Build Up Your People to Build Up Your Customers

The most successful product-driven companies are customer obsessed. Teams at these companies work relentlessly to get close to customers and represent the voice of the customer. This mindset allows your teams to develop a deeper understanding of the problems worth solving and build greater empathy for the people who face those problems.

Most leaders are able to acknowledge the importance of this. But too many leaders believe they can jump in, put a mandate in place, and see immediate results without having to put in the work themselves. If you want to build up your customers, you must first build up your people. 

Empathy gives rise to empathy. Trust gives rise to trust. 

You can’t expect your team to connect with and care deeply about your customers if you don’t demonstrate the same for your team. Attempting to build from a place of “do as I say, not as I do” is delusional and ineffective. But if you create this connection first within your team, it creates the foundation for a deeper connection with your customers.

“Operations occur at the speed of trust.”

— Jim Mattis

As a leader, this doesn’t mean you need to be in the weeds leading discovery efforts and research interviews with customers. But if you want your team to show up and care about your customers, you need to build that same empathy and trust within your immediate team. 

This can be as simple as using 1/1s to talk through challenges your team might be facing. You don’t always have to fix things or offer up solutions. Listen, make them feel heard, and connect to what they’re feeling about an experience. Then you can think about problem-solving together.

Retros are also a great way to build trust. But you need to lead by example, put something out there that you’re struggling with, and create a sense of safety for the team. When the team feels this, they’ll lean in together to lift each other up.

I’ve also found that providing actionable, thoughtful feedback after a big meeting or presentation can go a long way. Recognizing the specifics of what someone did well and what could be improved fosters a growth mindset. And reflecting on how to get even better as a team—what to double down on, what to work on—shows you’re working in the same direction.

Each day you have an opportunity to make people feel heard and to help the team push each other. Sprint planning, standups, quarterly planning, career conversations, engagement surveys, product reviews—every single touchpoint is an opportunity to lean in with your team.

Where this can break down is when we trick ourselves into believing top performers don’t care as much about these things. We tell ourselves they have their own work ethic and hold themselves accountable. We just need to focus on providing the right incentives and meaningful problems—which is certainly true in some capacity. But it’s a shortcut our minds take to avoid putting in the work and having real conversations. Staying in the shallow can feel easier in certain moments. But the truth is that top performers are also motivated by empathetic leaders who give a shit about their people. This connection is critical to their success and your team’s success.

“Understanding a person’s hunger and responding to it is one of the most potent tools you’ll ever discover for getting through to anyone you meet in business or your personal life.”

— Mark Goulston

By glossing over building a deeper connection with your team, you might end up with a marginally effective band of mercenaries who can keep the lights on. But you’ll struggle to connect with customers or achieve any sort of meaningful impact. It starts from the inside out.

And this is true at every level of your career. If you’re a product manager leading a squad, you must care about your team and building them up before you can think about delivering meaningful impact for customers. If you’re a middle manager, the same holds true of your direct reports—you must create a connection built upon empathy and trust. This provides your people the confidence to mirror this approach across both their teams and the customers they interact with.

If you want to increase your leverage and maximize your impact as a leader, start here. It’s a simple lesson but one that’s easy to lose sight of. By building up your team—showing up, listening, and instilling trust—you unlock your people to do their best work and show up at their best with customers. 

The Barbell Strategy for Your Timeframes in Life

If you follow the self-help genre, you’ve likely been bombarded with waves of conflicting advice:

Stay present, but make sure you spend time thinking deeply about what you want out of life, setting goals, and creating checkpoints to measure progress.

Find a flow state in your work, but expand your perspective of time so you’re assigning things their proper weight.

Drive results today, but sharpen your strategic mind by thinking multiple steps ahead and considering higher-order consequences to outmaneuver your opponents.

All of this advice on what timeframe to orient towards becomes exhausting. Am I over-indexing on the future and paying too little attention to today? Am I making shallow decisions and not thinking far enough ahead? Am I setting goals that match the optimal timeframes?

Each piece of advice on its own seems intoxicating. But when you try to reconcile these ideas against each other, it’s easy to get stuck. No one tells you how to achieve balance or what that looks like. 

The reality is there aren’t just two timeframes in life—present-oriented or future-oriented. These are just the bookends, there are other timeframes that sit in between. But the bookends are the most powerful timeframes to operate in. And the middle proves to be the most dangerous. 

A few weeks back, I came across a post on Twitter from @john_j_brown that provided me with a framework that created clarity…

While this post is geared towards investors, a similar model can be applied to the timeframes in our lives.

There are four timeframes in life…
1) Immediate = today
2) Short = days/weeks
3) Mid-term = months
4) Long-term = years/decades

The most rewarding life is found by pursuing a balance of 1 and 4 and avoiding too much time in 2 and 3. The most dangerous timeframes in life are the short and mid-term.

What’s the barbell strategy?

The optimal balance for these timeframes can be framed similarly to Nassim Taleb’s barbell investment strategy which proposes that you be as hyperconservative and hyperagressive as you can be, instead of being mildly aggressive or conservative.

