When I started a company in my early 20s, I didn't have a great way of dealing with uncertainty and stress. Even though we bootstrapped the company to an exit, I was miserable a lot of the time, and when I finally moved on, I wasn't sure I'd ever want to start another business.

Entrepreneurship felt like a calling, yet my lived experience of it had often been quite painful. I spent years in traditional talk therapy and reading self-help books to try and make sense of my experience, but I still felt stuck. I couldn't see myself doing anything else, yet I couldn't see myself being happy starting another company.

I'd always been a bit of a psychology nerd (I originally got into meditation after reading a meta-analysis of its positive effects), and one day I stumbled upon a book, Values in Therapy, that explored a little-known framework from behavioral psychology that was a lightbulb moment for me. It finally helped me understand why I was so unhappy running my last company, and I finally began to see how I might be able to approach the stress and uncertainty of entrepreneurship in a new way: one that was life-giving instead of soul-sucking.

The framework is called Acceptance and Commitment Therapy (ACT), and even though it's backed by 800+ randomized controlled studies, it is relatively unknown outside of therapy circles. This post explains the basics of ACT, how it impacted my life, and how you can begin to apply it too.

At a high-level, ACT (pronounced "act" not "A-C-T") looks at how our thoughts influence our behavior, and offers tools for debugging when our minds get us stuck. In my case, it helped me recognize where my mind was adding to the stress inherent in running a company, and how that additional stress had gotten in the way of finding meaning and enjoyment in my work.

In talking with friends—both founders and non-founders—I realized that a lot of people go through what I went through, and that what helped me could also help others. I started devouring books and research on ACT, and eventually trained in how to use it with others in a coaching context (when it's not therapy, we call it Acceptance and Commitment Training and still abbreviate it as "ACT").

In this piece, I'll teach you the basics of ACT and how this tactical framework can help you operate more effectively and stay connected to meaning when doing work that matters to you. By the end, you'll have an understanding of how you can use ACT to debug your behavior, and hopefully, to live a more meaningful and productive life.

Let's begin.

The ultimate goal of ACT is to help us move closer to what we care about in life. From an ACT perspective, the main thing that gets in the way of this is when our behavior becomes primarily about avoidance. When we’re focused on avoiding difficult thoughts and feelings, we’re not focused on moving toward what we care about.

Where other psychological approaches might try to resolve challenging thoughts and feelings by rationally reframing them or exploring childhood memories, ACT doesn’t see difficult internal experiences as problems in and of themselves–they are only seen as problematic to the degree that they interfere with living a meaningful and engaged life in the present.

Thus, much of ACT is about helping us change how our thoughts and feelings influence our behavior. Essentially, ACT teaches us how to stay oriented toward what we care about even in the face of negative thoughts and feelings—because those are a normal part of life.

ACT calls this ability "psychological flexibility," and outlines six core skills that we can practice to help ramp up the thoughts that bring meaning to our work and disengage from the thoughts that take us off-course.

The framework is called psychological flexibility, because when we're caught in avoidance, our behavior tends to narrow and become inflexible.

To learn how to apply this framework in doing work that matters, we'll explore each of ACT's six core flexibility processes and how you can apply them.

Here is a list of the 6 core processes that we'll explore in-depth below:

• Experiential Avoidance → Willingness

• Fusion → Defusion

• Past/Future → Present-Moment Awareness

• Rigid Stories → Flexible Perspective-Taking

• Lack of Direction → Clear Values

• Inaction → Committed Action

These processes are all interconnected, but we'll talk about each in step-by-step order, and show how mastering each can lead you to the next one.

Click here to read the full post on Every

We all make decisions in life that trade-off between what we do for money and how we’d spend our time if money was no object.

Even those who make a living doing something they delight in still have to contend with the money problem. For example, Lionel Messi gets paid to play the game he loves, and also spends time doing this:

The New Messi Chicken Sandwich

Is Lionel Messi passionate about chicken? Or American chain restaurants? I’d guess not. But even while earning over $100 million per year in compensation playing for FC Barcelona, Messi decided it was worth his time to ink a five-year deal with Hard Rock Cafe.

This may be a solid financial decision—athletes have a limited time window in which they’re a hot commodity, after which their earning power drastically drops. However, with career earnings of over $1 billion, I wonder how Messi will look back on this from his deathbed.

How much is a year of Messi’s life worth?

How about a year of yours?

This has been the core question I’ve sat with for the last decade—how to balance money and meaning on the entrepreneurial path. And there are three archetypal ways that I’ve seen people approach the question:

• The deferred life plan

• Being bivocational

• Choosing to integrate

I’ve had a front row seat to success and failure on each of these paths: I’ve pursued each of these strategies at various times and have helped hundreds of founders grapple with these questions in the communities I’ve built and in my individual coaching practice. 

So how does one choose which approach to take?

In this piece, we’ll explore what each of these strategies look like when done well versus done poorly, and how you can approach the question with more intention to decide how you truly want to spend your days.

Click here to read the full post on Every

Last year, I was chatting with a struggling founder who said something that stuck out to me:

“If this startup fails, I’m going to keep working on some variation of the idea for as long as I live until I make it work.” 

At first glance, this may appear laudable. In startup culture, we mythologize founders who were rejected by investors and then went on to build significant companies. Yet while perseverance is important, this felt different.

I got the sense that this founder was hanging on to his idea like a life preserver. If he kept working on the idea and one day it worked, then the project wouldn’t really have failed. More importantly, he wouldn’t feel like a failure.

This is a pattern that many of us fall into at times. We start a project because we’re excited by our dream of what it might become, and then fall into a rut where we become more motivated by fear than by vision. We stop playing to win, and start playing not-to-lose.

This happens when we contact a fear that feels so big it overwhelms us. When small worries arise, we may be able to experience them while staying connected to meaning. However, when something touches a core fear, our lives and work can become about managing that fear.

As a coach and former founder, there are five archetypal fears that I often see underlying people’s work:

• Unworthiness - the fear of not being good enough

• Death - the fear of insignificance and disappearance

• Uncertainty - the fear of not knowing who one is or where one’s life is going

• Insecurity - the fear of not having enough resources

• Rejection - the fear of isolation or letting people down

Click here to read the full post on Every

When Anna* came to me, she was interviewing for jobs after spending the past 18 months writing full-time.

Previously a product manager, some of her early writing had gone viral, and she had decided to quit and throw herself completely into her writing. She had hoped to build an audience, maybe get a book deal, and find a way to make a living doing something she loved… but things didn’t quite pan out that way.

Instead, her early success became a weight so heavy that she barely published any work. With each new piece, she felt like she had to measure up to the standard she had set with her past work or exceed it. She dreaded the thought of putting out something “low quality,” which she feared would lead her audience to turn on her, criticizing the work and leaving her irrelevant.

As a result, her creative output shrank to only a few published pieces in the year and a half she wrote full-time—and the whole process was fraught with stress, procrastination, and anxiety. Even though the writing she put out was well received, she came to hate the process and the craft she’d previously loved.

When we began to work together, what felt to her like a “failure” weighed heavy on her heart. She had decided to get a job back in product to take the pressure off her writing, but she still carried the weight of her unfulfilled dreams. The artistic medium that had once brought her so much joy continued to be a source of stress.

Goal fusion: stuck on dreams

While Anna’s dream was about becoming a writer, her story is not unique. I’ve met numerous founders and creators whose work has suffered under the weight of their aspirations.

In Acceptance and Commitment Therapy (ACT), we call this “goal fusion.” In lay terms, goal fusion is when we get stuck on a certain dream for our future and become fixated on closing the gap between our dreams and reality. When this happens, we become disconnected from the work we’re doing in the present and may not realize when our dreams are leading us off course. 

Click here to read the full post on Every

I didn’t fully understand how detrimental avoidance could be as a founder until after I’d exited my first startup and began working at a fund that acquired and operated SaaS companies.

There, I was involved with 4-5 acquisitions of businesses with $1-10M in annual revenue, and I noticed an interesting pattern; nearly all of the companies we acquired had been run by product-focused founders who had avoided sales and marketing.

Each of them had gotten quite far by being first to market and offering a quality product; yet over time, they had all hit a plateau. They spent years trying to grow the business through yet-another-feature launch. When they did invest in sales or marketing, it was usually a half-effort led by a junior employee and constrained by the founder’s discomfort around growth.

This was fine for the first years of the company—but then revenue stalled, the founders burnt out, and they decided to sell their businesses. After seeing this pattern, I realized I had been guilty of the same behavior in my previous startup.

This is one of the beautiful and painful parts of building a company–at some point, your comfort zone becomes the bottleneck in your business. Either you grow as a founder (and a person), or the company plateaus. Whether you're just starting out or are running a billion-dollar business, success depends on your ability to tolerate discomfort. 

In this post, we'll break down what a comfort zone is through the lens of Acceptance and Commitment Therapy (ACT) and discuss several ways to intentionally expand it so you're less likely to cause your life and projects to underperform.

Comfort Zones: An ACT Perspective

A comfort zone represents a set of behaviors that feel safe to us. Our brains believe that if we step outside that zone, something bad might happen, so we experience discomfort. To avoid it, we move back toward what feels safe.

You can think of it like an electric dog fence. While the border might be invisible to others, when you venture near it, you get a shock that sends you back toward safety.

Rather than the physical shocks used when training dogs, our brains use aversive thoughts and feelings to keep us in line. When we start to venture beyond our comfort zone, we experience things like fear, doubt, anxiety, and self-criticism—pushing us right back towards safety.

For example, when a product-focused founder starts doing sales and marketing, they might get hit with a wide array of aversive internal experiences:

• Thoughts: “This won’t work” or “I don’t know where to start.”

• Self-stories: “I’m no good at this.”

• Feelings: fear, shame

• Memories: past experiences of rejection or failure

• Urges: to distract oneself or work on something easier (like developing another feature)

If the founder gets hooked on these experiences, they are likely to retreat back to the comfort zone of product development in order to avoid discomfort. This is how a friend of mine ended up with, in his words, “18 microservices and not a single user.”

From an ACT perspective, comfort zones themselves are not a problem—they are only problematic in as much as they get in the way of doing what we care about. Much of the time, there may not be much of a cost to staying in your comfort zone. However, choosing to pursue a meaningful life at times requires us to venture beyond its borders… or shrink our lives to fit what feels safe.

Now that we understand the concept of comfort zones and their potential impact on our lives, let's explore how we can expand them to achieve our goals. 

Expanding Your Comfort Zone

When we leave our comfort zone, it may feel like we're a pinball hitting a bumper. Without even thinking, we end up right back where we started. 

However, it is possible to stretch and expand your comfort zone. From an ACT perspective, there are four key aspects to consistently getting out of your comfort zone in service of building a life that matters:

• Clarify what’s important

• Ramp up the costs

• Build discomfort tolerance

• Create commitment scaffolding

Let's dive briefly into each one.

Clarify What’s Important

When first stepping out of our comfort zone, it will be uncomfortable. So to begin, it often helps to start by reflecting on why we’re willingly choosing to open ourselves up to discomfort.

