entrepreneurship, mindset

Past Shapes Present

William Wordsworth, a well-known 18th century English poet, wrote:

“Life is divided into three terms – that which was, which is, and which will be. Let us learn from the past to profit by the present, and from the present, to live better in the future.”

Wordsworth was making a salient point: Our past experiences shape our present reality, and how we steward today impacts our future. Before founding Simple Modern in 2015, I worked for a non-profit ministry for nine years, and that experience powerfully shaped my approach to business and culture.

Three lessons, in particular, stuck with me as I began my journey as an entrepreneur.  Each of them directly impacts how I lead Simple Modern—both now and into the future.

Lesson 1: Creating A Culture Of Humility

Humility is one of Simple Modern’s core values, and it profoundly impacts our company’s culture and day-to-day operations. I would define humility as having a sober-minded view of self. It is not pretending that we aren’t any good in an area that we are truly gifted. Conversely, humility also is not having a puffed-up or overly elevated view of our importance or abilities. As a former leader of a ministry team, I experienced how critical it is to a team’s culture.

As with most non-profit organizations, our team was small but dedicated, usually consisting of 6-8 people at any given time. Everyone had to be willing to do the unglamorous day-to-day work needed to keep the ministry operating. No team member was above any task. Another area where humility was critical was in our self-awareness. Ministry is about helping other people to experience internal breakthroughs in how they view themselves and the world around them. Howard Hendricks once said, “You cannot impart what you do not possess.” It is impossible to help others have a higher level of self-awareness unless you have personally done the hard work of personal excavation.

Each of us has areas of our character that we consistently struggle with throughout life. For me, my pride has been the most consistent thorn in my side. I have learned that, when left unchecked, it leads to me having an inflated view of self. Humility is the antidote to pride. It neutralizes the poisonous effects that pride can have on our relationships and career. When we check our ego at the door, we become better teammates and better leaders.

One of the most impactful decisions I have made in my life happened about halfway through my college career. It started when I realized that I was far more flawed than I had ever been willing to admit. Up until that point, when I received negative or even constructive feedback, I would immediately respond with defensiveness. In my mind, it was up to the person offering the feedback to prove that their observations were correct. This epiphany led to a small but significant change in mindset. From that point forward, when I received unflattering feedback, I assumed that it was true instead of having the default assumption that it was false. This simple decision has transformed my self-awareness and led to countless growth opportunities as I have learned more about how others experience me. The key was my willingness to lay down my pride in search of a more accurate view of myself.

Giannis Antetokounmpo is one of the 2-3 best basketball players in the world. He is a two-time MVP and is now the reigning Finals MVP and leader of the world champion Milwaukee Bucks. Recently, a reporter asked how he dealt with his ego as he grew as a person and player. I thought his response was remarkable:

When we founded Simple Modern in 2015, we knew that humility needed to be a part of the foundation. Over the past six years, we have been fortunate to experience a lot of success. Our collective desire to prioritize humility has helped prevent competition, ego, entitlement, and pride from eroding our culture. Not only that, it has spurred tremendous internal growth for our team.

Lesson 2: It’s Not About The Profits.

The word non-profit means precisely what you would think. No profit. During my years in ministry, my team and I raised support to pay our salaries. All additional funds and resources went towards the organization’s administrative costs. In the non-profit world, the point of the money is to enable serving others. For this reason, in the ministry world, profit can seem like a four-letter word.

You can imagine the tension I felt when I first transitioned from ministry into the business world. In the business world, especially e-commerce, there is a bias toward numbers and profit. An organization’s success criteria usually revolve around what drives the most profit. I wrestled with this for several years before seeing how these seemingly contradictory ideas could work together.

Simple Modern’s culture is founded on the idea that generating profits makes generosity possible. As someone with non-profit and business experience, I now understand that profit is not necessarily bad. Profits can be redemptive and beneficial when used to care for and serve employees, partners and customers. For our company, this looks like giving generously to worthy non-profit causes, investing in our team members and their families, and offering premium quality at generous prices to our customers. In other words, in a healthy business, the profits make it possible to impact more lives positively.

Lesson 3: Explain The “Why”

In the non-profit world, you come to understand the need and importance of mission and vision. Mission and vision motivate people. In my non-profit leadership role, I wasn’t paying my team. We were all raising our salaries. To keep them invested in the ministry, I had to repeatedly articulate “why” we were doing what we were doing and coach and lead them using motivation.

Author Simon Sinek wrote a book called Start With Why. In his book, he explains the significance of starting with the question, “why,” as opposed to “what” or “who.” According to Sinek, explaining “why” we are doing what we are doing is critical. It unifies the team and creates a common reason for everyone to work together, leading to increased engagement and success.

This lesson translates to the business world. Whether it is sales or recruiting, leaders must get people to buy into the overarching mission and vision. When employees feel connected to the mission and vision of the company, they more deeply bond with their teammates, have greater job satisfaction and are ultimately more empowered to do their best work.

Antoine de Saint-Exupéry, a French writer and poet, captured the essence of this when he wrote:

“If you want to build a ship, don’t drum up the men to gather wood, divide the work, and give orders. Instead, teach them to yearn for the vast and endless sea.”

Rather than telling people what to do, communicate mission and vision, and tell people why they are doing what they are doing. Teach them to yearn.

Closing Thoughts

My perspective was irrevocably shaped by my years working in a non-profit context. That experience had a profound impact on how I view my life’s mission and the purpose of my career. Not surprisingly, the Simple Modern mission statement is straightforward:

We exist to give generously.

It is possible to fuse the most potent aspects of the non-profit and for-profit worlds to create thriving organizations. We all want our lives to be a part of impacting the world in a positive and redemptive way. When we lead with humility, generosity, and vision, it enlarges all our futures.

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entrepreneurship

Chapters

The early days of a startup are a singularly unique experience. You are bringing something new into the world, no one knows who you are, and no one cares. It is obvious quickly how difficult it is to gain traction and become relevant. When we started Simple Modern in 2015, the hydration market was full of established, well-run, strong brands. During the first couple of years, I was repeatedly asked questions like, “Aren’t you just selling a knockoff?” and “Why would anyone want to buy your product over the other options that already exist?”

Also, money is always scarce. Every startup that I have been a part of has been bootstrapped. While I am partial to this funding method, it all but guarantees that money will be tight for at least the first few years. Our foundering team did not draw any salary until the company was almost a year old. Our office in the early days was an upstairs room in my house or the local Panera Bread. We scrounged for ways to do things less expensively and conserved the limited resources we did have for inventory purchases. In contrast, during our first year of operation, two of our hydration competitors were bought by large corporations for sums approaching half a billion dollars each. After a couple of years, we swallowed hard and invested the money to attend the International Home and Housewares trade show. The day before the show was used by exhibitors for booth setup. While we admired the 6 figure displays that other competing brands had created for the show, we sheepishly set up shelving that we had purchased at IKEA. At one point, we watched employees from a competitor walk by our booth, literally pointing and laughing at us.

