My business made $1M+ when I was 29 years old. That was the beginning of the end.
Personal Note: This is one of my most personal posts yet. I share my journey to becoming a conventionally successful entrepreneur, then burning out from over-using discipline, and then ultimately rediscovering my passion and coming alive as a curiosity-based thought leader.
The article shares my story along with the lessons I learned so you can:
Avoid the mistakes I made (saving years of pain from forcing a square peg into a round hole)
Gain deeper insight and language into your own story (it’s hard to see the bigger picture when you’re in the middle of things)
Capitalize on solutions that work (I’ve found ways to marry curiosity, virality, and financial success)
The lessons I share are the most profound I’ve learned as a thought leader, as they impact almost every decision I make.
Paid subscribers receive a 90-minute masterclass along with a 19,000-word mastery manual I created on the topic for our Mental Model Club ($20 value).
I had pushed so hard for so long doing whatever was necessary to achieve the arbitrary $1 million goal that when we got it, I had nothing left in the tank. I was burned out, but I didn’t know it… yet.
In the following months, I stopped doing sales calls, and I started doing side projects I was passionate about rather than what the business needed to succeed or go to the next level. Revenue plummeted. Our reserves quickly vanished.
In the next two years, the business shrank, my time was spread among even more things, and I started going into personal debt. Eventually, my burnout reached its zenith. Soon after, the business dissolved, and I had nothing tangible to show for the 10 years I had sacrificed to build the business.
In retrospect, I was in the Discipline Doom Loop without knowing it…
It was brutal. It was humbling. It was depressing.
Fortunately, it was also the beginning of the beginning…
My Three Tenets To Building A Curiosity-Driven Life As A Thought Leader
In the beginning, my previous business was based on my passion. My girl friend (now wife) and I purchased a 32-foot tour bus, wrapped it, and traveled to college campuses speaking about entrepreneurship.
But, over the years, my passions and curiosities had evolved while the focus of the business had stayed the same. At first, I loved every opportunity to hit the road. But when I became a parent, traveling became much less exciting. Once I had seen every state for the first time, I wasn’t as excited to see it for the 2nd, 5th, and 10th time. Finally, while I loved the challenge and growth from speaking at first, over time I learned it wasn’t in my genius zone.
And, as much as I wanted my passion to stay the same and pretended that it had so that I could stay aligned with the business, I couldn’t fool myself. In some ways, I felt like I was impersonating my former self rather than embracing my emerging self.
As the business came to an end, I didn’t know what the next leg of my journey would be as an entrepreneur. But, I did have clarity on the foundational pillars I wanted the business to be built on:
I never wanted to sacrifice my personal growth to grow a business again. In the previous business, I focused on using discipline to do what the business needed to grow. More specifically, I worked backward from a long-term external goal to short-term goals to the day’s task without consideration for what was happening inside of me. This meant ignoring my curiosities that had no obvious and immediate payoff. It meant ignoring what was alive and bubbling up for me in the moment. It meant ignoring personal growth opportunities that arose during the day when they weren’t aligned with the day’s tasks.
I wanted a business designed to unleash my personal growth and learning. Rather than depending on my being the same, I wanted a business that rewarded my evolution. I wanted a business that rewarded me for exploring my curiosities and what was bubbling up for me. At the time, having a lifestyle business was paradoxically looked down on. In this new business, I wanted to start with living my ideal lifestyle and not hold it off until a future that might never come. I didn’t just want the business to support my growth, I wanted it to accelerate it.
I wanted to focus on building up a base of rare, useful, universal, and timeless knowledge. After having reduced my learning for the previous business in order to stay focused on production, I wanted to focus on learning that I could use for the rest of my life. This vision was clarified after researching and writing How One Life Hack From A Self-Made Billionaire Leads To Exceptional Success (in Forbes originally). Furthermore, I was inspired by Warren Buffett’s lifestyle of spending 80% of his time reading and thinking, and I wanted to do something similar. To learn more about how you can build up your base of timeless knowledge, I recommend checking out my Mental Model Club.
With these tenets, no matter what happened to the business over time, I would never sacrifice what was most important to me.
Unfortunately, coming up with these tenets was the easy part. The hard part was understanding how to realistically turn them into a lucrative business. Ultimately, to do so, I had to unlearn much of what I had learned in undergrad business school…
How I Made The Transition To A Curiosity-Driven Life
It all started when I began writing for Forbes, and I had to decide what I would write about. My normal inclination would be to do something strategic to help my current business. Instead, I gave myself permission to write about whatever I wanted to write about.
