One of the most useful exercises I perform each year is a “mid-year” review in June or July.

It’s great to set ambitious goals at the start of the year, but that plan often doesn’t survive contact with the real world for more than a few weeks. We’re like newborn babies flush with excitement for life, but who don’t yet understand how life works.

And looking back on the past year around January 1 is also a useful exercise, but by then it’s too late to make major changes. We’re like the elderly – full of hard-won wisdom, but without any time left to apply it.

But halfway through the year, there is a brief, liminal moment. You have enough information to know whether your goals are properly formulated, but there is also enough time left to change direction and finish the year stronger than you started.

This is a summary of my personal reflection process for mid-year 2021, which mainly involves a lot of reading, taking long walks, talking with the important people in my life, and journaling.

Its purpose is to check in with the , celebrate victories, and make any course corrections based on what I’ve learned.

1. Grow my email newsletter to 100,000 subscribers

This is my most important goal of the year, since the overall size of my audience drives every other business goal. In 2020 my weekly newsletter grew rapidly from 9,483 to 40,887 subscribers, or by more than 30,000. In the first half of 2021 I only added another 8,000, for a total of 48,352. In other words, growth slowed from 2,617 new subscribers per month last year to 622 per month in 2021, a 77% drop.

I’ve only begun to investigate why, but I have a couple solid hypotheses:

  • Email list growth naturally follows an “S curve” as strategies that worked before become less effective, and existing sources of new subscribers run dry
  • I spent little time and attention on it so far this year, in favor of growing the size of our cohorts and building the team

The deeper, underlying reason behind this plateauing is that I think I’ve reached the limits of what I can do as a solo creator sending emails on my own. I don’t have much interest in doing anything besides creating the content itself. I need someone to own this area of the business, from continuously finding new sources of subscribers, to managing the details of ConvertKit, to documenting and standardizing all the ways we use the email platform.

Half of this job will fall to our new Director of Course Operations, Dr. Monica Rysavy, who is working with our newly promoted Chief of Staff, Betheny Swinehart, on the operational side of email marketing. The other half will be the responsibility of the new Director of Content I’m hiring soon, who will manage the content side.

Besides building up this capability as a team, I’ve hired a promotional agency to work with us on the launch of my book over the next year. They’ve worked with some of the biggest names in online media on some of the biggest book projects of recent years, and will help us develop and execute a strategy for growing our audience as the primary lever in making the book a success.

2. Maintain our focus on our two flagship courses

I succeeded in staying focused on our flagship courses this year! Partly because of the accountability of having promised to do so on this blog.

I’m now beginning to think of our educational ecosystem in terms of three flagship courses: Building a Second Brain (BASB), Write of Passage, and The Art of Accomplishment (taught by our external partner Joe Hudson). Each of these courses trains people in an extremely important, yet challenging skill that can have a dramatic impact on their lives and careers – knowledge management, modern writing, and personal growth, respectively. They’re each taught by a uniquely qualified instructor, who is also dedicated to building it into a sizable business.

Each of these courses also checks all the boxes I look for in sustainable CBCs:

  • Includes both concepts and practical implementation
  • Professional/business-focused but including a strong personal growth component
  • Driven by or leveraged by technology and the Internet

These three factors are the moat around our programs. They are difficult for others to copy and require skills not commonly found together. They straddle traditional boundaries of education, which means existing institutions are unlikely to offer something similar. And they have some inherent friction which makes them difficult to scale easily, which means venture-funded startups are unlikely to take them on either.

When I think about these three programs as a symbiotic trio, I think their potential is basically unlimited. There is no reason they can’t each become a $10 million dollar business in the next 5 years. Especially when we take into account vertical integration into books, coaching, paid subscriptions, and physical products around the same intellectual property, each of them is like an extended universe unto itself.

3. Run a live cohort with 2,000 students at once

We got close on this one already, with cohort 12 of BASB reaching just over 1,600 participants including both new students and returning alumni. It was a wild experience, akin to putting up a pop-up liberal arts college in the span of a couple months.

