you’re naturally drawn towards, and where you find meaning. 

What are you naturally good at?

At 24, I was living in Nashville with no idea what I wanted to do in my life. One weekend, I forced myself to go to a coffee shop around the corner, put my headphones on, and write. It was the first time since I was eight years old that I was writing for fun.

Over previous months of reflection, I asked myself what I was naturally drawn towards in childhood and what skills I excelled at without trying as hard as other kids. I remembered that writing was one of those things so I pushed myself to reconnect with this. The connection was immediate and the state of flow I was able to achieve in writing was addicting. That’s how I knew I was on the right track. 

As I used writing to reflect on who I was, I also started to recall how industrious I was as a kid, working to generate extra money. From as early as I can remember, I was working my way through the neighborhood mowing yards, shoveling snow, or starting a mobile snow-cone operation on the back of a wagon that I’d roll door to door during the summer. I loved testing new ideas.

And finally, as I searched for how to fit the pieces together and what to focus on, I began reading for enjoyment again—another thing I loved as a kid and lost through school over the years. This allowed me to hone my sense of focus. I also began to develop stronger strategic thinking skills and stack mental models from different disciplines against each other to improve my decision-making.

All of this led me to a career in product management that I’m deeply invested in. Product demands an elite level of resourcefulness, focus, and communication skills. You have to be driven to create, take risks, and articulate stories in a way that resonates with different audiences. And you have to be able to quickly evaluate directions from multiple perspectives. These were all things I showed aptitude in from an early age. I just had to reconnect with those things and forget all the shit that happened between age 8 and 24 to get back there and align myself to that. 

Perhaps the most important aspect of this is that when you leverage skills that come naturally to you, you can outwork everyone else around you because the work itself is deeply rewarding and where you find your flow state. Your validation comes from the craft itself—internal, not external.

If your goal is mastery, the first step is reconnecting with your childhood interests and skills that come naturally to you. These are the places you must invest in.

To achieve alignment and build from a place of authenticity, you must first remember who you are.

What subject matter are you drawn towards?

During the early part of my career, I bounced between different industries—music, film, healthcare, and insurance. And what I learned through exploration was that those weren’t the things I cared deeply about. After a year or two in each, I was bored and struggled to sustain a connection with the problems we were tackling.

When I started my career in film production working on set for major music videos, I was barely able to sustain two summers in that line of work. It seemed glamorous from the outside looking in. But the inefficiency of working 22 hours for a three-minute music video drove me insane. And most importantly, I wasn’t willing to struggle for the end result because I didn’t connect with many aspects of the work that I was exposed to—whether finance, set design, project management, or cinematography.

I also found I didn’t have a natural interest in the entertainment industry or the value we were providing. And if you don’t care about the subject you’re focused on, it’s going to be tough to stick it out.

But early on, finding something that doesn’t resonate with you can be just as valuable as finding something that does. Because it helps you eliminate a direction and move on. The goal is to learn and refine to better align yourself with each move. 

Through trial and error, the subject areas that I’ve found a deeper interest in are philosophy, education, and finance. After close to a decade of exploration, before I applied to my current job, I knew I was going to stick with edtech and fintech as the sectors I wanted to work in. And it worked. Snapdocs is in the broader fintech category and I find the work endlessly fascinating. So I can stick it out despite the challenges and obstacles in the way of achieving our vision.

There are subjects you’re naturally drawn towards. Consider what you enjoy reading and learning about right now. That’s your starting place. The more you invest in these things, the better. Because it’s very difficult to sustain interest in a field or subject that you aren’t pulling from a deeper sense of curiosity about.

Mastery requires a relentless level of focus and effort.

Where do you find meaning?

And finally, you must also search for meaning. Because no matter how naturally talented you are and how interested you are in a field, you have to find meaning in the work or you’ll forever lack the persistence that mastery requires. 

This can show up in different ways but once unlocked it’s the force multiplier that allows you to endure. Whether it comes from the group of people you’re building alongside or the end result you’re driving towards or the brokenness you’re working to fix. There will be weeks and months that test your limits. If you lack meaning, it will be impossible to continue showing up. Mastery demands endurance. 

Almost nothing in the world can resist persistent human energy. Things will yield if we strike enough blows with enough force.
— Robert Greene

I find meaning in accelerating personal growth and pushing the confines of my current limits. I find meaning through the people I’m collaborating with on a daily basis to solve challenging problems. And I also find meaning in solving problems that translate directly to human outcomes. That’s one of the reasons I love my current position, I’m motivated to make the disaster that is the home buying experience less shitty. I want it to be accessible and more transparent for everyone involved. And it’s incredibly challenging. But worth it, because the end result we’re working towards is meaningful to me and I’m able to test myself along the way. 

Another way to think of this is asking yourself, what are you willing to suffer for? You’re going to struggle regardless of the line of work you enter. It’s going to be hard. There will be moments that piss you off or lead you to question what you’re doing. To get through these moments, you have to recognize and reconnect with a deeper reason that keeps you going.

Where do you find meaning? You can endure anything if there’s a deeper connection to your craft and the problem you’re focused on. Keep this front and center and you will be able to persevere when the inevitable obstacles stand in your way. Endurance is foundational in the pursuit of mastery. So what are you willing to show up for every single day?

Rising to the level of mastery

Once you’ve achieved alignment with the answers to these three questions, you’re on your way. But you still have to put in the work. You still have to show up. There is no path towards mastery without having skin in the game. 