It’s kind of like you’re sitting on an island surrounded by a swamp. All else being equal, it makes sense to stay on dry land. However, if there is a mountain you want to climb on the other side of the swamp, then you might be willing to get your feet wet.

When we are unsure about what we truly care about, it’s easy to default to familiar and comfortable behaviors. On the other hand, when we know what our discomfort is in service of, we experience that suffering as meaningful and are more likely to stay the course.

When we talk about what's important in ACT, we're often talking about values. Values are about what we'd choose our lives to be about, if we could choose anything.

Here are a few questions to help connect with your own willingness to go beyond your comfort zone:

• What is the “mountain” I want to climb that makes the “swamp” worthwhile?

• If I wasn’t bothered by fear/doubt/shame, what would I do? What would I want my life and work to stand for?

Ramp up the Costs

Staying in our comfort zone has short-term benefits and long-term costs. 

Click here to read the full post on Every

When our status is challenged, our body reacts like it's in physical danger. If you don't learn how to manage that reaction, you may find yourself in the status trap—endlessly chasing status as a way to try to feel safe and whole.

I experienced this myself when running my first company. We had been bootstrapping for a year when a competitor entered the space and raised $10 million.

This brought up a lot of insecurity. I was in my early 20s, with no real connections to mainstream investors. Our competitor was run by an ex-VC. Comparing myself to them, I felt like an outsider—like we were missing something or approaching the business wrong.

Years later, when I exited the company, this feeling stayed with me. I threw my energy into coming up with product ideas, hoping to start something new and get into YC. If I could do that, it felt like I’d finally be in the inner circle of tech and could call myself a Legit Founder™.

I’ve seen the same patterns in friends and clients. They feel like outsiders in comparison to tech’s “anointed ones,” and end up chasing external validation as a way to try to feel like they belong.

Instead of focusing on craftsmanship or doing work that matters, their life becomes about trying to get funded by Sequoia, go viral on Twitter, or give a TED Talk. External recognition becomes an end unto itself, often at the expense of their own values and vision. 

This is what I call the “status spiral.” When we compare ourselves with those we perceive as higher status, we feel insecure and doubt our self-worth. This in turn leads us to chase status as a way to try to feel better about ourselves.

However, status is a poor salve for feelings of "not enoughness." Even when we achieve status, it doesn’t necessarily translate into self-acceptance. In fact, striving for status can actually make us feel even more like something is missing or wrong in our lives.

Click here to read the full post on Every

If you want to be a great leader, you need to develop a worldview. You might think you don't have one—but you probably do. It's just implicit rather than explicitly articulated.

A worldview is a belief system that answers big, philosophical questions about life and existence. It's what guides our choices and how we orient ourselves in life. 

Understanding how to articulate and share your worldview with others can be a powerful tool for creating meaning in an organization. 

This came to light for me after I exited a travel company I’d started in the mid 2010s and spent a year studying theology and the psychology of religion.

When running the company, I hadn’t thought much about the deeper meaning behind our trips. But after learning about the study of worldviews, I realized that there were a number of core beliefs implicit in the experiences we offered:

• We believed in prioritizing life experiences over accumulating possessions.

• We believed in learning about oneself and human nature by coming into contact with people from other backgrounds and cultures.

• We believed in the importance of approaching work and projects from a place of intrinsic motivation.

• We believed that one should avoid the “deferred life plan”—that life is short, and one shouldn’t put off for the future what one really wants to do in life.

We never explicitly stated these things, but we could have—and doing so probably would have offered a greater sense of meaning to our participants, and given us a compass and greater sense of purpose as we built out the business.

Much like the bird at the front of the “V” makes flying easier for the rest of the flock, leaders who intentionally articulate and share meaning make it easier for everyone else in an organization to find meaning for themselves.

If leaders fail to do this work, members will either project their own meanings onto the organization or will fail to mark it as meaningful altogether. As an organization grows and new members no longer get facetime with the founder, this problem only gets worse.

In this piece, I’ll explore the basics of worldviews and ways to apply them in organizations. By the end, you'll have a better understanding of how to become a great leader by intentionally sharing meaning with others.

Worldview basics

“Worldview” as an idea was originally theorized by Immanuel Kant as a super-category that could include both religion and non-religious ways of viewing the world. The concept has been further developed in the past few decades by religious studies scholar Ann Taves and several others, defining worldviews by the Big Questions that they answer. 

These questions relate to six core domains within philosophy: ontology, cosmology, epistemology, axiology, praxeology, and eschatology*. They can be used to analyze many belief systems, from Christianity to Marxism, and can also be used to help articulate the core beliefs implicit in an organization.

Let’s look at each of these domains and the questions they explore:

• Ontology—what exists? (Gods, the natural world)

• Cosmology—how did we get here? (origin stories, secular history)

• Epistemology—how do we know what is true? (science, sacred texts)

• Axiology—what is the good worth striving for? (values, morals)

• Praxeology—how should we act to reach our goals? (practices, behaviors)

• Eschatology—how do we understand death and our own mortality? (afterlife, “YOLO”)

While religions offer explicit answers to these questions, we have implicit answers to these questions, revealed through our choices and behavior. When a worldview is implicit rather than explicit, researchers call it a “way of life.”

For example, if someone's goal is to become a scientist, their ontology may include a belief in the natural world, their cosmology may be based on the principles of evolution, and their epistemology may prioritize the scientific method for determining truth. 

As a leader, it can be helpful to explicitly articulate your worldview and understand the implicit beliefs of those you are trying to lead, so you can connect with your team on a deeper level and create a shared understanding of the world around you.

Of course, it's important to remember that everyone's beliefs are unique, and there is no one "right" answer to the Big Questions. The goal of understanding worldviews is not to impose your own beliefs on others, but to gain a deeper understanding of what motivates and drives people, and to use that knowledge to connect and collaborate more effectively through shared meaning-making.

Let’s look at how to think about articulating answers to each of the Big Questions as a leader along with some concrete examples:

Click here to read the full post on Every

If today was the last day of your life, would you be happy with how you’re about to spend it?

Steve Jobs famously said that he would ask himself this question each morning. I’ve found that continually asking this question is both one of the hardest and most valuable things you can do as a founder. 

It's hard because it's easy to get lost in the day-to-day grind of making your company succeed. It's valuable because the only way to make the stress worth it is to be working on something that matters to you. 

I learned this the hard way in the mid-2010s, when I was three years into running my first real business. What started out as a side project—a three-month hacker retreat in Costa Rica—had turned into a travel company doing half a million in annual revenue. However, as the business grew, I found myself in a role—and a life—that left me feeling unfulfilled.

In response to the pressures of building a bootstrapped business, I had become increasingly driven by loss avoidance. We made a few key decisions to make the business viable—raising prices and targeting higher-income customers—but these same decisions also moved us away from aspects of the work I had found meaningful and rewarding. 

Three years in, we had built a sustainable company, but one that I no longer wanted to run.

This happened because I'd lost touch with my values. Each individual business decision was economically rational but didn’t take into account what I ultimately wanted my life and work to be about. Altogether, they added up to a life that didn't work for me. 

If, instead, I'd been more in touch with what I wanted out of my life and work, I believe we could have built a business that was both viable and meaningful. But how can we stay in touch with our values as we go through the grind of building a company? 

Over the last several years, I've immersed myself in the values literature coming out of Acceptance and Commitment Therapy (ACT), and it’s been the most potent tool I’ve found for optimizing for meaning in life and work. 

In this piece, we’ll explore values in more detail and how they can help you stay connected to what matters, so you don’t end up with a business that works—and a life that you hate.

What are values?

In ACT, we think of values as what we ultimately want our lives to be about. They’re about how we want to live our moments, knowing that we’ll die someday.

If you were to ask the average person about what they value, they might say something like, “work,” “family,” or “spirituality.”

In ACT, however, we don’t see these as values; we see them as valued domains—areas of life within which one can express any number of different values.

Click here to read the full post on Every

“What is a normal goal to a young person becomes a neurotic hindrance in old age.” -Carl Jung

___

In The Second Mountain, David Brooks writes that our lives and careers are oriented around climbing one of two mountains.

The first mountain represents ego and striving in the world. It involves chasing outward success and cultural acceptance. We seek money, status, and power, all toward the end of feeling more secure in our lives.

Eventually, however, we come to desire more than the first mountain can provide. Either we reach the top and it disappoints, or we encounter some hardship in our life that reminds us of the quixotic nature of endlessly fortifying the self. In the end, no amount of resources or prestige can prevent the ultimate vulnerability -- our deaths.

At this point, we become aware of a second mountain: one motivated not by security and self-aggrandizement, but rather by an altruistic commitment to others. We no longer look to fill our existential vacuum with superficial achievements, but instead seek to dedicate ourselves to something beyond our ego -- a person, an ideology, or an organization.

Both mountains are important. We must find ways to survive and thrive in this volatile world, and the first mountain helps us find our footing. While spiritual practices may be meant to “relieve us of the bondage of self,” we must first develop a healthy sense of self before we can transcend it.

Yet, if we never move beyond self-orientation, we risk becoming what Buddhism calls hungry ghosts -- creatures who are never satiated, no matter how much they eat. In the words of Franciscan monk Richard Rohr, we must move our focus from doing “repair work on our ego container” and instead find the contents that are meant to fill it.

___

In generations past, religious traditions provided a framework for moving towards the second mountain -- a process known as “spiritual formation.”

Henri Nouwen, a 20th-century theologian, described this as a process of dropping from the head to the heart as a driving force in our lives. Through prayer, meditation, communal rituals, and a shared mythology of growth, people deepened in their religion and moved towards more meaningful and compassionate ways of being in the world.

In contrast, the modern, secular world has few overarching frameworks for growth. Perhaps this explains why self-help is a $10 billion industry and Americans spent $40 million on astrology apps in 2019 alone. We’re starved for something, anything, that can help us understand the world and our place in it. But instead of the Eucharist, we turn to Tim Ferriss and Tarot to fill the gap.

One reason the modern world finds classical spiritual formation inaccessible is that it usually comes wrapped up in orthodoxy -- systems of belief about the divine and our world. Growth processes are intertwined with a tradition’s myths and over-beliefs, alienating those who reject the supernatural or who do not wish to view their lives through the lens of a single tradition.

On the other hand, it is also possible to approach spiritual formation as an orthopraxy, rather than an orthodoxy -- a set of practices, rather than a set of beliefs. Many Western Buddhists, Quaker non-theists, and members of 12-step groups use this as a pathway into spirituality. They find value in the practices of a tradition even as they reject the original religious interpretation.

And yet, the above-mentioned environments are still too religious for many. Broad swaths of the secular world may never be able to look past talk of God at an AA meeting, or Pali chanting at a silent meditation retreat.

To reach the religiously unaffiliated masses and invite them into deeper meaning in their lives, we need orthopraxies of formation that are accessible to those of any faith and no faith.

How might we create these?