We tried a lot of different ways of making such a large group continue to feel intimate and personal. We had 30 Alumni Mentors delivering smaller breakout sessions each week. We created opt-in “feedback pods” where students could join a small group of students to discuss their progress and get feedback from each other. And we doubled down on making Circle the “town square” of the program. Hearing that people wanted a more real-time, chat-like environment, we also created a dedicated Slack just for this cohort, which we may reuse in the future.

Although each of these experiments was promising, I think we’re reaching a scale where we need to start putting limits on the size of the cohorts. I’m considering limiting the next one to 1,000 new students, plus 500 returning alumni. After that we can assess and decide whether to raise the cap incrementally, or standardize on that size so we can really master it. So much of the complexity of running cohorts comes from the uncertainty around how many students to expect, and although this limit would forgo some revenue, it will make our planning and the resulting student experience much better.

I’m also considering increasing the number of cohorts per year, from two to four, so we can continue serving more customers despite the enrollment limits. That would allow me to hire year-round staff instead of having to recruit a new group of mentors every cohort. And it would help us make longer-term decisions, in terms of semesters and academic years, instead of everything being a one-off.

4. Make operational excellence and customer service central pillars of our business

It’s been incredible to see the explosive interest in CBCs (Cohort-Based Courses) over the last year. The field is unrecognizable compared to when I started. Investment is pouring in, new startups are being formed, and it seems like cohorts are quickly becoming the default format for high-impact, premium educational experiences.

As excited as I am to see all this interest, it also means the landscape is becoming far more competitive. You can’t get away with a few casual Zoom calls anymore. Customers expect high production values, strong follow-up on their questions and comments, practical feedback on their work, real relationship-building amongst their fellow students, and a consistent and distilled experience throughout. I think we’re going to see a shakeout in the next couple years with quirky, personality-driven CBCs taught by solo instructors giving way to more professional, commercial programs run by teams. The plane of competition will shift from personal loyalty to operational excellence.

There are so many components and aspects to a CBC, and all of them are advancing rapidly. Which means we have a lot of work to do to discover, understand, test, and integrate new components. For example, here are some of the major areas of improvement we have our eyes on:

  • Data collection, management, and visualization – How do we combine data from all the different platforms and tools we use and turn it into tangible improvements to the student experience?
  • Mentor recruitment, training, and support – How do we double down on Alumni Mentors, and make their breakout sessions the most compelling and impactful part of the program?
  • Evaluation and testing – How do we improve and expand the Second Brain Snapshot that students take before and after the course, and turn it into a personalized curriculum for the program itself?
  • Live studio production – How do we upgrade the quality and reliability of our live broadcasts for the instructor, course staff, Alumni Mentors, and students?
  • Calendaring and notifications – How do we radically improve the course calendar, and its ability to blend seamlessly into students’ lives with useful reminders without being intrusive?
  • Video editing and distribution – How do we create a dedicated system for recording, editing, uploading, and distributing recordings of class sessions?

We’ve laid the foundation for making major investments into these areas, including hiring a Director of Course Operations, our first Customer Support Rep, and creating a series of internal systems to allow for more hiring in the coming months. We also built a solid support portal, including many FAQs and a support ticketing system for both the courses and inquiries in general.

5. Launch 100 Cohort-Based Courses through the Keystone Accelerator

We launched the first cohort of the Keystone Course Accelerator late last year, with about 35 participants teaching a wide variety of subjects.

The program produced some outstanding successes, but we also learned a difficult lesson: that there are SO MANY aspects of running a successful CBC, it isn’t realistic to expect any program to cover all or most of them. A CBC is a relatively advanced, mature product, meaning you need to have many foundational levels in place in order to make it work: an engaged audience of significant size; a team (or reliable contractors) you can lean on; an understanding of your customers and the most important need you can solve; an existing educational program that you know reliably produces great outcomes.

