Challenge Authority, Trust Your Judgment—Skepticism Powers Simplicity and Success
Ken Segall spent years watching how leaders at Apple and other major companies handled setbacks and gatekeepers. Time after time, he saw projects grind to a halt because someone in the chain—often a lawyer or risk-averse manager—declared 'it can’t be done.' Yet, Segall noticed that the people and teams who broke through always shared a trait: well-placed skepticism.
When a critical ad campaign faced last-minute legal objections that would have killed its impact, Jobs weighed the risks, quickly overruled the concerns, and ran it unchanged—nothing bad happened, and the campaign was a hit. On another occasion, facing trademark issues with the iPhone name, Jobs gambled on a handshake deal, then launched and settled the dispute afterward. This approach wasn’t recklessness, but a willingness to challenge expert opinion, trusting deep knowledge and judgment.
Behavioral research describes this as constructive skepticism—a willingness to question authority and process, paired with clear reasoning. Those who practice it consistently tend to produce more innovative, high-impact results and earn respect for independent thinking. Segall’s own lessons mirrored this: the returns for asking 'why not?' are worth confronting a little resistance.
Take the next opportunity to probe deeper when an expert, manager, or group says 'no,' and look for ways to solve the underlying problem rather than simply yield. Balance expert advice with your vision and what you know works; evaluate risks, but don’t always let fear override potential gains. If you believe in the value of an idea—even if it’s disruptive—take the initiative to move it forward and question established routines. Sometimes, breaking through the default resistance is the key to big progress. Try this attitude in one meeting or project this week, and watch what opens up.
What You'll Achieve
You will foster a mindset of creative possibility, strengthen judgment, and learn to balance respect for expertise with proactive, independent decision-making. This approach can lead to greater respect, career advancement, and personal satisfaction.
Question Rules, Experts, and ‘We’ve Always Done It This Way’ Thinking
When told 'no' or 'it can’t be done,' dig deeper.
Don’t accept a negative answer at face value. Ask, 'What would it take to make it possible?' or experiment independently.
Balance expert advice against your goals and common sense.
Weigh recommendations carefully, but don’t treat them as automatic orders if they conflict with your vision or context.
Push forward when you believe in an idea, even when it’s risky.
Sometimes process, legal advice, or tradition hold back big gains. Use judgment and calculated risk, and don’t let fear of rejection or criticism dictate your actions.
Reflection Questions
- Who (or what process) do you tend to accept without question?
- When have you pushed back and gotten a better outcome as a result?
- How do you balance risk and opportunity when challenging authority?
- What’s one rule or routine in your life or work worth re-examining?
Personalization Tips
- A student feels an assignment deadline is unfair; she respectfully proposes an alternative plan to her teacher, showing initiative.
- An employee asks if an outdated process can be replaced with a more efficient new method, backing up his suggestion with facts.
- A family member questions whether a vacation tradition truly serves the family’s current interests, suggesting a fresh approach.
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