How to Know When it's Time to Stop

In The Trenches

It's not hard to understand the importance of persistence to the entrepreneurial journey. Entrepreneurs who overcome substantial hardships on their eventual road to success are (rightly) applauded for the otherworldly persistence that they demonstrated in doing so. Yet many entrepreneurs are able to finally achieve success only after moving on from several prior ventures whose prospects eventually grew to become much less promising. These entrepreneurs are also (rightly) applauded, though this time it’s for the foresight, objectivity and courage that they demonstrated in making what must have been an incredibly difficult decision to “quit”. So, which is it? Should entrepreneurs persist at substantially any cost, or should they be wise enough to know when they’d be better off doing something else entirely? How does one know when to perceive persistence as an asset, and when to perceive it as a liability? In late-2020, I decided to step down as the CEO of my own company after approximately 7 years at the helm. Since then, I have spoken to countless entrepreneurs and CEOs wrestling with similar decisions. In each instance, they asked how I made my decision, which is why I’ve decided to write this post. Though I can’t tell you specifically what you should do, I can at least share with you the questions that I asked of myself in coming to my own decision.