Education & Freedom

Over the past couple months, I’ve been traveling extensively both for work and for pleasure. All of which:

A) Meant I didn’t write anything new to share here, and

B) Gave me a bit more space than normal for general reflection and personal well-being. 

When I have the time, one of the rabbit holes my mind ends up going down is  the question, “just how did I get here?” Like, what are the strands of existence that actually came together such that the facts of my life are true. This comes out even more prominently when I’m around extended family, and we rocked three different family reunions in three different Colorado mountain towns in the month of August, so I have some thoughts. Don’t worry, I’m not going to lay them all on you. Just one that’s deeply related to education - mine specifically, but maybe systems more generally. 

All systems are, to some extent, a game (which may explain a bit about why I have some issues with gamification). I think it’s because of my father that I internalized at some point very early in life that you can either play the game the system intends, or you can come up with your own game that works within the system and play that one instead. I tend to opt for the latter. 

I bet many of us know the games we’re meant to play as we conclude our secondary school education: load up on those AP/IB/Advanced/A Level courses, get into those leadership roles in as many clubs & societies as possible, and overall just polish up that college application. 

I’m not here to critique that game (too much - except to say that it’s a game whose implicit rules tend to advantage the already privileged, but that has little bearing on my own story as a cis white male raised in the suburbs). I just remember that as a teenager I couldn’t bring myself to play it. Dad was a university professor of high ideals, and he had imparted to his children the love of learning for its own sake, while developing in us rigorous critical faculties for thinking and engaging with the world. When it came time to get on the college prep pathway of loading up on AP courses, though, I mostly opted out. The problem, as I saw it, was that the college prep courses didn’t let me learn about the things that I was interested in. And they especially didn’t appeal to the way that I wanted to learn - I wanted to make and build and do and connect concepts to lived practice, not just internalize formulas in preparation for a high stakes test. 

I was fortunate: when I think back on the English & Language Arts faculty at my public secondary school, I now see that it was among the finest anywhere in the world. Four of those teachers - Mr. Anthony Maite, Mrs. Regina Meyer, Mrs. Diana Vance, and Mrs. Robin Brenneman - conspired with me to craft a different game than the one that everyone else was playing. Every one of them supervised an independent study course for me, helping me define projects and areas of study that fit within my interests. In doing so, they also challenged me based on my individual ability level rather than a general standard. 

Mr. Maite worked with me to build an entirely different pathway through a course I was required to take (which he happened to teach...not a coincidence that I ended up there). Mrs. Meyer gave me the recommended reading list for the AP literature courses that I didn’t take, and then just let me sign up for the AP tests if I wanted. Mrs. Vance helped me track down obscure texts in local public libraries. Mrs. Brenneman savaged my projects...and then always gave the most helpful feedback & guidance.

These people kind of ruined college for me (and I couldn’t be more grateful for it): when I eventually enrolled in university the projects were rarely as meaningful, the feedback rarely as personal, and that idea that “at university you have to take responsibility for you own education” - they helped me get on top of that when I was 16. 

I promise this isn’t just sentimental reflection. I promise this belongs in this newsletter about product & education, because here’s the thing: I got this experience because of people bending the system to make it work for me, but product in education is ecosystem building, and I’m curious about the different elements of an ecosystem that we could build to make this less of an exceptional case and more of a systemic solution. Which isn’t to say that I think this would be the right system for everyone, but I do think it could be a better system for a lot more people than we might imagine if we can just shift our paradigm a little bit. 

(BTW, there’s another “Buzzwords that won’t die” article in me around the term “personalization.” Let me just foreshadow a bit: none of what I’ve mentioned above is really about how to let someone move at their own pace through a standard curriculum)

What are some of the elements that would be necessary in the kind of products that would build a radically student-driven learning journey? Looking at my own experience, I can pull out a few strands:

•  Autonomy - making the process of learning dialogic between the learner and the teacher (and possibly even peers, if the environment wasn’t purely focused on individual outcomes?). This can apply to the “content,” but also the assessments in what is measured and how.

•  Authentic assessment - ways of assessing capabilities in application, and assessing them on a dynamic spectrum so that it’s not just a binary with a defined maximum. 

•  Light touch guidance - providing minimal initial guidance and then redirection, correction, or stimulation as needed rather than defining a rigid pathway forward. 