In life, the parallels are the immediate and long-term. Using the barbell strategy, we should spend 40% of our time focused on the immediate term, 40% on the long term, and only 20% of our time in the middle thinking about short or mid-term. Of course, this is just a mental model. No one is going to sit around and calculate how much time they spend in each category. But as a rule of thumb, it’s an effective way to keep yourself in check and balance the most effective timeframes to operate in. 

Why optimize for the immediate and long-term? 

1 and 4 are where I find fulfillment in the work itself and a connection to a more meaningful vision I’m working towards. 2 and 3 are where I become impatient, anxious, and scattered—anticipating that presentation next week which distracts me from putting in the work today, fueling unrealistic expectations before reaching sustainable growth, or making shallow decisions that optimize for comfort.

The immediate-term (1) allows you to be fully present and immersed in your work. It helps you remain focused instead of anticipating any sort of future payoff or conflict. This is what allows you to achieve a relaxed state of concentration. The gratification is in the work itself. 

While longer timeframes (4) allow for calmness, perspective, and compounding. Thinking in terms of years or decades connects you back to the bigger picture. It also combats the tendency to exaggerate the magnitude of conflicts we face on a shorter time horizon and guards you against deceiving yourself into short-sighted moves that favor comfort and predictability. The long term is what smooths out the anxiety and steadies the waves that can break your knees.

It’s when you become consumed by the short and mid-term (2 and 3)—the days, weeks, and months ahead—that patience and focus give way to restlessness and anxiety. In this timeframe, you’re anchored to unrealistic expectations of linear, short-term growth which compromises strategic thinking and your connection to your ultimate goal.

When you’re focused on the moment in front of you, you’re not anticipating. You’re absorbed in your work. When you’re focused on the longer term, you connect to something larger than yourself and expand your perspective of time. Ego is what operates in the mid-term. It breaks your flow state by anticipating rewards, results, and external validation. It’s what scares you into seeking predictability and comfort to protect yourself—limiting your available upside.

The allure of the short and mid-term is so strong because it’s easy. People who are better at talking than doing thrive in these timeframes. It allows them to create the illusion of progress through seemingly intelligent observations without putting in the work or holding themselves accountable to the long-term results. These are the politicians, the academics, the suits, and the startup flakes who prove unable to stick it out.

Many people live their entire lives here. They’re simultaneously distracted and not thinking long-term enough. They’re living for the weekend, their next vacation, or the comfort of their annual bonus. It’s the most comfortable place to operate, but the least rewarding because the short and mid-term are the most shallow timeframes.

Real depth is found in the immediate and distant—putting in the work today and building up the endurance to sustain for years. 

Certainly, you need some balance of the short (2) and mid-term (3) as checkpoints and it’s important to have things to look forward to. And of course, there are obvious exceptions. But sustainable results don’t appear over the course of weeks or months. They appear through years and decades of hard work and a constant connection to what you find meaning in. 

Growth is nonlinear

Remember, growth is nonlinear. People tend to overestimate what they can accomplish in the short term and underestimate what they can accomplish over the course of years. The power of small, calculated decisions grows exponentially over time. Especially if you have a clear vision that you’re working towards. Start small and let compound interest run its course.

Focus on the short and mid-term is what interrupts this. Because growth is not always observable in comparison to the previous week or month. When you expect linear results equivalent to the effort you’re putting in, you’re bound to give up too early or make short-sighted decisions that create the illusion of progress at the expense of sustainable long-term growth.

If you’re playing the long game, 1 and 4 are where you build up the resilience and endurance required to contribute your best work. This is what allows you to continue showing up or making difficult decisions that sacrifice comfort for growth. 

Optimizing for this balance of immediate and long-term timeframes allows you to persevere. To find meaning in the moment and the work in front of your face, while continuing to come back to your underlying strategy. One that extends beyond the weeks and months, but that you can advance in the moment. Dedicating more of your energy to 1 and 4 allows you to bring your best work to life by ignoring the distractions and noise that sit in between.

What’s in it for you?

When you adopt the barbell strategy for investing your time, you’re able to accelerate your trajectory and outpace those operating in the mid-term. Those who spend 80% of their time focused on the short and mid-term often end up stuck in dead-end careers. They’re prisoners seeking comfort and predictability in the weeks and months ahead. Their trajectory and growth are limited as a result.

The barbell approach encourages a deeper connection to your work and an understanding of what kind of life you want to live. If you know what you want out of life and you’re willing to put in the work, the competition crumbles. It becomes a race against yourself.

But you must never trick yourself into believing you are above the work. The work is where you find solace. Pairing this with the long term and what you’ve defined to be a meaningful life is what allows you to create enduring work and transform yourself. In both the moments you have today and in the decades ahead.

“As one achieves focus, the mind quiets. As the mind is kept in the present, it becomes calm. Focus means keeping the mind now and here. Relaxed concentration is the supreme art because no art can be achieved without it.”

— W. Timothy Gallwey, The Inner Game of Tennis

Immediate, distant, but avoid the in-between

When you’re focused on the moment in front of you, that’s where you begin to hone your craft and unlock a flow state so you’re able to do your best work.

