Over the past few weeks, I did something I’ve never done before: I read through all my old journals going back 10 years.


I’m not a hardcore journaler, as you can probably tell by the fact that only 7 notebooks cover a full decade of my life. Journaling is more of a crisis intervention tool for me. I turn to it in moments of challenge or opportunity when my thoughts are too confronting to keep inside and I need to pour them out.

These notebooks have been sitting on my shelf for years. I’ve always known they contained valuable insights into my past, but for some reason, it had never seemed worth the time to read them page by page. 

Until now. 

You see, as 2022 comes to a close, I find myself in the midst of a full-blown mid-life crisis. 

Mid-life crisis as opportunity

Contrary to popular belief, a mid-life crisis is a precious opportunity. It’s a rare moment when you are forced to question your basic assumptions, which can open the door to making profoundly positive changes in your life. 

Our lives are dominated by inertia and habit – a mid-life crisis is a chance to restart in a new direction.

I began reading through my journals looking for clues to how I’ve navigated such moments in the past. I seem to have had 5 mid-life crises before, separated by 2.8 years on average. Each one was triggered by a major life event, and confronted me with an existential question I had to answer in order to move into the next stage of my life:

  • 2009: I finished college and began to consider, “What path should I take after graduation?”
  • 2011: I returned from two years in Ukraine and began wondering, “What career should I pursue after returning from the Peace Corps?”
  • 2013: I left my consulting job on short notice and was immediately confronted with the question, “How can I support myself financially and independently?”
  • 2016: I recommitted to remaining a free agent after taking a job briefly, asking “What kind of business do I want to create?”
  • 2018: After moving to Mexico City, my partner Lauren and I wondered together, “What does life look like after leaving the San Francisco Bay Area?”

I began to find clues in my past writing that indicated a life stage was drawing to a close and a mid-life crisis was looming:

  • My usual sources of motivation stopped working
  • Pursuits that used to fill me with enthusiasm started to feel grey and flat
  • Contemplating a future filled with more of the same began to feel dark and depressing

I found that a mid-life crisis is characterized by a sudden, pervasive loss of energy. Like the engine that powers my psychology is grinding to a halt. My goal then becomes to find a new source of energy and motivation for the next chapter.

The BASB era

The current season has been the longest in my adult life so far, at over 4 years. It started in late 2018 as my then-fiancé Lauren and I packed up our Oakland apartment and moved to Mexico City. We wanted to go on an adventure, to wipe the slate clean and see what a new city and country had to offer.

We had the absolute time of our lives, meeting new friends, immersing ourselves in the local culture and cuisine, and traveling widely throughout Mexico. It was in that time of newfound possibility that I made one of the most fateful decisions of my career. After taking a year-long break from my online course Building a Second Brain, I decided to start teaching live cohorts again.

It seems like an obvious decision in retrospect, but at the time it filled me with doubt. Previously, I had severely burned myself out trying to run every aspect of the course myself, from marketing to content creation to operations to customer service. I didn’t want to go down that same path and end up in mental and physical exhaustion again. 

I decided to focus on two changes: properly marketing the course so that it would be more profitable, and using some of those profits to hire a team to help me manage it all.

Cohort 9 kicked off in the spring of 2019 and set the stage for explosive growth in the business a year later as the COVID pandemic hit. Since then, we’ve grown to a team of 10 full-time staff plus a dozen trusted contractors who allow us to deliver live cohorts to more than 1,000 people at once. 

My fateful decision to recommit to BASB started a slowly building avalanche of momentum that 3 years later culminated in the publication of my book Building a Second Brain, which incorporated everything I’d learned over the previous 16 cohorts. 

It’s been 6 months since publication, and the book has already far surpassed my wildest aspirations. Alongside all our other efforts of the year, the biggest milestones include:

  • Landing at #2 on the Wall Street Journal bestseller list
  • Amazon Editor’s Choice selection and Goodreads Choice Awards nomination
  • Foreign publishing deals in 20+ countries and languages
  • Reaching 127k subscribers on YouTube, 99k followers on Twitter, and 93k subscribers to our email newsletter
  • Receiving more than 1 million unique visitors to our two websites
  • Hiring our Social Media Strategist Claire, Course Manager Guia, Product Operations Manager DL, and Customer Success Specialist Erik
  • Speaking at Google Talks and World Domination Summit
  • Hosting the second virtual Second Brain Summit
  • Holding BASB meetups in São Paulo, London, NYC, Brooklyn, Miami, and San Francisco

Releasing my book to the world has been the adventure of a lifetime, but also the challenge of a lifetime. It took everything I had, and the cost was substantial. For more than 3 years I’ve had to focus relentlessly on a single goal, which required me to aggressively ignore any interest, curiosity, or side quest no matter how tantalizing it seemed. For someone who is naturally divergent and curious like me, such single-minded focus is painful. 