___

In an earlier post, we discussed three core elements that make an organization “church-y,” even if it doesn’t look like a traditional religious institution: contemplation, community, and contribution.

These are also what I like to think of as the three spheres of formation, and we can use them as a framework for building orthopraxies that meet the same needs as classical spiritual formation.

Contemplation

This sphere is about deepening one’s relationship with self and cultivating an experience of awe or transcendence. It encompasses rituals that invite us to slow down, touch the present moment, and make contact with our inner experience. Traditionally, this occurred through meditation, prayer, and time spent in silence. In the modern world, this also includes things like journaling, therapy, and intentional time in nature.

Community

This sphere is about cultivating interpersonal connections and seeing the shared humanity in another. Typically, it involves being part of a regularly meeting group where we can allow ourselves to be deeply known and learn to constructively navigate conflict.

It also involves building relationships with people across lines of age, ethnicity, race, and gender. Through these relationships, we become aware of the broader human story beyond our own individual lives, and we develop a deeper sense of belonging that we carry with us as we move through the world.

Contribution

This sphere is about channeling the energy from the practices above into movement toward the second mountain. It is about making sure personal or spiritual growth isn’t just navel-gazing, but results in committed action to reduce suffering in the world.

In the words of Buckminster Fuller, it is about asking, “What is it on this planet that needs doing that I know something about, that probably won’t happen unless I take responsibility for it?”

If we do not yet have an answer, this sphere is about experimentation and reflection -- exploring our vocational calling. On the other hand, if we already have some idea of an answer, this sphere is about making the daily decision to move toward the second mountain in the face of mainstream cultural influences.

…

Any well-rounded process of formation will include practices that encourage growth in each of these domains -- but what do they look like together in practice?

___

One of the best models I’ve seen of an orthopraxy of formation is at The Church of the Saviour, a little-known church based in Washington D.C.

Between 1950 and 2000, members of their congregation launched over 40 different non-profits in the D.C. area. Although the Church split into nine independent faith communities in the early 2000s, many of these non-profits are still around today, including a residential medical facility for the homeless,  recovery housing for people with addiction, and a local hub for community activism, among many others.

How were they so effective at activating their people toward social good?

The church was built around high-commitment small groups, each with a mission to serve D.C.’s most vulnerable populations. To join a group, you had to pledge membership for an entire year and commit to a number of practices in your daily life.

These included:

• A commitment to spend a specific amount of time in contemplative silence each day (meditation, prayer, etc).

• A commitment to make the weekly small group a priority in your life and allow yourself to be deeply known and loved by that group.

• A commitment to spend time with people across lines of difference, and use that time to nurture authentic relationships.

• A commitment to give proportionally of one’s time, energy, and resources.

• A commitment to use the inward journey to go outward, finding the place where one’s gifts and brokenness meet the world’s deep needs.

If we look at the above, we see that these commitments fall nicely into the three spheres of formation. They provide a balanced framework for how to grow as an individual, and the effect they had on members is evidenced through the community's impact on the local D.C. community.

Interestingly, while the Church of the Saviour was rooted in biblical Christianity, the commitments above are not explicitly Christian. Their orthopraxy is surprisingly secular-friendly, and can provide a foundation for individuals who are seeking the second mountain outside of traditional religious institutions.

___

After reading the above, you may decide you want to experiment with some of these disciplines in your life. Perhaps you realize that you want to carve out more time for stillness, or that you want to connect your existing meditation practice to more values-based action in the world. However, living into these commitments is easier said than done.

We don’t just decide once to move towards growth and then live happily ever after; it’s a decision we must continue making over and over again. Moving toward the second mountain can often feel like swimming against the current of mainstream culture -- when everyone around you is using a yardstick marked by status and fancy cars, it can be easy to lose sight of your own measuring tape.

This is why classical spiritual formation wasn’t just a set of independent disciplines, but was a holistic experience rooted in community -- scaffolding to help keep our bearings on the path. And yet, with a growing number of Americans identifying with no religious tradition (or dabbling in practices from multiple traditions), more and more people are creating their own piecemeal formation processes with no real support system.

If we wish to help the modern world move toward a second mountain, we need secular organizations that can offer the same formation experience that religion provided to generations past. Likewise, we need leaders in the secular world to step into their quasi-pastoral roles and take on the responsibility of inviting more meaning, connection, and impact into the lives of their people.

Though this is a big ask, we need not reinvent the wheel. Religious leaders have been doing this for millennia, and have generated a large body of academic literature around their process. While it may take some work to translate these learnings into a secular context, there is no greater task in our meaning-starved modern world.

___

Invitations for reflection:

• What mountain am I currently climbing? How would I name what’s at the top?

• In which spheres of formation am I currently moving? Where am I standing still?

• Are there any practices I feel called toward experimenting with after reading this post?

• Are my friends and colleagues pulling me toward the first or second mountain?

• Where do I have support on my path? Where could I support others?

___

PS -

A few friends and I started a “formation group” earlier this year -- a secular-friendly community based around the orthopraxy laid out above.

If interested in learning more, check out our full invitation and feel free to drop in one of our upcoming open gatherings.

PPS -

If you’re interested in implementing some of the ideas above in your community or organization, drop me a line. I’d love to chat.

However, in my early 20s, I got involved with the 12-step community. Going in, I knew nothing about the culture or history of 12-step programs, so when I found out that it was a spiritual approach to behavior change, I was... surprised.

Each meeting ended by holding hands and reciting the Serenity Prayer, and I was encouraged to learn several other prayers to recite at the beginning and of each day. As someone who formerly identified as a hardcore atheist, this brought up a fair amount of cognitive dissonance.

But I was at an emotional low point, so I gave it a try.

Over the better part of a year, I experimented with incorporating prayer into my daily life. I would recite the Serenity Prayer in my head before a challenging conversation, or the St. Francis Prayer before a work meeting. Occasionally, even though I had no real theistic beliefs, I found myself talking to God, the universe -- whatever was out there.

This was challenging at first, as the idea of prayer brought up a lot of resistance. I found it much easier to translate other aspects of the religious experience into a secular worldview -- embracing prayer always felt like it would mean turning off my rationalist filter and that I might start believing in all sorts of fanciful things.

However, rather than discounting prayer as I had in the past, I started to become curious about it as a phenomena. Prayer as a practice has shown up in societies across time, space, and culture. Even if I didn’t believe in a religious interpretation of prayer, I still wanted to know why so many people valued this practice.

Eventually, I came to a handful of secular interpretations of prayer that helped reduce my cognitive dissonance and to understand the role prayer plays in religious peoples’ lives. While I ultimately moved on from the 12-step world and let go of prayer as a personal practice, I still draw upon these interpretations to help bring meaning to my experience and cultivate empathy for others.

Below are a handful of these interpretations. May they be helpful for you as well.*

___

Finding hope

When people get sober, they tend to have lots of self-doubt and self-loathing. However, hope and belief in the future is important when making major life changes. Prayer can give people something to believe in when they no longer believe in themselves. It can allow them to tap into a strength that seems to come from beyond -- at least from beyond their negative self-identity. Even if it's simply a placebo, for many it still has a significant positive effect.

For the secular person, one can similarly look to believe in something beyond oneself at times of doubt and struggle. One way to think of this is as the anthropomorphization of an idea. We can view love, courage or compassion as tangible forces in the world that we are in relation to, that can visit us and lend us their strength. One can also engage with an internal representation of one’s ancestors, or with the universe itself. Even if these all are just projections of the mind, they can help us tap into more intentional ways of being during times of struggle.

Gladdening the mind

In the last few decades, we've learned a lot about the brain. One of those key learnings is that the brain keeps changing even as we get older, adapting to the experiences of our daily lives. Pathways in the brain are like grooves, and the more we travel those pathways, the deeper those grooves become. If we reach for a cookie or a smartphone when we feel sad or anxious, we’re more likely to do it again in the future.

One psychological interpretation of prayer and meditation is that it helps reinforce positive brain pathways. As one meditation teacher put it, it helps "gladden the mind." Examples of this are metta meditation in Buddhism or the Centering Prayer in Christianity, which both aim to cultivate emotions like love, compassion, and forgiveness. The more we experience these positive mental states, the more likely they are to arise again in the future. Eventually, they become such regular habits of mind that they turn from temporary states into personality traits.

Rubber duck debugging

In the tech world, some engineering teams engage in a practice known as rubber duck debugging. When a programmer encounters a bug they can't fix, before they go to a more senior engineer for help, they must first explain the problem and any ideas for potential solutions to a rubber duck on their desk. The idea is that in clearly elucidating the problem and possible solution space, engineers often solve the problem themself, without ever needing to bother their direct manager.

Similarly, even without a belief in God, one can understand the value of prayer as rubber-duck debugging. Whether we’re talking to God, the Universe, or a stuffed animal, by verbalizing the situation we're facing we may in fact stumble upon the solution ourselves.

Bonding

One of the ways that groups bond is through synchronous movement, singing, and speech. We see this in schools in the U.S. with the Pledge of Allegiance and at sporting events with the national anthem. We also see this in military bootcamp, where new recruits are forced to march and chant in unison for hours on end. These examples reinforce a sense of shared identity and communicate to each member of the group that they are part of something larger than themself.

Prayer as a method of group identification can also go far beyond the walls of a temple or church. For example, in the Orthodox Jewish tradition, there are prayers that one is required to recite at various points throughout the day. There is the prayer for eating, the prayer for sleeping, and even the prayer for going to the bathroom. At each of these moments, the prayer serves to remind a person of their religious and cultural identity, tying them back to the group.

In a more negative example, some cults use a similar tactic as a means to police the thoughts of their members. They'll compel their acolytes to pray constantly throughout the day, either out loud or in their own heads, such that there is no room in their thoughts for doubt or dissent.

In the secular world, one can utilize shared speech to create a greater sense of group-identification. A leader of a non-profit could have the team recite their mission as a group at the beginning of each weekly staff meeting, or a sports team captain could pick a call-and-response line from Remember the Titans and use it at the start of every game. These in-group memes can help transform a disparate group of people into a cohesive unit.

Sanctification

Sanctification literally means to make sacred -- it is a type of ritual that ascribes deeper meaning to an everyday activity, connecting it to "matters of ultimate concern." Whether it's work, food, or sex, sanctification serves as a bridge between the sacred and the profane, inviting a deeper sense of meaning into the mundanity of life.

Interestingly, sanctification has all sorts of positive benefits. Adults who sanctify marriage tend to have happier, more durable relationships. College students who sanctify sex tend to enjoy sex more, and have more of it. By intentionally ascribing deeper meaning to these activities, they both get better and become more significant in our lives.

One secular version of this is connecting daily behaviors to values -- the things you care about most in the world. This could look like intentionally tuning into a sense of compassion when speaking with your partner, or cultivating a sense of courage in the face of a difficult situation at work. These values can help heighten the high points of our life, and make meaning of the low points.

