This is the first year I decided to do a thorough mid-year review.

It’s usually enough for me to review my goals once a year, at the beginning of the year, and then spend the next 12 months powering through them. But the first 6 months of this year brought tremendous, unexpected changes for us.

We got pregnant with our first child at the beginning of January, moved back home to Southern California from Mexico City abruptly due to the COVID-19 pandemic in March, and at the end of May bought our first home.

Like a line of dominoes, each change seemed to usher in the next in quick succession, and I’ve felt a need to process a large backlog of changes. This was also the first year I shared my goals for the year publicly, and wanted to close the loop and check in on those. Having them out in the open has helped me tremendously to stay on track, so I think I’ll continue that tradition.

Goals Review


After more than a year of work, I got the book deal, which was a huge victory and relief. It’s happening, sooner or later. Finalizing the contract has taken longer than expected, and now I see that the whole process is going to take MUCH longer than expected.

The book won’t be published and on store shelves for another 2 years, which means my goal of 100,000 copies sold isn’t for 2020, but for 2022! This is a great example of how every goal relies on a certain set of assumptions about reality, and that when reality changes, the goal has to change. But I’m actually glad this gives us plenty of time to improve our courses, build the email list, and prepare the team for the onslaught of attention the book will (hopefully) bring.

Despite barely starting to work on the manuscript, I’ve already seen some benefits from clearing my weekday mornings for writing over the past couple months. I had to lean on the team more and remove myself as the bottleneck in as many decisions as possible. This boiled down to spending more time orienting/training them during weekly standing meetings, and constantly pushing for every commonly repeated task to be turned into an SOP or checklist or memo. These changes will continue to serve us as it allows everyone to make decisions faster and with less friction.


After a crazy last-minute push (thanks to a public deadline) I screened the first cut of my film for about a dozen members of my family a few weeks ago on my dad’s 70th birthday. The reception was fantastic and motivated me to get to work on the second cut, which I’ll screen for my subscribers using YouTube Instant Premiere on July 11. You’ll get the invite if you’re subscribed to my weekly newsletter.

I’ve learned so much from the process of making this film, which I plan on writing up as a blog post after the public screening. I also plan on doing an online workshop on how to create personal documentaries using widely available equipment and software, which is now possible for a tiny fraction of the cost once required.

I wasn’t able to screen the film in a theatre like I originally wanted. But I’m astounded by the prescience of what I wrote in January in light of recent events: “I believe amateur documentary filmmaking could be one of the most powerful sources of social change in our generation. With the proliferation of powerful smartphone cameras, easy-to-use editing software, and social media networks, that possibility is more feasible than ever. The only remaining constraints are our courage, our willingness to learn, and our ability to get ourselves organized and in action.”

I sound like I’m describing the Black Lives Matter protests against police brutality to a T. The first wave of smartphone videos have been short clips captured in the heat of the moment. I think the next wave will be short films made up of multiple pieces of footage, at higher quality, edited together to tell more complex stories that inspire people to action, not just outrage. I’m excited to contribute to the rise of personal documentaries as an individual, creative storytelling technique.


I haven’t been able to give Praxis the attention it deserves, due to the growth in most other areas of the business. Which is why I decided to join the Everything bundle, an online publication in which multiple writers join forces and combine their publishing behind one paywall.

What tipped me over the edge was that my subscribers would receive a wider range of excellent content on the topics I know they care about – productivity, organizing, effectiveness, strategy – without me having to change anything. I believe many more people will be exposed to my ideas through our combined platform, and those who only want my content can continue to subscribe only to Praxis. It’s a win-win with more options for everyone.

Ultimately, I just want to focus on creating the best content I can create. Dan and Nathan are committed to building a media company for the future, with all the work that entails, so I figured it made more sense to join them rather than continue postponing improvements to Praxis as I’ve been doing for a while.

We’re up to just over 1,200 members, which is a great milestone. It will be hard to count now given that many new subscribers will actually be Everything subscribers, but the ultimate goal is fulfilled: expose more people to my work who can benefit from it while maintaining a revenue stream that allows me to continue investing the time needed.


We ended up not pursuing any licensing deals so far this year. There were a few potential leads, but they were so speculative that we ended up investing all our attention in the public-facing online courses. For The Art of Accomplishment, our new group coaching program, we have a 9-person team from the same company joining one of our cohorts for the first time. It will be an excellent opportunity to test if we can add teams to our existing, public courses, rather than having to create a separate, private learning environment that doesn’t benefit from the ideas and energy of a larger group.

Once the book is out, that should also provide a boost to licensing deals. In fact, the foreign publishing deals we’re pursuing for the book could be seen as fulfilling the intention of this goal. Books are far easier to translate and license than courses.


