Courageous Possibility Questions
Replace defensive what-ifs with questions that expose a path to action.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 95%
Courageous Possibility Questions change the direction of attention without pretending that success is guaranteed. When the mind asks what happens if an effort fails or how others might judge it, deliberately ask what happens if it works. Then move beyond positive thinking by identifying what would need to happen, who you would need to become, what you would need to create or request, and what must be released. These answers convert possibility into requirements and expose the next action. The framework also allows for flexible timing: the desired result may take longer than expected while remaining possible. Its mechanism is attentional and behavioral—questions open a broader search space, while concrete commitments prevent the exercise from becoming fantasy. Use alongside realistic risk controls when the decision has significant downside.
Origin
Lewis Howes introduced these questions while discussing the “courageous questions” section of his book. Extracted from The Jasmine Star Show.
Core principles
- 01The questions you ask direct attention and imagination.
- 02Possibility questions reveal requirements rather than rehearse humiliation.
- 03Identity and action must both change to produce a new result.
- 04Optimism is useful when translated into concrete requirements.
How to run it
- 1
Capture the fearful question
Write the exact what-if statement driving hesitation. Identify whether it centers on failure, judgment, rejection, or another feared consequence.
Pro tip Use the words that actually recur in your mind rather than sanitizing them.
Watch out Do not treat a legitimate risk as imaginary merely because it is uncomfortable.
- 2
Reverse the possibility
Ask what becomes possible if the desired effort works. Hold the best plausible case in view long enough to examine it seriously.
Pro tip Describe a concrete outcome rather than saying only that things will be better.
Watch out This is an exploration of possibility, not a prediction or guarantee.
- 3
Identify the required identity
Ask who you would need to be to pursue that possibility. Name the qualities and behaviors the outcome demands.
Pro tip Connect the answer to a believable personal identity contract.
Watch out Avoid describing only external resources while ignoring your own behavior.
- 4
Map the requirements
List what you need to create, do, learn, request, or release. Convert each answer into an observable requirement.
Pro tip Include people you need to approach and uncomfortable requests you need to make.
Watch out A long requirements list can become another form of avoidance if it lacks priorities.
- 5
Take the next courageous action
Choose the smallest meaningful step that tests the possibility. Act while allowing the final result and timeline to remain uncertain.
Pro tip Prefer an action that produces feedback within days.
Watch out Do not wait for certainty before completing a reversible, appropriately bounded test.
In the wild
A consultant worries that launching a premium service will fail and damage her reputation. She asks what would need to happen for it to work, identifies the need for stronger proof and clearer positioning, interviews five ideal clients, and pilots the service with two existing customers.
→ The fearful abstraction becomes a bounded experiment with specific learning goals.
Common mistakes
Stopping at positive thinking
“What if it works?” is only the opening. The value comes from mapping what the possibility requires and acting on it.
Ignoring genuine downside
Possibility thinking should complement, not erase, safeguards for meaningful financial, legal, or safety risks.
Demanding your preferred timeline
An outcome can remain viable even when it takes longer than expected. Rigid timing can turn useful persistence into perceived failure.
Is it for you?
Best for
It is best for people immobilized by speculative failure, judgment, or uncertainty around a meaningful opportunity.
Not ideal for
It is not ideal as a replacement for risk analysis where safety, solvency, or irreversible consequences demand rigorous downside planning.
From the transcript
“But more so in a world of possibilities, if this could work out, what would I need to create, do, come ask for in order…”
“Maybe it doesn't happen in the timeline I want, but if it had to happen, who would I need to be?”
From the episode
You’re Not Stuck: How to Overcome Your Fears and Rewrite Your Identity with Lewis Howes
Lewis Howes