Where’s the line between stubbornly pursuing an idea that isn’t working and the patience and persistence needed to actually make it work? In other words — when should you give up and quit and when should you push on?
Since this is something Tim has struggled with, I came to the conclusion that I should reach out to people who might have a better answer. So, Tim sent the question to the following entrepreneurs, authors, and innovators:
Their answers are a thorough overview of how to assess your own ideas and opportunities, and determine which ones are worth pursuing. Enjoy!
Ryan Holiday (@RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy.
Ryan and Tim cover a lot in this conversation, including:
Meltdowns and how Ryan handles them
Workaholics Anonymous — How it works, what worked for him, what didn’t
The tipping points for his last book, The Obstacle Is the Way
External versus internal obstacles
Sherman versus Grant leadership and “success”
Howard Hughes versus Elon Musk
Thinking of “first principles”
If you only have 5 minutes, listen to what Ryan believes is one of the biggest threats to your creativity.