Unconventional Thinking Practice
Question inherited assumptions and test distinctive ways to create value.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 5
- Confidence
- 99%
Unconventional thinking is a repeatable practice for finding options that inherited industry assumptions conceal. The entrepreneur begins by releasing attachment to how a product, service, or business model has traditionally worked. Specific what-if questions then generate alternative revenue streams, offers, partnerships, or delivery methods. One promising option becomes a bounded experiment whose result is treated as information rather than a verdict on the entrepreneur. Because unusual ideas often fail, the owner analyzes what worked and what did not and uses those lessons to strengthen the next attempt. Constraints are inputs to creativity: they force the business to adapt, differentiate, and create value in ways competitors may overlook. The aim is useful originality, not novelty for its own sake.
Origin
Extracted from The Jasmine Star Show, where Jasmine Star framed unconventional thinking as an underrated strength for innovation, differentiation, adaptation, and business growth.
Core principles
- 01Established methods should remain open to challenge.
- 02Constraints can force valuable new solutions.
- 03What-if questions expand the available option set.
- 04Unconventional experiments are expected to fail sometimes.
- 05Every experiment should inform the next approach.
- 06Distinctive solutions help businesses adapt and stand out.
How to run it
- 1
Release inherited assumptions
Identify rules, formats, offers, or business models you maintain mainly because they are customary. Give yourself permission to reconsider them.
Pro tip Write the phrase “We have always…” and list every assumption that follows.
Watch out Do not discard a practice before understanding the purpose it currently serves.
- 2
Ask what-if questions
Generate concrete alternative conditions, such as earning the target revenue in one day, teaching customers, serving a narrow niche, or using a different funding model. Let the questions widen the solution space before evaluating feasibility.
Pro tip Include at least one question about the offer, delivery model, customer, price, and partnership structure.
Watch out Premature evaluation can kill potentially useful ideas before they are developed.
- 3
Choose a bounded experiment
Select an unconventional option that can be tested with limited time, money, and reputational exposure. Define the expected value and learning criteria.
Pro tip Prefer a pilot, presale, workshop, or limited package before a permanent transformation.
Watch out Unconventional does not mean reckless, deceptive, or unmeasured.
- 4
Expect imperfect results
Assume that some new ideas will not work and detach your self-worth from the outcome. Treat the test as a source of information.
Pro tip Predefine which failed outcomes would still produce valuable learning.
Watch out Acceptance of failure should not become an excuse for poor preparation.
- 5
Analyze and refine
Review what worked, what failed, and which assumptions were disproved. Apply that knowledge to strengthen the next unconventional approach.
Pro tip Document the lesson immediately while the evidence and customer feedback are fresh.
Watch out Do not repeat the same experiment unchanged while merely relabeling failure as learning.
In the wild
Instead of selling only a wedding cake, a bakery creates a package spanning cupcakes for the bridal shower, cookies for the bachelorette party, pies for the rehearsal dinner, and desserts for the wedding. It then builds referral relationships with wedding planners and photographers.
→ The bakery reduces decisions for the bride while increasing average order value, exposure, and referral opportunities.
A graphic designer sees low-ticket design work declining as clients adopt Canva and AI. Rather than competing only for shrinking project work, he offers workshops for marketing teams and a monthly subscription containing 30 customizable graphics.
→ The designer creates recurring revenue while helping in-house teams save time and produce more distinctive visuals.
A consultant notices that broad packages are becoming difficult to differentiate. She asks what would happen if one urgent problem for one niche were solved through a short paid pilot, then tests the offer with a small group before changing her core business.
→ The bounded test produces customer evidence and a clearer differentiated offer without requiring an immediate full-scale pivot.
Common mistakes
Pursuing novelty without value
An idea is not useful merely because competitors are not doing it. Connect experimentation to a real customer problem or business constraint.
Remaining attached to one experiment
An unconventional idea can fail even when the broader direction is sound. Analyze the evidence and change the next attempt rather than defending the original concept.
Stopping after an unsuccessful test
One failed idea does not invalidate unconventional thinking. Extract the lesson and use it to improve the next approach.
Is it for you?
Best for
It is best for entrepreneurs facing constraints, commoditization, changing technology, or crowded markets.
Not ideal for
It is not ideal for bypassing proven safety, legal, ethical, or financial controls merely for novelty.
From the transcript
“Number one, let go of how things have always been done.”
“Number two, ask what if questions?”
“Number three, Embrace failure as a learning opportunity.”
From the episode
The Most Underrated Strengths to Have in Business (And How to Develop Them)