The Road Between Employment and Entrepreneurship

02/17/2015 11:10 am ET | Updated Apr 19, 2015

Have you ever had someone pose something to you so powerfully that it literally stopped everything?

That happened to me a couple of days ago when I received an e-mail from Daniela Liscio of Eat for Sport. My interpretation of her words (my clarion call, really) are as follows:

"In order to show up powerfully as a coach who helps individuals transition from their desk jobs to entrepreneurship, I need to demonstrate that I myself know how to make the jump."

It seems obvious, but I must admit that even now (with a blog on The Huffington Post and everything), describing the world of entrepreneurship is a slippery concept. (Copying textbook definitions from Merriam Webster is easy. Describing what it's like to be an entrepreneur is to explain a concept that's continually shifting.)

I began to think about how I would describe it, and my thoughts immediately shifted to entrepreneurial mindsets because there are so many writings on this (a google search will easily produce articles and quotes all focused on helping you develop "the entrepreneur's mindset.") Yet I realize that before one even gets to mindsets, it's necessary to focus on being. What does it mean to be an entrepreneur?

After thinking a bit further, I came up with a visual representation of what entrepreneurship feels like. It goes like this:


You're at the edge of a forest. You walk in and are taken in by how foreign the forest looks. It's beautiful with dense, green trees. Your head turns to the right and you find a jewel (e.g., client/customer) by a log. You put it in your bag and proceed. Suddenly without warning, the scenery switches. You're in a raft floating down a raging river. You're surprised that the world beneath your feet has shifted, and immediately respond -- that is after praying that the raft will keep you afloat. You anxiously look around for paddles and find a pair. You grab them and then realize you don't know how to maneuver a raft with paddles. You do yor best to get down the river without crashing into the huge boulders jutting out of the water. You do bump into a few, but find that your raft is quite sturdy. On one of the boulders, you find another jewel. You manage to get hold of it just as you pass by and put it in your bag.

Scene change again. This time you're on a mountain with no trail to direct how you should proceed. Something in you tells you that you need to cross the mountain so you take a deep breath and proceed. At times, the inclines are gentle and you find jewels here and there amongst the rocks. At other times, the inclines are steep and you have to grab onto trees and vines to pull you up. You find a few jewels there too.

All of a sudden you're in a pleasant meadow with vibrant, beautiful flowers. The birds are singing. The clouds are dancing merrily in the sky. You stroll through the meadow, whistling and collecting jewels as you go along.

Scene switch. You're suddenly thrown into the middle of a large body of inky black water. It's colder than you'd like it to be, but after a few moments your skin adjusts to the temperature. You can just make out a few jewels on the water's edge. You tread water for awhile, and then you start swimming...

BEING an entrepreneur means consistently keeping yourself "in play" in this type of situation. Where you don't know what's coming next, yet you're committed to getting through whatever comes your way.

Last year I interviewed Daniela on how she took the leap from being a law firm partner to coaching amateur athletes wanting to incorporate healthier lifestyles and achieve their performance goals. You can find it here.