As 2022 ends and I start envisioning what I want my life to look like in 2023, I know it’s time for a fundamental shift in my priorities. The current season of my life has lasted more than 4 years. I’m long overdue for a change.

Changing identities

What my series of mid-life crises has taught me is that identities are malleable and temporary.

An identity is an information construct – a loose collection of beliefs, values, viewpoints, priorities, goals, and principles for living held together by a story about who you are. Humans cannot survive psychologically without an identity. It’s the narrative glue that gives meaning to the chaotic storms of electrical activity cascading through our brains.

Like changing clothes as the weather turns, identities serve you for one situation but not necessarily others. When your identity wears out and no longer serves you, it’s time to find a new one. As the saying goes, the identity that got you here won’t get you to where you want to go next.

At certain liminal moments of unpredictable change, such as during a mid-life crisis, the superstructure of our identity becomes especially fluid. There’s a brief window in which we have the chance to shake it loose and build another. 

It all begins with gathering the data you need to understand what life is asking of you: your symptoms, your learnings, your desires, and your questions. 

Over the past few weeks, through extensive journaling, deep conversations with people close to me, and revisiting my photos, notes, accomplishments, failures, and memories from the past year, I came up with my own.

Symptoms – What pains am I experiencing?

An identity is a solution to a set of challenges – surviving, finding love, obtaining food and shelter, feeling a sense of purpose. That’s why when inventing a new one, I like to start with the most acute pains I’m currently experiencing – what I call my “symptoms.”

My goal is to drill down into the abstract, vague complaints I have about life and identify exactly what isn’t working for me right now. My goal is to pinpoint the pain I’m feeling in the most objective, specific possible terms.

Here are mine, grouped by major area of life:


  • A feeling of dependence on coffee, like I’m not myself and can’t get excited without it
  • Constant sugar cravings, especially in the afternoon or in the evening after dinner
  • Tension and tightness in my lower back, hips, and hamstrings from sitting so much
  • Not having healthy, delicious food available at home when we’re hungry, leading to too many meals ordered in
  • Excess body fat and a sense of defeat that I’ll never be able to get rid of it


  • A feeling in the pit of my stomach, usually just as I’m falling asleep or waking up, of being lost or purposeless
  • A lack of motivation to pursue things I’m usually motivated by (writing, focusing, strategizing, reading, researching, planning, working in general)


  • A feeling of anxiety at the end of the workday with no particular cause
  • Not spending enough time with friends, and lacking connection to them
  • Feeling tired and listless in the afternoon even though I don’t work past 3 pm
  • Checking my phone and social media too often and feeling addicted to it
  • Difficulty mentally transitioning away from work at the end of the day


  • A hunger for more rest and unstructured time with family
  • Ximena (our dog) not getting enough attention and exercise, leading to her being neurotic and hyperactive
  • Our house being too disorganized and messy, making it difficult to rest and relax in the evenings
  • Not connecting with Lauren in the evenings, and feeling distant from her as a result

Notice that many or even most of these problems have direct, known solutions. None of them are unprecedented and there are many helpful books and how-to articles that will give me useful advice. In the past, I would immediately dive in and begin coming up with practical solutions to each one of them. And there’s a time for that. 

But here’s the thing about problems that I think most people don’t realize: you can’t solve them one at a time. Looking at the list above, if I were to adopt just one new habit or make one change for each symptom I want to address, that would be 16 new habits and lifestyle changes. It’s hard enough to change one habit, let alone 16 of them!

You have to address unwanted symptoms by addressing the root cause, asking questions like:

  • What is the source of the pattern that’s playing out across the different areas of my life?
  • What is the bottleneck in my thinking or behavior that is leading to all the other negative side effects?
  • What kind of life am I living that is producing these side effects?
  • Who am I being at my core that is manifesting these symptoms?

