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.

Shackleton’s Endurance and Lessons in Adapting Your Strategy

On October 26, 1914, Ernest Shackleton, captain of the Endurance, set sail with a crew of twenty-seven men comprising the Imperial Trans-Antarctic Expedition. Their goal was to complete the first land crossing of the Antarctic. With an expedition of this difficulty, there was no shortage of planning or coordinating involved.

Shackleton’s final itinerary planned to take the Endurance into the Weddell Sea before disembarking near Vahsel Bay with a team of six men and seventy dogs to sledge across the Antarctic. At the same time, a second ship directly across the continent would sail into the Ross Sea, setting down provisions along the intended route for Shackleton and crew. This would keep the men supplied until they reached their final destination at the McMurdo Sound base. 

Ten days after setting sail from Buenos Aires, the Endurance reached South Georgia and received disheartening news at the whaling station. The conditions in the Weddell Sea were the worst in recent memory. As the Endurance continued south towards the Weddell Sea, they learned this first hand. 

In an open ocean the Endurance covered close to 200 miles a day. But facing polar pack ice they were slowed to a crawl and by December covered less than thirty miles a day. 

As they came within 200 miles of Vahsel Bay, fierce winds struck and they were forced to shelter the Endurance next to a large iceberg. After six days, on January 24, 1915, the winds began to subside but the Endurance was frozen solid in pack ice as far as the eye could see. 

The crew did their best to free the ship, chipping away at ice with chisels and saws. But after a month, the ship was still trapped. As the days grew shorter, Shackleton knew there was no immediate way out and no way to communicate with the outside world. 

Shackleton’s neatly made plans to cross the Antarctic came to an abrupt halt. It was now about survival and the preservation of his crew, which demanded an entirely new set of strategies. He gave the order to prepare for winter aboard the Endurance.

On the open sea, each man had their assignment. There was work to be done and they remained in good spirits. But with the ship out of commission, they faced a lull. And Shackleton feared demoralization more than the threat of ice or sub-zero temperatures. 

In an effort to keep the crew engaged and morale high, Shackleton directed the construction of “dogloos” on the ice to protect the dogs. He sent others hunting to secure a supply of meat for the winter. And he created a series of social occasions with grog on Saturday nights, music on Sunday nights, and dog-sledding races. The men remained in surprisingly strong spirits through the depths of winter. 

But when spring arrived, the Endurance showed no signs of breaking loose. Quite the opposite. After being trapped in pack ice for nine months, the Endurance was being slowly crushed by the Weddell Sea. On October 27, 1915, Shackleton gave the order to abandon ship.

While sheltered aboard the Endurance, they had room to store equipment for every imaginable scenario. But Shackleton recognized they were in a new territory of survival which would require sacrificing preparedness for speed. There was no room left for luxuries.

Shackleton urged the crew to leave behind anything that wasn’t absolutely essential for survival. To emphasize the seriousness of his request, he tore a page from the Book of Job, placed his Bible in the snow, and set off without looking back. 

Shackleton and the crew huddled to set up camp on a large nearby ice floe. They hoped the drift would carry them towards the safety of Paulet Island, 250 miles away. Despite the dire circumstances, the men were relieved to have a plan. The indecision and speculation aboard the Endurance was over. Shackleton knew not to let ambiguity linger for too long. 

Even as storms carried the floe in unexpected directions, Shackleton operated with conviction. Whether in demanding patience during the drift or taking deliberate action to relocate camp and board the lifeboats during a last-ditch effort to reach land. 

As conditions changed, Shackleton’s strategies would shift. But he remained purposeful in his every move. The crew held a deep respect and admiration for this. It’s what held them together during their bleakest moments. 

It took everything he had, but nearly two years after setting sail aboard the Endurance, Shackleton reached the shore of South Georgia Island with five of his men in the last remaining lifeboat. The rest of the crew remained on Elephant Island where they were rescued three months later. 

Shifting Strategies

Shackleton could have relied on the same strategies he had up until the Endurance was trapped in ice, but that would have meant certain defeat. Instead, he avoided disaster through his ability to adapt and rethink his strategy as the situation required. Nothing could have prepared him for the circumstances he faced. But he willed his crew to survival at every turn. 

When Shackleton gave the order to winter aboard the ship, he shifted his strategy from one of operations and efficiency, to survival and engagement. With polar nights and a perpetual darkness bearing down on them, he knew the real enemy was a sense of restlessness and complacency among the crew.

Nine months later when they abandoned the ship, Shackleton had to pivot again, favoring speed over preparedness. It was the opposite of his strategy while originally planning the expedition or aboard the ship, but he knew time was of the essence. Every spare second wasted hauling around non-essential equipment could mean the difference between life and death. 

Strategies are frameworks to help you to think ahead and take thoughtful action. But strategies won’t provide a checklist of prescribed actions for your every move in life. As Shackleton knew well, no matter how strategic you are, there’s no replacement for true resourcefulness. And this is where people get lost. The map is not the territory. 

It’s easy to get locked into a rigid thought process with a single strategy if you stick to the map without ever looking up. But when you stop reaching for absolutes, you’re able to embrace the motion inherent to life. Everything is fluid.

Shackleton embodied this in a survival scenario. But the same concept holds true even when you’re not fighting for your life while floating on a sheet of ice in the Antarctic. At a certain point, the strategy that might have worked for you up until this point in time will falter. Resourcefulness matters. Allow yourself to adapt.

This article is an excerpt from my recent e-book, 7 Strategies to Navigate the Noise. It’s all about sharpening your strategic mind, taking thoughtful action, and living on your own terms. Grab your free copy here.

For more details on the story of Ernest Shackleton and the Endurance, check out Alfred’s Lansing’s book of the same name.