The Beautiful Mess
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New and Past Playbooks (Links)
With a lot of new readers, I wanted to make sure folks knew about some of my longer-form writing efforts, playbooks, etc.
3 hrs ago
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John Cutler
12
TBM 386: Understanding Enabling Constraints Using Shape Up (Basecamp)
After reviewing dozens (hundreds?) of operating systems in depth, I’m becoming increasingly convinced that the thoughtful design and deployment of…
Nov 3
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John Cutler
26
2
October 2025
TBM 385: "We Have To Simplify!"
“We have to simplify!
Oct 24
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John Cutler
61
6
TBM 384: Prioritization Starts With Strategic Prioritization
Enduring, differentiated advantages counter downward pressure. A powerful power (lol) resists decay and compounds future advantage. A feature that…
Oct 21
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John Cutler
70
2
TBM 383: Maximizers vs. Focusers
Many leaders (and successful entrepreneurs) are what I call “maximizers”. The quotes above come from “focusers”. Maximizers and focusers have a hard…
Oct 10
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John Cutler
102
7
TBM 382: Product-Centricity When You Don't Sell A Digital Product
I have been thinking a lot about the struggles of non-digital-product-selling companies when it comes to adopting more product-centric ways of working.
Oct 8
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John Cutler
38
5
September 2025
TBM 381: Stop Trying To Make Prioritization "Easy"
Hot take: We want prioritization to be hard.
Sep 30
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John Cutler
83
5
TBM 380: “But We Have To Try Something!”
You’ve likely heard the saying “The definition of insanity is doing the same thing, and expecting different results.” Humans have an intuitive sense of…
Sep 28
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John Cutler
54
4
TBM 379: Vertical vs. Horizontal Org Coupling
Sharing a 2x2 I’ve found useful lately (and wrong, of course).
Sep 19
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John Cutler
39
3
TBM 378: How To Effectively Pitch Constraints
One of my biggest personal career challenges has been advocating for the smart use of constraints. I strongly believe in concepts such as…
Sep 12
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John Cutler
31
2
TBM 377: Time Allocation ≠ Capacity Allocation
Spoiler: the concept of capacity allocation is fraught with misunderstanding, and companies waste a lot of money (and do a lot of damage) by mistaking…
Sep 5
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John Cutler
69
2
TBM 376: Why Are We Organized Like This?
This post is about understanding why your company is organized and designed the way it is.
Sep 2
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John Cutler
45
7
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