We are, I believe, in the third wave of online learning.

The first wave, known as Massive Open Online Courses (MOOCs), consisted of traditional educational institutions putting their lectures online. The bottleneck was basic tech knowledge, and the innovators of this era were those institutions able to set up a basic website, film and edit videos, and upload them. Coursera and Udacity are the modern descendants of this model.

The second wave was the aggregators, websites like Udemy and Skillshare, who served as marketplaces for online courses from a much wider variety of instructors. The bottleneck had moved to exposure, and these sites offered that by creating a “critical mass” of content that attracted more learners, who attracted more instructors, in a virtuous cycle.

The importance of exposure also influenced the format of the courses. Because a new course launch was the easiest time to gain exposure, it made sense to create more numerous, much shorter courses focused on narrower topics. This also helped boost completion rates, which led to more enrollments. Because these instructors weren’t necessarily world-famous experts who could bring in people on name recognition alone, they focused more on imparting skills, especially digital ones easily taught online.

But this explosion of online courses led to a new bottleneck: how in the world was anyone supposed to find the time to consume, much less put into practice, all this content?

This was where my first course, on GTD, came in. It took off on Skillshare because it was the only offering on the site that gave you the organizational and productivity skills to actually manage the dozens of courses you had signed up for.

But then investors came calling, and the aggregators were forced to cash in, taking an ever-larger share of the pie, and in some cases switching from an à la carte model (taking a commission on each sale), to a Spotify-like subscription model that paid out barely anything to the instructor. I saw my own revenues from Skillshare (now from 2 courses) drop overnight from $25 per sale to less than 25 cents. The promise was that they would make up for it in volume, but that never materialized. Another manifestation of this was the rise of flash sales: both Skillshare and Udemy offer 90%+ discounts on their libraries, which means creators have no control and no pricing power. The incentive is for the marketplaces to constantly discount, thus bringing in more users and improving their metrics, at the expense of instructor revenues, and therefore over time, quality.

The end point of the second wave was that you made more as an affiliate bringing in a sale, than as the actual content creator. It became crystal clear that it was more difficult to sell a course than to make a course.

Now we’re in the third wave, and the bottleneck has moved from exposure to accountability. It’s easy to get someone to sign up for a free course, and not that hard to get them to pay $15–30 for a slightly better one. But the overwhelming evidence is that doing so does not mean that they actually take the course, much less complete it, much less put into practice what they learned. Universities and other formal learning environments can be thought of as giant accountability machines: grades, tests, quizzes, GPA, honors, pass/fail, peer pressure, instructor pressure, financial pressure, family pressure, cultural pressure. The failure of the Udemy pilot at San Jose State University was the clearest wake-up call that “online” didn’t automatically translate to “better.”


We sailed into the glorious future free of the overbearing constraints of traditional education…and threw the baby out with the bathwater. It is not at all natural for humans to spontaneously dedicate large amounts of time and effort to learning things. The availability of content from the world’s smartest people is not by itself enough to motivate most people to make it a priority.

This article is my attempt to summarize what I’ve learned during 3 years on the front lines of online learning, and especially the last 3 months developing and delivering a 4-week virtual bootcamp on personal knowledge management called Building a Second Brain.

This won’t be a How To, a comprehensive survey of the industry, or a list of “interesting trends.” I’ll be jumping around wildly, touching on many different disciplines, and making some predictions that can actually be proven wrong.

It is very important to me that more people teach more subjects at a higher standard of quality online. It’s good for those creating the content, to express their ideas, gain a network of followers, and make some money on the side. And it’s good for the consumers of that content, to accelerate their learning, not have to reinvent the wheel, and advance their own careers. As I will argue, I think the boundaries between these two groups will increasingly blur over time.


I call this third wave Short Tiny Exclusive Virtual Experiences (STEVEs). They deploy a wide range of tactics to bring accountability back into the process.

Short: anything that is supposed to last a long time must necessarily be low intensity, which is exactly the opposite of what we’re going for. Anything that can be done at any time, tends to get done at no time.

Tiny: scale breeds anonymity, which is the arch-nemesis of accountability. These courses offer either limited enrollment that allows personal interaction with the instructor, or peer or small group structures that allow interaction with mentors or fellow learners.