Ironically, the difficulty of building a startup is also an important part of why the experience is so rewarding. Without the advantages our competitors enjoyed, we had to think creatively. We compensated for our relative lack of resources with sweat equity. There were long days and nights, but in the process, our early team bonded deeply. We developed a tenacious underdog mentality and a correspondingly big chip on our shoulders. I saw growth in my personal character and humility as my role called me to help lead us through challenging situations. As the business grew, it filled us with immense gratitude because we knew how difficult it had been to accomplish. When we talked about the future, it felt like a big place full of possibility and promise. The early days were an incubator of relational, personal, and professional growth for all of us.

My experience had taught me about the emotions behind running a startup. Before I co-founded Simple Modern, I had been a part of starting and scaling several e-commerce businesses. As a company grows, it is easy to focus on the future not yet obtained instead of enjoying the present. I would often spend my time thinking about acquiring the next group of customers, improving our processes to reduce chaos, implementing the latest technology, and achieving greater stability. As a result, I consistently had a feeling of wanting to graduate to the next phase. But when I looked back on those years, I realized that it was truly the process and not the destination that I had enjoyed. The clip below from The Office sums it up perfectly:

Because Simple Modern was not my first rodeo, I made a conscious effort to live in the present. Those early days were some of the best days of my life.

Growth

I vividly remember taking my son to Disney World for the first time in the spring of 2016. Simple Modern had just started selling water bottles the week before we left for our vacation. During our trip, I was struck by the number of water bottles and tumblers in the park. I began to take mental notes about the brands and types of water bottled I spotted the most frequently. When I returned, I set up a Slack channel called #inthewild where our team could post pictures when we spotted others using our products. Early on, I was surprised at how infrequently we posted on the channel. It turns out that you need to sell a LOT of products before you start to see them organically.

We were fortunate that Simple Modern quickly experienced product/market fit. As we released products, we saw our sales and brand presence continue to increase. A little after the company’s 2nd birthday, Target offered Simple Modern nationwide distribution. When my family revisited Disney World in the summer of 2019, I usually spotted several of our products each day. Not only were we successfully selling more units, but our brand was beginning to really resonate with customers. People loved our combination of premium quality, affordable prices, and dedication to generosity.

As our sales and customer base grew, everything else followed suit. We moved into our first office in May 2017, and by mid-2018, we had already begun looking at options for a larger office. The team also continued to grow. From our initial core team of 10, we slowly grew to 15. We had a strongly ingrained “slow to hire” mentality, but by the time we made our next batch of hires, it was obvious we had waited too long. After months of not hiring, we hired 5 people during one particularly hectic week in Fall 2019. The new reality was also impacting the company’s bank account. For the first time, it felt like we had a little financial breathing room. Although our circumstances had changed, things still felt very much like a startup. There were very few established processes, and most core leaders still wore several different hats out of necessity. At times, chaos reigned as we sprinted to keep up with our growth. I reminded my teammates to soak in the experience. I would say things like, “Even though things feel stressful and crazy right now, don’t be in a hurry to get to the next phase. In the future, you will remember these days and wish you could experience them again.”

The End of the Beginning

As we have been building Simple Modern, I have been squarely in the season of raising young children. When we founded the company, my son was four, and my daughter was not quite one. The experience of being a father has been one of the most enjoyable highlights of my life. Recently my wife and I cleaned out some old toys, and I was struck with a pang of sadness and nostalgia. I looked at toys that my children had once adored and thought about playtimes gone by. It was a poignant reminder that my kids are growing up. Someday soon, they will no longer be children. I have always been aware that is happening, but that moment underscored a gradual transition happening every day.

My work life has been filled with signs of transition as well. Last year our team moved into an incredible office that could serve as the company headquarters for years to come. We have grown from 3 co-founders to 45 amazing full-time teammates in just a little over 5 years. We now serve millions of customers worldwide and have the privilege to partner with some of the world’s leading retailers.

Last week our company experienced another significant milestone. The fifth person to join our team transitioned to his next adventure. He was a great teammate and friend. He had accomplished everything that he wanted to achieve with Simple Modern, and he is leaving on great terms with everyone. I am excited for his entire family as they will now live close to both sets of grandparents. Personally, it was a sobering experience for me. His transition was a concrete reminder that Simple Modern is no longer in its infancy. I realized that it was just like watching my kids grow up, it has been happening gradually all along, but this moment highlighted that we are at the end of a season. As I reflected on this reality, I was reminded of Winston Churchill’s words:

“Now, this is not the end. It is not even the beginning of the end. But it is, perhaps, the end of the beginning.”

I think our company has a tremendous future. I’m encouraged by the products we are developing, the customers we get to serve, and the opportunities to give generously that the business provides. We have the most talented team that I have ever had the opportunity to work with, and it seems obvious to me that there are decades of growth and expansion in front of Simple Modern. At the same time, it feels right to reflect at the close of a chapter in our story. The main question I am asking myself is, “As our company continues to grow, what should never change?”

A picture from our first annual company retreat in 2017

Always Day 1

Over the last 25+ years, Amazon has grown from a garage startup to perhaps the most significant company in the world. As it grew, one of the attitudes that Jeff Bezos consistently championed was a “Day One” mindset. “Day One” thinking acknowledges that although the internet has made a tremendous impact on our lives and our society over the last 30 years, we are still at the very beginning of its story. As Amazon grew, Bezos wanted the focus to lie on the vast possibility ahead instead of how much Amazon had accomplished and grown. When asked what “Day 2” is at Amazon Bezos said this:

“Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.

I’m interested in the question, how do you fend off Day 2? What are the techniques and tactics? How do you keep the vitality of Day 1, even inside a large organization?”

This way of thinking has helped Amazon stay innovative, agile, and creative even as they have scaled to a behemoth company with almost a million workers.

It is still Day One at Simple Modern. We have come a long way from the plucky startup that we founded 6 years ago, but we have just begun to scratch the surface of the impact that I believe we are destined to make. We started Simple Modern based on the belief that there is a better form of capitalism. We believe that so strongly that our company mission statement is “We Exist to Give Generously.” As we experience a growing company’s changing seasons, my goal is to keep a startup spirit and commitment to generosity central in everything we do.