The only condition I placed on myself was that I had to write about things that would feed my soul.
This meant that I ignored concepts I had learned in business school, like:
Everything I do should fit into a long-term vision and strategy.
I should get clarity on my niche upfront and target the largest, most profitable market.
Each article had to lead to an immediate sale.
Next, I had to actually find the time to write.
At the time, my kids were young, I was still wrapping up the previous business, and I had an undiagnosed gluten allergy. So I had no time or energy at the end of every day. And when I say I had no energy, I really mean it.
Fortunately, I had just been reading about Stanford researcher BJ Fogg’s work on tiny habits. He suggested that if you want to start a new habit, you should start with an extremely easy task. Thus, I made a commitment to myself that all I had to do once the kids had fallen asleep was to drive myself to the Barnes & Noble bookstore. Then I gave myself permission to do whatever I wanted once I was there. I could read any book. I could do nothing. I could write anything. Whatever I wanted.
Then something amazing happened. At first, I wouldn’t do much because I was tired. But, over time I started doing more and more learning and writing. Within a few weeks, as soon as I walked into the store, I would feel energy, excitement, and flow. Every night, I’d write until the store closed.
I wondered, where is this energy even coming from?
What I know now is that curiosity is literally its own energy source, and it’s a million times stronger than discipline.
For example, in the video below, Matthias Gruber, a cognitive neuroscientist in the Dynamic Memory Lab at the U.C. Davis Center for Neuroscience, shares a fascinating brain study he performed that shows how curiosity significantly increases our motivation and memory…
Source: This is Your Brain on Curiosity | Matthias Gruber | TEDxUCDavisSalon
To me the key quote in the clip comes at the very end:
Before I showed you that curiosity actually recruits the wanting system by itself. Here, I've now shown you that curiosity also benefits and drives interactions between the midbrain and the hippocampus. So it almost seems like that the brain's wanting system is warming up the hippocampus to get ready for the learning of upcoming information, regardless of whether this is the information that got you curious in the first place or not. Curiosity energizes us via the brain's wanting system so that we go out and seek new information. And curiosity helps us to make our memories stick.
—Matthias Gruber (researcher)
At first, I didn’t really have a process for writing each article based on curiosity and personal transformation. I just read stuff and wrote it out. But, over time, a consistent process emerged.
For every article, I followed these six steps…
6 Steps To Research, Write, And Monetize A Curiosity-Based Article That Transforms Your Life And Readers’ Lives
Wanderer, your footsteps are the road, and nothing more; wanderer, there is no road, the road is made by walking. By walking one makes the road, and upon glancing behind one sees the path that never will be trod again. Wanderer, there is no road — Only wakes upon the sea.
—Antonio Machado (poet)
I follow these six steps…
Follow my curiosity
Go down rabbit holes
Make sense of things
Create an original idea
Write and publish
Monetize my knowledge
Side Note: The articles I write for this newsletter are different than my normal process for articles that I have followed for the last 8 years. This newsletter is an exploration for me to find an additional format that takes less time and is still high quality. The median newsletter article takes me about 10 hours. My average Medium post takes 60+ hours and often significantly more.
Step 1. Follow my curiosity
When I think about what I want to write an article on, I think about what I’m most curious about as the primary motivation.
At the same time, I do now constrain this curiosity to:
What will be the most transformative for me.
What will most help the people reading my articles.
What is most closely related to thought leadership. (I’ve purposely chosen a topic that is on the one hand specific, as not many people want to be thought leaders, and on the other hand, it is very broad because the skills required to be a great thought leader are closely mirrored by the skills required to live life fully IMHO).
Takeaway: The important thing to know is that I don’t actually start the process of writing a long-form article with answers. Rather, I just start with a question and an openness to collecting diverse perspectives so that I can get closer to what’s true, useful, and original.
This approach is in direct opposition to starting with an answer and just searching for evidence to prove what you already believe. While this conventional process is more efficient in the short-term, in the long-term, it means learning less and having ideas that are less valuable.
Step 2. Go down rabbit holes
As I explore my curiosity, I’m introduced to information that triggers new curiosities, leading me to rabbit holes. Said differently, as I explore answers to a question, I’m confronted with new questions.
With each rabbit hole, I’m confronted with a choice:
Stay focused on the original question
Go deeper down the rabbit hole by exploring new curiosities and questions
Deep rabbit holes often start as cryptic clues that are easy to overlook...
