The Art of Quitting: Hang In or Hang It Up?

by placers on April 26, 2024 in Outside Insights



Here’s the thing – quitting shouldn’t be a bad word. But why does it often feel like it is?


At Placers, we champion values like results-driven performance and relentless hustle, epitomized by Winston Churchill’s wartime call to “never, ever, ever give up.” This motto resonated so deeply with me that it found its way onto t-shirts for the high school soccer teams I coached. My journey through rebuilding Placers after the 2008 recession and the pandemic has taught me the essence of perseverance—I even carry a coin in my pocket inscribed with “the obstacle is the way,” a nod to Ryan Holiday’s influential work.


The never give up mentality was instilled in me from the beginning. When I was young I wanted more than anything to be a Cub Scout. From the day I joined I was all in, and my mom even became our Den Mother. I loved everything about the Cub Scouts, from the pinewood Derby, the meetings, and merit badges. I loved it all until one day – I just didn’t anymore. One by one my friends dropped out and soon I realized they were what made the scouts so enjoyable in the first place. My parents encouraged me to honor my commitments and I stuck it out until the end of the year before informing them I wouldn’t be returning.


A little later in life, I worked tirelessly to make the senior baseball team at age 14 and was filled with pride when I learned I made the cut. Then, the day before the game, a star player—a 15-year-old who was bigger, stronger, and more skilled—suddenly joined the team. I felt intimidated, frustrated and I remember the distinct urge to quit washing over me. Again, my parents provided sound advice and urged me to contemplate whether stepping back was truly the right decision. In the end, I chose to stay the course and I’m glad I didn’t let my ego win that day.


As children we’re taught that quitting means “giving up”. The heroes in our storybooks never give up. Giving up is “weak” and being weak must be avoided at all costs. But, as uncomfortable as it may feel, sometimes quitting is the best thing you can do for yourself. 


Other people’s perceptions often get in the way of our desire for change. “What will my team think of me if I leave the company?”, “This partnership is no longer serving me, but I don’t know how to have the conversations that need to be had”, “I don’t have the bandwidth to give to this hobby anymore but I don’t want to disappoint my friends”, etc. Do these questions sound familiar?


As an entrepreneur I’ve faced numerous challenges that forced me to question my path both professional and personally. Over the years, I’ve narrowed down five questions that I use as a guide to determine if I would benefit more from persevering or allowing myself to embrace change.


Take a moment to consider a crossroads in your life or a big decision that has been weighing down on you for a while. Now ask yourself these questions:


  1. Sunk Costs: Are you continuing just because of the time and resources that you’ve already put in? Does the value of your past investment outweigh the current and future investment required to continue?
  2. Effort and Outcomes: Have you done everything possible to succeed? Is there anything you could change up to see if it would drive different results?
  3. Original Intentions: Why did you start this endeavor in the first place? Are you still reaping the intended benefits or have circumstances changed?
  4. Opportunities Upon Quitting: What new possibilities could quitting open up? I’m not just talking business here. Could quitting a side project open up space for you to pursue something more aligned with your goals? Could it bring you more energy to funnel into your family or wellness journey?
  5. Joy and Satisfaction: Does this path still bring you joy? If it doesn’t – the answer will always be to start looking for opportunities to change. There are always new ways to earn an income and dozens of projects waiting to begin.


Understanding when to quit and when to stay the course is a crucial skill, one that requires introspection and honesty. It’s about recognizing when a change of direction is necessary and being able to envision what awaits on the other side of a closing door.


Reply and let me know about a time when you quit something. What outcomes came from this change? What were you able to pursue as a result? Did you have any regrets?


Until next time, friends.



Our book is now available as a paperback, hardback, and Kindle on Amazon. We hope you will check it out here!

If you enjoyed this article, I recommend reading these past Outside Insights posts:

Our Theme is To Be

The Energy Vampires: Navigating The Draining Forces in Our Lives

Do You Have a Career Agent? You Should

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