Exclusive: a quirk of human psychology is that we don’t value anything that is available in abundance. Exclusivity, through high prices, application and selection processes, time-limited enrollment, or referral-only is a powerful signal that cuts through ambivalence.

Virtual: these courses still take place online, but using a whole new generation of collaboration and creation tools.

Experiences: this new generation steps away from the pure efficiency of highly condensed media, instead combining the unpredictability, humanity, and connection of live interaction with qualities borrowed from bootcamps: short, very intense, skill-based, forces you out of your comfort zone, develops camaraderie, and…you have to perform to stay in.

In many ways, STEVEs represent a return to intimate, almost tribal learning environments that are most natural for humans. They replace the abstract accountability of tests and grades with more visceral ones: peer pressure, scarcity, and FOMO.

Bootcamps as personality-driven brands

One of the most interesting and unusual aspects of these bootcamps is that the best ones are unapologetically personality-driven. See Jenna Soard of YouCanBrand — there is no question her entire brand is built around her image and her personality. You see it in everything from her photos and videos, to the wording and references she uses, to the people she partners with and co-promotes. It’s also outstanding content, by the way.

This brings up a truth about learning that I think has been almost entirely forgotten: we learn best from people we like and connect with. We may consider that one special college professor a fluke, but looking back over one’s learning career, I think it’s rare to find someone you really didn’t care for who was able to have a big impact. The internet gives us the possibility of such connection at scale.

This leads to something else I’ve noticed ever since teaching English to kids: the best learning is mostly entertainment. The rewards of education are too far off and abstract to appeal to our lizard brains — we need a reward now to stay engaged, in the form of amusement, surprise, drama, or laughter.

Which is why I believe the most important influence for understanding the future of online learning is YouTube personalities (known as YouTubers). Not the ones you and I watch — the weird ones that teenagers are obsessed with.

I had the opportunity a couple years ago to work with Paulo and Danielle Noce, who have one of the most popular YouTube channels for cooking in Brazil. They opened my eyes to a whole new world of media I had zero knowledge of: people like Zoella, one of the top fashion YouTubers, who is paid tens of thousands of dollars to try on a piece of clothing “on air,” even with full disclosure that it is sponsored.

Zoella’s YouTube channel

YouTubers churn out content at a blistering pace. Their entire lives become platforms for showcasing products, referring their audience to brands and services, and promoting their numerous online properties. They freely cross boundaries between genres (cooking to lifestyle to travel to technology), between formats (videos to photos to courses to online magazines), and between platforms (YouTube to Instagram to Snapchat to Patreon). Calling them “YouTubers” is actually a misnomer: these people control vast cross-platform empires of constantly evolving content, products, and services, all of which can respond instantly to the whims of an audience that they uniquely understand through dozens of digital and in-person channels.

This brings up an uncomfortable possibility for those of us not familiar with this corner of the internet: that creating profitable online content requires developing and leveraging a personal brand that can stand out from the crowd. This requires a set of skills never before associated with formal teaching: authentic personal sharing, irreverence and wit, surprising and delighting, and most of all, a continuous effort at what I call Whystorming.

It is easy in this multi-platform, rapidly changing content universe to lose sight of who you are, what you believe, what you stand for, and what you’re not willing to do. Whystorming is a continuous series of exercises and activities to uncover, refine, and reframe your purpose, your mission, your core values, and your goals in light of new information. It includes everything from MBTI and other personality tests, to branding exercises that “start with why,” to self-reflection and personal growth experiences that take us out of our comfort zone, to cultivating coaches and mentors that can tell us hard truths. You can’t wait for your paradigms to be overturned — you have to overturn them yourself. It turns out that the only way to give others perspective is to always be seeking it yourself.

The bottleneck of the bottleneck: marketing and sales

Of all the methods of limiting enrollment and keeping it exclusive that I’ve mentioned, the most important and interesting is price.

We’re witnessing the rise of truly premium online bootcamps: Ramit Sethi’s suite of offerings, Marie Forleo’s B School, and Seth Godin’s altMBA are prime examples, ranging in price from $1,000 to $10,000.

This is tremendously exciting, because it opens up the possibility of making a real living from teaching online. If these three represent the very top end of the market, there is plenty of room underneath for the non-famous to prosper. See Rebecca Katz’s $97 course on how to cook for cancer survivors. It’s also starting to address one of the biggest outstanding questions: can online learning ever replicate the engagement of in-person learning, and charge accordingly? It seems increasingly clear that it can.