We had more than 800 students in cohort 10 of BASB, which was incredible. There was so much palpable energy and so much enthusiasm around the course, like nothing I’ve experienced so far. I thrive on that energy and it was unbelievably fulfilling to see so much of it channeled through our newly recruited Alumni Mentors, as well as the course staff, who carried so much of the burden and went so above and beyond what I expected. I saw that my stepping back and doing less allowed others to arise as leaders. It didn’t look how I expected, but that’s ok. It’s not only ok, it’s critical to the future of this work finding its way to a broader audience.

Of those 800 students, 345 were new students. Which means we have a formidable goal in front of us, especially since we are only running two cohorts this year. To fulfill this goal, we are aiming for 655 new students in the next cohort in a couple months. It’s not impossible, but combined with the 50% price increase, it’s a daunting challenge. If we get anywhere near it, it will be an absolute blowout launch. We should easily have well over 1,000 students in the cohort total (including returning alumni), which is almost impossible to wrap my head around. What does it even mean for 1,000 people from around the world to come together to learn this new way of learning and working? I’m dying to find out.


Growing our email list was my top marketing goal for 2020, and I’m proud to say we’re well ahead of schedule. Growth in new subscriptions rapidly picked up from the beginning of the year, and is now at around 2,800 per month. That means we’ve just passed 23,000 subscribers, and should be around 40-50,000 by the end of the year, depending on how growth accelerates. It’s so gratifying to have made the investments in the newsletter that I made last year, and to see it bear fruit so fast and decisively.

I’m going to continue doing everything I’m doing, and knocking out email-improvement projects whenever I can. At some point we’ll want to level up our email game by implementing advanced strategies and potentially working with a consultant who specializes in this. But for now I think there’s a lot of growth potential just in continuing to stay consistent and producing the best content I can.


Write of Passage has continued to grow tremendously. It is in its rapid iteration phase, with 3 cohorts planned this year. The growth of that community has injected a lot of energy and ambition into the BASB community, and seeing David’s meteoric success has prompted me to look for other high-potential course creators. I’ve worked with Joe Hudson over the past few months on a new group coaching program called The Art of Accomplishment, which is my second in-depth collaboration to bootstrap a new program with another instructor.

I’m ready to retire Write of Passage growth as a goal of mine, since it doesn’t really need me and there’s not much I have on my plate related to it. I do have a goal to improve the cross-promotion of our courses, but not exactly sure what form that will take yet. Will revisit this at the end of the year.


This one was derailed by COVID, as we chose to leave Mexico in late March after the U.S. State Dept. warned Americans abroad that they might not be able to enter for some time. I’m really glad we made the choice to return, since the situation in Mexico has become truly horrible. Overall, I feel very fortunate that our lives in general haven’t been impacted much by the pandemic. Most of our work takes place virtually or is location-independent, and I feel more fortunate than ever for that fact.


The unexpected turn of events took us in a new direction which I’m very happy and grateful for. We spent a couple months living in an Airbnb after returning from Mexico, and a few weeks ago bought a home in Long Beach, close to both our families. We are expecting our first child, a son, in early October, and couldn’t be more excited to receive him in the beautiful home we are putting together now.

It’s been a lot of change in a short period, going from intrepid digital nomads to responsible suburban homeowners, but it’s a change I’m ready for. After 7 years (this month!) of self-employment, of putting everything I have into the growth of my business, I’m ready to take my foot off the brake a little and explore what a more relaxed lifestyle might look like. I honestly have no idea so it is indeed an exploration.


This TBD slot was filled with the The Art of Accomplishment program I’m running with Joe, which kicked off last Friday. It’s been a whirlwind getting it designed and planned, but it’s been extremely satisfying to not occupy the project/course manager role for once. I’m still learning the balance between letting things go and intervening when it really matters, but it’s done wonders for my well-being to not be at the center of all the action. It also dramatically opens up the possibilities for the kinds of joint ventures we can do in the future.

It was pretty amazing to ask something big of my audience – their commitment and trust in a brand new program at a much higher price point than we’ve ever charged – and to see them respond so forcefully. We’ve sold out all the spots in the inaugural cohort, and last week kicked off a completely new kind of online learning experience that is deeper, more personal, and I hope more impactful than anything we’ve done before (or anyone has done before).

7-Year Mindmap Review

At the end of 2018, I did a brainstorm about what I wanted my life to look like in 7 years. It’s insane to me that 21% of those 7 years has already passed. I feel like I made this just yesterday!

It took the form of a mindmap, with “7 years” at the center and each major branch representing one area or facet of my life. I used the MindNode app on my iPad, printed it out as a large poster, and posted it in our apartment as a reminder of my long-term vision.