Another way to approach secular sanctification is through tying something mundane to a greater story. This could be as simple as calling in the memory of your ancestors before a family meal, or connecting your day job to a broader story of human progress. Either way, it’s about taking an activity we’re doing and tying it to something that transcends ourselves in time and purpose. It is, as Viktor Frankl put it, ascribing our identity to something greater than ourselves.

___

We've covered a lot of ground, and I imagine not everything here will resonate with every reader. The devout atheist will probably find these interpretations lacking, and the deeply religious person will probably feel that I've missed the point entirely.

Still, for those of us who see the world not in black and white, but in shades of gray, perhaps these ideas may give us something to try in our own lives. At the very least, I hope they help the non-religious person better understand the function prayer might play in a devout person’s life.

And finally, while I no longer pray, I do often find myself using poetry the same way I may have used prayer in the past. I’ll recite a poem by David Whyte when I’m out on a hike, or reflect on a line from Carlos Castaneda when contemplating a difficult decision. Whether it’s Rumi, Mary Oliver, or Harry Potter, pulling in passages from great works of poetry and literature can help us tap into deeper human dynamics, with or without God.

So with that, I’ll leave you with two of my favorite Rumi quotes:

“Out beyond ideas of wrongdoing and rightdoing there is a field. I'll meet you there. When the soul lies down in that grass the world is too full to talk about.”

“Stop acting so small. You are the universe in ecstatic motion.”

___

Invitations for Reflection

• Where am I struggling to control that which I cannot?

• Where might I benefit by placing faith in something greater than myself?

• What states of mind do I find myself habitually inhabiting?

• How might I be more in touch with my values during the mundane tasks of my daily life?

• What are the texts that I find to be “sacred”? How might I use them to punctuate my life?

___

*Example of a quick secular prayer

But this wasn’t an early morning dance party; this was church.

I had come with a community-builder friend to check out C3, one of several millennial-focused Pentecostal churches that have popped up in New York City. We wanted to see if there was anything we could learn from them about ritual and community design.

C3 originally started as a Bible-focused dinner series, and has grown to 70+ weekly gatherings throughout the city. They also offer more conventional Sunday services in Manhattan and Brooklyn -- but these worship services are anything but traditional.

As an usher walked us to our seats, the energy in the room was palpable.

The young, ethnically-diverse band was playing Christian Rock in front of a larger-than-life LED crucifix. At crescendos in the music, a fog machine released mist onto the stage. The parishioners in the crowd swayed to the music, palms raised to the heavens while singing along with words projected on a giant screen behind the band.

As someone whose main exposure to spirituality had been through staid Buddhist settings, this was an entirely new experience. It was lively, energetic, and dare I say… fun.

“I could get used to this,” I thought to myself.

After about 15 minutes of music, an early 30s white man came onto the stage and introduced himself as the assistant pastor. Over the slow, vamping tones of the guitar and piano, he started telling a story:

“Welcome all. I want to tell you about one of our members and something that happened in her life this week.

You see, a few weeks ago, she was diagnosed with cancer. But she is a woman of faith.

She gathered together with her dinner party, and they prayed together. When she went in for a follow-up this week, the cancer was gone. Hallelujah!”

As the crowd echoed “Hallelujah,” my heart sank.

On its face, C3 had a lot to offer. Their dinner parties provided consistent community in a highly transient city. Their worship services felt like rock concerts. And the congregation itself was young, hip, and nearly always smiling.

Yet, alongside that experience of community was an ideology that included faith healing and the belief that homosexuality is a sin.

As a person rooted in secular agnosticism who also likes to drop in on worship services of various faiths, this highlighted a recurring challenge I’d encountered in my search for meaning and community in New York City.

On the one hand, I was looking to grow as a person and explore life’s big questions, things people often find through religion. On the other hand, I was allergic to any dogma or magical thinking, and had no interest in the wholesale adoption of someone else’s belief system.

In Manhattan, it was hard to one without the other.

__

In Varieties of Religious Experience, the 1902 book that kicked off the study of psychology of religion, William James talks about there being a shared, core mystical experience at the heart of various religions around which we form a number of “over-beliefs.”

Over-belief, he says, is a term for beliefs that require more evidence than we currently have. In the realm of religion, they are the stories we create to try and understand the mysteries of our world.

Beliefs about the afterlife are prime examples of this. For instance, the Christian belief in heaven and hell, the Buddhist belief in reincarnation, and even the atheistic belief that death equals absolute non-existence are all over-beliefs. It’s impossible to know what happens when we die, so these are all beliefs that exceed our current evidence.

James didn’t think that over-beliefs were necessarily bad. He himself was a pious man, and he felt that over-beliefs were what gave meaning to life. As long as they did not lead to intolerance toward others, they were something to be honored and respected.

However, while some over-beliefs may be useful, there are three types of over-beliefs that I believe are problematic:

• Stale beliefs -- beliefs that are increasingly untenable in the face of modern science. I.e., the literal interpretation of a religion’s creation myth.

• Social-control beliefs -- beliefs that are meant to control social behavior and reinforce societal norms. I.e., strict interpretations of marriage and gender roles.

• Group-protective beliefs -- beliefs that are meant to protect a group’s ideology and membership base. I.e., the spiritual punishment of non-believers or those who leave the church.

If we take a look at C3’s “What We Believe” page, we can see several of these types of beliefs in action:

Stale: “The Bible is our guide to life, not only because it is good, but because it is true... It is infallible, authoritative and everlasting and is the foundation of all Christian doctrine.”

Social Control: “(We believe) marriage was instituted by God, ratified by Jesus, and is exclusively between a man and a woman. It is a picture of Christ and his church.”

Group-protective: “(We believe) in the resurrection of both the saved and the lost, the one to everlasting life and the other to everlasting separation from God.”

These are all beliefs that may have served a purpose at one point, but which now serve to alienate an increasingly secular millennial audience.

This is really a shame, because C3 has gotten quite good at building community and designing transcendent experiences. If their beliefs weren’t so outdated, they could likely reach a much broader swath of New York City.

___

In reaction to these problematic over-beliefs, many people swing to the other extreme. In the spirit of Richard Dawkins and the New Atheists, they decide that all over-beliefs are bad, and that the world would be better off without religion or spirituality.  

Yet, when we do this, we risk erring on the side of under-belief -- attempting to explain away the mystery of life by reducing the world to a purely scientific understanding.

For example, in Stephen Hawking’s final book, Brief Answers to Big Questions, he discusses his lack of belief in God and how the Big Bang theory explains the universe.

This is all well and good, but when he touches on the mystery of what caused the Big Bang, he makes an argument that itself requires a leap of faith -- he argues that the universe just randomly happened.

He writes:

“What could cause the spontaneous appearance of the universe?

Travel down… to the sub-atomic level, and you enter a world where conjuring something out of nothing is possible... at this scale, particles such as protons behave according to the laws of nature we call quantum mechanics. And they really can appear at random, stick around for a while and then vanish again, to reappear somewhere else.

Since we know the universe itself was once very small—perhaps smaller than a proton—this means something quite remarkable. It means the universe itself, in all its mind-boggling vastness and complexity, could simply have popped into existence without violating the known laws of nature...

The laws of nature itself tell us that not only could the universe have popped into existence without any assistance, like a proton… that it is possible that nothing caused the Big Bang. Nothing.”

While this belief in spontaneous creation may work for Hawking (and perhaps for you), it is no more plausible than the theistic belief that some creator set the whole process in motion.

Since all measurable forms of matter came out of the Big Bang, we quite literally have no way of knowing what came before. And yet, Hawking tries over the course of several pages to explain away that uncertainty.

___

So, what’s the problem with under-belief?

At their core, under-beliefs are an incorrect map of reality. There are questions in life we can’t know the answers to, and under-beliefs attempt to eliminate those riddles through scientifically reductive answers.

Ironically, the New Atheist tendency to try to resolve life’s mysteries is driven by the same motivation as the religious fundamentalist. Uncertainty is uncomfortable, and life’s big questions don’t just go away. Even those without faith must still find ways to make sense of how we got here, where we’re going, and how to relate to suffering.

Moreover, a worldview based on under-belief can lead to a drought of meaning-making in our lives. We can slip into nihilism and lose touch with what Paul Tillich termed “matters of ultimate concern” -- deeper human dynamics such as love, loss, and vocation.

For those of agnostic-yet-spiritual persuasion, the challenge then is to find a middle ground between over-belief and under-belief -- as my friend Alexey put it, a “Goldilocks Approach” to spirituality.

If this is you, you may be asking:

• How can I cultivate our own “over-beliefs” that provide meaning and still take modern thought into account?

• Where can I explore these questions without being asked to adopt someone else’s belief system?

I’ve been thinking of this process as one of secular formation…. and that is the topic for a future essay ;)

___

Invitations for reflection:

• Do I tend to lean towards under-belief or over-belief?

• How have my over-beliefs changed over the years?

• Do I sense another change on the horizon? If so, how might I name that inkling?

• How might I test my over-beliefs and come to a finer view of reality? Is this important to me?

The esteemed Rabbi Zusya was dying, and several of his students came to his bedside to share their love for him and to hear his final teachings.

When the students gathered round, they were surprised to find the Rabbi distressed at the prospect of dying and God’s final judgment.

Curious as to why, one of the students asked,

“Great Rabbi, are you afraid that when you die and meet the Lord, he will ask you, ‘Why you were not more pious, like Joseph?'”

Zusya responded,

“No, for if I die and meet the Lord and He asks, ‘Zusya, why were you not like Joseph?’, I shall say, ‘Oh Lord, all-powerful, if you had wished me to be more like Joseph, you should have made me more like Joseph!”

Another student piped in, asking,

“Well, are you afraid then that the Lord will ask you, ‘Zusya, why were you not kinder, like Rachel?’”

Zusya again responded,

“No, no, for if the Lord asks, ‘Zusya, Why were you not more like Rachel?’, I shall say, ‘Oh Lord, Creator of the world, if you had wished me to be more like Rachel, you should have made me more like Rachel!’”

Finally, a third student asked,

“Well, great Rabbi, what are you afraid of?”

Zusya, gray in the face, answers,

“My fear is that when I die and meet my maker, He will ask me, ‘Zusya, why were you not more like Zusya?' And to that, how shall I respond?"

___

What does it mean to live a good life?

Every major religion is in some way a response to that question, and each one offers a slightly different answer. *

Religious scholar Stephen Prothero offers a model we can use to explore these answers. In his framework, religious ideologies can be broken down into 4 parts:

• Problem: a proposed core problem of life

• Solution: a proposed solution to that problem

• Path: a defined path people can follow to move from problem to solution

• Exemplars: archetypal figures from history who have shown what it's like to walk the path

Through this lens, we can look at Christianity:

• Problem: sin

• Solution: salvation

• Path: faith, follow the gospel

• Exemplars: saints and apostles

Or Buddhism:

• Problem: suffering

• Solution: letting go, being with reality as it is

• Path: mindfulness and heart practices, 8-fold path

• Exemplars: bodhisattvas and the historical Buddha

Prothero makes the case that while the mystical core of each religion may be the same, the belief system and lived experience of the everyday practitioner is vastly different from one religion to the next.