An interesting link in another article
A mention of someone I haven’t heard of
A new word or concept I have never heard of that seems relevant
A curiosity question that won't leave me alone
Something paradoxical that shouldn't be happening but is
Something that makes me feel alive even if it seems random
Rabbit holes are easy to ignore or explain away.
But, each time we follow a rabbit hole into its depths, we enter into a new reality that’s filled with more curiosities (i.e., interesting things that don’t quite make sense). Thus, in many ways, a rabbit hole is like a portal that takes us from the everyday world and into the worlds of mystery, wonder, and possibility. They are the chasm between order and chaos, known and unknown. The mythological call to adventure from the Hero’s Journey.
The best depiction I’ve ever seen of a rabbit hole comes from The Matrix movie:
I love this clip because it beautifully captures the emotional parts of rabbit holes:
Feeling that there is something more to life when we’re not quite sure what
Wanting to go on an adventure, but we’re fearful of the unknown
Experiencing a rabbit hole and trying to explain it away
The boredom of everyday life along with the seductiveness of the rabbit hole
The potential for distraction and even real danger
As a thought leader, I attempt to be a professional rabbit hole follower. I attempt to notice interesting questions. Then I Google them until I get to even better questions.
FUN DIVERSION: HOW MANY RABBIT HOLES DO YOU COUNT IN THE CLIP ABOVE?
This scene from The Matrix is the most rich depiction of rabbit holes I’ve ever seen. See if you can count all of the rabbit holes. Below are some of the ones I noticed...
1. Neo means new.
2. White rabbits symbolize magic.
3. He lives in room 101. Binary is the numerical symbol of the Matrix (a simulation).
4. The woman symbolizes rabbit holes.
5. Her seductiveness symbolizes the excitement of rabbit holes.
6. Her name is Dujour, which is French for “of the day”—temporary. Rabbit holes are portals that are only temporarily open.
7. Troy is metaphorical for the Battle Of Troy where a wooden horse full of possibility/danger was given.
8. Rabbit holes can distract and delay us from our plans. That’s why the woman is blamed for them being two hours late.
9. The scene uses religious words every chance it can—hell, hallelujah, savior Jesus Christ
10. The book is called “Simulacra & Simulation," because he’s living in a simulation (there is a real book and the directors asked the main cast to read it before they started filming).
11. The chapter he opens to is titled "Nihilism," the rejection of religious principles.
12. When we follow rabbit holes, our old reality starts to feel like a dream.
13. Troys says, “You don’t exist,” and it takes Neo aback for a second. This relates to eastern religion.Takeaway: Rabbit holes often have a negative connotation because they can be “distractions,” but in the context of learning, they are fundamental. So, in the beginning of the research process, I try to maximize the quantity and diversity of the rabbit holes that I explore. I explore the academic realm for theoretical wisdom. I explore the practitioner realm for applied insights. I explore the philosophical realm for implication/contextual wisdom. I search out ideas that attempt to disprove my deepest-held beliefs.
Step 3. Make sense of things
After a long time of more and more novelty via rabbit holes, the amount of novelty starts to decrease. Suddenly, I feel like I’m hearing the same ideas from the same people over and over.
When this happens, I know it’s time to shift from hardcore research mode to ideation and application. I play with the ideas in my own life and try to make sense out of them.
Thus, I have gone from:
Curiosity in the beginning…
To fascination, confusion, and overwhelm because of all the rabbit holes…
To order, as I begin to make sense of everything and see connections…
To boredom, as there is less and less novelty, and I see the same things more often…To exhilaration, as I develop unique ideas I haven’t seen talked about anywhere else in the same way I see it.
Takeaway: At times, it can feel like rabbit holes have no bottom, but they always do. At times, it can feel like rabbit holes will be dead-ends, but they never are. So, it is important to cultivate patience and faith that the process will pay off in ways that are more interesting than you could’ve ever planned.
Step 4. Create an original idea
In this stage, I try to extract insights that are rare and valuable that I haven’t seen other people share in quite the same way. I gain confidence about the idea in a few ways…
Because I have gone so broad over other people’s knowledge, I have confidence my idea is original.
Because I have applied it to my life, I have confidence that it works.
Because I share nascent ideas with many people in many formats before I publish them, I have confidence that online readers will resonate with them too.
Takeaway: It’s important to have an ideation process that you can run that predictably extracts and validates useful insights from everything you’ve learned. I will write about my personal process for this in a future post.
Step 5. Write and publish
Finally, I turn everything into a long-form article.
