4 Questions To Ask Yourself Before Quitting Something

The next time you feel like quitting, ask yourself these four questions first.

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Quitting can be seen as a failure in its simplest form; you either choose to stick with it or you realize it’s time to throw in the towel. This can be one of the most challenging decisions we can make as human beings, regardless of the circumstance surrounding the decision. Especially considering most of us grew up hearing the mantra, ‘Never give up.’ Whether it be a relationship, work, a new hobby, an entrepreneurial endeavor, or something else entirely, the final say one way or the other can be menacing. For those reasons, it is important that you take the time to ask yourself these very specific questions in order to gain the confidence necessary to choose one path or the other: either moving forward or switching paths.


Every worthwhile endeavor will have its challenges and setbacks. In the moments where it seems most trivial, it can become easy to become fixated on how dire things are so much so that we ignore the reason why we pursued the project or accepted the job offer in the first place.

Professor of management and psychology, Dr. Allison Gabriel Rossetti of the University of Arizona shared with Fast Company that when an employee finds themself in tough times at work, they should take a moment to remind themself why they accepted the job offer initially. By understanding their ‘why’ and examining whether or not it aligns with their role allows the employee to make a more rational decision as to whether or not they should stay or go. Should you find what you are doing still very much aligns with your ‘why,’ then it might be a sign that this is a challenge to weather.

Contrarily, if you find dissatisfaction in noticing your job is not as aligned with your why as you might have suspected, then quitting could be the smartest decision.


Typically, we want to quit something when it makes us either unhappy or uncomfortable (or both). While the first step is figuring out why you took it on in the first place, a second (and necessary) step is to figure out the reason why you are thinking of giving up.

Let’s say you are a new business owner who is currently facing financial uncertainty and as a result, you feel people don’t take you as seriously as they might the high-flying executive at a global corporation. You see your former colleagues living this lifestyle and indulging in all things lavish. Your pride mixed with all of these thoughts cater to the temptation to quit and go back to your former life.

But as recruiting specialist, Skip Hall, told Fast Company, pride or prestige should never be the only reason for making a move. He shares, “There are so many other factors to weigh in, even if they’re harder to see.” If you were to leave your corporate executive role because you were frustrated with the lack of autonomy and quitting your business venture meant returning to that, you will likely find yourself far less happy following the return to the corporate world in exchange for entrepreneurship.

In addition, if your values do not align with that you are doing, then you are likely going to find difficulty in making yourself happy long-term. Hall writes, “If you can’t go home at the end of the day feeling proud of the decisions you’ve made at work, it’s time to consider a move.” Will you thrive more as an employee or employer?

This methodology can be applied to nearly anything else in life that you are considering giving up on. Does your partner challenge the things you stand for? Are there more differences than parallels when it comes to values and priorities?


Frustration can oftentimes be prompted by a change in some variance. When life throws you curveballs such as these, the best thing to do is to embrace it. If you have tried a certain method once before and didn’t find success at the end of it, then you might need to try a different approach in order to drive different results. Entrepreneurs are notorious for this when they ‘pivot’ their business in order to find more success, broaden their audience of consumers, meet the increase in demand, or to make room for the outcome of short-term goals. If you do a little digging, it won’t be long before you find story after story of entrepreneurs who identified the need for change, rather than a screeching halt.

4. What do I have to gain by quitting?

Everything you do has an opportunity cost and sometimes quitting can allow access to more resources necessary to catalyze something that’s more important to you.

In “Barking Up The Wrong Tree: The Surprising Science Behind Why Everything You Know About Success Is (Mostly) Wrong,” author Eric Barker, shared the story of a man, Spencer Glendon, who suffered from chronic ulcerative colitis in high school. As a result of his weakened immune system, he was instructed to focus on accomplishing just one thing a day. Some days he would simply cook dinner while other times it was something else entirely. It wasn’t long before he learned that quitting something that wasn’t so important to him freed him to do the thing that was. This is one example of the opportunity to gain as a result of quitting.

Barker writes, “We don’t like to think about limits, but we all have them. While grit is often about stories, quitting is often an issue of limits–pushing them, optimizing them, and most of all, knowing them. Glendon could not deny or ignore his. He was forced to acknowledge trade-offs and focus his little energy on the things that mattered–and to quit doing everything else.”

The decision to quit is ultimately yours and no one else's and it is one that should never be taken lightly. It is understandable to have reservations specific to this decision and it is necessary that you understand not just that the options exist, but the reasons why you are so tempted to quit. New chapters often require the previous one to end and endeavors such as employment, relationships, and business ventures are no exception. So the next time you are stuck between ‘Should I?’ and ‘Should I not?’ ask yourself these four questions before answering.

Written by

Writer. Poet. Philomath. Dog Mom. Traveler. Creator. Wanderer. Teacher. Empath. Author of “Unapologetically Human” - available on Amazon

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