As I’ve gotten older I’ve learned that before jumping to solutions, there’s a lot of value in stepping back and looking at the complete picture these symptoms are painting for me. 

Using that lens, the picture I see is of a man who is overworked, pushing himself too hard on too many fronts, and using a combination of social media, sugary junk food, strong coffee, and distraction to salve the pain that causes. I see someone who is so tired and anxious that he doesn’t have the capacity to do the things he knows would make him less tired and anxious. I see someone who deeply wants to spend more and better time with his growing family, but doesn’t have clear enough boundaries between work and life to create the necessary space.

At the same time, I understand why these tradeoffs were made: to bring to completion the most important project of my life at all costs. Now I’m seeing the costs. Most of all, I feel tremendous sympathy and compassion for this man. And this is the key to the identity change that comes next: it has to come from a place of complete self-acceptance and self-love, not a desire to change someone who is bad or wrong.

As I move on to the next part of my annual review, I’m asking, “What kind of person could I become who would naturally and automatically make the changes needed to reduce my suffering?”

Learnings – What have I learned?

My next step is to summarize my most important lessons of the year. I want to thoroughly document the wisdom I gained to make sure it gets carried forward to inform my decisions about next year.

These are my top 10 lessons for 2022:

1. Don’t communicate emotionally charged messages via email or any other text medium; have a phone call

Communicating via text is efficient in a lot of situations, but I had to learn more than once this year that it isn’t ideal for messages with an emotional component. Sending emotionally charged messages in written form usually leads to the recipient making the most dramatic and negative possible interpretation. If there’s emotions involved, make a phone call.

2. No one creates better content or marketing in our niche than us – trust that we know what we’re doing and there are no big secrets out there

I always assume that we still have a lot to learn, but several times this year I found that when it comes to creating content or marketing in our niche of PKM, we are the experts. I’m resolving to trust our instincts on this front more next year, instead of relying on outside authorities, which will allow us to save money and move faster.

3. I am a Wisdom Worker, not a Knowledge Worker

Early in my career, I was an Information Worker – I spent most of my time taking in, organizing, editing, and manipulating information for others to act on. Later on, I became a Knowledge Worker, conveying tacit knowledge I’d begun to gather from experience. Now I increasingly see myself as a Wisdom Worker, letting go of the implementation details almost completely and instead helping others feel through uncertainty and fear to their truth.

4. There is no greater source of leverage in the world than ideas

Looking back, I realize part of my motivation for pursuing a traditional publishing deal for my book was that I lost faith in the power of ideas on their own. I felt it wasn’t enough to publish interesting ideas online; I needed to push them to their full potential and into a format that could spread to every nook and cranny of the world. But now that the book is out and I’m considering what to do next, I’m returning to the realization that ideas are indeed the greatest source of leverage in the world, and I want to spend more time with them.

5. It’s ok to change my mind

I worked all year long with a business coach for the first time, and through those conversations realized that I have a strong aversion to changing my mind about anything. I have an internal narrative that changing my mind means I’m inconsistent, flaky, and therefore can’t be trusted. While it’s sometimes valuable to persist stubbornly toward a goal, I’ve also increasingly seen the negative side effects of this attitude, such as sticking to decisions that make no sense or maintaining strategies that aren’t bearing fruit. In 2023, I’m embracing the fluidity and freedom to change my mind freely.

6. The CEO is the ceiling to the company

I came across this quote in my journals from a book I read years ago, and it instantly struck me once again. Now that we have a team, I can see clearly that the company is an extension of my psychology as the founder – all my strengths and knowledge get amplified and extended, but so do my weaknesses and limitations. My #1 job is to proactively work to uncover my blindspots because otherwise, they become permanent fixtures of the organization I’m trying to lead.

7. With great leaders, you don’t need a lot of their time

This phrase was uttered to me in passing last year as part of a couple’s retreat my wife and I attended. Seeing it scrawled in my notes, I know it’s time to really let it sink in. In the past, I demonstrated my commitment to my course, my projects, and my business through raw, brute force. I spent more time and exerted more effort than anyone else as proof of my commitment. But as we welcomed our second child, this attitude needs to give way to another: that the measure of my success as a leader is how minimal my intervention can be. I’m committed to stepping back and allowing others to make their own decisions and thus find their own voice as leaders.

