Refusing Permission and Embracing 'Unreasonable' Goals Gets You Farther Than Playing It Safe
Tim Ferriss stood in front of a class full of students at a top university, offering a round-trip ticket anywhere in the world to anyone who could complete an 'unrealistic' challenge—get a celebrity or CEO to answer three questions. Despite initial enthusiasm, no one attempted it, paralyzed by the belief that it was simply too hard. The following semester, when Ferriss challenged the same group but framed the possibility of failure as acceptable, several succeeded quickly. What shifted? It was realizing that the biggest goals have the least competition—most people are too afraid to start.
Ferriss himself won unexpected business deals, athletic competitions, and life experiences by setting bold, even 'unreasonable,' goals—then taking uncomfortable steps without waiting for permission. Over and over, he learned that striving for safe, incremental changes only led to mediocrity and boredom. Trying for the unlikely, while risking mistakes and looking odd, moved him forward faster than aiming for what others said was 'realistic.'
Studies in behavioral economics confirm that people systematically underestimate their capability and overestimate everyone else's. When you choose bigger, more exciting goals, your engagement and learning curve accelerate—mistakes become fuel for faster growth. Grant yourself permission for bold experiments, and success becomes more likely than you’d ever guess.
If you’ve been shrinking your dreams or waiting for a sign, now’s the time to test the unreasonable. Write down one goal that feels just a little out of your league—something you’d be secretly thrilled to achieve. Ignore the urge to get everyone’s approval and instead take a direct action: send a cold email, apply for the big opportunity, start the project publicly. Don’t beat yourself up if you stumble; instead, note what happens and use each bit of feedback to get smarter. The world rewards people willing to try the unlikely, so be bold and take your first wild shot this week.
What You'll Achieve
Break through self-imposed limits, expand your courage and learning capacity, and discover unanticipated successes by stepping beyond routine goals and permission-seeking.
Set a Challenge That Feels a Little Unrealistic
Pick a goal that feels a bit out of reach.
Instead of 'safe' or modest aims, choose something that excites you—and feels slightly intimidating.
Commit to taking the first visible step without asking for approval.
Rather than seek permission or consensus, do one thing that moves the goal forward—a bold email, call, or public commitment.
Learn from direct feedback or small failures, and adjust quickly.
Instead of perfectionism, let reality—and even rejection—teach you faster. Record what happens and iterate after each step.
Reflection Questions
- What’s the biggest ‘unrealistic’ goal you’ve ever secretly wanted to try?
- Who are you waiting for permission from—and is that really necessary?
- What’s the worst that could happen if you try and miss, and how would you recover?
- How might your attitude change if you prioritized bold attempts over safe wins?
Personalization Tips
- A junior employee applies for a speaking slot at a national conference, despite only working a year in the field.
- A college student builds a website and pitches it to potential customers before forming a club or seeking approval.
- A parent who always puts off creative pursuits submits artwork to a gallery for the first time.
The 4-Hour Workweek
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