Charging premium prices is so effective because it solves many problems at once: instantly filters out those for whom spending that much is out of the question; unmistakably signals the quality and personal attention being offered; frames it as an investment and level-upper; and of course, allows you to actually spend the time it takes to deliver on these expectations.

But increasing the price to solve for accountability introduces another bottleneck: the marketing and sales journey for selling a product at this price point is radically different than for commoditized $30 video-based courses. It takes not only a strong personal brand but a well-designed and constantly improving sales funnel, capable of building credibility over longer periods of time, with a large number of people, and in a semi-automated fashion. Building such a funnel is my main focus right now, as what I currently have is a disjointed and disconnected series of online properties that takes serious effort to make any sense of.

There are many innovative methods of promoting the product once it’s finished, which are all being updated and refined for online use. Some of the biggest ones are:

  • offering bits of content as “lead magnets” to incentivize people to give you their email address
  • bundling and discounting (i.e. get these 5 things that would normally cost $1,995 for only $499!)
  • upsells and limiters (upgrade now and get the bonus package for only $100!)
  • email automation (sending a series of pre-written emails at designated intervals, to slowly introduce the person to your content in small chunks)
  • retargeting (using cookies or Facebook tracking to show ads for your product across multiple sites, like when a pair of shoes you looked at on Amazon pops up on Etsy)
  • webinars (giving a preview of what your content will contain, leaving the how for those who want more)
  • summits (bringing together a bunch of content creators for “panels” or “interviews,” allowing them to “borrow” each others’ audiences)
  • free courses (as previews or introductions to more advanced, paid ones)
  • next-level testimonials (going beyond a quote and a headshot, the most common form is a video selfie of the customer saying what benefit they received)
  • guest instructors or interviews (providing your bootcamp as a platform for a bonus session or interview with another content creator in a related niche, providing value to your audience as well as a cross-promotional opportunity)
  • utilize existing platforms (publishers, aggregators, curators, thought leaders, publications, email lists, practitioner communities, traditional media, Facebook groups, etc. — a whole subject in itself)

Marketing as product definition

But the most interesting aspect of all this is “marketing” in the traditional sense — of defining and shaping the product to practically sell itself — and not in the sense of mere promotion and exposure.

The basic question is: how do I know what I’m creating is useful, valuable, and worth-paying-for for enough people to make the effort worthwhile? We want to avoid the two extremes: sticking to your guns no matter what anyone says, to defend your “artistic vision”; and sacrificing all your values and beliefs for the sake of “making what people want.”

This is the challenge of new product development, faced by every inventor and startup. It includes things like:

  • finding a clearly defined niche, unique “angle,” or point of entry into your audience (like the one my first course stumbled onto accidentally, selling productivity to creative types)
  • identifying a tangible outcome or deliverable that will make a real difference to their career or quality of life, and that they couldn’t get any other way (a customized “habit template,” not just “knowledge about how to create habits”)
  • offering “insider” or “secret” stuff that they “must have” (which usually requires some sort of unique experience — more on this later)
  • framing (what category does this product fit into? To what should it be compared? What are the expectations you want people to have?)

The truth is that this involves hard thinking, and there is no way to do it in isolation. You need layers of feedback and testing to refine the product definition through repeated iterations. Here is the basic sequence I followed for my bootcamp last month, to give you a sense of what this can look like:

  1. I started with a blog post almost a year before the course was developed. The comments on that post were pure gold to tell me how people thought about the subject.
  2. In December I emailed my newsletter list of ~1,300 people (accumulated over a couple years of blogging and other courses), asking for volunteers for a beta testing group.
  3. I chose 10 (plus a few friends), and asked them to commit to four 1-hour video calls with me over the course of a month, in exchange for a free ticket to the course once it was ready (note that this wouldn’t be worth much with a non-premium course) plus a promise to share what I learned from the experience (in the form of this blog post, plus a follow-up call to answer questions)
  4. Each weekly call required a little pre-work on their part (usually just reviewing something) and had a theme: content, marketing, format, logistics. I worked hard over the preceding week to have something tangible for them to give feedback on, and took careful notes during the call itself, following up on every point or question raised.
  5. Once I had the minimum content developed, I launched the sales page and began collecting money, which gave me the final burst of motivation (and accountability) I needed to finish things off.
  6. I promoted the sales page through every publication, email list, and partner I had access to, the most important being a new post on the Evernote blog, which was highly relevant to my target audience.
  7. To emphasize, I didn’t commit to building the course until I had the promise of a guest post on the Evernote blog in hand. I then proceeded to build the entire product around that post. That’s how important marketing is.