When I am 80 (if I get that long), what will I remember about the last few years? More than anything else, I will remember the relationships. The singular best part about Simple Modern is being surrounded by people that I deeply respect and enjoy. Being a startup CEO has helped me to grow immensly as a person. I have learned that career success pales compared to relational connection, and I have seen just how many weaknesses I have. I need to be challenged and loved by others who are for me. When I was younger, I thought the goal of leadership was to build organizations. Over time I realized a simple fact – in life, we are all passing through. Every person who works at Simple Modern will someday exit, even me. Organizations are simply containers that we pass through over the course of our life. I believe that what defines great organizations is that they help the people who pass through them flourish. As the chapter turns, I am thankful to have been a part of creating an organization that puts people first.

Here are some questions for refelection on this subject:

“What is an area of my life where I am in a hurry to graduate to the next phase? How is that impacting my ability to learn from and enjoy the experience today?”

“What will I remember about this season of life when I am 80? What are the areas that I am investing my time, money, or effort that will not matter to me when I look back on my life?”

“Where am I experiencing grief from a difficult transition? Who can I process these feelings with?”

“Am I taking regular time to reflect and express gratitude, or am I overly focused on the future?”

“Where am I scared to transition to the next season even though it is time?”

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entrepreneurship, mindset

Mistakes are Tuition

Over the course of his 84 year life, Thomas Edison acquired a record 1,093 patents and helped create the movie camera, microphone, the stock ticker, and even an early version of the tattoo gun. Edison famously only slept around 3 hours per night and could exist on such a small amount of sleep because of his frequent catnaps. He was also an exceptional promoter and businessman. His company, General Electric, is one of the oldest and most successful companies in US history.

His crowning achievement was the development of the incandescent light bulb. Over a several-year period, he worked to find an affordable and reliable solution to gas-powered lighting. The primary challenge centered around developing a filament that would be durable but cheap. In total, his team tested more than 6,000 possible materials before finding a solution made from carbonized bamboo. The process was expensive and full of prototypes that did not produce the desire results. However, when asked to reflect on these trials, Edison said:

“I have not failed 10,000 times. I have successfully found 10,000 ways that will not work.”

Edison’s mindset is worth examining. He did not view the thousands of unsuccessful experiments as failures. Instead, he saw them as the stepping stones that eventually led to the successful prototype.

How We Learn

There is a growing body of evidence that we learn most effectively by experimenting and analyzing the results. When we are young, we learn about the world around us by touching and tasting everything. No matter how many times we hear that a stove is hot, we ultimately have to experience the discomfort of being burned to understand. As a parent of two children under 10, I have concluded that good parenting includes allowing your children to fail in non-fatal ways.

In one recent study, researchers in Singapore examined how seventh-grade math students learned. Researchers divided students into a “direct instruction” group and a “productive failure” group. The direct instruction group learned how to work problems through a step by step tutorial from an instructor. In contrast, the productive failure group was allowed to struggle and fail at solving the problem. After allowing the students to attempt several unsuccessful methods of solving the problem, an instructor would help them analyze the failed attempts and find the correct answer. The study culminated with a final exam. The productive failure group significantly outscored the direct instruction group on all problem types. The most successful students were productive failure group participants who now could solve problems through several different approaches. The unsuccessful attempts had laid the mental framework for successful mathematical thinking.

The Cost of Wisdom

What are the implications? It means we don’t retain spoonfed wisdom very well. Instead, our learning correlates to its cost. Several psychological terms describe this tendency, like the sunk-cost fallacyendowment effect, and the Veblen good. One recent US Bureau of Labor Statistics study found that college students who worked a part-time job had an average GPA of 3.13, while nonworking students had an average GPA of 3.04. When you are washing dishes to pay for your classes, you are more motivated to absorb the information. We use the word tuition to describe the cost we pay to acquire wisdom and knowledge. Sometimes tuition is financial, but it can also be time, effort, reputation, or physical health. The more tuition we pay, the more deeply the experience impacts our future thoughts and actions.

At Simple Modern, we are deliberate about empowering teammates to make decisions and learn from the results. Sometimes this doesn’t go well. It could take the form of a new product that fizzles out before launch or a marketing campaign that fails to connect with our customers. Over the years, I have made two different leadership mistakes in these situations:

Mistake 1: Responding with frustration, anger, and disappointment. When I react this way, it expresses disapproval. If done repeatedly over time, this creates an environment of fear. It discourages innovative thinking and experimentation. I have learned a simple lesson about leadership – it’s never helpful to get angry.

Mistake 2: Minimizing the situation. It is equally unhelpful to sweep a disappointment under the rug. This behavior can be motivated by a misguided desire to protect ourselves or others. Unfortunately, it discourages honest assessment and introspection. It can also invalidate the disappointment others are feeling.

I am learning to respond differently to these situations. First, no one enjoys the feeling of disappointment. Give yourself and others empathy and grace. That will create a safe environment where real analysis can happen. After providing some time for introspection and reflection do a postmortem. What went wrong? Why didn’t things go as planned? If we could do this project over again, what decisions would we make differently? What unknown weaknesses did this situation expose? Just as Edison’s thousands of unsuccessful lightbulb filaments made his ultimate triumph possible, these clear-eyed evaluations are the foundation of personal development and growth.

A Million Dollar Mistake

Around the beginning of 2016, Simple Modern was about to launch its first insulated water bottle. We observed that the larger drinkware market lacked premium quality but affordably priced licensed drinkware options. Internally, we believed we could create the ideal solution, so we began the lengthy process of pursuing NCAA licenses while simultaneously launching our branded products. After building several samples, the University of Oklahoma agreed to be our first licensing partner. Shortly after, we had one of the most significant breaks in our company’s history when the retailer Sam’s Club agreed to consider our products. We were incredibly fortunate to show our product to a buyer that shared our vision and excitement. That meeting would set in motion a purchase of several hundred thousand units for retail programs in 2017. As you can imagine, we were ecstatic. Every consumer brand’s goal is to gain customer awareness. This program would be a massive shot in the arm for our new company.

There was a small but gnawing question in the back of my head. “Who is going to buy all of these tumblers?” Throughout the sales process we had been so focused on the product that we had not spent much time evaluating the order size. Everyone agreed that there would be a lot of demand for the product, but we would be launching something brand new. I pushed those thoughts to the back of my mind because there was plenty of other work to be done. We were simultaneously managing rapid growth in our branded business while executing on a complex order for Sam’s Club. In May 2017, our team spent almost two solid weeks unloading containers and loading trucks with over 500,000 NCAA licensed tumblers. In addition, we had discovered a packaging issue that required us to unpack scores of pallets, individually sticker the units, and then re-palletize the products. You can check out a time lapse of that process below.

One of my favorite memories from those days was a night where we loaded trucks until 10 pm and then went to watch a late-night showing of Guardians of the Galaxy 2. The picture below is a panoramic of all the product before we began to ship it out.

