How do the best go about building product? It can take years to build your own list of resources. This article is a curated, living guide to the best product books, articles, conferences, career development programs, and interview tools that will help give you a head start and sort through the noise.
A few years back I interviewed for a product role with an event management company. The beginning of the process was typical – I visited their local office for three hours of initial interviews, followed by another three hours of virtual interviews with their San Francisco office.
At that point, the fit was a maybe on both sides. And if it’s a maybe after 10 hours of interviews and preparation, that means it’s a no.
Instead of either of us calling it what it was, the company requested that I complete a four-hour homework assignment to gather just a bit more information. The circus continued with dozens of texts, emails, calls, and another on-site interview. And finally, I was extended an offer.
While I should have drawn the line before the homework assignment, the indecision on their part gave me a more accurate understanding of their product development approach.
How you hire your product team reflects how you build product. Slow, timid, and scavenging for just one more piece of information? Or knowing what’s critical, pushing forward, and making the best decision based on the available information?
There’s always going to be uncertainty and risk involved in hiring, just as there is in building product. But it’s the amateur product teams who spend weeks agonizing over decisions, failing to account for the value of time.
During interviews, if you experience tactics intended to stall or an exaggerated struggle to make decisions, there’s no reason you should expect anything different in how the product team operates.
I turned down the offer, despite the sunk cost, because of the worrisome parallels. You can tell a lot about product leadership based on the quality of communication and the speed of decisions.
This was one of the determining factors I used to evaluate my current position. It was a no bullshit interview process – the best I’ve ever been a part of. And the hiring process on our product team has proven to be an accurate reflection of our approach to product development.
Consider what your hiring process says about you and your team. If you’re drawing out your interviews for weeks, you’re likely asking the wrong questions or afraid to call a “maybe” what it is, a no. Instead, determine what you’re looking for, move quickly, and operate with conviction (strong opinions, loosely held).
For a better starting place, seek out high-integrity, curious people who add diversity of thought to your existing team. Questions should be geared around this, as well as some combination of analytical skills, creativity, cross-functional experience, and leadership.
And when you’re on the other side of the interview, consider the product, culture, and growth. But don’t give a free pass on the hiring process. If you look close enough, you’ll catch a glimpse of how the product is actually being built.
The best product teams know what they’re working towards – in both their day-to-day and hiring. They’re able to identify what matters, push things forward, and make quality decisions based on the available information. Seek out, and aspire to build, product teams who demonstrate this in every aspect of their work.
*This article was originally featured on Mind the Product
A few years ago, comedian Aziz Ansari released a Netflix special called “Live at Madison Square Garden”. During his set, he joked about the effort required to buy a new toothbrush. Not just any toothbrush would do, he had to have the best. He researched for hours, Googling “best toothbrush” and reading articles on the pros and cons of bristle strength. As he reflected, he questioned his indecisiveness and his desire to have the best when any toothbrush would have done the job.
For most of my twenties, I did the same thing. I researched every purchase – headphones, winter jackets, coffee grinders – in painstaking depth before making a decision. But, as I’ve learned, the quest for a perfect decision often does more harm than good.
Time is far more valuable than a marginally better solution. And if you’re leading product, the sooner you learn this lesson, the better. As a product manager, the worst position you can put yourself in is creating a bottleneck by making slow decisions.
When I started my career, I joined a team building a web-based patient portal for healthcare providers. At the time, I was unaware “product” even existed. But I was forced to learn the space out of necessity. My first manager, Eric, was a walking case study in how you shouldn’t handle product decisions.
With something as simple as our landing page, Eric went back and forth for months. His opinion fluctuated on a daily basis. Without the autonomy to make decisions, our development team wandered without any real sense of direction or progress.
Each week followed the same pattern. The team would align on the problem, collaborate on ideas, prioritize features to build and test, then have the tables turned on them a few days later. Eric was obsessed with surveying every available option. He operated with the constant fear that we might have missed something better. As a result, we wasted months of time and energy considering alternatives with negligible differences.
And if we were unable to make decisions on something as simple as the landing page, imagine what that did to our product which was heavy on integrations with practice management and electronic health record systems. Not to mention the most important piece–the user experience of patient-facing features.
The lesson: hesitation kills creativity, morale, and momentum.