When you’re immersed in a longer time horizon, that’s when you’re connected to something bigger than yourself and tap into your strategic mind, allowing you to drive towards your vision. 

But when you’re stuck in the middle, that’s where anxiety, anticipation, and ego take hold. Because it’s too soon for most results, distracts you from putting in the actual work, and leads you to cling to the comfort of the familiar in order to avoid the discomfort of introspection—who you are, what you want, the challenges you’ll face, and the work you need to do today to get there. 

The sweet spot is found by immersing yourself in your work, achieving a state of flow, and appreciating the moment. But also remaining connected to a greater sense of meaning you find in your life and harnessing the power of your strategic mind. 

The best endurance athletes in the world demonstrate this. Consider your strategy, focus on the mile in front of you, and dig deep to stay connected to the reason that keeps you going. The mid-term serves as a hydration station on your path, a place to refuel. But it’s nothing more than that—a brief checkpoint. Then it’s back to putting in the miles and honing your strategy. Leave nothing on the table.

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.

10 Lessons on the Road to 33

Birthdays and New Years serve as two natural checkpoints for me. Birthdays act as a time to reflect on what I’ve learned and consider lessons that have resonated strongest over that year of my life. Whereas New Years signal it’s time to set five primary goals and assess how well I did against the previous year’s goals. Most years I publish these reflections, the following are 10 lessons that stood out most over the past year. 

1) Show up, even when it’s inconvenient 

Fighting through canceled flights, delays, and traffic jams to show up for someone when they need it most, even if you’re only there for an hour, matters. Regardless of what plans you might have made for your evening or weekend. The timing of events beyond your control might be inconvenient. But the universe isn’t on your agenda. And there isn’t some perfect version of the future where your life is free of challenges. The challenges and obstacles are what give life meaning. You can point to those as your excuse, or you can show up anyway when it matters most. 

2) Commitment adds meaning

Just as obstacles add meaning, so too does commitment—whether your relationships, career, hobbies, you name it. Directions in life are mutually exclusive. In my early 20s, I optimized for optionality and never committed to anything. Many of these things were unfulfilling and left me restless. But once I started to cross options off my list and double down on the people and things I cared about most, life became far more rewarding.

Getting married to my favorite person in the world this summer after six years together has continued to deepen our relationship. The same goes for my career and the way it has been accelerated by committing to problems I care about solving and the vision we’ve crafted around solving those. 

3) You don’t have to agree with the entirety of someone’s opinions

Almost everyone has good ideas and bad ideas. And you don’t have to agree with the entirety of them. One good idea doesn’t mean every idea that a person has is worthwhile. Just as one bad idea doesn’t mean the entirety of that person’s ideas are garbage. This lesson shows up frequently for me in books. When I was younger, I would take the entirety of an author’s ideas in a book as truth. Now I find myself more often disagreeing with certain aspects, and that’s fine. This ability to balance multiple opposing views and perspectives is what leads to improved critical thinking. This also speaks to the danger of ideologies and blindly accepting a docket of opinions without thinking for yourself. Guard yourself against this at all costs. 

4) More music, less everything else

During the pandemic, this got away from me. I didn’t have my regular outlets at coffee shops or commutes to let go and listen to music. It was all work, all the time. And in the brief moments when I wasn’t working, we were watching Netflix. But music is the thing that allows me to reach a state of relaxed concentration where I do my best work. Making more time for this, creating focus blocks throughout my day to tune everything else out, and starting my day with music while reading or writing in the morning makes me happier. And the same goes for evenings at home. Just turning on music instead of the TV feels more rewarding than whatever show we might be watching. 

5) Focus on what’s within your control

As long as I’m around, I don’t think I’ll ever shut up about this. Focus more on yourself. Every second you spend projecting or losing yourself in imaginary conversations consumed by others’ opinions is truly wasted. Focus back on yourself. Most people waste away consumed by distractions without ever searching within. If there’s any sort of secret in this life, it’s figuring out what you want out of life, reframing that as an internal goal you can actually influence, and pursuing it with everything you’ve got. 

6) Happiness is knowing less about what’s going on in most people’s lives, not more

Comparison is the death of joy. Most people are far too connected and could use more distance. I can only speak to my life, but I am far happier when I know less about people outside of my closest group of friends and family. And that’s a group of about 10 people. Beyond that, it’s just noise. 

Certainly, you must care for your community. But your capacity to give a shit is limited. You have to pick your battles. Anyone who claims they can keep up with everyone and every cause is virtue signaling. Instead, focus on yourself and your family, fight for your cause, and ignore the bullshit. There’s only one way out of the noise most people find themselves consumed by—distance yourself.

7) In-person interactions hold company’s together

I’ve worked fully remote at different points in my career. I’ve never actively sought it out, it’s just worked out that way and I was rather indifferent to it. But over the course of the pandemic, I’ve changed my stance entirely. If your intention is to create an enduring company of top performers who band together to overcome challenging moments, co-located teams will crush remote teams. Fully remote teams sacrifice camaraderie, morale, and meaning in the name of short-term productivity. My expectation is that most fully remote teams will self-destruct over the next few years because they won’t be able to absorb the higher turnover caused by a lack of human connection. 

