Ask Christa! When Should I Leave? (S2E24)

Introduction – When Should I Leave?

Hi everyone and welcome to Ask Christa! the place where you can ask questions about how to work through business challenges and workplace issues. I'm Christa Dhimo and today’s listener question might sound more like a relationship question, which fits well into this Season, season 2, which has been about interpersonal dynamics and the various challenges so many of us experience in the workplace, from an interrupting boss to introducing a new idea to a rigid team, and from giving feedback to a defensive team members to what healthy workplace cultures feel like.

Like most of our listener questions, the listener offers context, too. Here it is:

“I’ve been at my company for 17 years, since I graduated from college. It’s a good paying job, and I’ve had a few managers—some better than others, but mostly good. I’ve had a few promotions also, but lately I feel like I want more. My ambitions have grown to be bigger than my job, and I keep talking to my manager about what the next step could look like, bringing different ideas, considering some roles we could create for me, and thinking about ways I can expand my responsibilities and move up.

”We keep having good conversations, but there’s no action, and I can’t get a straight answer as to why. I’m feeling antsy and want to leave, but a part of me also wants to stick it out. Plus, I don’t know how good the job market is—I keep hearing mixed messages, and again, it’s OK here. But that’s part of the problem: it’s just OK.

“When should I leave?”

Work is a big part of our lives while also supporting our lives.

I’m going to start with the flimsy answer everyone and anyone would give when asked this question, “only you can determine when you should leave.” But I also want to point out that our listener is asking the WHEN question and not the WHETHER question—whether they should leave of not, so I’m going to focus on how to work through the timeline of leaving your job for any reason: better growth, better money, better title, bigger responsibilities, even retirement.

And as a side note, if you work in a toxic environment or in a place where you just feel “icky” when you’re there, or can’t seem to find a way to finding your people within an organization… you need to think about leaving sooner than later. I always tell people that it's better to walk TOWARD a new job than run FROM and bad one. The former gives you more choices; the latter is you just desperately trying to get out of a bad situation… and there will be fewer choices because you simply want to move on. Quickly.

So. Timeline. This is again a personal decision, but if we think about how much of our lives we spend in a job or multiple jobs, and we think about how much energy we put into cultivating and managing a career, our work is a big part of who we are. 

Work isn’t just how we afford to live, but also how we get the bulk of our benefits and safety nets so we can live as well as possible, at least that’s the situation if you are working in the United States. It’s also where a lot of people find community, find their people, find a life outside of the home. We talk a lot about work-life balance so that our work doesn’t become our life; but there are those who feel that their work actually BALANCES out their lives, too.

Before going further, I want to acknowledge that a lot of people languish in their jobs or remain in toxic work environments because they cannot leave. They have a family to support, need health care and dental benefits, need a good way to save up for retirement. I’m focused on answering the specifics to this question, but I also know—and have personally experienced—there are times when the question about leaving isn’t WHEN, but a CAN I?

Two feelings about work, which helps with “fit”

That said, I do want to explore the two common ways people talk about work, which can be helpful to determine whether you are still a fit within an organization:

The first way people commonly talk about their work is through the lens of personal engagement, where we hope to grow and develop, find satisfaction, and fulfill our ambitions. There’s also the sense of camaraderie, feeling like we’re spending our days adding value and making a difference, and of course, being appropriately compensated and receiving what we consider to be fair for the value we bring. 

When we experience that level of engagement at our workplace, we also find deeper meaning and higher purpose in our work. People experiencing this level of engagement will say, “it’s more than a paycheck.” By the way, when this happens, the organizational performance soars and hopefully the organization has programs in place to keep their employees engaged and retained.

Then there’s the other way people commonly talk about their work, and that’s through a “supporting-our-lives” lens, which doesn’t always line up with fulfillment and meaningful work. This is when instead of hearing someone say, “it’s more than a paycheck,” you’ll probably hear, “it’s just a paycheck.” 

These jobs pay the bills, provide benefits, check all the usual life boxes. Employees likely feel camaraderie with their co-workers, but they’re OK if they don’t. These jobs have more of a transactional feel to them: I show up, I do a good job, I go home. And that’s OK. There are a lot of organizations that want their employees to show up, do their job, then go home, and there are a lot of employees who are happy with that arrangement for a variety of reasons.

But if you view your work through one of those two lenses and your workplace isn’t compatible—or perhaps becomes less compatible over time, that’s when the clock starts ticking. For example, with this episode’s question, the listener wants to grow, develop, fulfill their ambitions, promote upward… but perhaps those opportunities don’t exist or listener’s growth plateaus because they’ve hit a certain level—and this happens, especially with smaller and mid-sized companies. There ARE times when employees literally outgrow their organizations. 

