I recently hosted our first-ever in-person mastermind, unanimously dubbed “The Wholesome Mastermind,” at a retreat center in Ojai just north of Los Angeles.

I’ve been interested in masterminds for years, but the ones available never seemed quite right for me – whether because of the travel requirements, the format, or the kind of people who joined.

I thought: Why not create my own? So in January 2023, I put out a call for other online course creators to join me for a long weekend. To my surprise, eight of them said yes, and we came together in June to see what we could learn from each other.

I’ve always noticed that it’s quite difficult to summarize what exactly one gains from an experience like this one. People will rant and rave about how valuable and meaningful it was, yet when you press them for details, all they can talk about is “a new sense of perspective,” “renewed clarity” and other such ambiguous concepts.

In the spirit of transparency and accountability, I’ve distilled the 5 most important takeaways I walked away with to share with you…

1. The difference between being nice and being kind

As we took turns sharing our goals and challenges, one of the other entrepreneurs quickly identified that I had “people-pleasing tendencies.”

I had never thought of it this way, but he was absolutely right. I’ve always been the type of person who bends over backward to please people, accommodate them, and come off as a “nice guy.” Sometimes in a healthy way, but often in a dysfunctional way, by ignoring or minimizing my own needs in order to satisfy the needs of others.

I can trace this tendency far back into my past and could see in how many ways it had limited me. The trouble with repressing your own needs is that they don’t go away – they fester. Sooner or later, it all boils over in the form of angry outbursts or passive-aggressive resentment.

My entrepreneur friend pointed out a subtle but incredibly powerful distinction for us people-pleasers: sometimes when you’re trying to be nice, you’re not being kind. 

It’s kind to tell people how you truly feel. It’s kind to surface what doesn’t work for you, early and often. It’s kind to assume people can hear the truth (or at least your truth). But this isn’t necessarily going to mean you come off as nice. Sometimes you have to choose.

Usually, by the time I finally reveal a longstanding blindspot, there are multiple areas of my life where it is manifesting itself. And this was true in this case: several areas of the business that had seen lingering, chronic problems suddenly snapped into focus. I knew I needed to have some frank conversations that I’d been avoiding or downplaying for too long. It was time to choose being kind over being nice. 

2. Creative collaboration isn’t the same as people management

Another helpful distinction for me was to realize that there are two sides to my relationship with the people on my team: a creatively collaborative side – all about ideas, insights, experiments, and imaginative breakthroughs – and a people management side, which is about evaluating performance, measuring progress toward goals, and navigating conflicts.

I had assumed that as the CEO, I was supposed to have all the hard conversations. That’s what a leader does, isn’t it? The problem is, I’m not good at having hard conversations, nor any of the other responsibilities involved in management. They leave me incredibly drained even when they go well. Basically, I was running around the business doing all the stuff I’m not good at, leaving no time for the areas where I excel! Not exactly the formula for a thriving business.

I had assumed that I had to master both the creative collaboration aspect and the people management aspect, but a friend disabused me of that notion. Why spend years trying to master something I have no natural affinity for, while the business suffers and flounders in the meantime? 

I could instead separate these two aspects, giving all the people management duties to our new COO, Monica Rysavy. We’d already been moving in this direction for some time, but on my first day back, I made it official: she would run the business day to day, leaving me free to explore new creative frontiers, which is not only what makes me happy, but is also best for the business.

We moved all my direct reports to her, which frees me up to have a purely creative and collaborative relationship with each person on the team. Rather than holding back my feedback for fear of damaging the creative flow of ideas, I can step fully into my role as the thought leader and visionary creator that I fulfill best.

3. My dissatisfaction is the true north of the company

As a creator-led business, Forte Labs is designed to enable my personal creative and intellectual pursuits. It’s not like other companies that are product-centric or process-centric. We are idea-centric, and specifically, the ideas that I am currently pursuing and enlivened by.

As a result, I have to be very clear about what I want: the ideas I want to study, the projects I want to pursue, the learning I am being drawn to, and the investments that allow all those things to be monetized. This is why practices like journaling, meditation, retreats, coaching, and writing are so crucial – I literally cannot afford to lose touch with my burning passions.

Surprisingly, the conversations at our retreat revealed the opposite side of that coin: that my dissatisfaction is an even more powerful compass for the company. Since Forte Labs is an extension of me, I can feel problems brewing in any aspect of the business at an almost visceral level. I can sense things going wrong long before they become obvious, which means that being in touch with my dissatisfaction is like a superpower allowing me to see into the future.

Combining the three insights above, I’m beginning to realize that my effectiveness as a leader depends more on being able to sense problems brewing underneath the surface and raise them as quickly and loudly as possible, rather than trying to precisely diagnose and fix every problem myself. 

It’s far faster and more effective to hand off the resolution of a problem to someone else once it’s been identified, so I can focus on the next one. It’s like a never-ending conveyer belt of problems, each of which has the potential to become a new innovation or breakthrough. I am only the initial station on that conveyor belt, not the entire factory.


4. A product is defined by the consciousness that created it

Another attendee mentioned this phrase in passing, but it explained so many things I’d noticed over the years about the content and courses we’ve created.