8) Appeal to Your audience’s self-interest

Whether it’s a presentation, email, article, you name it, most people start by focusing on what they want to say. That’s exactly the wrong path if you’re hoping to land your message. Instead, ALWAYS start by putting yourself in your audience’s position and emphasizing the benefit from their perspective. Addressing the ‘What’s in it for me?’ question within the first 30 seconds is the only way to capture attention, disarm, and influence.

9) your first responsibility is to shut up and listen

I’m surprised at how common this problem is. A new hire joins the company, insecure and eager to prove their value, they immediately jump to providing feedback and solutions without having any context of the business, the product, or the team. And in doing so, they immediately erode any semblance of trust and have to work twice as hard to rebuild that over months. Seems like a fun way to start. This seems especially rampant in senior leaders who come into companies and should know this lesson better than anyone else, but they turn out to be the worst offenders. 

During your first 30 days at any company, just shut up and listen. Regardless of what level you’re coming in at. True confidence can look like keeping your mouth shut and simply listening. This will help you build deep relationships that will serve you far better than attempting to offer up empty feedback that lacks context and only draws attention to your attempts to overcompensate.

10) to command respect, be fearless

Timidity kills careers. Jump into the deep end. Raise your hand. Aspire to always have skin in the game and never act like you’re above the work. Regardless if you’re a middle manager, executive, or individual contributor, the work matters. You certainly have to know how to delegate. Otherwise, you’ll drown. But there will be occasional points where you must go deep on the subject and fight alongside your team in the trenches. If you avoid this second piece, you will never command respect from your team. 

Product and the Lost Art of Intuition

Discovery is a useful tool for Product Managers to get pointed in the right direction. But it only extends so far. It is not a neatly detailed map that charts the terrain and reveals every step you should make. 

That’s where most people get it wrong. Try as you might, discovery cannot be used to eliminate all uncertainty. Once you’ve used it to establish a deeper understanding of the problem, your users, and test high-level concepts, you must act. 

And when you do act, speed and correctness matter. The PM who gets it right in two iterations rather than six will run laps around the field, drive faster results, and unlock months of resourcing to focus on the next meaningful problem. 

The wasteland of mediocre PMs is littered with glorified project managers who build exclusively to customer requests, as well as those at the opposite end of the spectrum who have jumped off the deep end with the cult of discovery. The latter making up those who are content with never shipping anything of substance, instead creating the illusion of progress through a perpetual cycle of prototypes, personas, user testing, and exhaustive analysis. In other words, those better at talking than doing.

Discovery, within reason, remains a critical aspect of building exceptional products. It’s a tool to validate your largest and riskiest assumptions. To help get you started, Teresa Torres offers a helpful framework in her book Continuous Discovery Habits that features four quadrants where you map assumptions based on supporting evidence and level of importance. This provides a clear visualization of which assumptions to prioritize during discovery. 

But what we’ve overlooked is that intuition in product is just as valuable. 

PMs who are able to make better decisions, faster, win. PMs who fumble through months of discovery and analysis before moving, will lose. Just as those who only know how to build by taking orders from customers or stakeholders without any sort of research and refinement will also lose. There exists a golden mean. 

As it relates to intuition in product, this can take as many forms as the discipline of product itself. Once you’ve identified a meaningful objective to pursue, selected a direction, and validated or invalidated your riskiest assumptions, there are still hundreds of variations in how you might get to your desired end state. If you’re able to successfully anticipate second-order consequences, what’s going to drive the bulk of the value (80/20), how it advances the vision, and where your product has the highest likelihood of going off the rails, you’ll be able to deliver results in weeks instead of months, or months instead of years. 

At the heart of strong intuition is correctness and speed. In product, this will give a better idea of where to start, which iterations are worth pursuing, how to launch, when to scrap, and how to scale. 

The same logic applies to bigger swings and moonshots. These have an inherently higher likelihood of failure. PMs with strong intuition might only have a success rate of 25%. But a 25% success rate is worth exponentially more than 10% success rate. And as it relates to the 75% they miss on, they don’t drag out failures over multiple years, blinded by sunk costs in the name of discovery. 

The next obvious question becomes how do you hone intuition? Mainly through reflection, reading across disciplines, and experience. Get your reps in, ship often, and outlearn everyone around you. The best PMs codify each lesson the first time around—rather than having to relearn it dozens of times—and in doing so, cement that as intuition.

PMs with strong intuition focus on building a latticework of mental models. Product demands a multidisciplinary approach. The more flexible and wide-ranging your mental models, the stronger your decision-making and the less rigid your thinking. In product, this allows you to evaluate things from multiple perspectives and gain the right vantage point to find the best path forward.

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 product intuition. 

If you want a more actionable plan to hone these skills, here’s a list of deep-dive articles that I’ve written to get you started:

• Product resources to help you level up

• Unexpected books to help PMs hone a multidisciplinary approach

• Resourcefulness in product

• Indecision in product

The last piece—and perhaps the most important—in developing strong product intuition is that you must love product management or it’s going to be an uphill battle you’ll likely never win. Improving your intuition and judgment takes a lifetime of sustained effort. Endurance matters. Results happen over the course of years, not months or days. The motivation has to be there to stick it out.