I think this is the biggest blindspot that the CBC craze is missing: people are trying to make a CBC as their first ever paid product, or in some cases, the first significant project they deliver online. It’s entirely feasible to attract some friends or colleagues for the first and maybe second cohorts, but after this close circle is quickly exhausted I think we’re going to see many instructors realize they don’t have any foundation in place to keep it going, much less scale it.

So we’re pivoting Keystone to focus only on existing education businesses who have that foundation in place, and are ready for growth. Instructor Billy Broas is going to zero in like a laser on the true bottleneck for such businesses: the core messaging that drives every other tactic, strategy, promotion, and piece of content. Messaging (including positioning, storytelling, and differentiation) that is truthful, authentic, and most importantly of all, powerfully effective in moving people to take action. Messaging is the keystone of a successful online education business, and no one does it better than Billy.

6. Redesign BASB brand identity and apply it to new website

We kicked off this project last month, and the two designers I’m working with are well on their way. The early results I’ve seen are incredibly promising. We are creating a comprehensive visual system for the BASB brand that will give us years of runway. It will provide the cohesiveness and shared context we need to extend the ideas developed in the course into books, workbooks, videos, local events, physical products, coaching services, subscriptions, and other media.

I don’t have anything to share just yet, but stay tuned as I begin to share bits and pieces of the brand as it emerges. It will culminate in a completely new buildingasecondbrain.com website by the end of the year.

7. Grow YouTube following to 50,000

I’ve mostly ignored YouTube for the first half of the year, as my attention has been dedicated to finishing my manuscript (which is due at the end of this month!). But I have big plans for it in the second half of the year.

The first step has been remodeling our garage into a gorgeous, 360 square foot studio. I’ll have a lot more to share on this project soon as it’s been a fascinating learning experience. But the main goal is to have a completely dedicated space for not only working from home in general, but filming and livestreaming as well. We made every decision to maximize the usefulness of every part of the studio for creating video content.

In the meantime, here’s a playlist of periodic construction updates I’ve shared along the way.

8. Hire a personal trainer and train with them 90 times

I started working with a personal trainer I found on Yelp on February 11, and so far we’ve trained 37 times, about twice a week on average. This has been an interesting way of framing it for myself, because 37 doesn’t seem like a very dramatic or impressive number. But the 5 months of progress have already been transformational, like a whole body education in what it means to be holistically strong and flexible.

I’ve had to learn how to stay consistent and make room in my schedule for two hour-long sessions per week. I’ve had to learn how to eat better, before my workout to ensure I have energy, and after to make sure I’m capitalizing on my effort. I’ve learned a ton about correct posture and form, the relationships between body parts, and how to avoid injury. The pain and tension I’ve had in my lower back for years is gone, and I have more energy and sleep better than ever.

It’s kind of amazing in retrospect that so many of us walk into gyms and begin lifting weights without any training as to how to do it properly. I’ve had to unlearn many bad habits and correct mistaken assumptions gleaned from TV or watching others. It’s been a relief to accept that I don’t have the self-discipline right now to exercise regularly on my own, and to feel comfortable outsourcing that self-discipline to someone else.

But I think the biggest benefit has been psychological. I have a newfound pride in myself that I am taking care of my most fundamental and important responsibility, my health. It makes me happy that I am setting an example for my son, that health comes first. I’m beginning to think of myself as a cognitive athlete. It may not matter how fast I can run or how many pounds I can lift, but to the extent my body is the foundation of my mind, I depend just as much on it as any pro athlete.

9. Becoming a parent

This wasn’t on my list of goals, but becoming a father has of course been the most monumental change of the past year. Our son is almost 9 months old, and over the past 6 months his personality has really started to emerge.

It feels in many ways like I’ve entered a different dimension. An alternate reality that operates by different rules. Things that seemed critically important – launching new products, spending as many possible hours per week in deep focus, traveling extensively – suddenly don’t seem important at all. Or even desirable.