The initial sales data looked promising. A few clubs had sold through entire pallets in the first weekend. The program had launched right before Father’s Day, and our item had been a big hit as a gift purchase. It was a real mountain top moment for the company. In the weeks that followed, we realized something less encouraging. Father’s Day weekend was the peak of demand for the entire summer, and it was starting to look like we would not sell through all the two packs during the allotted program time. As the summer drifted towards August, it became evident that we had a problem. The product was great, and it had sold well, but we had shipped Sam’s Club way too many. When a retail program doesn’t perform to the sales plan, the brand leadership and buyer devise a strategy to fix things. In this case, there were tens of thousands of extra two packs that needed a home. During one of the conference calls during this period our buyer said something that has stuck with me when she observed, “Everyone talks about wanting to be a great partner but during situations like this you learn who really values partnership.” We were fortunate to be working with a buyer that was a true partner. Working together we devised a plan, but for it to work we had to make the painful decision to buy back almost $1,000,000 of product. It was the right decision, but company finances would be very tight for most of the next year and a half.

It was disappointing not to sell through all of our products, but the experience was not a failure. It was tuition. We had initially believed growing our brand required us to sell as many units as possible, but we learned that selling an appropriate amount of product is even more critical. Over the last few years, I have seen how learning from that tuition helped us grow into a more effective company. In 2020, we were preparing to ship another licensed order to Sam’s Club when the COVID stay-at-home orders went into effect. We worked quickly with our partners at Sam’s Club to modify the order’s size before it shipped. The result was a great program where everyone won.

When things don’t go well, it creates the perfect environment to grow and learn. We can convert our mistakes into the fuel for our growth. As Henry Ford once said:

The only real mistake is the one from which we learn nothing.

Reflection Questions

What is your most recent disappointing outcome? Did you view it as a failure or tuition?

When have you empowered someone else by reframing a disappointing outcome as an opportunity for growth?

What is an example of failing to use a setback or mistake as tuition in your own life?

Who are the people looking to you for leadership (at home, work, personal life)? How can you apply this principle to responding to their misstakes or missteps?

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The Eighth Natural Wonder

Seventy million years ago, a group of North American tectonic plates began to shift slowly. This movement produced tremendous pressure that lifted an entire region to almost 7,000 feet above sea level. For millions of years, not much happened until a small stream began to develop along the surface of the rock. Occasionally there would be a flood, and the stream would fill with more water and other objects like rocks.  These stones would serve as little chisels pecking away at the supporting rock below as the current carried them along. But every day, the stream grew bigger and burrowed a little deeper. Eventually, it was no longer a stream but what we now know as the Colorado River. Over millions of years, It carved one of the world’s seven natural wonders: The Grand Canyon.

Once you have experienced the canyon’s awe-inspiring scale, it seems inconceivable that it was once an unremarkable little stream. What makes this landmark unique and rare is how a focused action repeatedly happened for millions of years in a row. It is a quintessential example of compounding.

Compounding is when things grow in an exponential instead of linear pattern. Albert Einstein is undoubtedly one of the greatest thinkers the world has produced over the last few centuries. His theory of relativity has become a cornerstone for our understanding of time and how the universe functions. He plumbed the deepest depths of thinking about time and space, but he was the most amazed by compounding. Einstein’s fascination with the concept led him to observe: 

“Compound interest is the eighth natural wonder of the world and the most powerful thing I have ever encountered.”

Compounding can have a profound impact on our relationships, career, abilities, finances, and health. When harnessed, it has the power to improve our quality of life dramatically. It is as elusive, however, as it is powerful. As Charlie Munger put it:

“Understanding both the power of compound interest and the difficulty of getting it is the heart and soul of understanding a lot of things.”

Capturing the benefits of compounding starts with examining its core ingredients: action, focus, and time.

Action

We first learn about compounding as a principle for saving and growing our money. When I was in grade school, I discovered that when I put my money in the bank, it gains interest over time, and the total begins to grow exponentially. I initially thought of compounding as a passive process, but the opposite is true. The bank can only pay me interest if they are successfully loaning the money I have on deposit. If the bank stops generating new loans, it will not have the funds to pay my interest, and my deposits will not compound. Compounding requires action.

Every day we are faced with choices, and those choices manifest in our thoughts, words, and behaviors. Over time our life comes to be a cumulative result of these choices and actions. A fitting analogy is a garden. Plants begin as a small seed that, over time, can grow into a large plant. Not every seed will successfully grow to maturity, but only a planted seed has the potential to grow. Our actions are the seeds that define where compounding growth is possible in our lives. They are the starting point.

In entrepreneurship, one of the most important concepts is having a “bias to action.” When you start a new company, it has no sales and no customers. If you did nothing, it would be an absolute certainty the business would fail. Successful entrepreneurs make their best guess at what would help get the company off the ground and get moving. It’s much better than the alternative of doing nothing. A bias towards action is helpful in most areas of our lives. If I want to become fluent in another language, it is impossible for that future to exist until I take the action of learning my first word. In The Paradox of Choice, psychologist Barry Schwartz points out something interesting about how we reflect on our actions:

“When asked about what they regret most in the last six months, people tend to identify actions that didn’t meet expectations. But when asked about what they regret most when they look back on their lives as a whole, people tend to identify failures to act.”

In the movie Gladiator the protagonist Maximus says:

“What we do here today will echo in eternity.”

The actions we choose today reverberate for the rest of our lives and chart the course of our future.

In 1492 Christopher Columbus made landfall in China after an epic journey across the Atlantic Ocean. At least he thought he landed in China. During his preparation for the trip, Columbus made three significant mathematical errors while charting the course. The common thread was that they all resulted from overly optimistic assumptions on Columbus’s part. As biographer Samuel Morison noted:

“Of course, Columbus’s calculation is not logical, but Columbus’s mind was not logical. He knew he could make it, and the figures had to fit.”

I have seen the same tendency in my own life. As an optimist, I can assume that the future will be great and be overly generous in assessing my actions today. The inverse can also be true. Pessimism can discourage us from taking the steps needed to make our desired future possible. To harness the power of compounding, we have to take deliberate action today.

Focus

We all have areas of our life that we would like to see change. Every year over 50% of Americans will make a New Years’ resolution to change an aspect of their lives. Unfortunately, only around 8% of these resolutions stick for more than a few months. At the beginning of 2020, I resolved not to drink any caffeine. The first couple of months went great, but by March, I was back to drinking a couple of Coke Zeros per day. Anyone who has been to the gym in January has witnessed something similar. We are generally successful in taking initial steps towards change. Our problem is that we often lack the focus to sustain these actions.

