Embrace the Grind — Jacob Kaplan-Moss

Summary

Kaplan-Moss (co-creator of Django) argues that willingness to do tedious, unglamorous work is a genuine superpower. The core mental model:

1. Tedium as competitive moat. The magic trick analogy: a magician hides a playing card inside every single tea packet in a store — hundreds of packets, hours of painstaking work — just for one trick. The “trick” works because no reasonable person would imagine someone doing something so boring for such a small effect. The same dynamic applies to software, business, and career: the work that seems impossibly tedious to others becomes your unfair advantage when you’re willing to do it.

2. “I merely did something so boring that nobody else had been willing to do it.” This reframes “impossible” achievements. They’re not impossible because of technical difficulty — they’re impossible because the effort required is mind-numbing and everyone assumes there must be a shortcut. There isn’t. The shortcut IS the willingness to grind.

3. Automate and Elevate (not “laziness”). Larry Wall’s “virtue of laziness” for programmers gets reframed: the goal isn’t to avoid work, it’s to invest effort in reducing future effort. Build the labor-saving program, write the documentation, create the system. But sometimes the system IS the grind — there’s no further automation possible, and the only path forward is doing the boring thing hundreds of times.

Relevance

• SOUL.md — This should be a core operating principle. The AI COO’s job often IS the grind: processing inbox items, updating indexes, running health checks, doing the tedious maintenance that keeps the system running. The willingness to do this consistently, without drama, is the moat.
• 01-projects/phdata/career-transition — Career differentiation often comes from the grind that others won’t do: writing detailed documentation, building comprehensive test suites, doing the migration nobody wants to touch. These are the “magic tricks” that build reputation.
• 06-reference/2026-04-03-the-e-myth-revisited — The franchise prototype IS the grind. Documenting every process, creating every checklist, systematizing every workflow — this is tedious work that most founders skip. The ones who embrace it build businesses that scale.
• 06-reference/2026-04-03-company-of-one — The solo operator’s competitive advantage is often the willingness to do things that don’t scale, thoroughly and consistently. The grind is not at odds with the “enough” philosophy — it’s how you earn “enough” reliably.
• 06-reference/2026-04-03-part-time-creator-manifesto — The part-time creator who publishes every week, regardless of inspiration, is embracing the grind. Consistency over brilliance. The compound effect of tedious consistency creates what looks like magic to outside observers.
• 06-reference/2026-04-03-ladders-of-wealth-creation — Every ladder transition has a grind phase where the glamour fades and the real work begins. The people who reach the next rung are the ones who didn’t quit during the boring middle.
• 06-reference/2026-04-03-the-art-of-learning — Waitzkin’s “Making Smaller Circles” is the grind applied to skill acquisition. Practicing one move 10,000 times IS embracing the grind.

Open Questions

• Where is the grind being avoided right now? What tedious-but-valuable work is being deferred because it’s not exciting?
• The “automate & elevate” note in the original highlights is key: before embracing the grind, always check if the grind can be automated. But if it can’t, don’t let that stop you.
• What would it look like to make “embrace the grind” an explicit value? Not just tolerating tedium, but actively seeking out the boring work that others avoid as a strategic advantage.