Leaving your team in limbo without a sense of direction is a far worse position to be in than taking a wrong step. It’s easier to forgive a wrong decision than it is a painstakingly slow decision or the failure to make a decision.
“For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.”
If you’re wrong, you want to be wrong as fast as possible. Andrew Stanton, director at Pixar, uses a similar model to evaluate decisions on his films. When faced with two hills and you’re unsure which to attack, the best course of action is to hurry up and choose. If you discover it’s the wrong hill, you can always turn around and attack the other. But you will fail for as long as you continue standing still or running in between the hills.
There will be things you miss and ideas you haven’t thought of. But you’re going to learn more by putting yourself and your product out there than you will trying to make the perfect decision each step of the way.
For many product managers, faster decision making is the most significant improvement you can make. Especially when it comes to the trivial.
While somewhat elementary, the Pareto Principle should be foundational to your decision making. Which solution generates 80% of the value? Forget the other 20%. As Aziz points out in his toothbrush dilemma, perfection requires far more deliberation and research than it’s often worth. If your default position is hesitation – pausing to consider every alternative – you’ll stifle creativity and lose your team along the way.
You can also make immediate improvements by asking yourself a single question, “How reversible is this decision?” Tobi Lütke, Shopify’s founder and CEO, uses a similar strategy by asking himself, “How undoable is this decision?” Decisions that are reversible – most of the ones you make on a daily basis – deserve quick answers.
Better yet, if you have other product managers, developers, or designers coming to you with trivial decisions, empower them to make the call. Performance will improve when there’s a greater degree of autonomy and teams have more creative control over the product.
The decisions that aren’t easily reversible are the rare ones that Lütke spends his time deliberating before coming to a decision. In 2008, he had to decide whether Shopify would remain the lifestyle business he set out to build or shift towards a growth company. With venture capital implications, it warranted thoughtful consideration.[1]
Slow, deliberate decision-making can be a significant advantage in avoiding massive mistakes. But the reality is that most decisions you have to make on a daily basis aren’t permanent in nature. There’s a time and place to use this level of deep thought and consideration. Not when it comes to buying a toothbrush or choosing between two styles on a landing page.
Far too many product managers are focused on perfection from day one – an impossible task. Instead, with proper context, you should focus on making faster decisions. You’ll always be able to adapt along the way as you learn.
If you want to avoid becoming a bottleneck, just keep things moving forward. You’ll be better for it, your team will be more engaged, and you’ll be able to build better products. Decisions lead to progress because they improve the rate at which you learn.
Both life and product become much easier when toothbrush decisions aren’t monumental efforts. Learn to value your time over a marginally better solution. People appreciate decisiveness. And above all, that’s the sign of a true leader in product.
[1] Lütke still felt like he was far too slow in coming to this decision (lifestyle vs growth). To help speed up bigger decisions, he now tries to get as far ahead as he can in terms of vision and where the company is heading. In other words, being less reactive to inevitable, significant decisions that need to be made.
*This article was originally featured on Mind the Product
With each product I’ve built, things rarely come together exactly as planned. But it’s not the inconveniences, technical challenges, or misguided people that are the problem. It’s that we ever allow them to catch us off guard in the first place.
Anyone can operate under ideal conditions. But ideal conditions are the exception, not the rule. Eighty percent of your time building product will take place in a maelstrom of ambiguity and obstacles.
It’s naive to expect that the world should bend to your favor and promote ideal conditions. Most reasonable people acknowledge this. But when it comes down to it, many of us cling to expectations that our work should progress without pushback and our lives should follow a neatly charted map. We forget how much of life is negotiating egos and hidden variables along the way.
The best teams embrace imperfections beyond their control and create great products anyway.
The worst teams self-destruct because they’re too busy obsessing over inconveniences.
It’s easy to pick out the product teams who struggle with this. Each challenge appears to catch them off guard, demoralizing the team and throwing people into a state of anger or despair. This type of reaction points to two things: inexperience and fragility.
Improvement comes from experience and perspective–you’re prepared to face a wider range of potential scenarios. In turn, this allows you to develop a deeper well of resilience and resourcefulness.