8. My purpose is to bring people together over ideas, in inspired communities

Part of my reason for diving deep into my past journaling was to find evidence of my essential nature – what has always been true about me? And when I looked at the most fulfilling, most meaningful experiences of my life, they all had to do with bringing people together in inspired communities centered around the power and beauty of ideas. I want to return to this more purposefully next year.

9. I don’t play zero-sum games

Another common pattern from my past was that any time I was faced with a competitive, zero-sum game – a situation in which someone else had to lose in order for me to win, or vice versa – I chose to opt out of that game completely. At heart, I’m not a competitor. I’m a cooperator, and I’m drawn to environments where everyone can win. As the PKM space heats up and competitors flood the market, I’m going to look for the new, more exciting game I can play next.

10. It’s time to give up teaching the BASB course

This was the hardest one for me to acknowledge, and allowing the possibility to even surface in my mind required working through some uncomfortable emotions with my coach. 

Teaching Building a Second Brain has been the defining activity of my career and my life since that first small cohort in late 2016. I’ve given it everything I have – every ounce of energy, every good idea, every creative solution – but 16 cohorts are enough, and now it’s time to let a new generation of leaders take the reins.

In 2022, we made a series of changes that set the stage for this transition:

  • Centralized all our programs on Circle so the community is at the core of what we do
  • Changed from a one-time cohort model to a community membership model with year-round events
  • Increased from 2 to 4 cohorts per year, with each live session delivered twice in different time zones
  • Reduced the price of joining a cohort from $1,499 to $749
  • Launched Foundation, the first-ever self-paced version of BASB
  • Turned on “always on” purchasing for both Foundation and the Membership so people can join anytime

These changes effectively quadruple the number of opportunities to take our program over the course of a year – from 2 to 4 cohorts, with each one delivered twice in parallel. Participating in a cohort has also become far more accessible, with the price of entry dropping 50% from $1,499 to $749. 

For people who want to learn the fundamentals of the BASB method at their own pace, the Foundation self-paced course is even more accessible at $499. And for those who want to go deeper, the Membership now includes weekly workshops and other events throughout the year led by our most experienced members.

This is the new BASB ecosystem that I hope gives everyone a chance to build a Second Brain at a pace, price, and format that best suits their needs:

Cohort 16, kicking off on January 10th, 2023, will be my last time teaching the program as the main instructor (Join us!)

I have tears in my eyes as I write those words. It feels like the end of an era, but this decision will lay the groundwork for a brand new era: Cohort 17 with new instructors we will recruit and train to lead our flagship program.


When I think about what I want to turn my attention to next, I can start to feel the hidden embers of excitement coming to life inside me. There are vast new frontiers yet to be explored beyond the fundamentals of setting up a notetaking system and using it to be more productive. Among other things, I want to explore:

  • The Theory of Constraints and how it applies in a digital-centric world
  • The neurobiology of states of flow and how to create them
  • The new generation of “link-based” second brain apps and how they should be used
  • The potential of “just-in-time” personal productivity as the world changes faster
  • The subtleties of emotional intelligence and fluidity
  • How project management can be updated for an Internet-driven world
  • How sci-fi can help us visualize and prepare for the future

The possibility of everyone in the world having a Second Brain is more exciting to me than ever, but it’s time to lean on others to carry our educational programs forward. I’m so incredibly excited to see how our most experienced Second Brainers interpret the principles, explain the use cases, and teach other people how to apply them.

In the meantime, I’ll be returning to my essential nature as an explorer, experimenter, and innovator on the frontier.

Desires – What do I want?

Finally, we arrive at my desires, perhaps the most important element to emerge out of a year-end review like this one. I can summarize the essence of my annual reviews as, “discovering what you truly want for your life, again and again, in more subtle shades and deeper layers each time.”

Desires are different from objectives or goals in that they aren’t concerned with the “how.” Desires can’t be constrained by what is practical, reasonable, or affordable. They simply arise, daring you to reshape the world to make them real.