___

The problem-solution-path-exemplar framework can also be useful in exploring non-religious belief systems.

In fact, some religious scholars have argued that, rather than labeling ideologies as “religion” or “non-religion,” we may be better served by thinking of both as belonging to the broader category of worldviews.

From this perspective, ideologies like nationalism and socialism can be explored in the same way as Christianity or Buddhism. For example, we can analyze the worldview behind the American Dream in much the same way as the religions above:

• Problem: class immobility

• Solution: free markets, laissez-faire capitalism

• Path: sacrifice, work hard, take risks, and achieve success

• Exemplars: Andrew Carnegie, Mark Cuban, Oprah Winfrey

Similarly, here is a problem-solution-path-exemplar breakdown of the ideology running through the venture-backed startup ecosystem:

• Problem: working for a salary is a poor way to build wealth

• Solution: don’t work for someone else, have equity in the projects you work on

• Path: start a company, do things that don’t scale, focus on 7% weekly growth

• Exemplars: Mark Zuckerberg, Elon Musk, Drew Houston.

In many ways, YCombinator founder Paul Graham’s essays (linked above) function as a sort of sacred text for the startup world, laying out a clear ideology and opinion on a well-lived life.

To be sure, few people in tech would identify as “Graham-ites.” However, even if one does not explicitly ascribe to a belief system, it is possible to infer one’s worldview by looking at one’s behavior.

While there is nothing wrong with intentionally adopting someone else’s ideas -- I still refer people to Graham’s essays as some of the most distilled public thinking on startup life -- trouble can arise when one or two ways of thinking broadly permeate a culture to the exclusion of other viewpoints.

For example, if you work in tech, you likely hear Graham’s thinking reflected in the tech press, from your CEO, and in the aspirations of your colleagues. Or, if you’ve picked a different watering hole, you hear the IndieHackers crowd telling you that VC is evil and the real answer to living a good life is to bootstrap a SaaS company.

Whether you resonate more with Graham or the bootstrapper crowd, the more time you spend in a mono or duo-culture, the easier it becomes to mistake these worldviews as simply facts of life.

We become fish, and these worldviews become the water we swim in, unaware as our original values and goals fade away and are replaced by the cultural standard.

___

I think of the above as “worldview drift” -- when we unintentionally adopt someone else’s myths, path, and prescriptive goals as our own.

This is especially common with secular worldviews, as they are often implicit. Based on our peer environment and exposure to different success narratives, our internal compass can shift dramatically without us ever realizing it.

Which brings us back to the story of Zusya, or to paraphrase Ralph Waldo Emerson,

“How to be yourself in a world that is constantly trying to make you something else?”

Ironically, when viewed through the lens of Prothero’s framework above, this is just another interpretation of “the great problem” of life.  

To flesh out the full “be thyself” worldview:

• Problem: external pressures shape our lives in ways we wouldn’t freely choose

• Solution: self-express, live authentically

• Path: mindfulness, therapy, journaling, walking alone in nature

• Exemplars: Henry David Thoreau, David Foster Wallace, Mary Oliver

Viewed through this lens, the term “spiritual growth” becomes not about anything supernatural, but about reflecting more intentionally on what it would mean for each of us to “be more Zusya” in our lives.

Of course, much like the other worldviews above, “be thyself” is an aspiration; we may get closer and closer, but we’ll never fully reach our destination.

Still, perhaps this framework can help those of us who don’t affiliate with a traditional religion become aware of how we are living out our own answers to these questions, and notice when our worldview inevitably begins to drift.

___

Invitations for reflection:

• How does the problem-solution-path-exemplar framework resonate?

• What does my behavior implicitly say about my current worldview?

• How would I name the "problem" and "solution" of life?

• What would it mean to live in such a way as to be more you?

In his work with end-of-life patients, psychologist Irv Yalom remarked that,  “Cancer seems to cure neuroses.” He found that the dying tend to “trivialize life’s trivia,” rearranging their life priorities and deepening their relationships with friends and loved ones.

Yalom coined these as “awakening experiences” -- encounters with death that lead to a vastly more fulfilling life.

Interestingly, it wasn’t just those facing chronic illness whose lives were transformed by encounters with death. Any patient who was able to tap into a greater awareness of their own mortality had the capacity to move towards a greatly enriched sense of life.

These awakening experiences often arose when patients faced major life milestones, like graduations, weddings, illness, loss, or major decisions. Yalom would help his patients get in touch with the death anxiety that came up at these times, asking his patients:

“Why are you afraid of death?”

Their answers would nearly always point toward some sense of an unlived life. To the degree that a patient had lived their life on someone else’s terms or failed to prioritize what they held most dear, to the same degree they would experience anxiety around death.

For many, this inquiry became a compass, helping re-orient their lives toward more vitality and authenticity.

___

Over the past several months, the pandemic has reminded us of our mortality and vulnerability. As of this writing, we have seen nearly 80,000 coronavirus deaths in the U.S. alone.

No matter how grandiose our illusions of competence and control were before the pandemic, we have now come face to face with the limits of our agency in the face of external forces. We may have put men on the moon and built cities of millions of people, but our society can still be brought to its knees by a microscopic biological invader.

This awareness of death and vulnerability is not comfortable. Our natural inclination is to turn away from these feelings, and thus to try and maintain our illusions of invincibility.

During the pandemic, I’ve often seen this occur through minimization. My friends in their 20s say, “At least I’m not in my 30s.” My friends in their 30s say, “At least I’m not in my 40s.” My parents in their late 50s say, “At least I’m not 65+, the real high risk group.”

No matter where you fall on the spectrum, there’s someone else with higher risk. I’ll bet in In nursing homes throughout the U.S., you can hear people saying, “I may be 73, but at least I never smoked!”

This helps to distance ourselves from the anxiety of, “Oh wow. I might actually die.” Yet, this encounter with mortality may be the greatest gift the pandemic has to offer.

___

For many of us not on the front lines, quarantine has become the new normal. Our day-to-day experience is un-dramatic and marked mainly by boredom, loneliness, and a yearning to get back to our pre-covid lives.

While in the early days of the pandemic, there was uncertainty around how bad the situation could get, there is now a growing sense that the worst is already behind us. We seem to have successfully “flattened the curve,” and any sense of our lives being imminently at risk has faded or fallen away completely.

But here’s a reality check:

Hundreds of people in their 20s, 30s, and 40s have died of the virus in the past few months. Moreover, we’re beginning to see secondary effects of the virus on younger age groups, with young people now dying of strokes and children coming down with rare inflammatory diseases. Others who survive may have to deal with long-term lung scarring.

The reality is, there’s still a lot we don’t know about this virus. Your body could react poorly, and your life could drastically change, or even come to an end, over the next year.

Even if you come out alright, it’s possible that your friends and loved ones won’t be so lucky.

__

There is a scene in the movie Fight Club where the main characters abduct a convenience store clerk at gunpoint.

In the parking lot behind his store, they rifle through his wallet and find an expired community college I.D. The main character, Tyler Durden, threatens to kill the clerk, and then asks him a simple question,

Tyler: “What’d you want to be, Raymond K. Hessel?”

The clerk doesn’t respond, so Tyler cocks his gun and asks again.

Tyler: “The question, Raymond, was what did you want to be?”

The clerk frantically responds that he’d wanted to become a veterinarian, but found the schooling too hard, to which Tyler responds:

Tyler: “Would you rather be dead? Would you rather die here on your knees in the back of a convenience store?”

Eventually, Tyler lets him go, but says he’ll check back in 6 weeks to follow through on his threat unless Raymond is re-enrolled in school and on the path to fulfilling his dream.

As the clerk runs off, the main characters remark:

Narrator: “That wasn’t funny. What the f--- was the point of that?”

Tyler: “Tomorrow will be the most beautiful day of Raymond K. Hessel’s life. His breakfast will taste better than any meal you or I have ever tasted.”

Narrator: “You had to give it to him… it started to make sense… no fear, no distractions. The ability to let that which does not matter truly slide.”

[source]

___

In a sense, this pandemic has abducted each of us at gunpoint and invited us to reflect on what really matters. Yet, many of us have chosen to wake up the next day, pretend that nothing happened, and go right back to work at the same old convenience store.

In the coming weeks and months, I invite you to notice your own inclination to turn away from death and vulnerability. It’s a natural human instinct, but instead, I’d invite you to see if you can allow yourself to be touched by death, and in turn, to transform your life.

This is not only an opportunity for each of us to pierce our own illusions of immortality, but also to honor those we have lost and are about to lose. Their deaths do not have to be in vain; they can serve the purpose of giving those that survive a chance to wake up to a vastly more fulfilling life.

Do not let this pandemic go to waste.

___

Invitations for reflection:

• Why, specifically, am I afraid of death?

• If I were to die in the next year, what would I most regret?

• Am I making the most of time with loved ones that I might very well lose?

• How might I live in such a way as to minimize the accumulation of future regrets?

Their main innovation is this idea of the ecclesial minimum, or the minimum viable church. After studying house church movements in China and the Philippines that were growing exponentially (but looked very different from the American middle-class suburban mega-churches), they distilled their sense of what the “church” is down to three things:

• Community - gathering together with others

• Worship - centered around the gospel*

• Mission - serving the needy, the poor, or the unchurched

*interpreted from a conservative Christian perspective

As long as something had those three characteristics, they’d consider it a church, and have supported a wide variety of micro-churches, including:

• Beer and Bible - a Bible study that takes place over beers in a local microbrewery

• Mama Africana - a Christian mentorship program for young girls of color

• Well-Built Bikes - a non-profit bike shop that uses revenue to offer bikes to low-income city residents who can’t afford public transit

As a secular individual, I was surprised by how much I resonated with the ideology of The Underground. However, while they’ve cut out a lot of the “sacred cows” of traditional religious institutions down to what they believe is the core of the church, I believe the definition can be distilled further to take into account a secular & interfaith context.

Here is the adapted “minimum viable church” that I came up with:

• Community - gatherings where one can be deeply known and loved by others

• Contemplation - connecting with some form of the “sacred” or one’s inner life (journaling, prayer, meditation, etc.)

• Contribution - serving to somehow alleviate the suffering of the world

If you’ve read this far, I’d be curious to know:

• How do you resonate with this opinion on what it means to live a good life? (community, contemplation, and contribution to others)
  

• In which of these areas do you feel your cup is currently full? Is there an area that could use some nourishment?
  

• Is this definition of “church” missing anything? Does it change how you think about any of the organizations you’re currently a part of?

Foreword

I’ve spent most of the last 10 years building communities.

From building coworking and coliving communities across multiple continents, to organizing online conferences and hackathons that attracted thousands of people, I managed to get more right than I got wrong...

...but I often felt like I was flying by the seat of my pants. I had no overarching theory or framework within which to understand my experience.

That all changed in 2017, when I stepped back from the day-to-day leadership of my last community-based company, Hacker Paradise.