At age 23, I started working for a healthcare startup, building out a web-based patient portal. Each setback caught me off guard because I expected things to just work–a laughable statement for anyone who has worked in technology for more than a week. When I went on-site for the launch with our first big client, I was unable to anticipate the ways I was about to get torched.
There were technical challenges inherent to a complex healthcare organization and integrations with its existing software that we had to sort through. But the technical challenges were only half of it. The true test was handling stakeholders–internal and external–as well as the people who create noise and thrive on passive-aggressive emails.
Anyone who has worked in product is familiar with these challenges. There’s nothing unique about them. But I struggled to adapt because my expectations were off base. I lacked perspective. I was focused on perfection in our product and people pleasing–both impossible tasks–rather than creativity and resilience.
The best product managers are able to cycle through dozens of permutations and anticipate certain situations through dimensional thinking. But no matter how good you are, at some point you’ll get hit by something you didn’t see coming. Whether the feature you’ve been working on breaks or a “senior leader” steps in and changes the rules at the last minute, you will encounter situations that test your limits.
Your job isn’t to prevent these mistakes or eliminate every obstacle. Rather it’s to develop the ability to continue moving forward when the inevitable occurs. Leading product requires that you establish an unwavering sense of perspective and imbue this quality in your team. Then, and only then, can you build the resilience and resourcefulness to adapt, imagine creative solutions, and bring them to life.
Resilient teams who cause a few more quality issues will always beat out fragile teams who are only able to operate under perfect conditions. The difference is self-awareness and being able to step back to put things in perspective. This means assuming responsibility instead of feeling sorry for yourself because something you built didn’t work or someone criticized you.
This is not to say that you shouldn’t focus on promoting favorable conditions. You can’t create a complete shit storm for yourself and hope to come out better for it. But you should also understand that you’re never going to get ideal conditions. There are going to be things beyond your control. And that’s what keeps life interesting–the challenges and obstacles you have to learn how to overcome along the way.
Each team meeting, one-on-one, and retrospective is an opportunity to develop these qualities in your team. By challenging each other to maintain perspective and reflect on experiences, you can turn things back to what’s within your control–your attitude, the effort you put into your work, and the guiding principle that propels you forward.
In my experience, few things are more valuable to the morale and resilience of a team than holding retrospectives every few weeks. These are best done with your immediate team (keep things small so everyone can have their voice heard) in a low-stress environment, outside of work. There are multiple formats, but each person should have a chance to discuss what’s gone well and what hasn’t.
This provides a valuable outlet for everyone to air their frustrations, without judgment or repercussions, and remind each other of recent accomplishments. It also allows the team to come together and consider how you might frame challenges in a more productive light and course correct the things within your control.
Retrospectives are just one outlet to discuss experiences and rediscover perspective. And with the right perspective, you can begin building the resilience to navigate the conflict and uncertainty inherent to challenging work.
Creating more opportunities for reflection is the best way to harness experience and build perspective. It’s the first step towards realizing that imperfect conditions are where the majority of life takes place. Knowing this, you’ll be able to lead better teams, build better products, and live a better life.
Expect challenges. Expect unknowns. Expect ego. When you set your expectations accordingly, you’ll waste less time consumed by the things that have happened to you.
Anyone can operate under ideal conditions. But the best product teams don’t sit around waiting for the stars to align. Instead, they embrace the imperfections inherent to life, create their own momentum, and make things happen for them. To steal a line from Charles Bukowski, “What matters most is how well you walk through the fire.”
*This article was originally featured on Mind the Product.
Most people recognize the importance of hiring. Building something from nothing requires a core team of smart creatives with a deep well of curiosity. These are the innovators who are able to connect ideas between multiple disciplines and offer new ways of looking at the world.
But what’s valued in the hiring process–freethinking, curiosity, creativity–is often forgotten in the day-to-day. And it’s your job to preserve this, for both yourself and your team.
If you want to drive results, you need a better strategy than tightening your grip.
Not everything needs to be about efficiency, productivity, and deliverables. Breathing room helps nurture creativity and curiosity. Those who fail to grasp this nuance end up stuck in a one-track managerial mindset, unable to effectively lead.
Progress comes from having the autonomy to stray into the expanse of your mind and connect ideas in new and interesting ways. Focus on getting the conditions right so everyone has the opportunity to create these connections and find fulfillment in their work.