These are the clearest desires I’m feeling right now:

  1. I want to create immersive experiences for people where transformational breakthroughs happen naturally and continuously.
  2. I want to create a community of the world’s most passionate, curious, generous, and courageous people committed to personal growth and serving others.
  3. I want to maintain a portfolio of experiments pushing forward the boundaries of my field and exploring new frontiers.
  4. I want to be more present and mindful at home with Lauren, Caio, Delia, and Ximena – less time spent on devices, worrying about work, and mind-wandering.
  5. I want to create a business with a set of containers (courses, cohorts, memberships, summits, workshops) in which new ideas can continuously emerge and evolve, without us needing to pre-commit to any particular subject matter forever.
  6. I want to strengthen existing friendships and form new ones as rich, fruitful aspects of my life.
  7. I want to do more exploratory writing on topics that are currently fascinating me, blocking off my mornings exclusively for deep work.
  8. I want to place learning, traveling, and teaching back at the center of my life.

That final desire emerged from an interesting exercise I made up by drawing on the content of my journals. I noticed that all my favorite, most fulfilling experiences had to do with learning, traveling, and teaching, so I plotted them on a Venn diagram. 

I can see clearly that my greatest sense of satisfaction is found where those 3 activities intersect. Try it for yourself!

Decisions – How do I make it real?

My takeaway from this entire process is that it’s time to usher in a new season of my life. After an intense few years of all-consuming focus and convergence toward a goal, I want to turn my attention to something new.

To clear my schedule and create the environment I need to explore new interests, I will make the following decisions and changes effective immediately. Now is finally the time for practical solutions! 

I’m sharing them here in the hope that you, my readers, will hold me accountable to them. And if you think of any other way I can strengthen my commitment to this new direction, I’m all ears.

In 2023, I will:

  • Turn down all new BASB-related projects
  • Stop teaching BASB cohorts after Cohort 16 (and turn them over to new instructors)
  • Stop scheduling book-related interviews (except for the biggest names in podcasting, if they come calling)
  • Stop writing new BASB-related blog posts (unless a piece coincides with my current interests)
  • Only accept speaking engagements at my official rate (which is at the top of the market to filter for the biggest opportunities)
  • Clear mornings completely of meetings and other commitments
  • Start a standing bi-weekly meeting with the Product team (so I can inform their decisions while allowing them to work independently of me)

There are other symptoms to address and problems to solve, of course, but I’ve found that most of them largely resolve themselves when my priorities are right, I’m being honest with myself about what I want, and I have enough free time. 

By stepping back from teaching the cohorts I’ll open up time for writing, speaking, promoting my book to new audiences, connecting with other creators and entrepreneurs, and most importantly, spending quality time with my family.

My official theme for 2023 is Reinvention. I am reinventing who I am, what I do, and what I’m committed to for the next leg of this journey.

Questions – What are my favorite problems? 

The final step is to catalogue my open questions – I want to finish my review and start the new year with a divergent, generative set of open-ended wonderings. 

You can see clearly that they emerge directly from the symptoms, learnings, and desires above. I’ll add them to my favorite problems so I’m more likely to notice them over the course of next year:

  • How can we have other people generate new ideas using their energy and enthusiasm, instead of continuing to rely on me?
  • How do we make our community bottom-up instead of top-down?
  • How can I be the kind of leader and manager that inspires people to greatness without me needing to be there?
  • Which new rituals or routines do we need to put in place to create cohesion among everyone on the team?
  • How can I integrate cooking into my routines such that it saves time, instead of taking time?
  • What would life be like without coffee? What else could be the source of my joy and excitement? How will I produce intellectual breakthroughs otherwise?
  • What would it look like if my life wasn’t compartmentalized?
  • How could we treat the business as a prototype for a mass scaleable franchise?
  • What would it look like to make business decisions centered completely on what I want?
  • What kind of father do I want raising my son and daughter?
  • What gets me so excited I can’t sleep at night?
  • What makes me most angry about the state of the world?
  • What do I see that no one else sees?
  • What evokes wonder in me?

If you enjoyed this article and would like to do an annual review for yourself, join Cohort 16 of Building a Second Brain starting January 10th, 2023.

Using BASB principles, I’ll teach you how to capture the right information from the past year, organize and distill it to surface the kinds of lessons I’ve shared above, and then use all of that to craft a unique vision for your life in 2023. 


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