How do you know when to jump off the cliff?

One of my favorite entrepreneurial quotes is by Reid Hoffman, the founder of LinkedIn.  Reid wrote:  “The entrepreneurial journey starts with jumping off a cliff and assembling an airplane on the way down.”

This perfectly captures the essence of the fear, leap of faith, commitment and urgency that surrounds the entrepreneurial journey!  But it doesn’t answer the big question of “when to jump?”

Dave Girouard, the former President of Google Apps and founder of Upstart spoke at our Entrepreneurship Hour class last week and said that it was a really tough decision for him to leave Google and step out on his own.

“At some point you just can’t stop thinking about the idea,” Dave remarked when asked by a student how he knew it was time to leave Google?

This is, by far, one of the biggest fears and barriers most entrepreneurs will face and actually prevents many would-be-entrepreneurs from getting started.   People will carry around with them an idea for a startup for years but fail to execute on it for fear of letting go of what they have.

“I have found that if you ask people how much money they need to feel financially secure before leaving their job and their answer is always exactly 2x what they currently have in the bank,” says Jessica Ewing, a former Googler who recently moved to Ann Arbor.  “If they have 50K they tell you they need 100. If they have 10 million, they will tell you they need 20!”

Here are some techniques that people I’ve spoken with use to determine when is the best time to jump:

  • Analysis:  Spend some time weighing the pros and cons of the new opportunity against the lost opportunity you have when walking away from your current situation…  then set that aside and reflect on what is truly important to you and what type of impact you want to have on this world.
  • Carpe diem:  For some people, the opportunity to do something amazing is what finally pushes them over the edge.  Robin Williams summed it up best in Dead Poets Society when he said “Carpe diem.  Seize the days, boys.  Make your lives extraordinary.”
  • Take a shower:  “What is the idea that you think about most in the shower?” said Thomas Zurbuchen, Associate Dean of Entrepreneurship at the University of Michigan.  “When you find yourself thinking in the shower about your new idea more than the times you are thinking about your current job you know its time to leave”.

Ultimately, jumping off the entrepreneurial-cliff and starting your journey is a very personal decision.  I have been at the edge of the cliff multiple times in my career and I haven’t regretted the leaps I’ve made, the planes I’ve built or the crashes that have sometimes occurred.

For me, entrepreneurship is a way of life and I couldn’t imagine things any other way.




One thought on “How do you know when to jump off the cliff?

  1. Doug,

    I work in advancement at Pepperdine University and have been building the buzz around a Center for Entrepreneurship and Innovation for the past year and a half. I am passionate about creating a STRONG culture of innovation at Pepperdine and would love to pick your brain regarding my efforts and the plan I have built with alums, staff, and students. If you are available to connect, my email is above. Thank You and Godspeed.

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