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Should I Stay or Should I Go? 5 Questions to Ask Yourself Before Ditching That Toxic Job

Well-meaning friends and family often provide conventional wisdom that goes something like this: “Don’t quit your job until you have another one lined up.” Or, “It’s always easier to look for a job while you have one.”

I often break out in hives when I hear this brand of conventional wisdom.


The Role of Fear, Really

First, conventional wisdom is rooted in fear and assumes the worst: fear of the unknown, fear you won’t be able to pay your bills, fear that the next place will be the same (or worse), fear that this is the only time you’ll have this opportunity, fear that if you leave, you will feel like a failure, etc. Our brains are good at coming up with lots of fear-based reasons to stay.

The thing about fear, though, is that it doesn’t necessarily mean anything is wrong. What if feeling fear—and overcoming it—is exactly what we have to do in order to grow into the next best version of ourselves?

Fear may simply mean something is different. In human evolution, different = bad, while familiar = good. This explains why people may choose to stay in bad jobs, bad relationships, bad you-name-its. “The devil you know is better than the devil you don’t know,” or so we tell ourselves.

Whose Values Are They?

Secondly, this type of conventional wisdom is also rooted in a set of values that you may—or may not—share. Conventional wisdom asserts that safety and security = happiness. While we all need safety and security to be happy, what level of security we need may vary widely and just because we are safe and secure doesn’t mean we ARE happy. For some of us, we thrive on excitement, adventure and curiosity, which, you could argue, are anathema to safety and security.

Do yourself a favor and take a values inventory to see what’s important to you (not your well-meaning friends and family). Here are a couple free options:

Finally, what bugs me the most about conventional wisdom is that it doesn’t factor in the toll toxicity takes on your mental, physical and emotional health; on your family and other important relationships; on your career potential (yes, on your career potential); and most importantly, on your overall sense of wellbeing and happiness.

Conventional wisdom offers the promise of security, but how secure are you in a job you hate?

WWTCD (What Would The Clash Do?): Questions to Ask Yourself

If you’re feeling a lot like Mick Jones of The Clash: “This indecision’s bugging me,” you are not alone. Limbo sucks.

Whether you decide to stay or go, it’s important to examine your reasoning and make sure you like your answers. Here are some questions to consider as you think through your decision.

1. Let’s start with something fun: What if the Universe wants to help you fulfill your dreams?

What are some signs that the Universe supports your dreams? How would it change your behavior if you believed the Universe wants what’s best for you? (If your brain has trouble with this, try the converse: Why wouldn’t the Universe support you? How does that serve anyone?)

2. What’s your worst-case scenario?

Since fear is what paralyzes most of us, go ahead and allow yourself to imagine your worst-case scenario. Take 10 minutes and allow your imagination to run wild. What comes up? What’s the series of horrible things you picture? Write it down. (It's ok; just because you write it down doesn't make it true.)

Now, imagine you have just awakened the morning after the worst thing has happened. What’s your top priority? How can you take care of it? What are your resources—in terms of people, information, assets, etc.? What questions do you have and how can you get them answered?

While thinking about this isn’t fun, thinking it through, and knowing what you’ll do and having a plan can free up your mind for more productive thinking now about how to solve your current situation.

3. Do you need to detox from your job before you can look for a new one? When you think about quitting, are you imagining what you will be escaping from or are you motivated by what you will be moving toward? If most of your thoughts have to do with escaping, it’s a sign that you simply need O-U-T.

Sometimes an environment is so poisonous to our self-esteem and our health that we need to detox from it. In order to show up as your best self when interviewing or networking, you may need to take a break first—to rest, have fun, and remember what you’re good at. When we leave one toxic environment without taking a break, we can inadvertently re-create a negative pattern because we haven’t shifted our mindset. It may be necessary to take a break in order to correct a negative job pattern, which leads to the next question.

4. What job/career pattern would you like to break?

What buttons does your job push, and where else in your life do you notice these same button-pushing patterns? What do you tell yourself about your job? How do those beliefs serve you? As humans, we have thought patterns that are well-worn neural pathways, and while familiar, they aren’t necessarily helpful.

Answering these questions takes a great deal of self-compassion, honesty and curiosity. It’s important to examine what thoughts you have and how they contribute to creating a career pattern you’d like to break. Try not to judge yourself. Identifying a toxic pattern simply proves you’re human.

Before you leave this job, I recommend you find out what pattern you want to break. If nothing else, use your current job to discover the thought pattern that isn’t serving you. Because, once you know what your pattern is, you have the ability to change it.

5. If you decide to leave your job, how will your life be different?

What will be exactly the same? No matter where you go, there you are—so be sure you're leaving for the right reasons. If you need more advice, take it from The Clash: “If I go it will be trouble, if I stay it will be double.” How will you pay if you stay in the job? How will you pay if you leave the job? You get to choose.

Don't trust a punk rock band from the 80s for career advice? You can schedule a complimentary coaching session with me at

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