If product isn’t your thing and you’re not uniquely suited for a career in this space, it will be a struggle. As Naval Ravikant points out, “If you’re not 100 percent into it, somebody else who is 100 percent into it will outperform you. And they won’t just outperform you by a little bit—they’ll outperform you by a lot.” This mindset applies equally to both your career and intuition in your field.

In the world of product, there’s a tendency to overanalyze on one side and shoot from the hip on the other. You want to position yourself near the golden mean. Proper discovery matters, so you can refine your ideas and validate your riskiest assumptions to ensure the problem is worth solving. But intuition matters just as much. 

The speed and accuracy of your decision-making have a direct impact on the success of your product. If you’re able to make better decisions, faster, you improve your odds. You won’t always have months to complete an intensive discovery process, especially at startups where resources are limited and there’s nowhere to hide. 

Strong product intuition can be the difference between driving business results and achieving product market fit before careening past the end of your runway or sacrificing your competitive advantage. If you want to realize the vision for your product, achieve meaningful impact, and set yourself apart in the process, hone your intuition. 

The Danger in Projecting Your Most Important Thing

After graduating from college, I poured most of my time and energy into triathlons. That was my most important thing. And it stayed that way for most of my 20s. I optimized my days for training across each discipline—swimming, cycling, and running. 

When I went out on my bike, I’d ride with a group of cyclists twice a week. For years they would throw shade my way for not showing up to as many rides as they did. They couldn’t understand why their most important thing wasn’t mine. Their attitude towards me was dismissive—triathletes were just flaky, wannabe cyclists who couldn’t commit to one sport. And if we’re being honest, I harbored a similar sentiment in return. 

There’s a certain level of arrogance most of us hold with our own priorities. We believe, to varying degrees, that our most important thing is often the right thing for everyone. Our priorities take precedence.

But while it’s important to build confidence in your own path, presuming you know best and projecting that same path upon everyone else is hubris. To avoid spiraling past this golden mean, it requires humility. Without this, you become rigid and inflexible. You squander your limited time and energy on things beyond your control. And your relationships are worse for it. 

You are only responsible for yourself, your path, and identifying your most important things. Every second you spend consumed by what you believe other people should want is truly wasted. You are never going to change or help someone by prescribing what they should do with their life. You’re just going to piss them off. And in doing so, you’ll begin to stagnate as your focus drifts from your own life. 

The counterbalance to losing alignment with this golden mean—the place where you build confidence and trust in your own direction while respecting other’s differences—is reminding yourself that not everyone will share the same goal as you. Not everyone is your competition. Different people will have different priorities, and that’s okay as long as it isn’t harmful to society. All you can hope for is that everyone is thoughtful in their own approach. 

This manifests itself in different ways depending on your priorities. Consider your career and lifestyle. You might think someone is crazy to leave (or stay with) your company based on the opportunities available and the company’s trajectory. But that’s based on your vantage point, your level of engagement, and your aspirations. Rather than judging their decision—something beyond your control—all you can do is hope that they were thoughtful and made the best decision for themselves. What’s right for you right now will not be the same for everyone else you work with. And the same holds true for your lifestyle. 

When I was younger, it used to shock me that people would stay and raise their kids in the same town they grew up in. Weren’t they missing the opportunity to discover themselves and wreck their comfort zones by moving somewhere new? But my judgment assumed their priorities and mindset were identical to mine, which is exactly wrong. If someone’s most important thing is deepening their roots in the community they grew up in, all that matters is that they’ve aligned themselves to that. And while I will never have this experience, it’s something I’ve grown to appreciate as equally valuable.

Not everyone needs to see the world the same way as you. You don’t need to convince people you are right. The best you can hope for is to achieve a sense of alignment and authenticity within yourself. And respect when other people are trying to do the same. Besides, the world would be rather uninspiring if everyone held identical values and pursued the same paths. 

Your perspective and the principles you live by are what define you, your art, and your life. Trust that. Find solace in your direction. But don’t presume it’s for everyone. And don’t allow others to throw you off your game. 

The Greeks had a term for this—euthymia, which Seneca defined as “believing in yourself and trusting you are on the right path, and not being in doubt by following the myriad of footpaths of those wandering in every direction.” The key is that this starts and ends with yourself. 

Until I worked this out, I’d waste a soul-crushing amount of time judging and dismissing other people because of my own insecurities. It wasn’t malicious or all-consuming, but it was decidedly unproductive. When I developed the awareness to recognize this, I was able to better hone my own focus. In turn, this unlocked all the time and energy I wasted worrying about other people and allowed me to channel that towards my own growth. And that’s when I was able to define a stronger direction for my own life. There was nowhere to run when I faced uncomfortable conversations with myself. I couldn’t point to other people as a distraction to avoid self-reflection.

In my own life, self-sufficiency (within reason) is my guiding principle. I want to have skin in the game and make my own way, rather than spectating and criticizing from a distance. I believe voluntary hardship and forgoing too much convenience are key to living a fulfilled life. In moments that force me to choose between comfort and growth, I almost always choose growth. No matter how painful that is. But I no longer pretend to believe it’s for everyone. Directions in life are mutually exclusive. And it’s important to respect divergent paths because those differences are what make life interesting. 