Click the image to view in a larger size

I decided to revisit the mindmap and see what had changed about my future aspirations. I bolded the words and phrases that most resonated with me:

  • Purpose
    • Experiences with the kids to explore our inner selves
    • Foundation that funds promising new projects for the world
  • Nature
    • A deep connection to nature
    • Making a contribution to climate sustainability
  • Community
    • A close circle of deep friends who we share our lives and deepest selves with
    • More experience with psychedelics for healing
    • To be part of a community of seekers
  • Health and wellness
    • Yoga and stretching
    • High-intensity functional exercise
    • Stimulating vagus nerve
  • Learning and growth
    • New relationship with my throat pain
  • Presence and awareness
    • Solid daily routine of exercise, stretching, meditation, journaling
    • Daily experience of oneness and love for all beings
  • Homelife
    • Dedicated workspace supporting focus and mindfulness
    • Most meals cooked by us and eaten together
    • Bedroom free of devices and distractions
  • Business and work
    • Coaching a small group of world-class creators
    • Growth Board of strategic advisors
  • Art and creativity
    • Playing piano often
    • Drawing as a hobby
  • Family
    • Frequent visits to uncles/aunts/cousins on both sides
    • Everyone in my family supported and growing
    • Deep connection to our families in Brazil, Mexico, Philippines
  • Finances
    • Personal budgets in check with our long-term priorities
    • Diversified income through real estate
    • Angel investments or fellowship for promising creators

I always look for an unexplainable “resonance” as a sign that my intuition is telling me to pay more attention to something. In this list, I noticed that changes in my life circumstances have made certain parts of my life recede into the background, such as the ones about traveling or having diverse cultural experiences (which are made difficult by the COVID lockdown).

Instead, I was more attracted to themes related to spending time with children, family and friends (who we now live close to), regular exercise, and cooking at home (now that we have a full-size kitchen), and more right-brain activities like playing the piano and drawing.

In general, I’m a little bit shocked to find that I’m much less motivated by life goals than in the past. Throughout my 20s and early 30s, my list of goals was my north star. But I think the events of the past few months, combined with changes in my personal life, have reminded me of the preciousness of the basic things in life, and the people to share them with.

I’m also thinking a lot more about how I want to give back. I’ve watched the events of the first half of the year alternating between hope and heartbreak, depending on the day. I’m working on a new project that will allow us to make a contribution to the incredible movement for social justice we’re seeing play out on the streets of the United States. More on that next week.

In the meantime, I’m asking some questions of my team, to learn more about what we stand for and what we believe in, in a time where beliefs desperately need to be turned into action. These are the questions I’m sending them, drawn from a book called Reboot I’ve been slowly reading over the last few months:

  • How would our organization respond were we to hear all the things that are being said, regardless if they are being said with words or deeds?
  • What does it mean to be a leader at our organization?
  • How would we feel if our children were to work for the company we’ve created or the team we lead?
  • How has the unsorted baggage of what has happened to us shaped who we are as leaders?
  • When our employees and colleagues leave our sides and our company, what do we want them to say about our time together?
  • What do we believe to be true about the world?
  • What do we, as a community of people working toward a common goal, believe the world needs?
  • Regardless of the myths we are telling ourselves, what kind of company or organization are we truly building?

Perhaps the biggest insight from my own personal journaling has been that my #1 job is to empower leadership among my team. Their leadership is what will enable us to have the impact we want to have, while enabling me to lead the kind of life I want to lead. I’m hoping these questions will push us to look at ourselves more honestly, and to ask what kind of people we want to be in the face of all the changes rocking the world.

New Favorite Problems

Instead of a list of new goals, I found that the main output of my mid-year review was questions.

In my Building a Second Brain course, I have students generate a list of their “favorite problems” – open-ended, generative problems framed as questions that can drive their learning across many projects over many years.

Here are the questions that are most alive for me for the second half of 2020:

  • What future am I saying yes to with my actions?
  • What does it look like to be a channel?
  • What if I didn’t succeed? (What if I didn’t keep track of everything? What if I didn’t follow through? What if I let things slip through the cracks? What if I let things fail?)
  • What does excellence look like in a business that is all about prototyping, iteration, and publishing early?
  • How can I give up my need for control?
  • How can I make cooking and eating healthy a source of inspiration and creativity?
  • What is the source of my dissatisfaction toward the depth of relationships in my life?
  • How do I keep my heart open always?
  • Who would I be without the myths I’ve told about myself?
  • How is my way of being more powerful than what I do or say?

The clear pattern for me is the shift toward a more “normal,” more family-centered life as we welcome our new son in a few months. I can feel things shifting within me, the priorities and values reorienting around a new true north.

I’ve long heard about founders selling their companies and then plunging straight into a great unknown, ranging from depression to wandering the globe. Their identities get so tied to their company that once they step away, they don’t really know who they are.

I had always assumed that would never happen to me, because I’m never going to sell my company. Yet I find myself in a similar situation now, simply because work can no longer occupy the same place in my life that it has until now. It can’t be the anchor of my identity in the same way it has been.

I feel both a sadness and a bittersweet happiness at that thought. I’ve enjoyed that identity. It’s been a wild ride. But at the same time, I’m a little tired of it. It isn’t everything I am, or want to be. There’s a wider experience of life that I’m hungry for, that isn’t about pushing and pushing at all times and at all costs.

I’m just beginning to get my fingers around the wider edges of this new identity. Just beginning to get a sense of how it works. But I’m doing my best to welcome that discomfort with open arms.

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