Focus is the ability to concentrate our attention. It has always been an important skill, but I believe it has become even more critical in recent years. As a result of technological innovation, the world has witnessed an explosion of options, and one example is in TV shows.  A few decades ago, a handful of scripted TV show options existed. Then came cable and, more recently, streaming video. By 2009 there were 210 different scripted TV shows. By 2019 there were 532! There are more options to choose from than ever before, but It is becoming harder for a program to grab our attention. Once we choose a show to watch, if it suffers from a stretch of 2 or 3 mediocre episodes, we will quickly switch to one of the dozens of alternatives.

The more options we have, the more difficult it is to focus. Even if the show we are watching is outstanding, it is easy to imagine that one of the shows we aren’t watching would be even more enjoyable. Options seem to be freeing, but the reality is that they are often enslaving as they harm our ability to focus. Steve Job once remarked:

“Focusing is about saying no.”

We will meet thousands of people throughout our lifetime. Still, meaningful friendships with real depth and intimacy require that we focus most of our attention on a handful of people. The more that we focus our attention and efforts, the more profound the results will be. If you stand outside on a day when the sun is shining, you can get warm from the energy that the light contains. A magnifying glass can focus light into a smaller beam that produces enough power to start a fire. But If you focus light enough, it creates a laser that can cut through metal. The difference is the amount of focus. Focus is the discipline to say “no” to most of life’s options so we can concentrate our time, actions, and passion on the few things that we value the most.

Time

Alignment of our actions and focus creates powerful results, and when this goes on for an extended period, something extraordinary happens. Warren Buffet is one of the world’s wealthiest people with an estimated net worth of 87.1 billion dollars. Buffet began investing when he was ten, and it has been one of the central focal points of his life for over 75 years. Remarkably, 99.7% of his wealth accrued after his 65th birthday. It is counter-intuitive because exponential things don’t make intuitive sense to us. We tend to think about things in more of a linear progression. During the COVID pandemic of the last year, this was on full display. Viruses can grow exponentially, so by the time we realized COVID was in the United States; we already had a massive outbreak on the east coast. Because compounding is exponential growth, it becomes more powerful the longer it persists. Not surprisingly, Buffet’s says this about his long term perspective on owning stocks:

“When we own portions of outstanding businesses with outstanding managements, our favorite holding period is forever.”

It makes perfect sense. Once you are fortunate enough to be a part of something compounding, the most important thing is not to disrupt the process. It all begs the question: “What can we do to put time on our side?”

Throughout our lives, there will be many things that draw our focus. Some will be fleeting, others will last for a season, and a few will be focal points for most of our lives. The ones that persist will be the result of deliberate commitment. Our emotions and our passions will wax and wane over the many decades of life. For something to be a consistent focus, we must intentionally choose it. Commitment helps us to stands firm when our emotions and passions fluctuate. A great analogy is a marriage. Two people commit to a relationship with one another “until death do us part.” They enter this commitment without knowing what circumstances the future will bring. There is an old Puritan proverb about marriage that says:

“First you choose your love, then you love your choice.”

We choose the things we give our focus and actions towards, and then we commit to love those choices. Only then do we begin to recognize the fantastic compounding that comes with time.

The final piece of ensuring that time works in our favor is sustainability. In 1982, the Southern Methodist University football team finished undefeated and ranked 2nd in the country. It had been a remarkable rise to power for a school of only 6,000 students that lacked the pedigree of its conference rivals Texas, Texas A&M, and Arkansas. A turning point in program history had happened when future NFL Hall of Fame running back Eric Dickerson unexpectedly chose SMU in 1979. Dickerson became the focal point of the “pony express” offense that catapulted SMU to the college football world’s pinnacle. Soon rumors would begin to swell about SMU paying players. One of the most common quips was that Dickerson had taken a pay cut when he went to the NFL. In 1985 the NCAA handed down stiff penalties when a former player testified that as a recruit, he had accepted $5,000 to choose SMU. The NCAA didn’t know that many players at SMU had not only received money as recruits but were continuing to receive secret payments funneled to them via boosters. Instead of stopping the payments, SMU alumni decided to slowly “phase-out” the distributions hoping that the NCAA would never discover their existence. In 1987, these payments came to light, and the NCAA responded by giving SMU the harshest punishment possible: the death penalty. It would be two years before SMU would be allowed to play another football game, and the school would manage only one winning season in the next twenty two years.

Compounding requires sustainable behavior. When we cut corners like SMU, time starts to work against us. It becomes a countdown until implosion. Over the course of my life I have witnessed people experience short term success with unethical behavior, but that success usually evaporated over time. Sustainability comes from pursuing our goals with integrity, empathy, honesty, and humility. We should listen most attentively to those leaders that have achieved sustained long term success.

Take action today to plant the seeds of compounding in your life. Intentionally and deliberately ignore 99.9% of options to focus your time and effort on the .1% that matters. Do it with commitment and integrity so it can last for decades.


Questions for Reflection:

What is a dream that requires you to plant seeds with your actions today? What is preventing you from taking the first step today?

Write out the five things you want to focus on the most in your life and rank them. How does this list compare to how you are allocating your time, thoughts, and finances?

What is one thing about your behavior in the last year that could make growth unsustainable? What can you do to make a change in this area?

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entrepreneurship, mindset

The Power of Practice

Game 6 of the 2013 NBA finals was one of the best games in basketball history. The Miami Heat entered the game behind 3-2 to the San Antonio Spurs in the best of seven series. The entire game was close, with the lead seesawing between the teams until the Spurs took control in the last two minutes. With 28 seconds left, Manu Ginobli sank a free throw to put the Spurs up 5 points. 

Bill Simmons recounts his experience watching this part of the game:

“During that now-fateful timeout with San Antonio up five, Jalen Rose and I watched NBA officials wheel the Larry O’Brien Trophy into the runway to our right. It couldn’t have been farther than 15 feet from us. We watched security guards assume positions around the court, and we watched Heat employees hastily sticking up yellow rope around the courtside seats. Like they were cordoning off a homicide scene. Even after LeBron’s second-gasp 3, I still thought we were going home. Some Heat fans had already trickled out. We watched them leave in disbelief.”

The game seemed over for all intents and purposes. What followed was an improbable and frantic finish culminating with this incredible Ray Allen 3 pointer that would send the game into overtime.

Everything about this shot is remarkable. The coolness under pressure. Allen’s mental awareness that he had to shoot a 3 for the Heat to have a chance. The balance to avoid falling out of bounds while dribbling backward, and the presence of mind to make sure that both feet were completely behind the line before shooting. This iconic play was a shining moment for one of the game’s all-time greatest shooters. We all get to see the amazing shot, but that shot was only possible because of the thousands of hours of training and practice that preceded it. Allen was once asked about how he became such a great shooter and said:

“I’ve argued this with a lot of people in my life. When people say God blessed me with a beautiful jump shot, it really pisses me off. I tell those people, ‘Don’t undermine the work I’ve put in every day.’ Not some days. Every day. Ask anyone who has been on a team with me who shoots the most. Go back to Seattle and Milwaukee and ask them. The answer is me — not because it’s a competition, but because that’s how I prepare.”

