Knowing when to Quit

The following is a guest post from the Backpacking Entrepreneur Reggie Black behind Sticky Inspiration, an inspiring art project using only a sharpie and post it notes.

The phrase “I quit” is forbidden in the world of business. It’s typically a sign of weakness, lack of consistency and belief.

The world of business needs to be completely redesigned, along with the rest of the world. Their notions and unethical practices have dehumanized the culture so their opinions are inaccurate.

Quitting obtains more power than anyone can imagine. Kanye West once asked,

You got the power to let power go?

Drake followed that question with an affirmation of his own,

How long they choose to love you will never be your decision.

However, my love for the idea of quitting and owning your power is rooted beyond those lyrics. It started with one of the brilliant minds of our time and one of my idols, Seth Godin.

In 2011, someone suggested I read “The Dip” by Seth Godin. The timing was perfect. My life was a hurricane; my creativity had reached its peak, and my fashion brand, BLACK Collection was upside down. My life as a designer didn’t have much fuel in the tank but I wanted to continue to drive the car because I was afraid to get out and face reality. I even had visions of launching a new project, Sticky Inspiration, but fear held me hostage.

In Seth’s book he talks about the importance of understanding the highs and lows of life, and creativity, which he refers to as “The Dip.” He also elaborates on the importance of knowing when to quit. There’s a fear that’s bigger than the idea of quitting. Seth explains that the fear of giving up on producing average work is the hard part. Most people would prefer to create in comfort, to do average work, as opposed to quitting, which he defines as redirecting your mission to create risky work.

Earlier this year, I had the privilege to meet Seth. I was selected to participate in his “Agenda Session”, a weeklong, life-changing experience with 14 other people. The weeklong experience took place in his office Upstate New York. It was the most aggressive, thought provoking experience I’ve ever encountered. Seth challenged us to push harder, risk more, and ship regardless.

Quitting my fashion line led me to start Sticky Inspiration, a project where I post a POP art philosophical musing on a sticky note everyday, my initial goal being to inspire one person a day. I worked hard. I battled fear, doubt and insecurity. An Instagram community grew up in support. I found a partner who shared my vision. And it lead to my meeting an idol who only does work that causes a ruckus, as Seth Godin puts it.

So when should a person quit? It’s all case by case.

People should quit when it’s no longer fun, when they find themselves operating from values that don’t matter to them, or when they find themselves doing stuff because of what others might think.

Deep down you’ll know when you’re not doing your best work. If you’re stuck producing averaging work but afraid to leap into new things because you’re getting comfy it’s time to quit.

It’s best to do it on your terms too. If you quit, you can recreate yourself. If the market dictates when you quit, its hard to get your confidence back to go forward or to start a fresh.

So as Seth puts it, the question to ask yourself is:

Are you causing a ruckus?










Big thanks and photo credit goes out to Steph Norton