Throughout this entire process, the extent to which the content itself could be changed was limited. I had something to say on some topics, and not on others. I can’t generate insight on any subject on demand. What was much more mutable and subject to quite radical change was the framing and crafting of the offering: which metaphors and terms to use, which problems and interests to appeal to, what kind of person to speak to, which expectations to set and which to deemphasize. In short, how to clearly describe what this bootcamp was about and what it promised.

The feedback I received from the beta testers was immensely valuable. It helped me extricate myself from the curse of the expert: to be deeply immersed in the content in order to teach it, but blinded by that very immersion to the needs and interests of people not familiar with it. Many times I was shocked to hear that what I found to be a fascinating subtlety was, for others, a meaningless detail. What I thought was an obvious building block turned out to be a challenging claim. This is the kind of “beginner’s eyes” that cannot be bought, begged, or stolen — only borrowed.

Another valuable part of the experience was having my assumptions and preconceptions challenged:

  • Is this content really about new ways of doing, or new ways of thinking?
  • Do people really feel the need to “be more creative,” or do they just need tools for utilizing the knowledge they already have?
  • Are people relying on you to tell them what to do, or what NOT to do?
  • What is the largest “chunk” of content someone can reasonably consume in one sitting?
  • Does adding more “features” to the offering improve it, or just dilute the benefits?
  • What does the system you’re outlining actually do for them in their day-to-day life?
  • What are the habits, routines, and practices that go into making such a system work over the long term?
  • What is the nagging worry that keeps people up at night, in regards to the digital information they consume and manage?

All questions I hadn’t thought of myself. And the answers to all of them were very insightful as I strived to simplify my message and make it more concrete.

One last thing I want to point out: all these methods are available to anyone at some level. If you don’t have an email newsletter list, you have probably almost the same number of social media followers. If you don’t have fans that will volunteer to beta test, you have friends and colleagues that would be happy to do so over lunch or coffee. If you don’t have world-class expertise in a subject, reduce the boundaries until the niche is small enough that you do.

STEVEs and Just-In-Time Education

I see online learning dividing into two camps: STEVEs for intense, skills-based, behavior change-driven experiences; and Just-In-Time Education for modular, searchable, on-demand solutions to specific problems. In this sense the San Jose State pilot taught us a valuable lesson: the success of online education cannot be measured by a blunt instrument like “completion rates.” The successful JIT learner knows how to enter and exit multiple forms of content with surgical precision, weaving together and combining lessons to fit their context, not just check a box.

Increasingly, the question every online learner will need to answer in order to decide between the two camps is this: in a given area of my life or work, do I want sustainable behavior change, or just a straightforward answer to a question?

The journey ahead

All this points to a tremendously exciting and fruitful future for online learning. It’s so clear to me that we’ve barely begun to scratch the surface of what is possible.

Sure, there’s all the fancy stuff coming down the pipe like virtual/augmented reality, self-tracking, personal analytics, AI, and wearables. But what really interests me is how the evolving nature of online learning is enabling new ways of working, collaborating, and living.

Much of the emphasis has been on how anyone can now learn outside the walls of a formal institution, with MOOCs and the like. I’ve argued that that is largely an illusion for the kinds of intensive learning that really make a difference. The people most likely to have the time, resources, self-discipline, background knowledge, and meta-skills necessary for self-directed learning are precisely those who already have plentiful access to formal institutions.

The key, I believe, is to focus on the supply side of the equation: how do we get thousands of people, with existing knowledge and expertise in valuable fields, to summarize and package up what they know in a format that gives people accountability, social interaction, and follow-through? We long ago solved the “content” bottleneck — there is infinitely more published every single day online than anyone can hope to consume in a lifetime. What is needed is new formats and tools for helping subject matter experts (even if that subject is very, very niche) to take others on an accelerated version of the journey they’ve already experienced.

