Step 03 of 07 · Pain · free

Pain Discovery Worksheet

Fall in love with the problem, not the solution. Most failed startups didn't fail because the team couldn't build — they failed because they built something nobody actually needed badly enough to switch.

Instructions: First name your beachhead — the narrow market, and the one person inside it. Then list the pains you are weighing. Score each one: how often it hits, how badly, how many real conversations you have had about it, and what would prove it is not worth solving. Read the verdict at the end, and save the worksheet as a PDF. Remember — score ranks your pains, but conversations decide which one is real.

Already mid-flight? You can run this compass on its own — it doesn't need the earlier stages first. To follow the full sequence, start at Purpose.

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The discipline

Score = Frequency × Severity. Validation = conversations had.

  • Frequency — how often the pain hits. Daily (5) → Weekly (4) → Monthly (3) → Quarterly (2) → Yearly (1).
  • Severity — how bad when it does. Blocker (5) → Major (4) → Annoying (3) → Minor (2) → Trivial (1).
  • Conversations— how many real users have described this pain to you in their own words. Zero = it's your guess, not a customer's.
  • Disconfirmation— what would prove the pain isn't worth solving? Written down so you can't pretend you didn't see it.
1Beachhead2Score the pains3Your read
1

Define your beachhead

Before scoring any pain, name the narrow market you're actually serving and the specific person inside it. Pains scored against “everyone” are unfalsifiable. (Borrowed from Bill Aulet's Disciplined Entrepreneurship — the beachhead discipline.)

Where to listen

Primary — the only thing that counts as a Conversation.

One-to-one with a real person in your beachhead. The Mom-Test discipline: ask about their past behavior, not their future intentions. After every conversation, write down a verbatim quote — if you can't, you have your paraphrase, not their words. Aim for 10–20 conversations before treating any pain as “Validated.”

Secondary — where founders find what to listen for.

Use these to discover the pain language your beachhead persona actually uses, and to find people to interview. Read posts and comments where they're already complaining out loud:

  • Reddit — find subreddits your persona lives in (r/Entrepreneur, r/SaaS, r/IndieHackers, plus the domain-specific ones). Search “[problem keyword] sucks” or “why does [tool] always”.
  • Indie Hackers + Hacker News — read “Show HN” comments and “Ask HN” threads in your space.
  • Twitter / X founder threads — search for the persona's job title plus “hate” / “wish” / “why doesn't”.
  • Substack & newsletter comments — long-form audiences leave detailed grievances under posts.
  • Industry forums & LinkedIn comments — domain-specific (e.g. legaltech, dev tools, etc.) — where practitioners vent about workflow.
  • Founder communities & Slack groups — if you're building for founders, search for channels where they vent about workflow, fundraising, hiring, or product decisions. The complaints are the pain catalog.
2

Score the pains

#1

Score

16

Validation

Suggestive
#2

Score

12

Validation

Speculative
3

Your pain read

Almost — keep listening.

“Founders waste hours each week guessing what to build next.” scores highest, and you have some real conversations behind it. That makes it suggestive, not yet validated.

Aim for 10+ conversations in your beachhead before this earns serious build time.

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Your turn

Rate the Pain compass