Other things that I’d never given much thought to have become paramount – improving our family’s dietary habits, spending as much time as possible with my parents, understanding and healing intergenerational trauma (I’m reading a book called It Didn’t Start With You that has been very moving on this subject).

I think the deepest shift is that my own life – my goals, priorities, and freedom – is not the central focus of my life anymore. Instead, my attention is dedicated to what my spouse and my son need, want, and will become. It’s jarring to realize that I’ve had the great privilege of focusing entirely on myself until now.

Becoming a parent has also changed how I view a lot of “life advice.” A lot of advice that makes complete sense for single 20-somethings or childless 30-somethings makes absolutely no sense once you have kids. They are like different worlds with little communication between them. As I approach 40 and identify less and less with hard-charging 20-somethings giving their career or business every last drop of their energy, I can see that the content I create and the lessons I teach are going to change as well.

As a parent, I have far less time, and especially solo, focused time, than I did previously. My sleep is far more unpredictable. We are fortunate to have childcare until about 3pm each weekday, but that means that my workday effectively ends at 3pm. Whereas in the past I would get a whole second wind to work through the afternoon and into the evening.

Now I’m looking to other sources for inspiration. Not so much productivity gurus, but fellow parents who seem to live with ease and grace. Not so much the puritanical extremes of human performance, but the messy middle. I’m interested in leaders and business owners who are somehow able to maintain and even expand the impact they have without sacrificing the needs of their growing families. I feel like a beginner again, and that is a precious gift.

3 areas of innovation

I’ve long had this idea that the business just needed to mature, and then we’d reach this mythical plateau of stability where we’d have everything figured out and just sail smoothly into the horizon.

But now I understand that the only plateau is the plateau of stagnation. That change is the only constant, and it is our prerogative to get good at navigating it.

I’m starting to realize that every single year of the business requires a different strategy and even business model. We are growing quickly, approximately doubling revenue each year. Each doubling demands a different mix of goals, different roles for our team, and different kinds of partnerships and advisors.

From 2013 to 2017 I was in “solo creator” mode, experimenting with a broad range of projects, pursuing whatever resonated with me. In 2018 my Building a Second Brain course really took off, and the whole business reoriented to support it.

In 2020 we started hiring, ushering in a new stage of building a team that could deliver the course to a much larger number of students. We now have a team of 8 across two flagship courses. It’s been a wonderful experience to go beyond what I can deliver by myself, to watch others learn and grow alongside me, and to envision our future as a real company.

Now it’s time to shift once again. As strange as this sounds, it wasn’t until the past year that I truly committed to our future as an education business. There seemed to be so many interesting topics to learn about, and so many promising pathways to explore. Why would I commit to just one?

But the growth of the course alongside my newfound conservatism as a parent have combined to make it very clear to me that BASB is my big idea, the course is the breakout product, and the release of my book in just about a year is an opportunity to make it the definitive methodology on knowledge management, and productivity in general, on the planet. What GTD did for personal productivity, we can do for personal knowledge management (PKM).

Interestingly, this leads me to the conclusion that there are really only three areas of life that I want to innovate on:

  1. My personal growth
  2. My child’s education and upbringing
  3. Ideas related to PKM

Each of these areas are ones where 1) I believe I can make a real difference, and 2) The existing defaults if I don’t act aren’t very good. One is for myself, the second for my family, and the third for the wider world, like concentric circles.

All the other areas of life, such as my marriage, home, family life, hobbies and free time, friends, and the running of the business, I want to be as mundane and boring as possible. Not “boring” in the sense that it lacks excitement, but in the sense that it draws on the timeless wisdom of the past instead of trying to invent a radical new future. We’re even considering buying a mini-van.

I take seriously Gustave Flaubert’s advice to “Be regular and orderly in your life, so that you may be violent and original in your work.” I’m discovering that the more violently original I want that work to be, the higher the percentage of the rest of my life that needs to be regular and orderly.


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