Without this, you’ll face a barrage of apathy, burnout, and unrealized potential. And once you lose engagement, meaningful progress becomes impossible or short lived.
This is not to say that you shouldn’t set deadlines or establish goals. You need this, too. But if you want to sustain engagement and encourage innovation, allow the people you invested the time to hire to do what set them apart in the first place. Let curiosity and creativity lead the way. This puts your team in a far better position to create something worthwhile.
Leaders fight for a balance between deadlines and exploration.
Designers need freedom to explore creative directions.
Developers need freedom to explore new technologies.
Product managers need freedom to explore different visions.
There’s a sense of artistic expression to each. Creating this space helps build morale by pushing each person to find a deeper sense of satisfaction and meaning in their daily work. It also lays the groundwork for innovation by encouraging people to bridge disciplines, offer new ideas, and test different angles.
This mindset is foundational to every high-performing, rewarding team that I’ve been on. Most recently at Asurion, during a recent year-long effort to drive messaging volume, my team reached a place where we were slowing down and struggling to sustain engagement. To rebuild momentum, we created space to explore how we might leverage a few of our ideas in the smart home–a new space we were all interested in.
We balanced this with our primary initiative, as it wasn’t immediately evident how it would fit in or what was technically feasible. But a few weeks later, we finished building out an Alexa skill which allowed customers to speak with our messaging experts asynchronously via text to speech.
We were able to create something entirely new with the capacity to change how our customers interacted with us. But even if we failed and came out with nothing to show for it, the change of pace held value of its own. It allowed us to reenergize and refocus.
What mattered most was that we gave ourselves space to explore.
There won't always be a one-to-one translation between what you’re exploring and the objective you’re working towards. Sometimes pursuing an idea out of a sense of wonder, is reason enough.
Engaging your curiosity and creativity will help expand your perspective and build momentum. Allow yourself to be distracted from time to time and follow the random ideas that strike your interest, regardless of where they lead.
The most brilliant minds throughout history infused their work with a wandering sense of curiosity.
Leonardo da Vinci embodied this better than anyone else. His entire life followed a series of digressions from his career as an artist.
Leonardo allowed himself to be distracted and seek knowledge for its own sake. This led him to study human anatomy, conduct dozens of dissections, create schemes to divert rivers, choreograph pageants, investigate the flight of birds, and create diagrams of technical innovations such as human flight machines.
Some consider this to be a lack of discipline, which only served to pull him away from more important work. But when you study his life in its entirety, you begin to see how these detours helped shape and inform his art. His obsession with human anatomy, for instance, helped him breathe life into the finest details of his paintings, as he worked from the inside out.
As for the more fantastical detours, such as schematics for flying machines or giant crossbows, I doubt Leonardo would consider this wasted time. It was a channel for his relentless curiosity and creativity–the very things that made him who he was, and a source of pure fulfillment.
Creativity and curiosity are the building blocks of engagement.
Everyone needs space to wander, much like Leonardo, and explore new technology, ideas, and interests. Otherwise, you’ll miss the opportunity to piece together your own insights.
Do you want a team of lemmings going through the motions? Or would you rather have a team that’s imaginative, engaged, and curious?
That’s the difference between driving your team into the ground with a relentless focus on productivity and allowing them breathing room to channel their own creativity.
Your first responsibility is to the people immediately surrounding you–not the product, goals, or traditional measures of productivity. You’ll achieve more in the long run when you have morale, engagement, and innovation on your side.
Many smart creatives have lofty ambitions — a desire to create something meaningful, make a difference, improve the world. But it’s easy to get caught up in these aspirations and overlook your most important responsibility.
Each of us has the capacity to directly impact (and improve) a handful of people’s lives on a daily basis through our work. This is our obligation to each other — no matter how high our position or perceived impact.
When you come into work each morning, your first job should be to improve the quality of life for your immediate team. It doesn’t matter if you’re an engineer, analyst, designer, manager, or intern. Everything starts with the people around you. Take your ego out of it. Only then will you be able you branch out and improve, as a group and individuals.
Building the morale of your team is what precedes creating anything of lasting value. If you don’t get it right at this immediate level, it’s impossible to sustain at higher levels of performance with multiple moving pieces.