As tempting as it might be to distance yourself from the work and make it easier on yourself, this works in opposition to mastering your craft. You can never be above the work. This also helps ensure your incentives are aligned and you have a vested interest in the outcome. Because even when you come up short, you can always take solace in the fact that the credit belongs to the man in the arena. 

When you’ve aligned yourself to skills that differentiate you, subjects you’re naturally drawn towards, and focused on where you find meaning, this all acts as a force multiplier for your work. 

You are uniquely positioned to bring certain things to life. You can’t be everything. And if you want to maximize what you’re giving back to this world, the sooner you focus on mastering what you’re uniquely positioned to contribute, the more fulfillment you will find.

Top 4 Books for Better Mental Models

In a world of specialization, mental models are the most powerful argument for adopting a multidisciplinary approach. The concept behind mental models is that broad exposure to a range of subjects enables you to leverage the most useful knowledge from each and make better decisions.

When you position yourself at the intersection of multiple disciplines, you develop the ability to connect seemingly unrelated dots in a way that the vast majority are otherwise incapable of discovering. It’s here where true creativity and the most innovative solutions are found.

Charlie Munger coined the term “latticework” of mental models–which is exactly what you’re aiming for. The models you pick up should be intertwined with one another, as well as with your personal and vicarious experience. The more connections, the faster you’ll be able to navigate the latticework of your mind, and the stronger your cognitive ability.

You can begin building better models by going straight to the source. If you read and study those who have demonstrated mastery over their specific fields–regardless of industry–you can improve your decision-making ability considerably.

Over the past year, I’ve read (and reread) over 70 books in search for the best systems. These have served as the foundation for improving my own mental models. I’ve distilled what I’ve found to be the most important methods and strategies down to just four books. Each documents real models from some of the most intelligent, imaginative minds in history.

While these are in no way comprehensive, it is my hope is that they will provide a useful starting place to build your own latticework.

1) Mastery — by Robert Greene

You would be hard-pressed to find a more profound, relevant book, no matter your position in life. If I had to recommend a single book of Greene’s to get you started, this would be it. He begins by defining mastery as the sensation we experience when we feel that we have a greater command of reality, other people, and ourselves. The book offers a deep dive into every element of mastery–including insight for those just starting out and searching for their life’s task. True to form, Greene also provides detailed accounts and models from some of the greatest masters in history–Leonardo da Vinci, Benjamin Franklin, Charles Darwin, Albert Einstein, Paul Graham, and dozens more.

“The pain and boredom we experience in the initial stage of learning a skill toughens our minds, much like physical exercise. Too many people believe that everything must be pleasurable in life, which makes them constantly search for distractions and short-circuits the learning process. The pain is a kind of challenge your mind presents–will you learn how to focus and move past the boredom, or like a child will you succumb to the need for immediate pleasure and distraction?”
— Robert Greene

2) Tools of Titans — by Tim Ferriss

A collection of interviews with hundreds of the most talented entrepreneurs and thought leaders consolidated into their most useful sound bites. It follows the same format as his popular podcast. Ferriss lays the framework for building better, more productive mental models. Rather than suggesting a checklist of X-Y-Z required to set yourself apart, he emphasizes strategies and tactics which can be applied more broadly. A few of my favorite sections feature Naval Ravikant (entrepreneur/investor), Josh Waitzkin (chess prodigy), and Alain de Botton (philosopher). There are sure to be a handful of ideas that will resonate with you and help improve your own mental models. It’s a book I revisit with regularity–especially when I’m in need of a new perspective.

Most people think they can wait around for the big moments to turn it on. But if you don’t cultivate ‘turning it on’ as a way of life in the little moments–and there are hundreds of times more little moments than big–then there’s no chance in the big moments.
— Josh Waitzkin

3) Antifragile — by Nassim Taleb

Taleb introduces his concept of antifragility, which explains that certain things–including us–benefit from a degree of randomness, chaos, and disorder. While comfort, convenience, and predictability, breed the opposite–fragility. He presents this as part of what he calls ‘the central triad’ which ranges from fragile to robust to antifragile–the key to personal growth. As he explains antifragility, he discusses the value systems that hold us prisoner, ancestral vs. modern life, and Seneca’s version of Stoicism. It’s a dense read, but worth it for a glimpse into the originality of Taleb’s models.

With randomness, uncertainty, chaos: you want to use them, not hide from them. You want to be the fire and wish for the wind.
— Nassim Taleb

4) The Daily Stoic — by Ryan Holiday and Stephen Hanselman

I’ve found Stoicism to be the most effective philosophy for modern life. If you’re unfamiliar with Stoicism, you’re probably operating under the misconception that it’s synonymous with a lack of emotion. In actuality, it’s a school of philosophy focused on cultivating an unwavering sense of focus, appreciation, and rationality. The Daily Stoic is a great introduction to some of the most memorable Stoic philosophers and their models for living a better life, including Epictetus, Seneca the Younger, and Marcus Aurelius. The book offers daily wisdom–366 short sections–focused on the most important Stoic themes. This is not a philosophy textbook filled with abstract concepts. It’s an accessible overview of Stoicism and its emphasis on the art of living.

Take a good hard look at people’s ruling principle, especially of the wise, what they run away from and what they seek out.
— Marcus Aurelius