•  Rich feedback - integrating qualitative definitions of strength and growth alongside quantitative measures of achievement. 

•  Starting from inquiry - rather than beginning with information to be consumed, starting from questions to be explored. 

To be clear, we all know of environments that exist that exemplify all of these things (and if you don’t, check out some of the links below), but most of those environments aren’t broadly accessible. And this isn’t a challenge that has only a product- or design- based solution, but if we want to think about what systems for empowering education look like, they’ll need products to support their vision and principles. 

Some dank links…

  • The Agora School in Holland sounds like a dream. The Dutch, they really do everything better, don’t they?

  • Todd Rose’s book The End of Average is a good lens for thinking about how to move away from “one size fits all” systems to those that are more built around the learner.

  • Apropos of nothing, the latest issue of Craig Mod’s newsletter Roden on the implicit contacts we enter into with different types of media is just so good. About once a month, Craig drops a 3000-5000 word essay that is always worth the time investment.

The Recipe for the Secret Sauce

Or, as it will be known henceforth, “The Sauce”

There was a time in the place where I work that people were taken with talking about “The Secret Sauce,” this precious and special thing that we had that was somehow ineffable. For the record, I do not work in the food industry. We couldn’t describe it or name it, it was just there in the ethos. Me, I want to figure out how to make such things reproducible, so one afternoon I sat down with our co-founder and COO (to whom I would provide a link, except he’s apparently some sort of international man of mystery), and we hammered out our recipe for the Secret Sauce.

I swear it isn’t just Thousand Island Dressing…

I’m sharing this here for two reasons: first, because building product in education by necessity is about scale, so if you have some magical secret sauce in what you’re doing, you need to figure out how it grows with your product; and second, while I don’t think this recipe will apply to any and every education product, I do think the future of education is less about optimizing the process of knowledge transfer and more about the formation of identities, mindsets, attitudes, and beliefs. There’s still a whole lot that we’re figuring out in my little corner of the world about all of that, but I do think we have some things to say.

Alright, before I turn into every other recipe website on the internet and make you scroll and scroll and scroll to get to the thing you really want, let’s just get into it:


  1. Connection to a big mission that transcends any one person.

  2. Focus on ethical self leadership. 

  3. Environment where students lean on each other more than “the professionals.”

  4. A high standard of excellence that is made explicit.

  5. Hands on practice of leadership & reflection on what they are learning about themselves as leaders. 

  6. Opportunities to play, have fun, and not be too serious

  7. Measurable, visible learning (optional)

  8. Opportunities to build new things (optional)


  • Start by articulating the big mission in such a way that everyone can see themselves playing a part in it. Ask them to define what their part in it might be. Let them share their own and see what others have to say as well. This begins to mix ingredients 1 & 3

  • Take ingredient 4 and underscore the value of the ALU opportunity and how special people are who get to be a part of it. Balance out an equal sense of feeling honored with a burden of feeling entrusted with something big. Expect them to live up to the standard of excellence from day 1, and treat them as people who already embody ALU’s values. 

  • Take ingredient 3, and ask students to accomplish things together - these can be applied challenges, classroom experientials, anything that gets them actively engaging with each other and recognizing the value that their peers bring to their experience. Try to say yes to their ideas, or find the parts of their ideas that are worth saying yes to and call them out as valuable. Mix with ingredient 5 liberally. 

  • Take ingredient 2, and ask them to reflect on key elements of their identity: their values, their sense of mission & purpose. We don’t always call this “ethics,” but just by asking them to think about the values that guide them, we implicitly tell them that we make choices based on what’s important to us, not just what’s expedient or convenient. Revisit this frequently throughout their time with us. Allow them to grow and change their mind, but to reflect on why those changes have taken place. Use ingredient 2 and ingredient 5 together as much as possible. 

  • Wherever you add ingredient 5, make sure to also add at least a pinch of ingredient 6. Sometimes you’ll need to add more - like a handful. They’ll engage better with the serious stuff when they can let their guard down, not take themselves too seriously, and not worry about bruising their fragile egos. 

  • Balance ingredients 7 & 8 by telling them what the things are that we intend for them to learn and showing them their progress along the way, but also ask them to create their own things that represent what they want to learn & how they want to grow. Ask them to look at things in different ways (reimagine them, if you will), particularly things they are passionate about.