This can be better understood as a five-tier model, similar to a rather famous hierarchy of needs.
Improve the lives of those on your immediate team
Elevate the quality of individual and group contributions
Establish and grow the culture
Advance the overall mission and purpose
Contribute something meaningful to the world and improve people’s lives
The people around you come first. Before the customer. Before the experience. Before the achievements.
Improving the lives of those around you doesn’t mean making things easier, and it doesn’t mean people pleasing. What it does mean is engaging, challenging, collaborating, and empathizing. And it all must be authentic —everyone’s different, it takes time to build trust and develop your own cadence and rapport.
Environments where people care and know how to push each other, produce better outcomes. This is where the seeds of cultured are sown.
While it’s an individual attitude at its core, you can also structure teams in a way that facilitate this type of growth and interaction. Small empowered teams — what we refer to as journey teams — encourage people to check their egos and focus on coming together. It’s the same mentality in startups — lean, resourceful teams who care about each other, their values, and their mission.
Those who are only in it for themselves will struggle to survive in this type of an environment.
There’s less room to hide behind personal brand — or whatever garbage they disguise it as. While this might work in a more rigid, corporate hierarchy, true motivations become glaringly obvious on self-sufficient teams. Pretending to care about the people around you because you’re supposed to, is not the same as actually being invested. You can’t fake that. At least not for long without breeding resentment and disengagement.
Authenticity, purpose, and challenge are each important if you want to keep smart creatives engaged and contributing their best work. This is one of the most significant obstacles that companies face in today’s business world. That’s why so many people are on the two-year plan, bouncing from one opportunity to the next. It’s difficult to sustain a high level of engagement for years on end.
The best way to combat this is by building a community of people who not only challenge, but care deeply about each other. It’s a true competitive advantage that’s not easily replicated. It’s hard work, that’s why it’s so rare. But few things have a more powerful, direct contribution to your overall wellbeing than this type of work environment.
If you want to make a difference, start by making a difference in the people’s lives immediately surrounding you, then build from there. This remains true regardless of what aspirations you hold.
Show compassion and interest towards the people you work with. Discover meaning in your work, together. Enjoy your time together, struggle together, and strive to improve each other’s lives.
If you want to achieve what you’ve set out to, you’re going to need people who care about and challenge each other. That’s what it takes to bring an idea to life and contribute something meaningful to the world. When you make this your first responsibility, everyone will come out better for it.
Six years ago, I found my way into product management out of necessity. I was beginning my career at a healthcare technology startup in what was supposed to be a marketing/communications position. But during my third month on the job, I was thrown on-site at a regional hospital to help facilitate a go-live with our software. As it turns out, job titles don’t always predict the scope of your work in startups.
That day, it became obvious that there was a significant gap between key stakeholders, customers, and our development team. It was impossible to prioritize or build the right thing because we weren’t close enough to the end user. As a result, we ended up working exclusively on client requests–perhaps the least effective way to develop a product. We needed someone to step in, close the gap, and work alongside our small team of five developers. Cue my newfound career path.
As companies learn the importance of evolving into product-driven organizations, there are increasingly greater opportunities for those with a specific skill set — see below — to explore product management. Over the past few years, I’ve put together some of the key lessons I’ve learned from leading product at my own startup, as well as from the innovative, hardworking teams that I’ve had the privilege to be a part of.
Broad exposure to a range of subjects enables you to leverage the most useful knowledge from each and make better decisions. Specialization gets a lot of attention these days, but it doesn’t fly here. Product requires seeing things from multiple angles and being able to quickly navigate a latticework of mental models. On any given day, you need to be able to evaluate the user experience, assess the feasibility from a development perspective, identify and sort relevant data, communicate key experiment results, and determine how a feature aligns with the overall vision.
Developing a multidisciplinary approach should also help to set you apart, as most who work in technology are focused exclusively on concepts and trends native to the industry. The majority will miss the important lessons and models from other fields of study that can be applied more broadly.
But the ultimate reward is that by positioning yourself at the intersection of multiple disciplines, you develop the ability to connect seemingly unrelated ideas 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.
