The End of an Era & an Agenda Going Forward

A Playing to Win/Practitioner Insights Book Club

Source: Roger L. Martin, 2026

It’s the end of an era. On October 5, 2020, I published The Role of Management Systems in Strategy, which I wrote to provide practical advice on how to think about the fifth box in my Strategy Choice Cascade. Every Monday since, I have published a piece and just finished five years of the Playing to Win/Practitioner Insights (PTW/PI) series. I am moving on to something different starting next Monday and I will describe what I plan in this piece called The End of an Era & an Agenda Going Forward: A Playing to Win/Practitioner Insights Book Club. As always, you can find all the previous PTW/PI here.

The Era

I would have never imagined when I posted my first piece that it would become a series, let alone one so lengthy. It has ended up being more than five years (5 years and 4 months) because I have published a number of year-end summaries (like last week’s), best-of lists, and reflections on the series (like this one) in addition to the 260 original pieces, averaging a little over 1800 words/piece for a total of 470 thousand words.

To put that in perspective, Playing to Win, my 2013 book with AG Lafley and the inspiration for the series, is 67 thousand words (of content, not including index, endnotes, and foreword). That means PTW/PI is equivalent to (just over) seven Playing to Win’s. That is, I have written seven books-worth of strategy in just over five years.

I think this is unprecedented. I don’t think any business author has published just under half a million words in five years. And certainly not for free — yes Medium is $50/year for the platform, but PTW/PI is republished on my free website and now on Substack (free subscription).

I do get questions such as: Roger, who is writing all this stuff? Do you have a group of writers that produce content for you? Is this AI generated? Nope. I wrote and edited 254 of the 260 entirely by myself. The other six are my co-authored pieces. But for each of those six, I was as much of a writer as my terrific co-authors. Unlike many ‘authors’ out there today, I write my own stuff.

To put the magnitude in context, Peter Drucker is unquestionably the greatest management thinker of all time. One reason is that he was both bold and brilliant. He created rather than followed. I will be eternally grateful that he was a vocal supporter of my work in his later years. But another reason for his prominence is sheer volume. Peter wrote a stunningly huge amount— 39 books and 1500 articles, including 39 Harvard Business Review (HBR) articles — the most in the history of the magazine. My estimate is that he published four million words — extraordinary.

It makes me exceedingly happy when knowledgeable people like longtime former HBR editor-in-chief Adi Ignatius refer to me as the 21st century Peter Drucker. Adi (I miss him already!) may have a somewhat HBR-centric view. I published 27 of my 34 HBR articles during his time as editor-in-chief, and that total of 34 — all but one of which has been published in the 21st century — is approaching Drucker’s lifetime record of 39 — all but five of which were published in the 20th century. So, from an HBR standpoint, I was Adi’s 21st century Drucker.

I will be very lucky to be publishing HBR articles when I am 96 (his last HBR article was published in early 2006, a few months after his death at age 95). But I am on a good pace. My 34 total is the most HBR articles ever prior to age 70 (coming up in August 2026 for me) — compared to leading HBR writers such as Michael Porter (26), Clay Christensen (21, before his untimely death at age 67) and Drucker (22).

I am far behind Peter in total words published. I estimate my total thus far at 1.6 million words — from 12 books (my 13thwas an edited volume), 350 articles, and the PTW/PI series. While it is less than half of Peter’s monumental total, I believe that it is more than any other business writer.

Of course, it certainly isn’t all about volume. It is about reach and impact. Happily, Playing to Win has enjoyed lots of both, as have other of my best-sellers. For example, The Design of Business is the second most cited publication in design thinking. In terms of articles, Social Entrepreneurship: The Case for Definition is the most downloaded article in the history of The Stanford Social Innovation Review, and numerous of my HBR articles are included in various HBR Must Reads on ‘x’ compilation books.

But with respect to the PTW/PI era specifically, the series has garnered 3 million views, 1.1 million reads, and 150 thousand claps. The Medium editors deemed 43 of Year V’s 52 pieces to be worthy of a boost. In slightly over five years, my Medium followers have grown from zero to 266 thousand — the fifth most of any writer on the platform (and not terribly far off the #1 at 327 thousand). The growth has been organic. I have done no promotion (paid or otherwise) or search-engine optimization — l just re-post the articles a single time both on LinkedIn and Twitter/X.

I view the era with more than a little bit of pleasure and pride and am thankful for the many avid readers.

Where from Here?

Several months ago, I started a migration from Medium to Substack, during which time I have posted on both platforms. I appreciate my time on Medium and the content up through this piece will continue to be found on Medium. But I have also replicated all 260 original pieces on Substack.

But now that I am cutting over fully to Substack, to continue to receive my content, you need to subscribe — for free — to me at https://rogerlmartin.substack.com.

