Side Project Evaluator
Pressure-test your side project idea before investing time you don't have.
Side projects fail for predictable reasons: no clear customer, no sustainable motivation, and scope that grows until it collapses. This workflow helps you evaluate your idea honestly and design it for the reality of part-time work.
The Workflow
Describe the idea clearly
State what the project is, who it's for, and what problem it solves in plain language. If you can't do this, the idea needs more development first.
Run the evaluation
AI stress-tests your assumptions before you spend six months on something that won't work.
Pressure-test my side project idea. Project description: [PROJECT_DESCRIPTION] Target customer: [TARGET_CUSTOMER] Problem it solves: [PROBLEM_SOLVED] How I plan to make money (or if not, what the goal is): [REVENUE_MODEL] Competitive alternatives my customer could use instead: [ALTERNATIVES] Time I can realistically commit: [WEEKLY_HOURS] hours per week My relevant skills: [MY_SKILLS] Skills I'd need to develop or hire: [SKILLS_GAPS] Timeline to first version: [TIMELINE] Please assess: 1. The three biggest risks to this project succeeding 2. The core assumption I haven't validated that, if wrong, makes everything else moot 3. A simpler version that could prove the concept in 30 days 4. One thing about this market I might not know that's worth researching first 5. An honest gut check: does this have a clear path to being worth the time I'd put in?
Replace: [PROJECT_DESCRIPTION], [TARGET_CUSTOMER], [PROBLEM_SOLVED], [REVENUE_MODEL], [ALTERNATIVES], [WEEKLY_HOURS], [MY_SKILLS], [SKILLS_GAPS], [TIMELINE]
Build a 30-day start plan
If the project passes evaluation, create a first-30-days action plan that respects your time constraints.
Build a first 30-day action plan for my side project: [PROJECT_NAME] My available time: [WEEKLY_HOURS] hours per week, usually [PREFERRED_WORK_TIME] My starting point: [WHAT_I_HAVE_NOW] The core assumption I need to test first: [CORE_ASSUMPTION] Create a day-by-day or week-by-week plan that: 1. Validates the core assumption before building anything 2. Produces something real and shareable by day 30 3. Fits in my actual available hours 4. Has a clear stop/continue decision point at day 30 Week 1 should include talking to at least [NUMBER] potential customers before writing a single line of code or creating any deliverables.
Replace: [PROJECT_NAME], [WEEKLY_HOURS], [PREFERRED_WORK_TIME], [WHAT_I_HAVE_NOW], [CORE_ASSUMPTION], [NUMBER]
All Prompts for This Workflow
Pressure-test my side project idea. Description: [PROJECT_DESCRIPTION] Target customer: [TARGET_CUSTOMER] Problem solved: [PROBLEM_SOLVED] Revenue model: [REVENUE_MODEL] Alternatives: [ALTERNATIVES] Time available: [WEEKLY_HOURS] hours/week My skills: [MY_SKILLS] Skills gaps: [SKILLS_GAPS] Tell me: the three biggest risks, the unvalidated assumption that could kill it, a 30-day proof-of-concept version, what I should research first, and an honest assessment of whether the time investment is worth it.
Replace: [PROJECT_DESCRIPTION], [TARGET_CUSTOMER], [PROBLEM_SOLVED], [REVENUE_MODEL], [ALTERNATIVES], [WEEKLY_HOURS], [MY_SKILLS], [SKILLS_GAPS]
Write a customer validation script I can use to interview [NUMBER] potential customers about [PROJECT_IDEA]. My core assumption: [CORE_ASSUMPTION] What I need to learn: [LEARNING_GOALS] How I'll find people to talk to: [CUSTOMER_CHANNEL] Generate: 1. An email or DM I can send to request a 20-minute call 2. Five interview questions that test my assumption without leading the witness 3. Three follow-up questions for answers that reveal something interesting 4. What a "successful" validation looks like vs. a signal to pivot The script should sound conversational, not like a survey. And remind me: don't pitch the product during validation calls.
Replace: [NUMBER], [PROJECT_IDEA], [CORE_ASSUMPTION], [LEARNING_GOALS], [CUSTOMER_CHANNEL]
An honest assessment of your side project's three biggest risks, the unvalidated core assumption, a simplified 30-day proof-of-concept, and a go/no-go recommendation based on your stated time constraints.
- →The simplest version of your idea that proves the concept is almost always the right place to start. Ask AI to help you cut your idea in half.
- →Talk to 5 real potential customers before building anything. This single step eliminates most side project failures.