For the first time in my career, I had time to slow down and reflect on my experiences. A month into my sabbatical, I came across a book that completely changed the way I think about creating connection and belonging: The Purpose-Driven Church, by Rick Warren.

In the book, he describes how he built a 20,000-person mega-church from scratch in Orange County, California. As someone who was raised secular, I’d never been exposed to the church-planting world, yet I found the concepts and frameworks directly applicable to my experience leading secular communities.

I realized that community-building doesn’t have to rely on gut instinct -- it’s a learnable, teachable skill-set, and religious leaders and activists have been honing these skills for millennia.

From there, I started reading everything I could on community design and the psychology of religion and mass movements. I interviewed countless other community practitioners, and began experimenting with putting these ideas into practice in my own organizations.

In this mega-post, I’ll share the key concepts and frameworks that I’ve found most useful. These are the ideas I come back to over and over again when designing communities and gatherings for a deep sense of connection, meaning, and belonging.

Moreover, not only have I found the ideas in this toolkit useful when building community for others, but also in cultivating deeper relationships and meaning in my personal life.

I hope you find these ideas fruitful as well.

We’ll be following up on many of these ideas with future posts that will provide in-depth explorations of each topic.

For now, I present to you -- The Little Black Book of Community.

#1 - The Unbundling of Religion

We live in an increasingly secular, urban, and isolated world.

25% of Americans and 40+% of millennials are religiously unaffiliated. 80% of Americans live in urban areas. 70% are on Facebook, Twitter, or Instagram. Against this backdrop, people are yearning for something to fill an unnamed void -- a void  that former generations met through organized religion.

The landmark research on this topic was done by Angie Thurston and Casper ter Kuile at Harvard Divinity School, where they explored how organizations like Crossfit, SoulCycle, and Creative Mornings are giving people some of the same connection, meaning, and belonging that previous generations experienced at church every Sunday, a phenomenon that some academics have described as the “unbundling of religion.”

Skillful community-builders are aware of this and think intentionally about what it means to help their members find meaning and deep connection within their groups.

In my own experience running a travel community for digital nomads, it’s the difference between describing ourselves as merely a “community for people who can work and travel” vs. tapping into the idea of “pilgrimage,” tapping into what it means to punctuate a life with travel and tying our modern-day travels to the stories of travelers throughout the ages who have left home, yearning for adventure.

Key Takeaway:

When leading a community, or any kind of organization, you will probably find that your members are looking for something more in their lives: deeper connections, a sense of values, and help understanding the world and their place in it.

#2 - Transactional vs. Worldview-Oriented Communities

Some communities provide deeper meaning and belonging, while others are purely transactional.

Many professional communities fall into the latter category. If you asked members why they participated in a happy hour or other networking event, chances are they’d mention job prospects or other opportunities for self-advancement.

In these communities, members probably don’t feel a strong sense of identification with the broader organization. These communities mainly serve as a clearinghouse for certain kinds of transactional relationships, and the value of the community to their members doesn’t go far beyond that.

On the flip-side, there are what I call worldview-oriented communities. These communities take a stand on some of life’s big questions, sharing their own stories, symbols, and rituals that ascribe meaning to their members’ experiences.

One way to think about the difference between transactional and worldview-oriented communities is to check whether they meet 3 fundamental psychological needs:

• The need for connection and belonging

• The need for a framework to make sense of uncertainty and make decisions in an uncertain world

• The need for meaning-making and dealing with death anxiety

If an organization just brings people together but doesn’t offer a broader ethical framework or help their members connect their story to the broader human story, chances are those are transactional communities.

If an organization has an opinionated view on what it means to live a meaningful life, and particularly if that opinion helps their members deal with suffering and death anxiety in a more meaningful way, chances are they’re a worldview-oriented community.

To gain a sense of a secular, worldview-oriented community, check out this Harvard Divinity School interview with Crossfit founder Greg Glassman on the topic of Crossfit as Church, which even includes an exploration of Crossfit’s own meaning-making around death and mortality.

Key Takeaway:

Some concepts and frameworks are broadly applicable to all communities, and some apply more specifically to worldview-oriented communities and organizations.

The first half of this post will go through general community-design principles, and the second half of the piece will address ideas and frameworks that narrow the focus to worldview-oriented communities.

Community Design

#3 - Phases of Community Maturity

Richard Millington, in his book Buzzing Communities, outlines the 4 phases of community maturity, particularly with regards to online communities:

• Inception - 50-100% of growth & activity driven by community manager

• Establishment - 50-90% of growth & activity driven by members

• Maturity - 90+% of growth & activity driven by members

• Mitosis - plateau-ing of growth & activity, splitting of larger community into smaller sub-communities

One important insight from this framework is the idea that growth tactics vary according to a community’s stage of development.

In the inception stage, community-builders should be individually inviting outsiders to join the community, initiating many of the discussions, individually prompting members to participate in discussions, and building 1-to-1 relationship with members.

Once the community has hit critical mass and 50+% of activity in the community is initiated independently of the community-builder, leaders can then focus on encouraging referral growth, undergoing promotional growth tactics (PR, blogging, etc.), scaling up community processes, and working on activities that build a sense of community among members.

Key Takeaway:

If you’re trying to grow a community, you must know where you are in its life-cycle (based on % of activity initiated by members) so that you apply the appropriate approach.  

If you have not yet reached the threshold of 50+% of the activity initiated by members, you still need to be seeding content, sending personal invitations, and creating invitations to discussion!

#4 - Rick Warren’s 5 Cs -- Circles of Commitment

One of the biggest challenges I experienced in my early years of running Hacker Paradise was deciding how much of a commitment to ask for from participants.

We had some people who were super engaged in what we were doing and wanted to be as active in the community as possible. At the same time, we had people who were much less interested in participating in group activities.

In the early years, it felt as if we could either design trips for the lowest common denominator (the least committed person), or we could require a higher commitment and potentially lose people who weren’t ready for it.

Then I read The Purpose Driven Church by Rick Warren and came across his framework for how to design communities around different levels of commitment.

Rick talks about the 5 concentric circles of commitment around which he designed Saddleback Church, his 20,000 mega-church in Orange County, California:

• Community -- the broader community of people of which Saddleback is a part, particularly people who have come to Saddleback once or twice.

• Crowd -- the people who come to Saddleback regularly, but have not yet committed to becoming members.

• Congregation -- the people who have taken a formal membership commitment.

• Committed -- people who volunteer and take on a ministry in the church.

• Core -- the people who help organize the volunteers and other ministers within the church.

One interesting idea from the book is that Saddleback’s Sunday services aren't meant for Church members — they’re meant to be services to which an existing member could bring a non-believing friend. Sermons focus on practical ways to interpret the Bible for modern life, and music is hip and modern.

It’s only once a person becomes a formal member of the church, when they enter the Congregation stage, that they’re required to join a weekly small group, come to the Wednesday evening services meant for members, and tithe a percentage of their income to the church.

What’s more, to transition between each stage of commitment from Crowd —> Core, Saddleback requires you take a class and participate in a formal commitment ceremony, where you learn about the next level of commitments and why they’re important, and then explicitly commit to following them.

Key Takeaway:

You can and should find ways to create events and experiences for members at each level of commitment.

Meet people where they are, but also have higher commitment levels that they can step into.

#5 - Charles Vogl’s 7 Principles for Belonging

One of the first books I recommend to folks on the topic of community-building is Charles Vogl’s Art of Community.

Drawing from his studies at Yale Divinity School, his book outlines 7 ways that secular communities can create a sense of belonging, inspired by traditional religious institutions.

His 7 Principles are:

• Boundaries -- having a clear delineation of who is and isn’t a member of the community.

• Initiations -- an explicit process for marking when someone becomes an official member of the community.

• Stories -- shared stories about what the community values and its history.

• Rituals -- shared group activities that help members bond, make meaning, and express the unique values of the community.

• Symbols -- images, phrases, songs, or other items that have shared metaphorical meaning within the community.

• Temple -- a gathering place for the community, whether online or offline, where members know they can go to find each other.

• Inner rings -- ways to grow and progress within community based on one’s knowledge, experience, or commitment.

We’ll be releasing future posts to dive deeper into each of these ideas, and I highly recommend checking out the full book, which makes a great complement to Rick Warren’s The Purpose Driven Church.

Key Takeaway:

You can create a stronger sense of belonging and engagement in your community by intentionally designing your boundaries, initiations, stories, rituals, symbols, temples, and inner rings.

#6 - Ideal Gathering Sizes -- Priya Parker & Robin Dunbar

Many people are familiar with Dunbar’s number -- the idea that humans can manage only around 150 relationships at any given time. This number was theorized by Robin Dunbar, an anthropologist from Oxford, who saw that tribes tended to break down once their numbers got above 150.

Priya Parker extends this in her book, The Art of Gathering, and talks about other archetypal “tipping points” which change the way a facilitator should approach their gathering. She noted these as:

• 4-6 people

• 12-15 people

• 25-30 people

• 100-150 people

Robin Dunbar has written about similar thresholds in follow-up research relating to the ways social networks operate, noting that most people have:

• 1-2 special friends

• 5 intimate friends

• 10 “best” friends

• 50 good friends

• 150 acquaintances

• 500 very loose ties

Each of these group sizes leads to different approaches for creating intimacy and belonging.

For example, with 4-6 people, it’s easy to make sure everyone participates in a group conversation. This is much more difficult when facilitating groups of 50-150 people, and one needs to get creative to find ways that allow for active rather than passive engagement during a gathering. More on this below when we discuss liberating structures.

Key Takeaway:

Be aware of your overall group sizes when designing gatherings; when managing a community, think about what gathering sizes you currently hit and what sizes you might be missing.

#7 - Scaling Community through Small Groups -- Rick Warren

In a 2005 New Yorker article, Malcolm Gladwell described Rick Warren’s mega-church as a “cellular church.”

What did he mean by that? Well, most of the members of Warren’s congregation, Saddleback Church, meet weekly in 6-12 person Bible studies.

It’s easy to get lost in the shuffle in a 20,000-person mega-church, which is why Warren has placed such a strong emphasis on funneling people into small, tight-knit groups. This gives people the experience of a smaller, intimate community within the larger community.

He considers small groups to be the “cells” of the church’s body, and the Saddleback team puts a lot of effort into maintaining small group health. In one of his sermons on the importance of small groups, he sums up his philosophy: “If the cells are healthy, then the church is healthy.”

Burning Man is another great example of this -- tens of thousands of people flock to Black Rock City for Burning Man every year, and while all of the participants agree to a certain set of core principles, one’s main sense of community and connection comes from one’s camp, which again provides a mini-community within the broader community.

Key Takeaway:

Most community-builders I know think it’s hard to scale community, believing that once a community gets above a certain size, you inevitably lose the intimacy that was there at the beginning.

This is only partially true. While it may become more difficult to cultivate intimacy as a community grows, you can still have intimate community at scale. You just have to be more intentional about funneling people into small group experiences where they can experience the intimate relationships early members of the community developed by default.