I am going to shift gears a bit going forward. Creating 1,800 words of new content every week is too much. I have probably spent over 100 days/year on the PTW/PI series over the past five years. Going forward, I will continue to publish every week — readers seem to look forward to receiving a post every Monday morning.

But I will write new pieces more infrequently — only when I feel compelled to speak on a strategy subject — not because I need one for Monday. On the other Mondays, I will reprise my most popular PTW/PI pieces and provide commentary on each. I hope this will help newer readers. One piece of feedback I get is that the volume is massive and new readers have a hard time getting caught up on the old pieces. Hopefully, this will help readers.

I have ranked the 260 original pieces on a combination of views, reads, and claps — again with the help of friend and colleague Darren Karn. Thanks Darren! From that ranking, we have identified the Top 37 in terms of reader feedback. Why 37, you might ask? The 260 original pieces are equivalent to seven Playing to Win books. So, one-seventh of the pieces — 37 of them — is the equivalent of one book.

So, next week I am going to initiate a book club of sorts. I will comment and reflect on one of the 37 pieces that, together, are the equivalent with one book. Plus, I will write 15 entirely new pieces. That is the plan for the next year. I may end up doing more than 15 new pieces and, if so, the exercise will take more than 52 weeks. That is the agenda going forward.

The Top 37 PTW/PI

With respect to the Top 37, I am not going to do a countdown. Statistically, when a sample is way out on the tail of the distribution, it is not clear that an exact ranking adds much value. Instead, I used a randomizer on the Top 37 and will present them in the random order that it produced. I will, however, identify the Top 3 because their rankings are distinctly higher than the other 34.

Looked at collectively, there are five types of pieces that made it into the Top 37, with three types making up 80%.

1) Practical advice on an element of the Strategy Choice Cascade (SCC) or Strategic Choice Structuring Process (SCSP) (14)

This is the biggest category of highly ranked pieces, and they are all elaborations of a box of either the SCC or SCSP. In these pieces, I explain and give examples of how that box works in practice. Examples include The Role of Management Systems in Strategy about the fifth box of the SCC and What Would Have to be True? about the third box of the SCSP.

2) Help on understanding the context for strategy (11)

This second largest category provides advice to the reader on how to think about strategy in general — i.e. helps define the context for strategy. Examples include Strategy vs. Planning: Complements not Substitutes, which helps distinguish strategy from planning, and What is Strategic Thinking?, which helps the reader understand the characteristics and components of strategic thinking.

3) Screeds! (7)

This third large category — getting us to over 80% of the Top 37 — is what I fancifully call screeds. This is when I tee off on a subject because I believe the prevailing dominant theory is flawed and bad for the practice of strategy. Examples include Stop Letting OKRs Masquerade for Strategy and The Strategy Lesson from the Bud Light Fiasco. They are among my most fun to write and I am pleased that seven of them made the Top 37.

4) Personal development in the domain of strategy (3)

The first of the two small categories provides personal development advice in the domain of strategy. Examples include Being ‘Too Busy’ Means Your Personal Strategy Sucks, which advises on using the SCC to become more effective in your own personal work, and What Makes for a Great Strategist?, which describes how to develop your personal skills as a strategist.

5) Relationship between other books and Playing to Win (2)

The other small category is comprised of pieces that describe the relationship between Playing to Win and another popular business book. I did ten of these in the series, all in response to requests from readers who wanted to know my views on a particular book — to what extent is it consistent with or in conflict with Playing to Win? Two of those pieces made the Top 37, Good Strategy/Bad Strategy & Playing to Win and Business Model Generation & Playing to Win.

Concluding Thoughts

I am simultaneously gratified and wistful.

I am gratified that the series has helped me get out of my head and onto paper nearly half a million words on the practice of strategy. Many of those thoughts would otherwise expire with me because I hadn’t ever written them down or had anybody else. Over and over, I was amazed that a client or reader question caused me to dredge out of the recesses of my mind things that only existed there. And I wouldn’t have realized that they were in there if I hadn’t been spurred to recall my thinking on the subject in question. I would never have imagined that, in addition to the million-plus words that I had previously written, there were half a million more words in there. But there were — and I am glad that body of knowledge is now available for everyone.

At the same time, I am somewhat wistful that I am getting off the steady drumbeat of a new post every week. It has been a good forcing mechanism. But it has been just too much. So, I will work to achieve a sustainable cadence.

But right now, I would ask all readers on Medium (who haven’t already) to subscribe to my Substack to continue receiving my posts — here at https://rogerlmartin.substack.com.

For those of you who don’t — goodbye and be well. For those of you who have or will — I look forward to continuing with you on Substack.