Curiosity-Led Side Project Ladder
Turn dissatisfaction into a small experiment, traction, and a new career option
- Difficulty
- Moderate
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 94%
The Curiosity-Led Side Project Ladder begins with dissatisfaction, boredom, or a repeated observation inside ordinary work. Instead of treating that feeling only as a reason to disengage, identify the better method or unmet need that has captured your attention. Build the smallest independent project that tests the idea, expose it to real users, and watch for sustained traction. Commitment rises one rung at a time: curiosity leads to an experiment, the experiment generates evidence, and evidence can justify turning the project into a larger business or career. The Skim example illustrates the ladder: its founders questioned long-form television news, tested a concise inbox format while employed, and later left their jobs once the project had enough momentum.
Origin
Extracted from Marketing Against The Grain through the discussion of The Skim's founders and the broader question of using side projects or side hustles to accelerate a career.
Core principles
- 01A job does not define the limits of what you can learn.
- 02Boredom can signal an overlooked opportunity.
- 03Side projects create low-commitment tests of better approaches.
- 04Traction should precede a major career commitment.
- 05Curiosity can reveal opportunities outside a current vocation.
How to run it
- 1
Reframe dissatisfaction
Identify whether boredom or frustration points to a method, product, or experience that could work better.
Pro tip Write the opportunity as a specific contrast between the current and desired experience.
Watch out Not every unpleasant task represents a market opportunity.
- 2
Confirm genuine curiosity
Check that you are interested enough in the problem to investigate it outside the obligations of your job.
Pro tip Choose a problem you voluntarily keep thinking about.
Watch out A side project driven only by escape may be difficult to sustain.
- 3
Build the smallest test
Create a lightweight version of the better approach without making an irreversible career decision.
Pro tip A newsletter, manual service, or simple prototype can test demand quickly.
Watch out Respect employment agreements, intellectual property, and confidentiality.
- 4
Seek real traction
Put the project in front of potential users and evaluate recurring use, sharing, requests, or revenue.
Pro tip Look for repeated behavior rather than compliments.
Watch out A successful launch day does not establish sustained demand.
- 5
Climb commitment gradually
Invest more time or leave the current role only when evidence and personal circumstances justify the next rung.
Pro tip Set explicit traction and financial thresholds in advance.
Watch out Do not confuse excitement with readiness for a full-time transition.
In the wild
Two NBC associates believed people could consume news more efficiently than through long morning shows or traditional newscasts. They explored the idea through a concise email product while employed and eventually gained enough momentum to pursue it full time.
→ Workplace dissatisfaction became a tested media format and then a standalone business.
An analyst repeatedly sees small companies struggle to interpret a weekly metric. She creates a weekend email explaining that metric for five companies, then expands only after recipients begin referring others and requesting paid support.
→ A constrained side project validates demand before a career change.
Common mistakes
Quitting before testing
Leaving a job before the project demonstrates demand converts a reversible experiment into a high-risk bet.
Building on employer property
Using confidential information, company time, or protected intellectual property can make the project unethical or legally unsafe.
Following boredom without interest
Dissatisfaction can identify a problem, but sustained curiosity is still needed to work through it.
Is it for you?
Best for
It is best for professionals who see an opportunity but need to test it before leaving stable employment.
Not ideal for
It is not ideal for people who cannot ethically separate a side project from employer time, data, or intellectual property.
From the transcript
“It's like what side projects or side hustles can I start to do to accelerate my career.”
“And sometimes the dissatisfaction or boredom of in your role is actually not just boredom, it's an opportunity for you to go and disrupt a…”
“We gave you a ton of examples today of businesses that were started that wasn't what that person was doing for their job or their…”
From the episode
Curiosity is a Billion Dollar Skill