Stakes and Worst-Case Check
Name what matters and expose the fear beneath a high-stakes decision
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 5
- Confidence
- 96%
Begin by stating the decision or event without defending your preferred outcome. Ask what is genuinely at stake, then distinguish tangible consequences from embarrassment, ego, or imagined judgment. Next, describe the worst thing that could happen and keep probing if the first answer feels superficial. The useful insight often appears beneath the obvious fear: Jasmine initially considered public failure, but discovered that her deeper concern was learning she did not want the business she had planned to build. Giving that possibility explicit language reduces its emotional control. The output is not an automatic yes or no; it is a clearer account of the real risk, which enables a more deliberate response.
Origin
Extracted from The Jasmine Star Show during Jasmine Star's preparation for a recorded conversation with Gary Vaynerchuk.
Core principles
- 01Unspoken fears gain power
- 02The first fear named may hide a deeper concern
- 03Separating ego from consequences improves judgment
- 04Accepting a possible outcome makes honest action easier
How to run it
- 1
State the decision
Describe the upcoming choice, conversation, or commitment in neutral terms. Avoid beginning with a defense of what you already want to do.
Pro tip Write the decision as a single sentence.
Watch out A vague decision produces vague fears.
- 2
Ask what is at stake
List what could be gained, lost, exposed, or changed. Include both practical consequences and emotional concerns.
Pro tip Notice whether embarrassment or identity appears alongside business risk.
Watch out Do not dismiss ego-related concerns before naming them.
- 3
Name the worst outcome
Describe the most difficult plausible result rather than a dramatic but unlikely catastrophe. Say what that outcome would force you to acknowledge or change.
Pro tip Ask what would be painful even if nobody else knew about it.
Watch out The first answer may be socially acceptable rather than true.
- 4
Find the deeper fear
Probe beneath reputation and performance until the concern explains why the decision feels charged. Distinguish fear of failure from fear of discovering that you want something different.
Pro tip Complete the sentence: “If that happened, I would have to admit…”
Watch out Do not outsource this interpretation to an adviser.
- 5
Accept the terms
Acknowledge that the feared outcome is possible and decide whether you can proceed without changing your behavior merely to avoid it. Use the clarity to enter the situation ready to listen.
Pro tip Treat acceptance as preparation, not pessimism.
Watch out Acceptance does not mean the outcome is inevitable.
In the wild
A founder plans to ask an experienced operator whether her holding-company vision is realistic. She initially says the risk is public embarrassment if the plan fails. After applying the two questions, she realizes the deeper fear is hearing credible evidence that she does not want the company’s actual costs and must reconsider what to build.
→ She enters the conversation prepared to receive information rather than perform confidence.
A team lead fears that abandoning a stalled product will make the previous year look wasted. The check reveals that the deeper concern is losing the identity and status attached to leading the initiative. Naming that distinction lets the team evaluate customer evidence separately from personal pride.
→ The pivot decision becomes evidence-led rather than identity-protective.
Common mistakes
Stopping at embarrassment
Public failure may be the easiest fear to name while a more consequential private truth remains hidden.
Treating the worst case as destiny
The exercise surfaces a possibility so it can be evaluated; it does not predict that the possibility will occur.
Using an adviser as the decision maker
External input can provide an indication, but the owner must interpret the cost and make the decision.
Is it for you?
Best for
It is best for founders and leaders preparing for high-stakes conversations, pivots, or public commitments.
Not ideal for
It is not ideal for routine choices with limited consequences or decisions requiring primarily technical analysis.
From the transcript
“And the question is, she wanted me to ask was, number one, what's at stake? Number two, what's the worst thing that can happen?”
“And that's one of those things that if you give it air, it loses all its power.”
“And it feels good because I've identified it. Yeah, and then I accept the terms of it.”
From the episode
Eavesdrop on a Private Call with Me and My Business Mentor