For my best work, I do 15 drafts. And for each draft, I aim to improve it in a specific way. For example, below are a few of the lenses I use for different drafts…
Hooks
Understanding
Readability
Devil’s Advocate
Comprehensiveness
Kill Your Darlings (to shorten the length)
Titles
Quotes
Visuals
Etc.
I will talk more about this process in another post.
Step 6. Monetize
Over the years, I’ve explored and had success with many different forms of knowledge monetization:
Book publishing ($100,000+)
Speaking (Millions)
Subscription/Newsletter ($1M+)
Courses (Millions)
Agency/Consulting (Hundreds of thousands)
Through this process, I’ve gotten to know the pros & cons of many different paths—many of which takes months or years to play out. Furthermore, some constrain curiosity more than others.
My two favorite approaches by far are:
High-Ticket Coaching Programs. This allows me to work closely with individuals, see the impact, and get incredible feedback so that I can rapidly improve the program. On-demand programs provide little feedback. Furthermore, it’s much easier to make a living serving a few students per year than marketing to hundreds or thousands.
Paid Newsletters. I love the paid newsletter model, because I can focus almost 100% of my time on reading, thinking and writing, and the revenue is reoccurring. I don’t need to spend time creating marketing funnels, sales pages, and marketing campaigns. There is nothing wrong with these, but they’re not in my genius zone.
Takeaway: How you monetize your knowledge has huge implications for where you spend your time. By choosing a monetization model that isn’t aligned with your curiosity/growth, you can easily find yourself building a business that takes you away from reading and writing. Originally, my fear was that having a business based on curiosity would cause me to make less money on a personal level. The opposite has been true.
After years of following this six-step process, several surprising things started to happen to my brain, business, and life
Because the whole process was designed around personal growth, I started spending most of my days on it, which meant I started evolving faster than I ever had in my life.
I started realizing that my real product wasn’t each article that I produced, the impact on others, or the money I earned. Rather, it was me.
Through my own personal evolution, my ability to create more and more transformative ideas and programs increases over time.
Below are a few ways that following the six steps above had a surprising impact on my brain…
My curiosity increased exponentially over time
I learned that the dots of curiosity always connect in reverse
My ability to come up with original ideas increased exponentially
I came upon a new way to make transformative decisions
The perfect niche for me emerged on its own
Surprise 1. My curiosity increased exponentially over time
The larger the island of knowledge, the longer the shoreline of wonder.
—Ralph Sockman
As I gained more knowledge, I saw that my curiosity became a stronger and stronger source of motivation. I didn’t have words for the phenomenon until I watched the video below by Ian Leslie, author of Curious: The Desire to Know and Why Your Future Depends On It:
Source: Ian Leslie on Why We Must Continue to Learn and be Curious
Takeaway: In short, curiosity is fundamentally based on knowledge. Thus, as you gain more knowledge linearly, curiosity seems to grow exponentially. Over time, a learning lifestyle seems to lead to a life that is filled with curiosity and wonder.
Surprise 2. I learned that the dots of curiosity always connect in reverse
My fear in following my curiosity was that it would lead me in random, disconnected directions and not lead anywhere interesting.
Fortunately, the opposite happened.
Furthermore, the more I followed my curiosity, the more I started seeing how the dots I collected in research actually connected into bigger ideas that I didn’t and couldn’t have seen in advance. Said differently, every article I’ve written has become a lego block for a larger idea.
As I saw this happen over and over, I started to have faith in the wisdom of curiosity even if I didn’t see an immediate payoff. I knew that it would take me somewhere far more interesting than a specific goal could have.
Suddenly, Steve Jobs’ famous quote made sense:
You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something—your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.
—Steve Jobs
In addition, I gained a deep appreciation for why curiosity is central to science. The following advice from a Nobel Laureate is a perfect example. When his graduate students suggest a topic for research, if they are deeply curious about it, he automatically gives them the go-ahead. He does this because he knows if his students follow their curiosity, the dots will eventually connect.
Source: "The best kind of research is curiosity driven research" - Barry Marshall, Nobel Laureate
Surprise 3. My ability to come up with original ideas increased exponentially
My hypothesis, informed by reading Creativity, was that as I built up a larger and larger base of timeless knowledge, I would be able to come up with more and more original ideas more and more quickly. This has proven to be true.
As our knowledge base of rare, useful, and timeless knowledge increases linearly, our ability to come up with ideas increases exponentially.
Surprise 4. I discovered a new way to make transformative decisions
As I followed this process, which hastened my personal evolution, I started appreciating the feeling of evolving more and more. I realized that I didn’t just love learning new knowledge; I loved being transformed by that knowledge. I loved discovering new preferences, values, ways of experiencing, and points of view. I loved feeling more alive. And that was an end in and of itself.