Building confidence in your own path is a critical skill if you want to live a meaningful life. It’s the golden mean between self-doubt and hubris. Find your thing. Trust in your path. Figure out what you’re after in your own life and double down on that, knowing your priorities are unique to you. 

When you stop worrying about what everyone else is focused on and play your own game, you can better navigate distractions and channel that energy towards the things that matter most—actually listening to those around you and making meaningful progress towards your own priorities. 

“There are hundreds of paths up the mountain, all leading in the same direction, so it doesn’t matter which path you take. The only one wasting time is the one who runs around and around the mountain, telling everyone that his or her path is wrong.”

— Hindu proverb

When to Quit and When to Stick It Out

One of the most challenging aspects of your career is knowing when it’s time to move on to your next opportunity.

As you reflect on where you are and what’s next, dozens of questions race through your mind. Is there more to learn here? Should I double down on my current role? Do I still have room to grow and level up my skills? Is this a passing moment of doubt where I feel like quitting because this is hard? Or is it because this experience has run its course and it’s time to move on?

Throughout my career, I’ve pushed the limits of staying too long at certain companies. But I’ve also had moments of doubt where I felt like leaving early because things were hard. Together, these experiences have allowed me to consider the decision point between sticking it out in a current position versus transitioning to something new.

Leaving to pursue a new opportunity at the right time can be one of the best ways to accelerate growth and properly time the Sigmoid Curve—an S-shaped curve that tracks learning, growth, and decline. The goal is to make calculated leaps when you’re at the pinnacle of growth before you reach the decline phase. Otherwise, you risk stagnating and handing back gains you’ve made. But the trick is knowing how to self-assess and recognize once you’ve reached this point.

In October of 2019, I felt like I was reaching the end of the line with my then-current company. But I couldn’t quite articulate why. One afternoon, I took a coffee break with a close friend and colleague. We talked about the challenges we were facing and the patterns we noticed. We also reflected on the problems we were trying to solve as a team and as an organization. 

I voiced my struggles contemplating whether or not it was time for me to move on and try something new. I mentioned how I wasn’t sure if I cared about solving the problem we were focused on anymore. Not just on our individual team, but the underlying problem the company set out to solve. And with this passing thought, I started to identify my true litmus test for knowing when it’s time to look for a new job or double down on the current one. 

I asked myself two questions to better understand my level of engagement:
1) Do I still care about solving this problem? 
2) Would I take this job if I were offered it today?

If the answer to the first question is no, that’s when you know it’s time to move on. It’s also an indicator you’ve reached the decline on the Sigmoid Curve and it’s time for your next leap. 

If the answer to the first question is yes, but the answer to the second is no, maneuvering within your current company to a new role remains a viable option to jumpstart a new phase of growth. 

But if you continue to idle in your current role without being invested in the problem you’re attempting to solve, you’re allowing both comfort and fear to dictate your career. To be fair, it’s easier to sit by and complain than it is to put yourself out there and try something new. It’s also the hallmark of a fixed mindset and the fastest path to unrealized potential—limit all risk and failure. 

There are certainly circumstances and economic conditions when you have to suck it up and deal with it. But you should always be working to anticipate this decline—where learning and growth begin to slow—so you’re able to stay in front of it. 

One alternative to overstaying is flaking from one job to the next. As soon as things get hard, you bail. But the truth is that if you want to make a meaningful difference in your work and the problem you’re facing, you have to be willing to suffer. The same is true for growth. If you’re unable to stick it out when things get tough, a lack of resilience will come to define you. Both your work and experiences will forever lack depth.

On a surface level, those who float from one job to the next might seem like the polar opposite of those who stay too long in a single position. But both are attempts to do what’s easy. When things get hard, the easy thing to do is retreat and cover your ass so you’re not the one who’s accountable. Just as when you’ve started to stagnate and growth has tapered off, the easy thing to do is stick with the familiar and your routine—no matter how unfulfilling it is—rather than putting yourself back out there. 

Instead, do the hard thing. Fight for what you find meaning in. Aligning yourself to this requires reconciling when an experience has run its course versus when quitting is the easy way out. From here you can find the courage to take new risks or push through challenging moments. 

“What man actually needs is not a tensionless state but rather the striving and struggling for a worthwhile goal, a freely chosen task.”

— Viktor Frankl

You’re a better version of yourself when you’re working on problems that you find meaning in. Meaning is a force multiplier for your own engagement and growth.

When you pick a problem you find meaning in, things won’t always be perfect and there will still be noise to sort through. Engagement is cyclical. There will be times you feel close to burning out or struggle to sustain engagement. You will hit low points that you have to push through. But observe your reactions in those moments. Is it because you genuinely don’t care about solving the problem anymore? Or is it because you’re tired, it’s been a hard week, or someone pissed you off? The latter is an indicator that you need to step away and recharge before digging back in. 