When to leave and the role of the organization for retention

It doesn’t mean you have to leave right away, but it DOES mean you have to begin thinking about moving on so that you can fulfill your ambitions in a workplace that is more suited to your growth needs. It’s no longer a WHETHER you should leave. It’s become a WHEN you should leave, and that WHEN needs to be based on how much you want your work to be more than a paycheck. Because if you’re under-employed or have outgrown your job, it is already in large part transactional. You show up, you do your job, you go home.

Conversely, if you want to show up, do your job, then go home, but suddenly your company is asking you to take more initiative, become more involved in ways to improve the business, find ways to engage differently with your team, use a portion of your work time to get involved in other programs or activities or tasks, that’s a mismatch, too. 

From a strategy and organizational performance perspective, and as an expert, I’ll say this: you need a mix of employees to get the best out of them: those we call “Steady-Eddy’s,” who will consistently show up, do the work, go home, and those who will go beyond… But remember: those who go beyond will at some point want and deserve more. And if organizations cannot offer more, then… it’s not a matter of WHETHER you’ll lose those employees, but WHEN.

As a final thought, asking the question “When should I leave?” by definition requires a condition, so flip it to be a statement that you have to finish: “I should leave when…” and the ending of THAT statement is the answer to your question.

Additional Resources

There are a lot of resources to help you with these decisions, but I’m offering three that are great resources to help you navigate your career.

The first is from Keiran Setiya, and I’m offering his 2019 article, called, “Facing your mid-career crisis,” because it is written in a highly relatable way for anyone asking the “when should I leave” question… which, as you’ll learn from the article, is common for those entering into the middle part of their careers, usually late 30s into your 40s and beyond. If nothing else, you may find some comfort in understanding the phenomenon of how many of us shift and change as we enter into the middle years of our career.

Building on this perspective, I included an article written by Jack Kelly called, “How to successfully navigate the three stages of your career.” It will provide more details and insights for the various stages of our careers, and it’s accurate. It’s always helpful to know we’re not alone—that what you are feeling in terms of it being time to leave—asking the question WHEN—is typical of a lot of employees, especially if you’re somewhere into the 15th year, give or take a couple years.

And—I did something I NEVER do: I’m including an article from Indeed. It includes a video, too, and the only reason I never include articles from job sites is because I prefer to provide articles that are either backed by research or offers insights extrapolated by research and written by people with a lot of experience who can offer support.

Remember, I offer resources in every episode so you can learn more at your pace.

But this article, written by Jennifer Herrity in June 2025, is focused on 15 signs that it’s time to move on, reasons 1, 2, and 4 are all related to this listener’s question. I can also tell you that the majority of what she writes about is in fact supported by research related to employee retention, so… it passes the muster.

Final Thoughts: Leaving Because of Bad Boss Behavior

I do want to say that if you’re in a toxic environment or work with an abusive boss who yells, belittles, or disrespects you in other ways, like outwardly embarrasses you or chronically takes credit for your work, find a way out when and if you can. If you live in a small town and that’s the best job for you within 100 miles, then obviously it’s not easy to just leave, but it’s still important to manage it in a way that doesn’t lead to an impact on your health. 

Bad boss behavior is exhausting at best, and really harmful at worst—and it’s not about whether you can take it, but whether you SHOULD take it. Good humans cannot thrive in those environments. 

If you want to take a hard-nosed approach and challenge me: Christa, you shouldn’t be so soft… then that tells me two things: first, you don’t know me that well, and second: you think of a job as a transaction. A pay check. 

And that’s fine. But I can be hard-nosed, too. If you want a more successful company, if you want higher and more predictable performance, then treat your employees well. THEY can think of their job as just a paycheck. But YOU cannot think of them as “just employees.” 

Unless that’s all you want from them.

That’s a Wrap! Looking Ahead…

OK, that’s a wrap for episode 24 and the final episode for Season 2! The next episode starts up Season 3, which focuses on a lot of business topics—which may be less dramatic than the workplace dynamics questions in this season, but my show is about answering any and all questions about business challenges and workplace issues, so… 

I’ll be answering listener questions that ask about business basics, so there will be a 6-episode series called “Business Basics.” I’ll also tackle questions like how business can be less intimidating for those who don’t consider themselves “business people,” as well as how much finance you need to  know in order to be good at business (here’s a preview: about as much as you need to know about managing a household…).

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Thank you—your questions are fueling my show, and I appreciate your support. And remember, if you have a business challenge or a workplace issue—Ask Christa!