Don't Stop Be Leaving: Knowing When It's Time to Move On

In his book Necessary Endings, Dr. Henry Cloud offers a powerful perspective on the importance of recognizing when to walk away. Whether it's a business relationship, a personal endeavor, or a job that no longer serves you, knowing when to move on is just as crucial as knowing when to stay. Too often, we hold onto roles out of fear, loyalty, or the belief that things will improve. But trusting your instincts and your skills can lead you to something better.

The Power of Necessary Endings

Cloud explains that pruning—removing what no longer serves us—is essential for growth. Just as a gardener trims dead branches to allow healthy ones to flourish, professionals must recognize when their career has stalled due to staying in the wrong role. The key is to embrace endings not as failures but as necessary steps toward success.

How Do You Know When It’s Time to Leave?

Recognizing when it’s time to move on from an employer isn’t always easy. However, there are clear indicators that signal it may be time to explore new opportunities. If you identify with any of the following, it may be time to trust your instincts and make a change:

• You’ve Stopped Growing – If your current role no longer challenges you or offers opportunities for learning, you risk stagnation. Growth should be continuous, and if your employer isn’t providing that, it’s time to seek it elsewhere.
• Your Work Is Not Valued – If you consistently put in effort but feel unrecognized or underappreciated, it can lead to frustration and burnout.
• Toxic Work Environment – A culture of negativity, poor leadership, or lack of respect can be emotionally and mentally draining. If your workplace leaves you feeling anxious or unhappy, your well-being should come first.
• Your Values No Longer Align – If the company’s mission, ethics, or direction conflict with your personal or professional values, staying can feel like compromising your integrity.
• You’re Not Compensated Fairly – If your skills and contributions exceed what you’re being paid, and your attempts to address this are ignored, it’s a sign to look for an employer who recognizes your worth.
• Opportunities Are Limited – If promotions or career advancement seem unattainable due to company structure or favoritism, your long-term success may require a move.
• You Dread Going to Work – If Sunday nights bring dread and weekdays feel like a battle, your mental and emotional health could be at risk.
• Your Gut Is Telling You to Move On – Often, your instincts recognize what your mind resists. If you have a persistent feeling that you should leave, trust yourself.
• Don't Stop believing is played at an all hands meeting - The staff gets all pumped up, next up are the awards for "best place to work" and more. Then dead silence when the next words are "we have been acquired". So even if you love where you work and love the culture, be aware that a business can be sold at any time.

Embracing the Transition

Leaving a job is never easy, especially when uncertainty looms. However, staying in the wrong place for too long can hinder your potential. The key is to recognize that endings create space for new beginnings. When you take control of your career path, you position yourself for greater fulfillment, success, and happiness.

If any of these signs resonate with you, consider making a strategic exit plan. Update your resume, network, and start exploring opportunities that align with your goals and values. Trust yourself—you have the skills and instincts to navigate the next chapter.

As Dr. Cloud says, "Getting to the next level always requires ending something, leaving it behind, and moving on." So don’t stop—be leaving.