When you’ve reflected on these questions, if it’s time to move on to something new your response won’t be riddled with emotion. It’s an observation and acceptance of a fact. Not an impulsive reaction. It’s just time to move on. 

This is the realization that I came to in my last position. I cared about the company and the people I worked with. I just didn’t care about the problem anymore. I felt like I had given all that I was capable of. That was my reality. And accepting it helped me identify the best path forward. 

From here you’re able to make the necessary moves to position yourself for your next leap and optimize for learning and growth. Whether you’re able to make your next move in days, weeks, or months, it’s important to find an outlet to immediately immerse yourself back in a learning phase. Even if you have to pursue this outside of work by writing, reading, or learning a new skill while you search for your next opportunity. 

As your progress through your career, what matters is that you pick a problem you care about. One that’s worth suffering for and resonates with you at that moment in time.

But you must also be able to recognize once an opportunity has run its course. Not because it’s hard. But because the problem you’re solving doesn’t generate the same level of sustained engagement as it once did. That’s one of the best signs that it’s time for your next leap. And timing your leaps is one of the best skills you can develop in your career.

And if you find that deep down you still care about the problem, there’s no better indicator that you’re in alignment and focused on the right thing. 

Using a Growth Mindset to Overcome Your Obsession with Perfection

“We’re ditching you.” I stopped in my tracks, engulfed by a sea of classmates rushing towards the buses lined up alongside Cherry Tree Elementary. This was the drama of fourth-grade in my class of abnormally social ten-year-olds. After I “broke up” with my girlfriend at the time, I was deemed not cool enough to continue hanging out with my current circle of friends. 

We were a strange group of kids, as our parents will likely attest. We did our best impression of teenage life—watching Total Request Live on MTV after school with Dunkaroos and Mountain Dew. We were all new to the dating scene, which at that age consisted of writing on a paper note your “Top Five,” ranked in order of who you wanted to date. If you matched with another person, that made if official. The carousel of dating remained in constant motion, as one’s “Top Five” was subject to change on an almost hourly basis.

While the entire situation seems decidedly stupid now, my friends ditching me was traumatic at the time. Kids are ruthless. And at that age, it felt like the end of the world. It was an early lesson that taught me to keep my ass down. 

I learned to quit drawing attention to myself and found ways to block myself off from criticism and rejection by limiting my exposure to situations where I might fail. This was a defense mechanism driven by my need for acceptance and belonging. It helped me create a sense of safety—however false—as I navigated adolescence.

This became most obvious at school where I was afraid to speak up because I didn’t want to be wrong. Despite being a strong student, this trapped me in a low-learning state for years. The only way I was able to combat this was by reaching for depth outside of the classroom.

In my late teens and early twenties, I largely escaped this by channeling my contrarian nature. Fortunately, I’ve never struggled with peer pressure or listening to myself. But old thought patterns—especially those from childhood—require a deep awareness and years of work to overcome. It’s not an overnight thing. And without having done the self-work, I fell back into this mindset at the beginning of my career.

During big meetings I would feel myself sinking into a corner. I worried the room would judge my every word. Who was I to volunteer my opinion and ideas when everyone else in the room held years of industry experience? 

As author, Carol Dweck points out, this is the hallmark of a fixed mindset which traps you into a low-learning state. The way this reveals itself is through a judge-and-be-judged framework. Your mind projects judgments of others and fuels your own fear of being judged. And this becomes your baseline.

But the antithesis is a growth mindset which shifts the emphasis to learning. Instead of a judge-and-be-judged framework, everything becomes based on a learn-and-help-learn framework. And this is how you better orient yourself towards a high-learning state.

Once you establish self-awareness, it will continue to take years of hard work, patience, and commitment. I still keep this written down in my journal as one of my top areas to focus on for the year. This reminds me to read and reflect on it on a weekly basis so it’s always near the top of my mind. 

But the real benefits of a growth mindset are the threats it allows you to overcome and the bias towards action that it helps you create. 

A bias towards action

One of the biggest advantages of making a conscious shift towards a learn-and-help-learn framework is that it lowers the stakes. It allows you to step back, put things in perspective, and see that not every word has irreversible consequences to you reputation. This frees you to focus on advancing the conversation and exploring different directions, rather than holding yourself hostage to the perfect answer. 

I’ve found in my own career that there’s a tendency to lean on and look towards those with seniority. But everyone’s voice matters. You have a unique perspective that’s all your own. Your own experiences are just as valid. Besides, those who share your commitment to a growth mindset will appreciate where you’re coming from.

A bias towards thoughtful action accelerates the rate at which you learn.

“Becoming is better than being. The fixed mindset does not allow people the luxury of becoming. They have to already be.”

— Carol Dweck

When you find yourself silently judging others, it’s a sign of insecurity and concern over being judged yourself. You become fearful based on the past or anxious about the future. This makes it difficult, if not impossible, to remain present. And growth requires some degree of action in this moment or else you’ll never get started. 

By learning how to recognize and navigate this fear, you create more room for action. To perform at your best, you want to achieve a relaxed state of concentration where you’re focused on the task in front of you and what’s within your control. Not the externals and surrounding noise. 