Thus when being confronted with a decision about what to write, I started gravitating toward articles that would be the most self-transformative. I also started using the same logic with other major life decisions. Rather than searching for options with the highest expected value, I started making decisions based on the desire to discover new versions of myself and feel more alive.
The person who speaks about the most eloquently on this shift in decision-making, based on my research, is philosopher LA Paul in her book, Transformative Experience. She condenses her research in the following talk, which I then clipped even more to give you a quick overview:
Source: University Of North Carolina - Chapel Hill
The end of her book, in particular, highlights the decision-making shift I’ve made as I’ve come to appreciate the revelation of discovering new versions of myself:
When we choose to have a transformative experience, we choose to discover its intrinsic experiential nature, whether that discovery involves joy, fear, peacefulness, happiness, fulfillment, sadness, anxiety, suffering, or pleasure, or some complex mixture thereof. If we choose to have the transformative experience, we also choose to create and discover new preferences, that is, to experience the way our preferences will evolve, and often, in the process, to create and discover a new self. On the other hand, if we reject revelation, we choose the status quo, affirming our current life and lived experience. A life lived rationally and authentically, then, as each big decision is encountered, involves deciding whether or how to make a discovery about who you will become. If revelation comes from experience, independently of the (first-order) pleasure or pain of the experience, there can be value in discovering how one’s preferences and lived experience develop, simply for what such experience teaches. One of the most important games of life, then, is the game of Revelation, a game played for the sake of play itself.
—L.A. Paul (philosopher)
Surprise 5. The perfect niche for me emerged on its own
Finding a niche can be hard for someone who encourages their curiosity. Curiosity has a life of its own, and it can feel very unpredictable. It’s impossible to predict what we will be most curious about in 2 months or 2 years.
For example, over the last 10 years, I’ve gone through the following niches:
Work-Life Balance (2 months)
Relationship Building (2 years)
Learning (8 years and counting)
Thinking (5 years and counting)
Thought Leadership (4 years and counting)
Ultimately, the challenge becomes, how do we pick a niche we might be in for years when our curiosity constantly changes?
For me, the answer emerged as I followed and analyzed my curiosity:
First, I noticed the the longer I’ve had a passion, the longer it will remain moving forward. I became a voracious learner when I was 16 years old. I started journaling an hour everyday since I was 18. I used to set aside time when I was younger just to think, and I always enjoyed asking people deep questions about life. This gave me confidence that I will likely be passionate about learning, thinking, and writing for many years.
Second, I noticed that going meta to my curiosities helped me find more fundamental curiosities. In other words, let’s say I have a passion for tennis. We can go meta to that and ask, what is it about tennis that I love? What’s the meta-passion? For me, what I loved learning was constantly changing, but my passion for learning (the meta-passion) was only becoming stronger.
Bottom line: We don’t have to start with a perfect niche established. All we need to start is one question we’re extremely excited to explore.
Bringing It All Together
Making the decision to live a learning lifestyle and write curiosity-based articles has been fulfilling and transformative. In this article, I attempted to give words to my journey and lessons learned, even though I’m still on the journey and still finding the right words to express internal shifts that I’m still making sense out of.
At a deeper level, the past 10 years of my life have been about unlearning things I learned in business school and in culture more broadly. And more about learning to value my own aliveness and trust in the wisdom of curiosity.
I am grateful to my younger self for making a decision to value my inner world and to adopt a process that only gains more and more momentum and possibilities over time rather than a stale process designed for fast publishing of mediocre ideas.
Take The Next Step As A Curiosity-Based Writer (For Paid Subscribers)
If this article spoke to you, then I have a resource for you that could change your life. At least that’s what it did for me.
I call it the Stepping Stone Mental Model, and I learned it from studying the book Why Greatness Cannot Be Planned by two of the top AI researchers in the world. Their research gave me words and a framework for what I was feeling internally. More specifically, they demonstrated that the biggest creative breakthroughs don’t actually come from a goal setting algorithm. They come from a novelty algorithm.
This book had such a big impact on me that I spent dozens of hours building upon it by synthesizing the ideas in the book with research on:
Creativity habits of Nobel Laureates
Curiosity
Hidden downsides of goals.
Next, I created a 90-minute masterclass along with a 19,000-word mastery manual for our Mental Model Club ($20 value).
As a bonus for paid subscribers, you can access the class and manual below…