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  • Writer's pictureMatt Chung

Should I Leave My Job? - 5 Things to Consider When Deciding to Quit Your Job

Updated: Nov 6, 2023

Are you contemplating leaving your job? If yes, here are 5 things you should consider first to make sure you won't regret your decision later.

When you're thinking about leaving, it's crucial to ensure that you're making an informed & thoughtful decision because it's often tempting to believe that the grass is greener on the other side, especially when the desire to leave is strong. In this post, I'm going to share the 5 things you should think about or start doing first if you wanna sure you're taking the right step toward your true career aspirations.

  1. One: Define and Clarify your career goals:

The first step you should take before making any career-related decisions is to define your career goals. Without clear goals, it would be impossible to make coherent choices that will guide your career in the right direction. In fact, you wouldn't even know what the right direction is. This is why so many people go through a large part of their career only to regret their actions or feel lost. Yes, our goals or aspirations may change along the way, and that's perfectly fine, but it's always better to know where you're going at the moment so that you can direct your energy and focus accordingly.

If you have not defined your goals and do not know how you want your career to progress, making any strategic decision about leaving would be extremely difficult. At best, you will likely look for whatever is more convenient at the time or only go after short-term benefits, which may be detrimental to your long-term advancement.

It may be that the current situation is unpleasant, but it could also be the most helpful experience you may gain for your future development. Or vice versa, you may feel like everything is smooth sailing and hunky-dory, but the current job may be taking you further away from what you want to achieve, in which case, you may need to change your job even if you do not have any push factors immediately. This is why goal setting is the most fundamental step before making any career decisions, including leaving a company.

  1. Two: Get clear on why you want to leave

Once you are clear about your career goals, the next step is to carefully examine the actual reasons why you want to leave. Often it's a combination (or mixture) of several factors, situations and emotions that drive us to want to leave our job. If we are not clear about our biggest motivators, we may end up making a rash decision or find ourselves in another dissatisfying opportunity again. Not only that, but by identifying the key reasons for leaving, you can be that much more intentional about the positions, companies, and industries you should target as your next move. Ask yourself the following questions.

  1. What aspects of your current job are dissatisfying or unfulfilling?

  2. Which of the above factors is of the highest priority (or urgency) to you? How would you rank them in order of significance?

  3. How realistically will these problems disappear by moving to another company or industry?

  4. How can I ensure that I will not end up with similar situations in the new company?

  5. Number Three: Are there still learning / growth opportunities left?

Another crucial question is how much learning potential is still left in this position. Even if many (current) factors are unfavorable (such as compensation, work hours, locations, and etc.), if you know that you are still growing and are moving in line with your career goals, it may be premature to leave yet.

I'm sure you've heard stories (or personally experienced instances) where some of the most demanding and challenging experiences at work being the most helpful foundation for future success.

A friend of mine who is extremely successful in the finance industry once told me the story of his first job. Even though it was a decent opportunity, he hated going to work because he felt his boss was micro-managing him and was nit-picking everything he did. He was this close to leaving his job but in the end decided to stay largely because he realized, at the end of the day, that he was learning and growing because of the constant feedback from his boss. And afterward, he realized those years that he did not enjoy actually helped him build the foundation he needed to advance quickly in the later years.

I am aware of countless others who regretted their decision to leave a place where they were still growing due to short-term factors such as compensation, title, or personal preferences and ended up losing several years of their career.

Of course, I am not saying that you should never leave a company if you're still learning and growing. Every situation is different and we simply cannot make a general blanket statement like that. Even if there is great learning potential, if the work environment is too toxic or beyond repair, leaving could be the best decision for yourself. What I am saying is asking yourself this question will help you make a more rational decision, especially regarding your long-term destination.

  1. Number 4: Have you done what you can to resolve/improve the situation?

In my opinion, this is one of the hardest questions to ask ourselves but also one that could offer the most valuable lesson. Throughout our careers, inevitably, we will encounter problems and difficulties. And often, the easiest thing to do is to avoid the situation by leaving the job. However, if this becomes our default mode of dealing with challenges, we will have to move constantly because these things are bound to happen again. And most tragically (seriously), we will never be able to mature.

When there are conflicts with colleagues, bosses, or when our work is not recognized, or other factors, if we simply choose to leave, we will never learn how to overcome similar problems in the future (which, again, are likely going to repeat at some point). Instead, it is by learning to take uncomfortable steps such as (for example) conflict resolution, building or mending relationships, drawing healthy boundaries, and learning to market yourself, that we gain skills hat will help us advance in the long-run, professionally.

Even if the situation doesn't improve despite your best effort and you do end up leaving, you will not be doing so as a way of escape or running away from problems, and you will have matured through the process as a result.

  1. Number 5: Start acquiring skills and knowledge

Once you have concluded that it is time to leave and you're sure about what you are looking for, it's time to do an inventory of whether you have enough skills or experience to obtain the kind of opportunities you're targeting. And you feel that you lack certain expertise, you can start working on it through additional certification, training or education to enhance your knowledge and prepare yourself.

But that's only half the story. If you want to truly stand out as the ideal candidate in this competitive market and actually get your dream job at your top-choice employer, you also need to be strategic in your job search too. This includes learning how to write a consistently attention-capturing resume, tailoring your cv to target each position, identifying the biggest needs of the employer, positioning yourself as a solution to those needs, and convincing the employer that you're the ideal person for the job.

Because the truth is, how the employer will feel about you at the end of the day will be determined by your ability to sell and convince them during the job search and interview process. Therefore, learning the skills to present yourself in the most relevant manner and prepare for key questions in advance is one of the best investments you can make for your career advancement. On the flip side, failing to do so will be one of the most direct disadvantages you can give to yourself.

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