Top performers who take risks in their work certainly face their share of doubts. And if we’re being honest, a fear of judgment that ebbs and flows. But the difference is that they don’t allow that to dissuade them from creating and putting themselves out into the world. A bias towards action wins out because they better align themselves with a growth mindset that favors the impact of doing and learning over the fear judgment. 

This also manifests itself in how we teach others. One of the easiest ways to identify those who are trapped in a fixed mindset is how they react when someone doesn’t know something they deem to be obvious. It becomes a joke and an opportunity to soothe their own ego at the expense of someone else.

Those who focus on a learn-and-help-learn framework see this as a learning opportunity to step back, provide context, and test their own ability to articulate the idea in a simple way. Rather than teasing that person, they appreciate the fact that they spoke up to ask the obvious and gain clarification. 

Feedback isn’t a threat

For the same reason that a growth mindset encourages healthy risks and a bias towards action, so too does it help you reframe the feedback you receive along the way. 

There’s a difference between feedback and criticism. The more sensitive you are to judgment, the more that line becomes blurred. Feedback is constructive and the more important of the two. Criticism is destructive and often comes from those without skin in the game who don’t have your best interests in mind. 

But a fixed mindset takes everything personally. A person trapped in this state considers mistakes a reflection of their character. Everything is an attack, regardless of its source or validity.

Feedback is only a threat when you’re locked into a judge-and-be-judged mindset. 

With a growth mindset, you disarm this threat. Feedback no longer feels threatening to your character and the stakes don’t feel insurmountable. You don’t have to be perfect or know the right answer every time. You’re able to contribute and push the conversation forward because you’re curious and driven to better yourself, rather than being consumed by the risk of judgment. 

The learn-and-help-learn mindset views these as lessons that are just part of life. They don’t mean you’re any better or any worse of a person. Instead, the missteps, unknowns, and difficult feedback become an opportunity to learn and grow. 

When you come to this realization, you’re able to properly sort between criticism and feedback. The criticism loses its sting. The feedback becomes actionable. 

Reinvent and try new things 

This mindset also manifests itself in how you explore new interests and allow yourself to evolve. With a bias towards action and the ability to reframe feedback, you create an openness to try new things. There’s less anxiety about failing when testing a new approach or exploring new interests.

Every data point, especially failures, are an opportunity to discover more about yourself—what’s worth doubling down on, improving, or moving away from. 

Those who view learning favorably as a chance to grow, rather than obsess over the failure or perception it could create when they stumble, are far more inclined to find their niche during each chapter of life. They’re able to go wide, reassess their interests and reinvent themselves when things get stale. Because they don’t allow a fear of being judged or laughed at dictate every move.

With a growth mindset, your deepest fear becomes reaching a plateau in what you’re learning and your own abilities. Life is motion. Attempting to stand still and preserve an identity, worldview, or set of interests that made sense years or decades earlier but no longer resonates with you will leave you empty. Escaping a fixed mindset also allows you to escape the confines of comfort. 

“The secret to happiness is this: let your interests be as wide as possible, and let your reactions to the thing and persons that interest you be as far as possible friendly rather than hostile.”

— Bertrand Russell

A fixed mindset locks you into a place of hesitation. If you’re only concerned about consequences and people’s interpretations, you’ll learn at a fraction of the speed. You’ll be less inclined to jump into action or try new things that you might suck at.

This is not just relevant to your twenties when you’re trying to find your place in life. It’s relevant in each decade. As your sense of authenticity and identity evolves, you can’t expect to remain still. Finding harmony in that motion requires growth of your own and trying out new things. You’ll never be able to find meaning in new areas of life if you’re unwilling to put yourself out there time and time again, regardless of age. 

An opportunity to grow

A shift into this mindset begins with awareness—being able to step back and recognize when your instincts are pointing you towards a fixed mindset and operating within a judge-and-be-judge framework. Once you train yourself to identify this, you can create a buffer before acting and nudge yourself back towards a growth mindset. 

This allows you a moment of reflection to remember that feedback is a learning mechanism each step of the way—rather than something to be feared. Whether you’re in your twenties or sixties, each moment you face is an opportunity to grow. You don’t need always need to have the perfect answer. 

With a mindset built upon a learn-and-help-learn framework, what might have seemed like a sign of failure before becomes a positive sign that you’re putting yourself out there. And that’s how you grow. By showing up and being the one who steps into the arena.

In contrast, those who find themselves stuck in a judge-and-be-judged framework withdraw from contributing their own ideas and shut down when they receive anything less than praise. They watch from a distance.

Everyone acknowledges this at a surface level—some sort of feedback loop is important to progress. But far fewer people can actually face the feedback that it takes to grow. Whether embracing a difficult conversation or acknowledging an imperfect answer. It’s easier to settle back into the coping mechanism that is passive aggression or judgment without taking risks of your own. 

If you want easy, it comes at a cost. But those committed to growth understand that life is about learning, no matter how painful that might be.

If you want to develop yourself, you’ll need to hone your own bias towards action, a deep appreciation for the present, and an openness to challenging feedback. It’s not about perfection. It’s about building the right mindset to carry with you.

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.