Yeah, we got a few links this week:

  • Baking Innovation Into Your Design Process - worth remembering, you innovate toward something, you don’t just innovate for the sake of innovating. The best stuff comes from really understanding what your user needs.

  • Usable Knowledge - I really do think this site from Harvard Graduate School of Education might be the most accessible presentation of research for practitioners. You won’t have to dig too long to find something useful and interesting.

  • The Battle of Grace Church - Wherever you think you stand on matters of education, get ready to experience some moments of discomfort when you read this one.

  • The Boy Who Played With Fusion - a fun thought experiment: what product, service, or environment do you design to create more Taylor Wilsons?

Last word: the thread experiment of last week was an epic fail. No worries - around here, we’re cool with low risk failure. I’ve got a card or two up my sleeve for the coming weeks to see if we can’t get some real dialogue happening here. Watch this space…

Getting to the Actual Story

So…what do you do to get the Actual Story when talking with your users?

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The Official Story and the Actual Story

(And why we want one but end up with the other)

Here’s the scenario: everyone has agreed across the board that it’s important to talk to your [choose word: users/participants/customers/students] in order to understand their needs and the problems that you need to solve. Some people you work with have bought into it grudgingly, so you need to show why this part of the process of building a great product is so important. So...what do you do?

Maybe let’s start with what you don’t do: don’t tell the person you’re interviewing your idea about how to solve their problem and then ask them for feedback. (Even worse: don’t put the fully built product in front of them and ask for their feedback). Here is what will happen: people will basically tell you that it’s fine and maybe make some cursory suggestions of tweaks, and you will fail great like you totally nailed it, and then no one will actually use it, and you’ll feel bewildered, and the people who grudgingly bought into this process will point their fingers in your face and be like, “See, we should never have done this in the first place.” And then they’ll open up the lions’ den and throw you in, where you will be devoured. that much is obvious, and none of us would ever imagine doing such a thing anyway. In my experience, though, we often engage in the discovery process in a way that gets us to the Official Story, when what we want to get is the Actual Story. 

First, some terms:

•  The Official Story is the thing that the person being interviewed knows they’re supposed to say. They’re familiar lines, and they can sound good because they give us so much confirmation that we’re headed in the right direction. The Official Story brings us comfort and reassurance. The only problem with the Official Story is that it isn’t the Actual Story. 

•  The Actual Story is what’s really going on. It’s the skeletons in the closet that people don’t want to bring out, the actual obstacles they’re facing that they don’t want to own up to. It’s the real problem, and it’s often messy. To make matters worse, because it hasn’t been translated into the Official Story, when you talk to a dozen different people they might talk about the same Actual Story in a dozen different ways. Getting to the Actual Story is messy and hard. The only good thing about it is that the Actual Story is the thing you should actually be working on. 


Wood-paneled table? Check. Microphones and cameras (plural)? Check. All set to get the Official Story...

Why do we so often end up with the Official Story? The short answer is: because we ask the wrong kind of questions. Let me give you some examples of question stems that lead to the Official Story:

•  Can you tell me about a typical...?

•  What is the average  like?

•  How do you [do thing x that we think is related to the problem]?

•  What do you think of [thing x that we think is related to the problem]?

On the surface, these don’t seem like bad questions. They seem like they should be informative and useful. The problem with them is that they ask people to remain at the most superficial level, and so the insights you’ll get will remain superficial. In the best case scenario, they will help you understand the functional requirements you need to fulfill (but probably not - instead they’ll tell you what the interviewee thinks the functional requirements are, even if they aren’t). What you won’t get - and what you need - is an understanding of the emotional requirements for your product. 

Reworking those questions to get to the Actual Story isn’t a monumental uphill battle though. The main factor to keep in mind is the word “story” itself; to get to the Actual Story, you need to task the interviewee to tell you stories about real, actual experiences. Some question stems that start to get you there:

•  Can you tell me about the most recent time you...?

•  When did you feel the most [excited, frustrated, confused, confident, etc...emotional adjectives] about...?

•  The last time you needed to [do thing x], how did you go about it?