The idea is that the maker of something – whether a piece of writing, a slide presentation, a website, or a physical product – inevitably leaves an impression of their consciousness on the thing they’ve created. No need to get metaphysical about it: this can simply mean that the state of mind one is in indelibly shapes the decision-making that goes into a new creation.

When I am in a deep flow state and all parts of myself are aligned and working in harmony, I produce things that flow logically, are internally aligned, and function harmoniously. However, when I am in a chaotic state, internally conflicted, or aggravated, the writing or designs, or emails I produce reflect that.

I’m not saying we should only create things when we’re in a perfectly balanced, zen-like trance. All states of mind have their use. In fact, many of my best inventions happened when I was feeling manic, depressed, nervous, angry, or in inner turmoil. This isn’t a moral imperative, but a functional one: to be aware of how your internal consciousness is influencing everything around you, especially anything you create out of that consciousness.

Speaking practically, this insight was the final confirmation I needed to feel confident in giving outside facilitators full control over our cohorts. My consciousness had shaped the nature of the Building a Second Brain course and how it was taught since its inception. That had given it a coherence and a personal style crucial to allowing it to break through the noise. But now we needed more kinds of consciousness to contribute their own ideas, and to allow BASB to evolve in ways that aren’t possible when I am in the driver’s seat.

5. It’s time to curate people, not ideas

My fifth and final insight wasn’t something anyone said directly. It emerged in my mind like a prophecy, fully formed, like it had been waiting in plain sight to be found. It was the phrase, “It’s time to curate people, not ideas.”

As the intensity of my book launch has wound down over the past six months, I’ve started looking to new horizons for the “next big thing.” After years of extreme convergence, I’ve been feeling the hunger to swing back to divergence and indulge my curiosity without a specific outcome in mind.

I’ve spent time trying out a new generation of second brain apps like Obsidian, Tana, and Mem. I’ve immersed myself in the AI revolution, experimenting with various generative AI tools. I’ve started getting back into personal growth again, after a long hiatus focused on raising our two young kids.

All this learning has been wonderful, but there has been something nagging at the edges of my mind the whole time that I can now see clearly: the way I explored new things in the past isn’t going to work anymore. In the past, my default approach to learning was obsession – eating and breathing the “new thing,” staying up late into the night tinkering, spending all my time on it, even changing my social circles and my environment to feed my hunger for new information. 

That was exhilarating and gratifying, not to mention being a fantastically effective approach to accelerated learning. But I can’t do it anymore, and wouldn’t want to even if I could. I have a beautiful family and a healthy, grounded daily routine. I have a profitable business and a world-class team I can rely on. That’s a lot of people I have affection and responsibility for, and I’m not interested in neglecting them in order to throw myself at something new.

My typical obsessive approach to learning, as exciting as it can be, also has a major flaw: it is tremendously wasteful. You have to spend hundreds of hours pursuing leads that don’t pan out. You have to get into the weeds, since there is usually no curriculum or map to follow. And let me tell you, the weeds can consume vast amounts of time with little to show for it.

One afternoon at our retreat, I was in the “hot seat” with a question: How can I explore the emerging generative AI landscape without taking my usual obsessive approach? The answer my friends and fellow entrepreneurs came to almost immediately was obvious in retrospect: lean on the people around you. 

The major difference between me today and me 10 years ago is I now have a network of people aligned with my mission and eager to contribute to it. I’ve built an audience of people who are already at the frontier, already doing the work, already learning and innovating, and discovering the important lessons of this new AI landscape. 

I don’t have to strike out toward that frontier, by myself with a pickaxe in hand, to mine for gold nuggets at some random stream. I can call up an army of intrepid explorers who aren’t just willing to join this adventure, but eager to do so. I can step into a new role, providing the infrastructure, leadership, and resources to fund this grand expedition. I don’t have to go it alone anymore.

I spent the first decade of my career curating individual ideas, carefully noting them down in my notetaking system and then systematically reviewing and synthesizing them into new creative works. That has been such a gratifying experience. But now it’s time for a new chapter – to go up a level, and become a curator of people. 

Perhaps my greatest takeaway from our first mastermind is uncovering an unexpected desire within myself: to serve creators and entrepreneurs who are doing important work in the world. 

I discovered that such people are out there, and they need help, and I have a unique ability to offer that help. I learned that I do know how to create environments and experiences that provide profound value to them. Environments that evoke vulnerability and authenticity, where people can show up as their full selves while also taking away transformational business and strategic insights. 

I want to spend the next chapter of my life contributing to a community of creators, entrepreneurs, writers, teachers, artists, and experts who share a common vision of serving humanity to their fullest potential. I want to connect them to each other so they can see that they’re not in this alone. 

It’s time for me to learn the subtle art of gathering people together, and showing up naturally and fluidly in such spaces so I can express myself without fear. It’s time for the last remnants of that shy, introverted, socially awkward identity to dissolve away. 

I have no idea what that’s going to look like exactly, but I also know that figuring that out is not my job alone. My job is to curate the right people in the room and watch the answer emerge.

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