The best companies look for diversity on their teams in terms of background and experience, as well as hard and soft skills. This range of skills includes analytics, communication, design, development, research, strategy, synthesis, and user empathy, to name a few. Figure out which you’re good at and commit to developing those skills further.
That’s not to say you shouldn’t listen to feedback about where to improve. But you distinguish yourself by becoming very good (top 25%) at two or three skills.
Reaching this level demands years of dedication to your craft and the discipline to continue learning. You’ll only be able to sustain this effort if you allocate more energy to the skills that you’re naturally drawn to and enjoy immersing yourself in for indefinite periods of time.
“You make yourself rare by combining two or more ‘pretty goods’ until no one else has your mix.”
Any job with “manager” in the title carries an immediate connotation that you’re overseeing people. There’s no worse approach to product or faster way to alienate your team. Your sole focus should be on building the best product and user experience. This means collaboration with your team, not management. And if you’ve developed at least a few skills in the top 25%, you should be a true contributor.
Those who resort to managing people often do so because they lack the willingness or ability to contribute to the experience being built. Make yourself an indispensable part of the process.
You can’t possibly have the answer to every question, nor should you pretend to. The most intelligent, respected leaders are always aware of the limitations in their knowledge. But you can help your team clearly articulate questions and begin to uncover answers through conversation.
If you’re able to help others think more rationally and find their own answers just by talking it through, you’re naturally going to get more buy-in than you would by telling someone what to do. It’s human instinct to feel more invested in answers and solutions you’ve helped come up with.
When everyone on your team is engaged, contributing, and learning from one another, the quality of work improves significantly. This skill demands exceptional listening and learning how to ask better questions. If you do it right, you will be able to promote transparency, self-awareness, and better orchestrate the perpetual moving pieces.
First-order consequences are those that are immediately evident and often end up in contradiction to long-term gains. Failing to think beyond first-order effects often results in poor decision making. For example, most of us might not enjoy the rain. But we wouldn’t wish away rainy days because the subsequent-order consequences–drought, wildfires, famine–are in direct opposition to our best interests.
While product is slightly lower stakes than climate, tunnel vision is a common struggle when building out a feature that’s intended to drive a key metric. You might be focused on retention, but how is that affecting the bigger picture? What if you’re compromising the experience for customers who are your strongest advocates? What if the strategy contradicts the identity you’re working to create?
It’s important to move fast, but it’s also important to navigate between these different levels so you have fewer headaches down the line. You’re not always going to have a definitive answer, but this thought exercise should help you consider the future implications of your decisions.
This is one of the biggest struggles I see from entrepreneurs across the board. Everyone wants to pour money into their project because they’re convinced it’s a million-dollar idea. But very few have the humility to prototype a product, put it out there, and seek honest feedback. And unless your risk tolerance borders on insanity, this is the cheapest, most effective way to assess the viability and potential market for your idea.
As a product manager, the story remains the same. You want to figure out the fastest, cheapest way to test your concept. This often requires hacking something together, getting it in the hands of your users, and actually listening to what they have to say. Great product managers find creative ways to gather customer feedback at the earliest stage possible.
“Human beings are complex and fickle, so it’s impossible to predict how they’ll react to a brand-new solution. When our new ideas fail, it’s usually because we were overconfident about how well customers would understand and how much they would care.”
The momentary discomfort that comes from seeking brutally honest feedback is far less of a risk than taking off in a blind sprint based on intuition. You want to limit the potential downside and wasted effort whenever possible. The earlier you’re able to correct potential flaws in your product or assumptions, the greater your likelihood of success.
Most people never venture past the surface level of the “fail fast” mentality. We acknowledge that failure comes with the territory when working on disruptive ideas, but we forget to consider the underlying importance of this sentiment.
The goal should never be to force an idea to work, no matter the cost. It should be to assess if there’s a “there” there, as quickly as possible. There’s a fine line between sharing an overall vision and becoming emotionally entrenched in the success of a specific feature. The latter blinds you from objectively assessing outcomes and often leads to bad practices, i.e. “massaging” the data.
As a product manager, your job is to take chances and determine which opportunities show promise. When one of those efforts doesn’t result in the next big thing, there are still positive takeaways. You definitively know that it’s better to allocate energy elsewhere, which is valuable knowledge that will help shape your company’s direction. With the right approach, failure is a sign that you’re committed to pushing the realm of current possibilities–a necessity if you want to evolve your product and position yourself for long-term success.