I think Allen’s answer is a powerful insight into how we can unlock the highest levels of achievement. His point is not that he has a lack of God-given talent but that his jump shot is largely the result of countless hours of practice. There are likely thousands of people with a comparable amount of natural talent as Ray Allen. Still, only a handful have honed their ability to shoot a basketball to such an elite level.

In his book, Outliers, Malcolm Gladwell examines what enables some people to achieve at remarkable levels. It is always difficult to tease apart talent and practice to find how much each had a role in a person’s success. One of Gladwell’s more compelling examples is students who have successfully gained admittance to a top music school. Without a doubt, there is a relatively high level of required talent to be admitted to a school like Juilliard. Once a student achieved admission, Gladwell wondered, what was the biggest leading indicator of future success? Fortunately, the data paints a clear picture:

“Once a musician has enough ability to get into a top music school, the thing that distinguishes one performer from another is how hard he or she works. That’s it. And what’s more, the people at the very top don’t work just harder or even much harder than everyone else. They work much, much harder.”

Successful musicians are forged from a combination of natural talent and exceptional practice ethic. In some fields, the natural talent required to succeed is a high bar. The NBA only has around 500 active players at any given point in time. Even if you include international professional basketball leagues, there are only a few thousand professional basketball jobs available at any given point in time. As a result, the amount of natural physical gifting needed is relatively high. If you are 5’6″ tall, it’s borderline impossible to have a career playing professional basketball no matter how hard you practice.

In contrast, one of the great things about entrepreneurship is that the world economy needs millions of business owners. Countless people possess the natural aptitude and talent required to be an entrepreneur. Creating a business doesn’t hinge on how you look, where you were born, or what level of education you received. Instead, just like Ray Allen’s jump shot, success in entrepreneurship is largely about mindset and a willingness to put in the practice.

Practice Cultivates Talent

Recently I have been listening to the audio version of the outstanding book, The Body, by Phil Bryson. In the chapter on how our body responds to the food that we eat, Bryson notes:

“By whatever means you measure it, we are pretty good at removing energy from food. Not because we have an especially dynamic metabolism but because of a trick we learned a very long time ago – cooking…It is widely believed now that cooked food gave us the energy to grow big brains and the leisure to put them to use…the few plants we can eat are the ones we know as vegetables…but we can benefit from a lot more foods by cooking them. A cooked potato, for example, is 20 times more digestible than a raw one.”

Cooking exponentially expands the number of things that we can eat. It protects us from harmful diseases and bacteria. It changes the texture and taste of food to make it more appetizing. It even increases the amount of nutrition that we derive from food. Without cooking, our body would require us to spend our entire day eating in our quest to get enough calories. But what does cooking have to do with entrepreneurship and practice?

In the same way that cooking cultivates and enhances food, practice cultivates and enhances our natural talents and abilities. Practice unlocks our full potential and amplifies our effectiveness, but it requires a great deal of time and commitment. For example, one study of 20-year-old violinists divided them into 3 talent groups based on their conservatory teachers’ scores. Those judged “best” had averaged 10,000 hours of deliberate practice since taking up the violin. Those judged “better” averaged 7,500 hours. And those judged “good” averaged 5,000 hours. One thing that is worth noting: Considering their age, all of these violinists had spent an incredible number of hours practicing. If you assume these students began playing violin at age 5, then 10,000 hours of practice had required 11% of their life to be dedicated to training!

Our mindset profoundly influences how we view practice. In her classic work, Mindset, Carol Dweck makes a compelling case that most people can be categorized as having a predominantly “Fixed Mindset” or a “Growth Mindset.” Fixed mindset people believe that the talents and abilities we are born with define what we can do. The idea of practice is somewhat antithetical to this self-view because your abilities are almost exclusively the result of your natural abilities. Fixed mindset people are more easily discouraged by setbacks, take feedback poorly, and view exertion of effort as proof that someone does not have talent in that area. Challenges are, therefore, something to be avoided.

In contrast, the growth mindset is characterized by a fundamental belief that our capabilities can expand and grow over time with dedication and practice. They believe our skills come from hard work and persistently working through challenges. They actively seek out feedback and would assert that effort will be necessary for any significant accomplishment. Dweck illustrates how powerful a growth mindset can be through several examples. One of the most compelling is through art. Drawing is widely considered to require a good deal of natural artistic ability. Still, even a small amount of regular practice by someone with a growth mindset can make a remarkable difference. Below is an example of a before and after picture one artist produced from just a few hours of practice and instruction.

One artist’s initial drawing compared to a drawing after a 12 lesson course.

Entrepreneurship requires a growth mindset. Over the past 12 years, I have been fortunate to be a part of co-founding several businesses. One of the best parts is the immense amount of practice and learning in a new company. Running a business requires being able to execute at a reasonable level in a lot of different areas. Below are some of the many needed skills that come to mind:

Recruiting
Casting Vision
Crafting Strategy
Negotiating
Motivating
Selling
Establishing Culture
Strategically Quitting (Read More About this Here)

Our natural giftings and personality give us a different base level of competence in these areas. But no matter what our starting point, excellence is impossible without a tremendous amount of practice. Here are 5 tangible suggestions of how to apply this in your life:

  1. Openness to feedback. There is a reason that the best golfers in the world still have a swing coach. No matter what level of performance we reach continued growth requires feedback. One of the ways that I grew the most in my teenage years was through being a part of basketball and track teams. Teams provide a context where others can observe your behavior, your attitude, and your habits. Your teammates become the single best place to get honest and vital feedback.

