Aug 13 • Challenges
Challange Three
“If you woke up tomorrow and every person in your life—your parents, spouse, friends, former colleagues—questioned your judgment and considered you foolish for abandoning ‘security’ for an uncertain path, and if you had to watch others around you receive predictable paychecks, enjoy employer benefits, and take guilt-free vacations while you scraped by on inconsistent income for the next two to three years with no guarantee of success, would the vision you’re chasing still feel worth it when you’re alone with your thoughts at 3 AM?”
This weeks challenge addresses the
social isolation that comes with rejecting conventional paths.
Most people will not understand your choice, and some will actively discourage you or view your struggles as self-inflicted.
The psychological weight of uncertainty. Entrepreneurship isn’t just about working harder—it’s about tolerating profound ambiguity about your future while everyone else seems to have their lives figured out.
The real timeline of building something meaningful. Those overnight success stories are largely myths. Most successful ventures take years of grinding through periods where progress feels invisible.
Your relationship with failure and judgment. You’ll be wrong about many things, and unlike employees who can blame systems or bosses, every failure will feel personally yours.
The question also reveals whether your motivation comes from running away from something (which rarely sustains you through hard times) versus running toward a vision so compelling that external validation becomes secondary.
If reading this makes you uncomfortable or second-guess your decision, that’s not necessarily a red flag—it might be the clarity you need to either commit fully or recognize you’re not ready yet.
Where are you in the journey??
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Challange Three
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