Simon’s Red Flags for Knowing When It’s Time to Quit Your Job

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  • Understand the importance of securing a new job before quitting your current one, backed by research showing hiring biases against the unemployed.
  • That said, learn to identify critical indicators, such as (truly) toxic environments or conflicting organizational agendas, signaling when it’s time to move on.
  • Gain valuable insights and guidance from Simon Sinek on navigating workplace challenges and making strategic career decisions.

There are countless reasons why one might feel unhappy at work. However, abandoning ship is almost never the best solution. As Simon emphasizes, every job, no matter how challenging or disheartening, presents an opportunity for personal and professional growth.

“Working at a challenging job, even one with a bad boss, can actually provide one of the greatest educations,” he says. Rather than waking up with a sense of dread, consider reframing your mindset to view it as a form of higher studies. Essentially, you’re earning a master’s degree in leadership and gaining invaluable insights into what not to do.

Moreover, it’s a well-established fact that finding a new job is easier while you are still employed. Research indicates that organizations often exhibit a hiring bias against those who are unemployed.

That said, there are situations where quitting might be the appropriate decision, especially if you have ensured some financial stability to pursue new opportunities. According to Simon, here are the major red flags that suggest a company or organization is no longer worth your time.

1. The work environment is certified, Grade-A toxic

The term “toxic” is often used to describe workplaces, but here we are referring to genuinely toxic work environments. “True toxicity,” Simon says, “involves consistent public humiliation, berating in public, or even physical aggression.”

It’s important to recognize that every job involves some degree of office politics, shifting strategies, negative tension, occasional lapses in communication, and even moments of fear. As human beings, it’s our responsibility to navigate these challenges, support one another, and move forward.

However, if you find yourself in a truly toxic work environment, prioritizing your well-being is crucial. Such environments, characterized by high stress and toxicity, can severely impact your self-worth and confidence, making it challenging to pursue better opportunities.

If this sounds like your situation, you are not alone. Recent reports indicate that a hostile work environment is a top reason for employees quitting, with Gallup noting that approximately one in two employees have left a job to escape a bad manager or environment.

2. You’re getting lazy with nowhere to go.

If you are content with coasting at work with little to no effort, if you’re in a phase of life where having an easy job fits (like after having a baby), or if you’ve achieved a level of stability that satisfies you, feel free to skip to the next red flag.

However, if your job is so unchallenging that it’s causing you to lose passion in other areas—and you’re finding that your organization is unwilling to negotiate new opportunities within the company that might satisfy your growth ambitions—it might be time to look for something new. 

“This isn’t about the occasional slow day; it’s about a persistent lack of engagement and challenge,” Simon says. “The issue is that the job has become so easy that you’re becoming lazy.”

3. Your organization has an agenda that runs counter to your principles

This could stem from various factors, including cultural differences, political divides, or even company values. Working against who you are and what you believe can be detrimental to your mental health, regardless of the paycheck.

“You’re going to have disagreements at work, and you want people to have diverse thoughts, opinions, and politics. It makes for better teams,” Simon says. “But the issue arises when the company doesn’t value diversity of thought. If you are the outlier, it can be hard to continue in a job that forces you to silence your own beliefs.”

At the end of the day, it’s about feeling included and valued, which is essential for a healthy work environment. If you don’t feel like you matter in your company, you should find somewhere where you will—because you do.

4. You want to be an entrepreneur

As any successful entrepreneur will tell you, juggling a full-time day job and the demands of building a new business simultaneously is nearly impossible.

“The right approach,” Simon suggests, “is to balance your job and your entrepreneurial pursuits until your side project requires full-time attention. When it becomes too busy to manage both, that’s when you decide to quit.”

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