    I have found that it is not easy to get others to share candid feedback, especially with a superior. To have a feedback-rich environment, you must continually ask for feedback from others instead of assuming that they will offer it if there is a way that you can improve. When you do get critical/constructive feedback, listen and seek to understand instead of responding defensively. Responding negatively to feedback communicates that you are not really open to feedback and that sharing it with you should be avoided in the future. Do people feel comfortable sharing feedback with you?
  2. Root out fixed mindset thinking. Although you can generally categorize people as having a growth mindset or fixed mindset, the reality is that all of us have at least some of both. I tend to lean pretty heavily towards having a growth mindset, but there are areas of my life like music and foreign language where I am prone to fixed mindset thinking. In general, the less natural talent I have in an area, the more tempting it is for me to have a fixed mindset. What are the areas in your life that you are living with a fixed mindset?
  3. Focus on process over results. Results orientated people are primarily motivated by outcomes. For example, “I will practice piano every day so that I can win the talent show in the spring.” Practice is a means to an end. In contrast, process-oriented people are primarily motivated by achieving a higher level of intrinsic skill at a particular endeavor. For example, “I will practice piano every day because I get joy from playing beautiful music. I want to know how beautifully I can play this instrument.” At some point, our ability to persist in practice has to be based on something deeper than results. It requires that we intrinsically love the process of finding out what we are capable of. Where are you more results-oriented than process-oriented?
  4. Be picky in what you practice. Recent psychological experiments have shown that our brains are not able to multi-task. Unsurprisingly, we are also unable to practice many things simultaneously. Choosing judiciously where to focus our time creates the opportunity to invest meaningfully in the areas where we most want to grow. Are you trying to grow in too many areas at the same time? What are the most important areas for you to be growing right now?

What area of your life do you want to focus on practicing the most over the coming year? Was there something that stood out to you in this article as helpful? Please share your thoughts in the comments.

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entrepreneurship, mindset

The Art of Quitting

Over the past 12 years, I have been a part of starting several companies. I’ve been fortunate to be a part of some incredible successes, but I’ve also seen my share of flameouts. I am constantly seeking to understand how to be a better leader and entrepreneur. In this blog, I hope to share some of the things that I have learned along the way.

What personality traits are the biggest predictors of success? Historically experts have identified things like intelligence, raw talent, and charisma. Newer research shows that our mindset might be the most important predictor of future achievement. Specifically, a mindset of persistence may be a more powerful leading indicator than raw talent. In Angela Duckworth’s acclaimed book Grit, she says this about the necessity of persistence in pursuing excellence:

“…there are no shortcuts to excellence. Developing real expertise, figuring out really hard problems, it all takes time―longer than most people imagine….Grit is about working on something you care about so much that you’re willing to stay loyal to it…it’s doing what you love, but not just falling in love―staying in love.”

That aligns with my experience. It’s impossible to build a business, a relationship, or any expertise without staying the course. But I’ve learned another paradoxical truth. Successful entrepreneurs are simultaneously skilled at persistence and at the art of quitting.

2nd Time is Not the Charm

In October 2009, I was a part of a team that launched an online auction business. Against all odds, it was an incredible success that surpassed our wildest expectations. We were young and naive; at 30, I was the oldest person in the company. Emboldened by our success, we began planning a 2nd e-commerce startup in 2011. Abundant time, money, and passion were poured into the 2-year buildup to launch. Confidence was high that this new venture would be another huge success. The concept was an online store where customers could shop for any product in mainstream categories. During the checkout process, they would play a short flash game to win a discount on their order. We believed our creation would add excitement and entertainment to the shopping process. We finally launched the website in 2013 with high hopes. We were exhausted but excited.

By the time the first customers saw the website, I had personally invested thousands of hours and a large amount of personal savings into funding the project. I eagerly watched to see how customers would respond. The early results were…terrible. The average customer was not responding at all. Potential customers were bouncing off the landing page like it was a trampoline. It would be hard to overstate our discouragement at the initial results. Internally, company morale sank as the reality began to set in.

In retrospect, we made several missteps in the process of launching:

-We didn’t spend enough time talking to potential customers
-We did not create a minimum viable product (MVP) and tried to launch a polished product
-We were overconfident because of the success of our first company
-We underestimated how quickly Amazon was consolidating market share in e-commerce
-We picked a technology that would soon be extinct (Flash)
-We designed around desktop instead of mobile

It’s quite a list of missteps now that I type it all out. And yet, I don’t have many regrets about the mistakes we made in launching. Hindsight is always 20/20, and anytime you try to do something new, there is a decent chance that people won’t get it. The question before us was “What do we do now?”

“Don’t Give Up”

Back to the research on the mindset of successful entrepreneurs. Conventional startup wisdom affirms the value of the statement “Don’t give up.”  There are epic stories of people who refused to give up and were rewarded for their persistence.  One great example Business Insider recounts here is Pandora: 

Pandora was not able to pay its employees for an astounding two years between 2002 to 2004 while it worked on producing a viable commercial product. Not paying full-time employees is very, very illegal in California, where Pandora is based.

“We had no idea we were breaking the law,” Westergren said.

Over that period, Pandora accumulated $2 million in back wages owed. Westergren himself ran up a $500,000 debt on “maxed-out cards” while he paid bills and as many salaries as he could afford. 

He paid a little at a time in the order they were due, an experience he describes as like “playing Tetris” with his finances, which he “[doesn’t] recommend.” 

Two employees sued for back wages. And Pandora’s original model of licensing out its Internet music recommendation engine to retailers and labels was not working out. 

But Westergren, a musician by training who had little to fall back on if he defaulted on the debts, managed to keep most of the team together. To keep employees motivated, he gave speeches upon speeches, encouraging them that the potential market was huge, and so was Pandora’s potential impact on music and culture. 

Somehow — Westergren says he is not sure how — the company was able to close a $9 million round of funding in 2004, when money was much harder to come by than it is today. 

Westergren called an all-hands meeting for everybody in Pandora that same day. Everybody was expecting another stirring speech, he says. Instead, he pulled a stack of envelopes from his back pocket and paid out the $2 million among the 50 employees right then and there. 

“Everybody thought it was a bad joke, like it would bounce or something,” Westergren says.

What an epic story! The scene of Westergren handing out envelopes full of back pay is incredible.

This story can serve as a reinforcement to my natural disposition to be persistent. I don’t like giving up on things.  I am the kind of person that will keep working on a brainteaser longer than other people just because it drives me nuts if I can’t figure it out.  Hearing the Pandora story only strengthens my resolve. “No matter what – don’t ever give up.  Sometimes success comes from sheer force of will.”

The problem with lionizing stories like the one above is that it lacks two important pieces of context.

1. Why was Westergren so convinced that he should bet everything he had to keep going? Was there clear evidence that they were on the cusp of a breakthrough? Was it obvious they had product/market fit? Was their main challenge a temporary disruption to fundraising due to the tech bubble bursting?

2. How many stories exist where things didn’t turn out so cheerfully? Survivorship bias tells us that using anecdotes and stories of successful entrepreneurs is dangerous. How many times has the founder of a company “played Tetris” with their finances only to see it end in bankruptcy? We never hear that multitude of stories because they don’t get articles in Business Insider.

The point I am driving at is this: What if persistence isn’t always the answer? What if sometimes persistence prevents success?