As we acquire experience it’s natural to wonder what we would change or tell our younger selves. It’s all the more intriguing when the question is posed to the entrepreneurs we admire.
The one consistency I’ve found is that few advocate altering the course of their lives. The entrepreneurs we consider successful don’t wish away past events or decisions they’ve made. When asked if there’s anything they would do differently in their careers or lives, they reject the question entirely. They’re comfortable with the decisions they’ve made and the obstacles they’ve faced because it has led to where they are today.
At an individual level, this a productive, if not essential, behavior. But some of the most brilliant minds also have a tendency to prescribe their past decisions as a blueprint for others to follow–advice that’s in direct contradiction to their emphasis on the importance of making it their own way.
The reality is that there is no single path to success and it’s impossible to make the optimal decision every step of the way. But you stand a far better chance if you leverage your unique abilities and embrace the direction you find for yourself, instead of attempting to replicate the decisions of those who have experienced past success.
The Greeks defined this as euthymia. Seneca explained it best 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.” Some will call this fate. Seneca referred to it as tranquility.
Once you trust in the direction you’re heading, you’re able to better negotiate one the most formidable obstacles you face–yourself. As you move out of your own way and out of your own head, you free yourself to make meaningful progress instead of second guessing.
It should come as no surprise that most successful entrepreneurs embody this lesson. But their unequivocal belief in themselves and their ideas often makes it difficult for them to refrain from projecting their path upon those with open ears.
Queue the contradiction–advocating the importance of your individual path and choices, then turning around and prescribing specific actions to others attempting to reach similar goals. It’s something I encounter on a weekly basis, with advisors directing early-stage startups to emulate a specific set of actions because it worked for them once upon a time.
To be fair, this seems to be a human tendency–regardless of the degree of success experienced. But pay careful attention to the next podcast you listen to when the inevitable, “What advice would you give your 20-year-old self?” comes up. Is the line drawn after relevant insight and a useful aphorism, or does it digress into advice for listeners to follow an exact sequence of events?
This is a useful way to identify the smartest entrepreneurs in the room–those who understand that their choices are their own and could never be replicated by anyone else. They accept that there is no standardized path for getting from A to B.
While it’s important to trust in your own direction, pretending like every decision you’ve made has been the optimal choice and that others might follow your exact path, is ego at its finest.
The belief that your route and your decisions were the only possible combination to get to where you are today is just not true. At best, it’s a foolish narrative we tell ourselves that takes the concept of fate too far. At worst, it’s pure arrogance. The concept of euthymia is only relevant at an individual level.
The likelihood that anyone has made the correct decision every step of the way–or that there is even a “right” decision to begin with–is an impossibility. Each one of us, including the most successful, have made the wrong move at certain points in time. And that’s okay. Some decisions carry greater weight than others, obviously you want to avoid the fatal errors. But more often than not, it’s about what you do next. What’s your next move? How can you use this decision as leverage to get closer to where you want to be and better yourself?
Success, as defined by you, is far more about resourcefulness than a checklist of prescribed actions.
There are dozens of ways to get to any single point. What’s important is your strategy for dealing with obstacles and learning from failures, not your attempts to replicate someone else’s career or life progression. The likelihood of the latter working is infinitely small and would require far more energy in attempts to exert control over random events.
The more productive route is to harness the energy from random encounters, breaks, and obstacles that are unique to your own life, and turn them into momentum.
“There are routes to success that are nonrandom, but few, very few people have the mental stamina to follow them.”
This is not to say that you shouldn’t learn from the mistakes and lessons others have faced, whenever possible. But to a much greater extent, the course of your life will be determined by your resourcefulness and willingness to learn when you come up short. Sustainable success is built by having skin in the game–as Taleb advocates–and learning as you go.
Advice to follow a template of decisions should be approached with caution. The individual path and environment that worked for someone else, no matter how successful, is irrelevant to your current position.
You will never be able to replicate the lives of the entrepreneurs that you admire. But you can examine the systems and mental models that give them their competitive advantage. This is where you’ll find the truly valuable lessons that you can apply to your own life, direction, and decision making.
