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The Grand Game of Software Engineering

Stories, often even humor, from the dark side of corporate culture.

The Performance Theatre Years

5 min readOct 4, 2025

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A story of Tolstoy sized manuals, Teams pep talks, and own brand teabags.

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“Image generated using OpenAI’s DALL·E.”

There’s a very distinct period of time during the growth of most newly minted companies¹, with perhaps 20 or fewer employees, where they can be a genuinely fun place to work.

I say most here, of course, as we can just immediately dismiss anything to do with cryptocurrency as throwing money on a fire whilst the founders disappear when things go awry, anything SaaS¹ as just copying something else that already exists, and pretty much all “AI” startups as putting a UI on top of an OpenAI API key.

Anyway, you know the kind of thing with these fledglings. Starry-eyed ex-developer founders with hope in their eyes, a distinct lack of MBAs on the payroll, even CTOs that can actually code coherently and know how to use git, lots of developers that get to make real and meaningful decisions and stay late into the night of their own accord, and the complete and utter lack of a coherent management structure and absolutely no HR department at all.

Bliss personified, indeed, with minimal process, a virtually non-existent company manual (a pamphlet at best), and the high likelihood of it cranking out useful solutions to actual problems³.

As a company grows the weeds start to drift in and take root, filling the tiny cracks, expanding…

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The Grand Game of Software Engineering
The Grand Game of Software Engineering

Published in The Grand Game of Software Engineering

Stories, often even humor, from the dark side of corporate culture.

Dr Stuart Woolley
Dr Stuart Woolley

Written by Dr Stuart Woolley

Worries about the future. Way too involved with software. Likes coffee, maths, and . Would prefer to be in academia. SpaceX, X, and Overwatch fan.

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