• Rick Warren on the importance of Small Groups (video ~1 hour long)

#8 - Evaporative Cooling

This is one of the most powerful ideas in this list, and once you learn it, you will likely find it sheds light on a number of your past experiences in community, both good and bad.

Evaporative cooling is the idea that there is an average quality bar for members of a community, and over time, the average quality of a group tends to trend downwards.

In a professional community, quality might mean work experience, connections, or potential. In a workout community (like Crossfit), quality might relate to one’s commitment to fitness and the morale boost they give to the rest of the group.

Evaporative cooling is the idea that communities are most attractive to people who are below the average quality bar in a community. This means that unless there is an intentional vetting mechanism to keep quality high, the quality of a community tends to decrease over time.

This in turn leads to the highest quality members becoming less engaged and eventually leaving the community, which then leads to a further decrease in the group’s average quality bar. This leads to even lower quality people joining the group, which lowers the bar again, continuing in a downwards spiral.

This vicious cycle only stops once the community establishes a way to vet new entrants to the community -- or when community quality degrades to a point where the only people it attracts are happy to be associated with the group’s former reputation and don’t realize the community is no longer worth joining for the people it originally attracted.

There are two main ways to prevent evaporative cooling:

• Through an intentional application and vetting process, often with explicit membership criteria.

• By having gatherings that in some way encourage people to self-select out.

An example of clear vetting criteria is the Entrepreneur Organization (EO) community, which only accepts people who have founded companies with $1 million or more in revenue.

An example of a self-selecting gathering is a Crossfit workout, which is intense enough that it attracts only people with a certain set of goals, values, and orientations toward exercise.

Key Takeaway:

Be aware of what quality means for your community, and do what you can to make sure your incoming stream of new members meets or exceeds that average quality bar. This is most effective when you can explicitly define membership criteria.

#9 - Liberating Structures

Liberating structures are a number of exercises used to “free” participants in a gathering from the “tyranny" of a speaker or facilitator by encouraging participation from all members.

The most basic exercise from the liberating structure tool-kit is “1-2-4-all,” which involves:

• Inviting people to reflect on a topic individually for a set amount of time (1)

• Talking about it in a group of 2 for a set amount of time (2)

• Combining pairs into groups 4 to continue discussing for a set amount of time (4)

• Coming back to the large group and inviting people to share highlights of their discussions (all)

Key Takeaway:

Next time you’re presenting information, whether it’s giving a talk or welcoming people to an event you’re organizing, try out this approach above as a way to inspire your participants to talk to each other and to actively participate in the gathering as early as possible.

For more examples of liberating structures, check out their book.

Worldview-Oriented Communities

As we mentioned in the beginning, there are a number of frameworks that are more relevant to worldview-oriented communities. In the second half of this post, we’ll walk through a handful of them and how they might be applied.

#10 - Problem-Solution-Path-Exemplars

In his book, God is Not One, Stephen Prothero discusses some of the differences between 8 of the world’s “Great Religions.”

His main framework for dissecting each religion can be thought of as Problem-Solution-Path-Exemplars and is useful when distilling any community's worldview and reason for existing:

• Problem -- the great problem of life, i.e. suffering, sin, pride, etc.

• Solution -- how to deal with life’s great problem, i.e., non-attachment, salvation, submission, etc.

• Path -- individual and group techniques for moving from the problem to the solution in one’s life

• Exemplars -- people who have successfully navigated this path from problem to solution

This idea is similar to Vogl’s inner rings and Warren’s concentric circles - it’s the idea that every community should inspire its members to grow in some way, further and further embodying the values and belief system of a community.

Key Takeaway:

When designing a community, ask yourself:

• How do you view the “problem” of life?

• How does your community help solve it?

• In what way should membership in your community help members grow?

• Who already embodies the values of your community and can serve as exemplars to new and current members?

#11 - Six Big Questions

In the past few decades, scholars have been searching for a broader term than “religion” or “spirituality” that can apply to the life experiences of secular individuals and encompass other types of ideologies, like Marxism and nationalism.

The term that is being increasingly used to encompass religious and secular ideologies is “worldview.”

Worldviews can be thought to answer six “big questions” about life and the human condition:

• Ontology -- what exists?

• Praxiology -- how should one act?

• Axiology -- what should one strive for?

• Cosmology -- how was the world created? How did we get here?

• Epistemology -- how do we know what is true?

• Eschatology -- how do we relate to death and mortality?

An interesting idea from worldview studies is that we all have a worldview — it's just that for some of us, they are more explicit than for others.

Even if we can’t name or explain our own axiology or eschatology, the way we act contains implicit assumptions about each of the above and can be analyzed by outsiders viewing our behavior.

In the words of Carl Jung, “Until you make the unconscious conscious, it will direct your life (community), and you will call it fate.”

Key Takeaway:

As a community-builder, you may find it helpful to explicitly reflect on what your personal answers are to these big questions of life and how they’re expressed through your community, events, and growth path for members.

Engaging with your community’s worldview on these levels can help your members reflect meaningfully on their lives and come up with their own answers to the big questions.

#12 - Collective Storytelling -- Marshall Ganz

Marshall Ganz is a professor at the Harvard Kennedy School of Government who spent 25 years as an activist organizing farm workers in California.

He currently teaches courses on “organizing for action” and “collective storytelling,” and his frameworks are some of the best out there for distilling your community’s mythology and shared stories.

The big idea in his work is that we need three stories to motivate action:

• Story of Self -- our own history and values, why we are called to action

• Story of Us -- values shared by those who are called to action

• Story of Now -- talk of an urgent challenge to those values that demands actions now

A great example of these three stories can be found in  Barack Obama’s 2004 speech that launched him into the public eye.

Ganz also teaches about how some emotions inhibit action and some emotions motivate action, a lesson he learned while mobilizing activists in California.

At their best, our stories take us from inhibitory emotions to those that spark action:

• Inertia → urgency

• Apathy → anger

• Fear → hope

• Isolation → solidarity

• Self-doubt → you can make a difference

If you’d like to dive deeper into Marshall’s work, you can find some readings online here, or if you’d like to go deeper, his entire Harvard course is up on Youtube.

Key takeaway:

Work on distilling your story of self, story of us, and story of now to increase engagement in your community or organization!

Make sure everyone in your organization is familiar with your key stories, and help them come up with their own story of self that ties into the broader organizational mission.

#13 - Fowler’s Stages of Faith Development

James Fowler, a researcher in the 1980s, came up with the idea that people go through different stages of maturity in their belief systems, inspired by Piaget’s theories around childhood psychological development.

In adult communities and organizations, it can be helpful to reflect on where your organization sits in his stages of faith maturity.

Fowler’s first two stages of development relate to childhood, so they are less relevant to adult communities and organizations

Here are stages 3-5 in his model of faith development:

• Stage 3 — one’s belief system is heavily influenced by those with authority in a person's life. There is a strong emphasis on the authority of institutions and “sacred texts.”

• Stage 4 — one has an internal sense of what is right and wrong, often criticizing or leaving one’s childhood faith; the individual is highly judgmental of others’ beliefs.

• Stage 5 — one awakens to a broader perspective, allowing for the validity of others’ beliefs even if they contradict one’s own.

When looking at political organizations, religious groups, and even companies, one can find a number of organizations that embody earlier stages of maturity.

As much as possible, aim to create a “Stage 5” community or organization.

Key Takeaway:

Do your best to create a community that respects each individual’s internal locus of authority and respects others' beliefs and practices.

#14 - Sanctification

Sanctification is a specific type of ritual that connects an everyday activity to a sense of the “sacred.”

It’s basically a way of intentionally ascribing greater meaning to everyday activities, resulting in more enjoyment and impact for its participants.

And the ritual or activity doesn't have to be inherently religious in nature — in one study, researchers found that couples that sanctified sex enjoyed sex more… and had more of it!

For builders of secular organizations, it can be helpful to reflect on what activities your community holds to be “sacred” and to find ways to invite individuals into a sense of connection to something larger than themselves.

How to define the “Sacred” in a secular setting? I like to think of this as reminding people of their connection to something larger than themselves: nature, a group, a virtue, or the broader human condition.

Key Takeaway:

Reflect regularly on how your community connects your members to something larger than themselves. How can you help them cultivate that connection on a regular basis?

Conclusion

Each of these ideas and frameworks is immensely powerful, and with study and practice, can change the way you lead groups and help you to bring more connection and meaning to other peoples’ lives.

Moreover, the above only scratches the surface… We'll be following up with more in-depth explorations of these and other ideas in future posts.

Have another framework or concept that’s changed the way you think about community and organization design? We want to hear about it!

Ping me on Twitter, and would love to learn more.

I just got back from a 7-day silent retreat, and one thing that surprised me was how creative I became after cutting out all outside influences for 3–4 days. Ideas were so exciting, because they were the only stimulation I had! It reminded me of how I felt during some of the creative projects I did as a kid, pre-Internet in a house that didn’t have cable.

This in turn got me thinking of the Montessori approach to learning. From what I understand, their innovation was realizing that young children have an innate drive to explore and interact with their environment. So, if you create an environment that they can learn through interacting with, they will learn by default. Put them in that environment, and just by naturally being a toddler, they’ll pick up the things they need to know.

I think we adults have a similar innate drive to create, and that drive can be supported or stifled by the environment. And, I think that instead of creating environments where we are creative by default, we live in a world where we are distracted by default.

In a vacuum, we have ideas and projects that want to see the light of day. However, with phones in our pockets mainlining the Internet into our veins at any moment, our minds never have the uninterrupted quiet we need to let the creative juices flow. It’s hard for the seed of a not-yet-fully formed idea to compete with Candy Crush or checking HN / Twitter / Facebook / Gmail for the nth time that day.

What if quiet, stillness, and boredom are the fertile soil in which creative ideas can blossom? Cal Newport has written about the importance of carving out periods of deep work in one’s schedule, but what would it look like to make that the default?

Here’s a stab at what a “creative by default” lifestyle might include:

• No phones for most of the day

• Internet only at pre-allotted times, 1–2x / day

• Documentation, Stack Overflow, programming libraries, and design templates locally hosted and available offline

• Immersion in nature

• Extended periods where you can only meditate or create — no socializing or passive consumption of material.

• Regular, planned social periods outside of the silent work / meditation periods

• Healthy, low glycemic index foods

• Alarm clocks, analog calendars, and other “dumb” devices to reduce dependency on a smartphone

• An emergency contact # (maybe a land-line) where family / friends / colleagues can contact you if an emergency arises during the extended offline periods

• Perhaps a typewriter or other device that never touches the Internet

• Intentionally chosen pieces of content to consume around the creative life and process (poems, essays, talks)

And, in a group setting:

• Having one terminal with Internet access for as-needed connectivity throughout the day

• A place to store phones if needed where everyone can see, again using social pressure to encourage limited use

• Designated places to collaborate / brainstorm that won’t spill over into the silent creative space

After being in that environment for a week, I strongly felt like I didn’t want to let the stillness and creativity go when I left the retreat. So, since coming home, I’ve begun to implement some of the above practices in my life, like only connecting to the Internet a few times per day, getting a flip phone to use in case of emergencies, and spending more time in nature.

