Hard Thing About Hard Things

Q: What is a Claude Code skill and how does the Hard Thing About Hard Things skill fit in?

A Claude Code skill is a SKILL.md file that lives under ~/.claude/skills/<name>/ and tells the Claude Code CLI agent how to perform a specific task (instructions, prompts, allowed tools). Skills are auto-discovered at session start. Hard Thing About Hard Things is one of 67,000+ skills indexed in the open ClaudSkills catalog, classified under the Security category. Learn more at https://claudskills.com/learn/what-is-skill-md/.

Category: Security · Sub-category: security-misc · Last updated: 2026-08-04

Applies Ben Horowitz's "The Hard Thing About Hard Things" framework (The Struggle, wartime vs. peacetime CEO, no-easy-answers decision making, the Law of Crappy People, hiring for strength vs. lack of weakness, taking care of people/products/profits in order, managing your own psychology, firing/demoting fast but respectfully, good vs. bad process, organizational debt) to hard leadership, CEO, hiring, firing, layoff, org-design, or crisis-decision problems. Use whenever the user wants a "hard thing about hard things approach," mentions "The Struggle," "wartime CEO," "peacetime CEO," "Law of Crappy People," "organizational debt," or is wrestling with a decision that has no good options, a layoff, a firing, a demotion, or how to keep functioning while a company/team is under real stress — even if they don't name the book.

Security AStatic scan found no risk patternsHow grading works ›

From the source SKILL.md

Apply this skill to CEO/leadership problems that don't have a clean textbook answer — Horowitz's core claim is that most management books cover how to do things right, but the hard part of running a company is what to do when there's no good option, only less-bad ones.

What this skill does

Hard Thing About Hard Things is a community-contributed Claude Code skill in the security-misc sub-category. It ships as a SKILL.md file that Claude Code auto-discovers under ~/.claude/skills/hard-thing-about-hard-things/ and loads when your prompt matches the skill's trigger.

When to invoke it: Use whenever the user wants a "hard thing about hard things approach," mentions "The Struggle," "wartime CEO," "peacetime CEO," "Law of Crappy People," "organizational debt," or is wrestling with a decision that has no good options, a layoff, a firing, a demotion, or how to keep functioning while a company/team is under real stress — even if they don't name the book.

Who uses this skill

The Hard Thing About Hard Things Claude Code skill is built for security engineers, penetration testers, DevSecOps practitioners, and development teams hardening codebases and infrastructure. It's part of ClaudSkills (also referred to as Claude Skills or Claude Code Skills) — the open community-curated registry of 176,000+ SKILL.md files for Anthropic's Claude Code agent and the wider Claude ecosystem (Claude API, Claude Agent SDK).

How to install

Free

Manual install (2 steps)

mkdir -p ~/.claude/skills/hard-thing-about-hard-things
curl -L https://claudskills.com/skills/hard-thing-about-hard-things/SKILL.md \
  -o ~/.claude/skills/hard-thing-about-hard-things/SKILL.md

Or just download SKILL.md directly and drop it into ~/.claude/skills/hard-thing-about-hard-things/. Claude Code auto-discovers it on next session.

Skills live at ~/.claude/skills/hard-thing-about-hard-things/SKILL.md on macOS/Linux, or %USERPROFILE%\.claude\skills\hard-thing-about-hard-things\SKILL.md on Windows. See the full install guide for step-by-step instructions.

📱 Install from your phone or desktop Telegram

Open @claudskills_bot on Telegram, tap Open Desktop App, and the desktop app installs this skill for you. Or share the bot link with a colleague — they get the same one-tap install. Learn more →

Pro

One-click install via the desktop app

The ClaudSkills desktop app installs any skill directly into ~/.claude/skills/ with one click — no terminal required. Pro starts at $9/mo or $149 lifetime.

Pro

For the full experience including quality scoring and one-click install features for each skill — upgrade to Pro.

See pricing → Download desktop app

Frequently asked questions

How do I install the Hard Thing About Hard Things Claude Code skill?

Install via the ClaudSkills desktop app (one click) or copy SKILL.md from the source repository to ~/.claude/skills/hard-thing-about-hard-things/SKILL.md and restart Claude Code. Both flows are detailed at claudskills.com/install/.

What does the Hard Thing About Hard Things skill do?

Is this skill free to install?

Yes. ClaudSkills is an open registry — every skill keeps its source repository's license, and manual install via copy is free. ClaudSkills Pro ($9/mo, $79/yr, or $149 one-time) adds one-click install via the desktop app and a multi-signal Quality Score.

When should I use the Hard Thing About Hard Things skill?

Use Hard Thing About Hard Things when your Claude Code task falls under the Security category — specifically in the security misc area. Claude Code auto-discovers installed skills and invokes the right one based on the task description, so you can also ask Claude directly (e.g. "use Hard Thing About Hard Things" or describe the task and let Claude pick). Browse related skills at /category/security/.

What is a Claude Code skill and how does the Hard Thing About Hard Things skill fit in?

A Claude Code skill is a SKILL.md file that lives under ~/.claude/skills/<name>/ and tells the Claude Code CLI agent how to perform a specific task (instructions, prompts, allowed tools). Skills are auto-discovered at session start. Hard Thing About Hard Things is one of 67,000+ skills indexed in the open ClaudSkills catalog, classified under the Security category. Learn more at /learn/what-is-a-claude-skill/.

Attribution & license

Source: https://github.com/DamiMartinez/book-skills/blob/HEAD/skills/hard-thing-about-hard-things/SKILL.md
License: MIT
Author: DamiMartinez

Cite this skill

If you reference this skill in a blog post, paper, or documentation, you can cite it as:

APA

DamiMartinez. (2026). Hard Thing About Hard Things [Claude Code skill]. ClaudSkills. https://claudskills.com/skills/hard-thing-about-hard-things/

BibTeX

@misc{hard-thing-about-hard-things-2026,
  author    = {DamiMartinez},
  title     = {Hard Thing About Hard Things [Claude Code skill]},
  year      = {2026},
  publisher = {ClaudSkills},
  url       = {https://claudskills.com/skills/hard-thing-about-hard-things/}
}

Embed this skill

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Badge

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Security scan

Grade A · scanned 2026-08-04 — free static scan against the OWASP Agentic Skills Top 10.

No risk patterns were found in any of the ten OWASP-aligned categories. How grading works ›

✓ Prompt injection
✓ Data exfiltration
✓ Supply chain
✓ Reverse shell
✓ Credentials
✓ Execution
✓ Filesystem
✓ Persistence
✓ Obfuscation
✓ Network

Show this grade on your repo (click to copy):

[![Security: A](https://img.shields.io/badge/Security-A-2e7d32)](https://claudskills.com/skills/hard-thing-about-hard-things/#security)

More Security skills

Browse all Security skills in the ClaudSkills registry, or explore these other picks from the same category:

Browse all Security skills → Top 100 skills

Part of ClaudSkills — the open registry for Claude Skills & Claude Code Skills. · What's New · Install guide · About · llms.txt

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