When to Walk Away: Signs It’s Time to Leave a Job, Business, or Relationship

Many people stay in jobs or relationships long after they’ve lost their essential mojo. Recognizing the signs that it's time to leave a job or relationship can be difficult. Similarly, how to know when a business or career is failing is crucial for making strategic decisions. Whether personal or professional, understanding when to pivot and how to take action can make all the difference.

This article explores warning signs of decline and offers strategies for reviving a struggling business or relationship before it’s too late.

In his masterpiece book, “Things Fall Apart”, the writer Chinua Achebe uses the dissolution of society in post-colonial Africa as a metaphor to explore why and how things deteriorate. The lessons in his book can be applied to any relationship, company, or society. While the book focuses on the decay and dissolution of the society he was describing, the lessons that he conveys in the book are universally applicable to any system that is in decline.

John Hein, a radio personality who worked on the Howard Stern Show, also coined the phrase “Jumped the Shark” to apply to when a TV show was no longer relevant and began its decline to cancellation. The phrase tried to pinpoint the moment when the show no longer had its essential creative spirit even though the show often kept running for years more.

All man-made things go through the process of entropy and decay without a constant renewal of core principles driving them forward with creativity and awareness.

The time it takes for something to decline depends on its complexity and structure—it could take days, months, years, or even decades. There is always a specific point when a company or relationship begins its decline, though it is often only recognized in hindsight.

Unfortunately, people don’t usually identify this “in the moment” and it is only in retrospect that this point is identified. Even when the people involved recognize their effort has “jumped the shark,” few are willing to abandon something that is currently successful and known for the uncertainty of something new.

Jerry Seinfeld was able to do this with his show “Seinfeld”. The show ran for nine seasons and could have run for many more, making everyone involved millions per year. Yet Jerry had both the insight and the courage to realize and act upon his knowledge that it was time to end the show. He clearly avoided “jumping the shark.”

My question is how do we develop the same insight and courage to do this in our own lives? How do we know when to pivot in a new direction or breathe new life into our current effort?

I see this in people’s relationships, jobs, and within companies. Many people ignore the signs it’s time to leave a job or relationship, staying due to fear, security, or sunk costs. Consider a marriage that no longer has love and purpose but people stay in for comfort and convenience. Many people I counsel stay in jobs at companies they no longer love because they think their stock options will be worth something someday or that the company will turn around even though their gut is telling them to start looking.

From a market perspective, there are many instances where this knowledge would be useful to investors. I remember my mother being convinced that Bell Telephone would exist forever. For business owners and professionals, knowing when a business or career is failing can mean the difference between reinvention and collapse.

From a different perspective, if you are running a company, how do you determine whether the decisions/choices you are making will lead to growth or decline? Everyone tries to make the right choices but we all make mistakes. Is there a litmus test for a choice that will lead away from entropy and toward life? I think there is.

When I counsel and work with people and companies I spend a lot of time focusing on values, ethics, and purpose. The key to reviving a struggling business or relationship is realigning with core values and making decisive changes.

“Success is not about selling more, it’s about aligning the entire organization with the reason the company exists, and even if this adjusts over time, enrolling the employees in that reason for existence. In the long term, revenue and profits follow excellence and customer value, not the other way around.”

A relationship example would be when a family is transitioning from a nuclear family towards the children going to university or moving out of the family home. For many parents, raising children is their central mission. While this will always be a component of their union unless that couple redefines and renews their relationship to reflect their new reality, their marriage often either falls apart or becomes lifeless.

This happens with companies too. If a real estate company is focused on small commercial real estate and then starts buying warehouse buildings, a similar decline can happen unless the bedrock mission and purpose of that company clearly changes to reflect the new focus and all of the employees and prospects are enrolled in the new mission.

Finally, there is the hard-to-define aspect of the “soul” of a company. There are always certain people that define this within a company and their departure creates a downward progression unless a new visionary leader is found to replace them. If you look at really successful companies like Oracle or Microsoft you can see the importance of holding this purpose at some level and finding the right person to embody this at each step. Clearly, Larry Ellison continues to provide the guiding ethos for Oracle. Microsoft was successfully able to pass this from Gates to Ballmer to Nadella.

As an aside, this is why private equity companies so often kill the companies they invest in. Ethos is not a dollars and cents measure yet it is vitally important to continued success.

What are the warning signs that a job or relationship has "jumped the shark"? What specific strategies can be employed to realign a company's mission to prevent decline? In what ways can one cultivate the insight and courage necessary to make transformative changes in their life?

Recognizing the signs it’s time to leave a job or relationship or identifying how to know when a business or career is failing allows you to make empowered choices.

If you’re facing these crossroads, my advice is to spend time looking at meaning, purpose, values and ethics to ensure you’re moving in the right direction. Is there alignment with the activities that are happening? Whether it’s changing paths or reviving a struggling business or relationship, the most successful transformations come from clear awareness and decisive action. Recognizing the right time to leave or reinvent is an act of courage. Don’t wait until circumstances force your hand—align with your purpose, take decisive action, and move toward a future that serves you.

This article was originally published on LinkedIn.