In each of these question types, you’re asking the person to provide real, tangible details about an actual instance of something of interest to you. These stories will be rich and provide ripe opportunities for follow-up questions and deeper probes. They will reveal at least the contours of the skeletons in the closet, and if you make the person feel comfortable and safe and probe delicately you might get to meet those skeletons face to face. And when you hear a lot of people talking about the same skeletons, that’s when you know you’re onto a valuable problem to solve with your product. 

The mechanics of how to do those interviews, distill insights, and translate that into problem statements is a whole other can of worms, so here’s what I’m going to do: Substack just debuted a “thread” feature. Let’s take it for a test drive. I’ll follow up with a thread for anyone interested to either pose questions or share some of their own effective tactics for great customer discovery. If it seems like an itch worth scratching, I’ll synthesize and edit it into a follow up post within the next couple weeks. 

Need some good links?

AltSchool closing down - on the one hand, it was an ambitious approach to ecosystem building. On the other hand, they never really had the education & learning expertise that they needed, instead building what I would call the surveillance school model of collecting and analyzing troves of data. They aren’t going away entirely, but with this move they are becoming more of a pure educational software company while jettisoning their physical schools.

Interviewing for Empathy - you can never go wrong with the Stanford for this stuff. This handy one pager gives a quick conceptual overview and provides some very practical tips. 

A bit more on gamification...

It’s been a few weeks. Since last you heard from me the ALX Xcelerator graduated its first class, and ALU Mauritius did the same. The latter was a long time coming and a feat that occasioned a solid week of celebrations.

A great question from my friend Jorian regarding Buzzwords That Won’t Die: Gamification

Can everything be gamified?

I love this question, and I think the answer goes back to the question of interest posed by Dewey. Some things don’t need to be gamified - the level of inherent interest is already high enough (think about some major scientific breakthroughs, and a lot of scholarly work in general - people don’t need a game element to stimulate interest); some things don’t need to be gamified because the existing reward system attached to them is already strong enough inducement (this is basically the entire financial system, but also a lot of things where there could be prestige or recognition associated). In both of those cases, people will do things that are difficult and possibly even mundane because there’s some greater goal that they already connect to.

The class of things I think you’re asking about are things that may be difficult or tedious or both. In those cases, I would say that gamification can be a short term bridge from an initial spark of interest to achieving a level of competence, but it won’t necessarily be sustained. There has to be some initial level of interest, though, regardless of why that interest exists in the first place. One of the great examples of this that I remember was a game that was developed to teach safety standards to train operators - they created a story-based game that was about a terrorist attack on a train, and the only way to stop it and regain control of the train was through following certain safety standards. The game itself was basically just a repetition of this structure:

•  narrative, leading to

•  Task-based challenge, leading to  

•  pretty straightforward information consumption (like, read some text on a screen), leading to 

•  decision-based gameplay applying the information just consumed, leading to

•  Advancement of the narrative

I think of that as good gamification - it draws on the fact that these people are already interested in this topic because it’s necessary for their job, but learning about safety is tedious, so they appeal to the existing interest and make it more interesting in order to stimulate learning.

But games won’t always be the best way to stimulate existing interest - I would see something like Strava as a good example. It seems like one of the least “gamified” fitness apps, built what it appeals to instead is social connection. (Note: I don’t use Strava...this is based entirely on my interactions with Strava users showing me their routes and the responses they received from other people)

So, long story short, I guess the answer is: everything probably can’t be gamified, but everything can probably be made more fun - at least for a short period of time (and that period of time is directly related to some combination of how strong the initial interest is and how much the intervention stimulates further interest). I don’t think there’s necessarily an easy heuristic by which to figure out what that is, aside from good old understanding the end user. 

•  While we’re here, Mena sent me this article about gamification for civic initiatives. It seems like a lot of good examples of attempts to make difficult things more accessible through gaming. It also includes this gem, “ shoe store Zappos and hotel giant Marriott are among the companies to have learned to their cost that designing a game that is both fun to play and promotes a beneficial outcome can be devilishly difficult.” You don’t say...

•  If you want to go a bit deeper on this, check out Institute of Play, and if you really want to geek out a bit then see how some good gamification practices are being applied at Quest 2 Learn - a game-based learning school in NYC. Side note: since I first drafted this IoP has announced that they’re shutting down, but the resources they’ve developed over the years are still great (and I’m happy that they’ll live on through the Connected Learning Initiative at UC Irvine).

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