Toxic Persistence

The last 20 years have seen an explosion of reality TV talent shows. One of the most notable is American Idol, which has led to stars like Kelly Clarkson and Carrie Underwood. Several years ago, American Idol was must-see TV for my wife and me each week. Without a doubt, the most cringe-worthy part of each season was the compilation of failed auditions. The clip below is a fan’s “top” 10 worst auditions of all time.

The hardest part of watching these auditions was not the off-key singing. It is how contestants responded to negative feedback from the judges. Instead of introspection, contestants would often reply with something like, “I’m not giving up on my dream!” or “I’ll prove you wrong!” These contestants are exercising persistence, but it is the darker side of persistence. I call this type of persistence “toxic persistence” because it harms us.

At its core, persistence is continuing on the same course despite difficulty or adversity. Belief is what fuels persistence. A belief that if we keep going, better days are ahead. But when we are heading in the wrong direction, the last thing we want to do is persist! Unfortunately, our psychological software has a bug called “belief perseverance.” When we sincerely hold a belief, we don’t process new evidence properly. Several studies have shown that being presented evidence contrary to a deeply held belief can strengthen the incorrect view. When evidence contradicts our beliefs, we tend to choose our beliefs. Ironically, aspiring entrepreneurs can be the most susceptible to toxic persistence precisely because they are so committed. Author C.S. Lewis once observed:

“Progress means getting nearer to the place you want to be. And if you have taken a wrong turn, then to go forward does not get you any nearer.

If you are on the wrong road, progress means doing an about-turn and walking back to the right road; and in that case, the man who turns back soonest is the most progressive man.”

Quit isn’t a Four Letter Word.

As I told you earlier, the second launch I led as an entrepreneur could not have gone worse. We made countless strategic errors leading up to the launch. However, when I reflect on this period, I don’t think it was the mistakes I made before launch that I regret. I regret the decisions I made after launching far more.

I regret not giving up sooner. It was clear that our business hypothesis was wrong. Not just that we were in the wrong zip code, more like we were on the wrong planet. In the face of plentiful evidence that we were not on the right path, we continued to push ahead. Over the next year and a half, we would waste even more time, resources, and morale trying to redeem a project more supported by belief than market evidence.

Why? I think the primary reason is identity. When you pour a lot of yourself into something, the lines can begin to blur. The project can transition from something you are working on to something that defines you. Once your heart makes that jump, it is excruciatingly difficult to allow it to fail. The project becomes a referendum on your worth as an individual. You become willing to prioritize belief over evidence because a failed project means laying off friends and painful conversations.

Another reason that we resist quitting is the sunk-cost fallacy. When we have invested significant time or money into something, we develop an irrational attachment to it. Imagine you buy a used car. A month later, you discover that it will require repairs that exceed the value of the car. Studies have shown that we are likely to pay for the repairs even though it isn’t rational. 

I kept going because I was too afraid to quit. That’s not helpful. In fact, it will actively prevent you from accomplishing your goals. It is a bottomless pit that can devour all of your devotion, time, passion, and money. The more you indulge it, the more dangerous it becomes.

My point is that persistence must be paired with another skill to be valuable. Knowing when to quit. Our culture celebrates starting things and mourns ending things. Our emotional and societal incentives all discourage quitting. I call it the art of quitting because it requires judgment, maturity, and humility. In Seth Godin’s book “The Dip”, he examines the importance of strategic quitting and makes the observation:

“Winners quit fast, quit often, and quit without guilt.”

W.C. Fields surely agreed with this sentiment when he famously said:

“If at first, you don’t succeed, try, try – and then quit! No use being a fool about it.”

Toxic persistence is pressing on when quitting would be wiser. Quitting saves us from devoting our resources to efforts that are destined to fail. It stimulates growth and learning while bolstering our humility. It is the foundation that future success is built upon. As Mulla Nasrudin observes:

“Wisdom comes from experience, and experience comes from failure.”

Redemptive Persistence

Redemptive persistence is flexible and adaptive. To use an example from above, imagine someone who deeply loves music and wants a career as a singer. For a variety of reasons, including talent and circumstances, this might not be possible. Toxic persistence leads to a mindset that the only path to success is by becoming a professional singer. It would lead someone to continue to pursue a career in singing even when all the evidence from the market is that they don’t have a future as a performance artist. Redemptive persistence would lead someone to incorporate feedback and explore other areas to find a career in music. How many successful producers, songwriters, and agents only unlocked their full potential when they quit trying to be a singer? Redemptive persistence is about pursuing a career that engages your love of music while being open-handed with the specific context.

I recently read the biography of a man who dreamed of becoming an officer in the British military. He gained his first significant military assignment at the age of 20 and commanded troops by 21. He distinguished himself for courage and bravery in several battles, but after a few years, it became apparent that he would never be able to advance to a higher rank because of where he was born. After several years of service in the British military, he quit and pursued a new career in farming and politics in Virginia. Years later, he would unexpectedly realize his dreams of leading in a military context when he was appointed General of the Continental Army. As you have probably guessed, that man was George Washington. Washington’s willingness to resign from the British military instead of pressing forward created the context and opportunities that culminated in serving as the first U.S. president. How would the world be different if he had pressed on instead?

Conversely, it was Washington’s redemptive persistence that made him such an exceptional leader during historic times. He had not attended college and was woefully underprepared to serve as General of the Continental Army. He made repeated mistakes during the Revolutionary War and won very few significant battles until receiving substantial French aid. He was always low on resources and troops. But America won the war, in large part, because of Washington’s persistence. He correctly observed the enormous financial cost of the war for the British. Even though the battles weren’t going particularly well, America could win the war with endurance. He successfully held the ragtag army together until the British bills mounted and the French joined the war as allies of America.

Final Thoughts

How can we identify when our persistence is toxic or redemptive? I’m going to tackle this more in future posts, but I would offer two thoughts.

  1. Redemptive persistence is almost always predicated on evidence that objectively points towards possible future success. It is flexible and adjusts to feedback. Toxic persistence is often a defiant “doubling down” in the face of the evidence. It is characterized by a rigid definition of success that we become unwilling to change.
  2. This highlights the important role of judgment. We don’t know what would have happened if Washington had continued in the British military. Maybe it would have led to his promotion to leadership despite being born in the colonies. Conversely, many contemporaries of Washington believed the Revolutionary War was a lost cause at points. This mental model does not remove the need for judgment; rather, it highlights the necessity to carefully and strategically choose when to quit and when to press on.

In 2012 I started working on what would be the most significant professional failure of my life. It took me almost a year and a half to break free from a mindset of toxic persistence. That failure was one of the best things to ever happen to me. It helped me learn the art of quitting, and I am a better leader and entrepreneur. It would turn out that my most significant professional failure would set the stage for the highlight of my business career so far: Co-founding Simple Modern.

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