I’m also interested in exploring these practices in community, as I feel like having a group of people intentionally doing this will make it even more powerful. If you’d be interested in trying out these practices in a 4–7 day retreat, sign up here and I’ll reach out when I have something concrete.

Or if you have ideas / want to get involved, you can email me at casey@recesslabs.com.

Also, follow me on here if you want to hear more updates on my experiments with living a “creative by default” lifestyle!

I was recently chatting with a friend of mine who was learning to code. A psychology researcher at a major university, he wanted to create an app that would make it easier for researchers to collect patient data.

Ultimately, he wanted to turn it into a software product and sell it to researchers at other universities. However, since he didn’t know any programmers and couldn’t afford to hire someone to build it out, he thought his next best move was to learn HTML and Javascript.

This is a fundamental mistake I see non-technical entrepreneurs make when getting into the startup world, and it’s understandable.

Everywhere you look nowadays, people are talking about how “software is the future,” “programming is like literacy,” and “everyone should learn to code.” And, while programming is a useful skill, there are higher ROI things you can be doing as a non-technical founder.

If you’re trying to start a company, you shouldn’t start by learning how to code. You should start by learning product design.

When you’re exploring a startup idea, there are two main types of risk: technical risk and design risk. You can think of the distinction like this:

• Technical risk — can this be built?

• Design risk — if we build it, will anyone really want it?

Most product ideas are not that technically complex. This means that most of the risk is design risk, and that if you can lower the design risk, it’ll relatively simple to build the product you’ve designed.

How does one lower design risk?

The main way to do this is talking to potential customers to get feedback on your ideas. Luckily, there is an entire field of study around this process, called “product design” or “design thinking.”

My two recommended starting points for product design are this awesome Coursera course from UPenn and this list of resources from Stanford’s design school.

Now, you might think you need to actually build something to get feedback on your idea, but by using prototyping software, like InVision, you can get feedback on a high-fidelity prototype without having to write any code. These prototyping tools are pretty robust, and the learning curve is much shorter than learning web development from scratch.

Once you’ve gotten your product in front of potential customers, you’ll either have learned that people want it, or that you need to go back to the drawing board and incorporate some of the feedback you received.

If you need to do another iteration, that’s great — you just saved yourself a bunch of time by figuring that out now instead of after you’ve built the whole product.

If, on the other hand, people clearly want what you’re building, that’s also great. Having talked to users and verified your product assumptions will have put you in the 99th percentile of people looking for technical cofounders.

If you have people who want to give you money, or even better, have pre-ordered your product, that’s even better.

At this point, you can try and find someone technical who is looking to get involved with a startup or a project outside of work. Chances are, once you’ve found someone, they’ll be able to implement in under a month what would have taken you significantly longer to build.

Since you’re not spending your time learning to code, you can continue to iterate on the design, or you can start reaching out to other potential customers so that way you’ll have revenue from day 1 once you launch the product.

At the same time, all the above doesn’t mean you shouldn’t necessarily learn to code.

If you’re looking to transition into a career in software development, for example, then by all means, learn to code. Software developers are well-paid, tend to have good work / life balance, and get to do creative & engaging work, so if you’re looking for a new vocation, software is pretty sweet.

If you’re starting a company, you still might want to learn a bit about how the underlying technology works.

Also, there are probably code-related things you can learn to help automate tasks in your daily life, for example learning how to do web-scraping, more complicated mail-merges, or data manipulation. Often, the best place to start is by automating tasks you do regularly.

Overall, though, you should focus on how code can make you more effective at the job you have or want.

And, if you’re doing a startup, focus on the area where you’ve got the most risk: design!

“And then there is the most dangerous risk of all — spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.”

— Randy Komisar, partner at VC firm KPCB

I was 19 when I read “Are You a Pirate?”, Michael Arrington’s treatise on life as an entrepreneur. In the article, he argues that entrepreneurs are motivated by a unique approach to risk. Instead of avoiding it, they seek it out for adventure, much like the pirates of the 17th century. For them, he writes, risk itself is the reward.

At the time it was published, I was interning as an analyst at an energy company in Philadelphia. I remember sitting in my cubicle, reading the article, and thinking, “This is what I want to do be doing with my life.” I began doing some unpaid work for startups on the side, and within a year, I’d quit my job and was working on a startup of my own.

In the beginning, I was thrilled just to be building something. I loved the idea of inventing the future, and I was excited to have startup friends with whom I could bounce around ideas for changing the world. Sure, I was interested in creating a lucrative business, but like the pirates in Arrington’s piece, the potential riches were in many ways an excuse for the adventure.

Over time, though, things began to change. I compared myself to the people who were “killing it” on TechCrunch, and I began to crave an exit. I started exploring less risky ideas and began looking for the surest path to success. Ultimately, I ended up working on a product that I thought had potential, but that I really didn’t care about, hoping that it would do well enough so that down the line, I could live the life I wanted and work on something I found meaningful.

Ambitious young people are flocking to San Francisco, London, and other startup hubs. Fueled by coffee, Red Bull, and other nootropic substances, they work 80-hour weeks at below-market wages while chasing “unicorns” and “rocket ships. If all goes well, they hope to get a piece of the insane amount of money that is getting thrown around.

This is not so different from the “dream” sold to investment bankers. New recruits work like crazy for their first two years in hopes of eventually becoming partner or finding a job at a hedge fund. If they can make it through the ringer, they are promised tremendous wealth and prestige.

A big part of why I got into startups was a reaction against this mentality. I hated the idea that you should defer what you care about in life, devoting yourself entirely to your career until you’ve reached success. I wanted to enjoy my work in the present, and I didn’t want to sacrifice my youth for a job.

Yet, that’s exactly what ended up happening. As I became more obsessed with getting to an exit, I started feeling guilty whenever I wasn’t working on the business. I began to neglect my health, hobbies, and personal relationships. I stopped working out, ate more fast food, and would cancel plans with friends if I felt I hadn’t been productive enough to warrant social time.

This went on for a period of 6–12 months. I lost any intrinsic joy I had in my work, and it got to the point where I had to drag myself out of the house every morning, dreading the day at the office. I remember lying on my back at the top of the stairs one day, staring at the ceiling and thinking to myself, “Why the hell am I doing this?”

I didn’t have a good answer. I never wanted to be someone who cared solely about amassing wealth and success, yet that was what ended up informing most of my decisions. That values conflict wore on me everyday, and eventually, I just couldn’t continue. I told my co-founder I needed to step back, and after some discussion, we decided to wind down the venture.

For a time afterward, I wasn’t sure what to do. I had some ideas for startups, but I was so burnt out that I couldn’t bring myself to actually begin working on any of them. At the same time, I felt guilty that I wasn’t working. I felt like my life and career were stagnating.

For awhile, I’d been feeling like everything I did had to be on the direct path to success, because I wanted to get there as fast as possible. Then, one day, it hit me — my approach to work was making me utterly miserable.

I realized that given the choice between reaching success in 5 years while hating the day-to-day and reaching success in 20 years while enjoying the journey, I’d rather take the slow road and have some time to smell the roses.

In some ways, this is a false dichotomy. Rarely is it the case that you need to explicitly choose between the fast and slow path, between being happy or being miserable at work. Yet, looking back, I could see that many times I had sacrificed my personal happiness to pursue what I thought was the shortest path to success. I had optimized for that over everything else, and all of those small decisions added up to me feeling incredibly unfulfilled.

Founders and early employees of tech companies often pay a high personal cost. Most of my tech industry friends have gone through major burnout at least once in their careers, a result of a culture that idolizes workaholism. This is heartbreaking, as most of the people I know in the startup world are in their twenties and early thirties — the prime years of their lives.

This is a unique period in one’s life, when you’re free enough to travel the globe with only a backpack or pick up a new hobby on a whim. You can dive headfirst into art, meditation, or a whirlwind romance, and really explore who you are and what you value in life.

Yet, many people I know are spending these years hunched over a computer, thinking of few things besides their company, their career, and how to “make it” in the world. They’ve bought into the same deferred life plan as the 22-year old banker at Goldman Sachs; it’s just sugarcoated with words like “disruption,” “ownership,” and “innovation.”

After I realized that my drive for success had been causing so much stress, I decided to start prioritizing happiness in the present over finding the quickest path to prosperity. Bit by bit, I began to allow myself to pursue things just because they seemed fun or interesting. Over time, I realized that before jumping into another startup, I wanted to spend some time exploring the world and working on side projects.

So, I found some freelance work and bought a ticket to Costa Rica. Along the way, I met a hotel owner who was looking for ways to fill his hotel during the off-season, and ended up pitching him on inviting a bunch of developers and designers down there to work remotely and hack on side projects.

Things snowballed, and eventually, this turned into my main gig: Hacker Paradise (we organize trips around the world for people who want to work remotely or focus on side projects). Through it, I’ve met some amazing people, and in the last year, traveled to places like Vietnam, Bali, Thailand, Barcelona, Berlin, Tokyo, and Taipei (I’m writing this from Vietnam). More importantly, though, it’s gotten me back in touch with the joy of creating things for their own sake.

If you’re out there working on a startup, I’d ask you… why?

Don’t get me wrong; there are good reasons to work on a startup. Startups mean more autonomy than you can get elsewhere, and they can be a great way to learn quickly, gain a ton of experience, and express what you believe about the world. They can be an incredibly effective way to solve a problem, and indeed, there are certain classes of problems that essentially require venture funding.

Still, the beautiful thing about a startup is that there are no rules.

You don’t have to be in Silicon Valley chasing venture money and paying $2,000 for a tiny apartment in the Mission. Instead of building an organization that you hope will buy you happiness in 5 years, you can build one that will bring you happiness today.

And, if you do find yourself dreading the grind and waiting for the day when you can finally start living… throw a wrench in the system.

Move to Paris on a whim. Bike from Hanoi to Saigon while working remotely. Build a side project and then give it away for free. Join a band. Learn a new language. Love with reckless abandon. A startup can be rewarding, but so can all of the above.

The real risk isn’t in getting off the traditional path; it’s in staying on it and missing out on the full range of experience life has to offer.

And, if you do decide to do a startup, keep an eye out for the deferred life plan. Even if you decide to raise money and swing for the fences, you can still find ways to enjoy the day-to-day. Try to build an organization that you’d want to be a part of for 10, 20, or 30 years to come.

I’ll end with one more quote by Randy Komisar from his book, The Monk and the Riddle:

“At key points in my life, I’ve found it helpful to ask myself a simple question about what I was doing at that moment:

What would it take for you to be willing to spend the rest of your life on [it]?”

“Don’t concern yourself with exit strategies.”

(The Monk and the Riddle, p.77, published 2001)

Have a job that lets you work remotely? Thinking about taking time off to work on your own projects? Consider joining one of our upcoming trips to Bali, Thailand, or Portugal.