I don’t mean that everyone can or should be full-time online entrepreneurs. Imagine what a difference it would make for anyone to have an interesting side project they look forward to working on, a public showcase of their work to show potential employers, a collaborative open source project that helps them learn new skills, or just a little extra income to save, invest, or smooth out the rocky parts of our volatile economy.

The leverage and precision that online teaching offers opens up new possibilities that weren’t available before: with little or no marginal cost for each extra enrollment, it becomes easy to offer scholarships and targeted discounts to people who wouldn’t normally be able to afford them. It becomes a no-brainer to actively seek out more diverse participants — in the productivity space especially, this means women, people of color, the differently abled, people in developing countries, etc. With zero marginal cost, recruiting these groups becomes not an “expense” to be borne, but an investment in cognitive diversity, which is more needed than ever.

Because you can teach a virtual bootcamp from almost anywhere, with less friction on getting to and from a classroom multiple times per week, it is possible to be both a teacher and a practitioner. This is essential to keeping your ideas fresh, relevant, and results-oriented. I find that the cross-pollination between corporate consulting and training, direct-to-consumer online teaching and coaching, and other projects is my most important source of new ideas and practices, and helps me test things in diverse environments. Maybe, eventually, we could subvert the fundamental assumption of all teaching: that those who can’t do, teach. If teachers became practitioners, that means practitioners (the rest of us) could also easily become teachers. Teaching would not be some strange, rarified profession for self-sacrificial martyrs, but an inherent part of living and working in the 21st century.

Each of us could stand on the shoulders of giants, but those giants would be each other, in as big or small an arena of knowledge as we are ready and willing to master in each season of our lives.

Outstanding questions

Let’s run an experiment. I’ve noticed that these premium, bootcamp-style courses are very difficult to get access to. Thus it’s difficult to learn from their mistakes and their successes.

I’m going to list here my 3 biggest outstanding questions and areas for improvement, and ask you to contribute any examples or best practices from your experience, especially relating to any premium online course you’ve taken.

Please respond by commenting on this article below. If appropriate, I’ll summarize or package up these follow-on learnings in a Part II.

1. Balance between optionality and accountability

I put a lot of emphasis on accountability in this article, but the truth is, it’s a fine balance with optionality. It’s not necessarily a bad thing if someone wants to just peruse your content, focus on one or two parts, or just hear what you have to say for kicks.

When this becomes a problem is if it creates a “spectator effect.” If too many are just along for the ride, any form of online interaction can become a ghost town. We’ve all been part of Facebook groups or Slack channels with nothing going on.

How do you create forms of accountability that exert a helpful pressure to complete the course, while also allowing for more flexible and needs-driven forms of interaction?

2. Exercises and activities

A major difference between passive, video-based courses and virtual bootcamps is that the exercises and activities are central to the experience. A book or video might give you a prompt or question “to reflect on,” but a bootcamp throws a challenge at your feet and dares you to move. This includes applying new techniques to real problems participants face, which is critical to making the knowledge stick.

But as important and carefully designed as these exercises may be, they are ultimately optional. I’ve noticed a funny phenomenon: for low-priced courses there is little sense of investment to complete the exercises, but for high-priced courses people figure they are paying so much, they shouldn’t have to do any extra work!

How do you structure exercises and activities to convince participants to complete them, building to a final outcome while also delivering immediate value?

3. Follow-through and support

I think this is probably the least developed aspect of online learning today. The “graduate” of such a bootcamp is a powerful asset — able to bring others into the fold, influence how organizations run, and help others in their own learning, whether inside or outside your offerings. But very little effort is put into retaining and supporting them after the course ends.

I think we’ll need to look at traditional groups to see how such leadership development is done: community organizations, clubs, schools, political organizations, sports teams, even religions and cults. Every message worth sharing needs a mechanism for turning students into teachers.

How do you provide ongoing support and follow-through to people who complete online bootcamps, in a way that is both effective and sustainable for everyone involved?

Thank you for reading, and I’ll look forward to hearing your thoughts.


Follow us for the latest updates and insights around productivity and Building a Second Brain on Twitter, Facebook, Instagram, LinkedIn, and YouTube. And if you're ready to start building your Second Brain, get the book and learn the proven method to organize your digital life and unlock your creative potential.