Terrified to Leave a Comfortable Job? Here’s How to Get Over Your Fear

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It's scary to leave the job you’re in because of the uncertainty of where you could end up. We’ll help you combat that with a few strategies.
Mar 14, 2024 11 min read

It's scary to leave the job you’re in because of the uncertainty of where you could end up. There is a common phrase that can describe this situation: “The devil you know is better than the devil you don’t.” But although it may be scary, the feeling inside of you that tells you that things aren’t right may be the same feeling that’s pushing you towards something greater for you and your career.

In this article, we explore:

  • A psychological understanding of the fear of leaving a job.
  • How to get over that fear to blaze a new trail?
  • Strategies on how to assess your goals and skills to see where you fit in the ever-expanding job market.
  • How to get all of your ducks in a row, with real-world examples of how to leave a company well.

What’s so scary about leaving a job?

Every single day, you are given so many choices that you learn to make choices on the fly. Whether it’s going to the grocery store and choosing between name-brand and generic products or choosing which route you will take to get home, you are hard-wired to make decisions.

But although human beings are good at making little choices, often the big choices are difficult for us. As soon as we choose to make a life-altering decision like changing jobs, alarms start going off in our heads.

Whether it’s fear of the unknown, fear of failure, or financial concerns, all the fears we feel are real and should be acknowledged. If not acknowledged, the fear can fester and develop into full-blown imposter syndrome when we finally get that job offer. Below, we’ll dive a bit deeper into each of these fears:

Fear of failure

The more that we desire something, the more it can cause us to feel fear. This fear is tied to a fear of failure, of losing that thing that we want so dearly. James Clear, in his book Atomic Habits, puts it like this:

The pain of failure correlates to the height of expectation. When the desire is high, it hurts to not like the outcome. Failing to attain something you want hurts more than failing to attain something you didn’t think much about in the first place. This is why people say, “I don’t want to get my hopes up” (Pg. 263).

When you daydream and think about how much a new job could change your life, it creates a deep desire inside of you to get that job.

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To address your fear of failure, make a list of all of your skills and abilities and do some research in the job market to learn how highly valued your skills are. Knowing that your skills are highly valued can help to calm the fear of failure inside of you.

Fear of the unknown

You may also be afraid to venture out into something that you don’t know or understand. We know things aren’t always better in other companies. Even if you’re in a fairly dysfunctional–or even toxic, work environment–you can’t help thinking that maybe things won't be better if you go to another company.

At this moment, you may not know all the options that are available to you. Gaining knowledge and understanding more about the jobs that are available to you and the companies that are hiring can help you understand a little more about the job market.

One of the best things you can do right now is to build a strong network of professionals within your market. Learn a bit more about the companies that they work for, the roles and responsibilities that they have, and gain a better understanding of what the job market looks like.

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Take baby steps as you plan out your career progression. You can learn a bit more about similar companies to the one that you work for in your city or region.

Financial concerns

Within upper management circles, there’s a common phrase being tossed around to employees who are given incentives to stay at their company longer than they’d like to: “golden handcuffs”. Those who feel shackled in their career through golden handcuffs, feel like they can’t leave their job because of how highly compensated they are through their salary and benefits package. Those in this situation feel like they can’t leave because they’ll never be able to make as much money as they're making right now.

Finances can be a big concern when switching to a different job. You always want to be making more money as you progress through your career.

But salary alone doesn’t make up
the full compensation package that a company can offer you. Here are some other things you can think about when applying for a position include:

  • Benefits (medical care, dental care, vision care, etc.): Benefits can play a significant role in whether you take a position. If you have young kids who need braces or an elderly parent who needs medication, benefits may be a huge contributing factor to whether or not you take a role.
  • Paid time off (PTO): Creating a better work/life balance through paid time off can certainly be a draw to a company. Consider this: one company is offering you $65,000 a year with 10 vacation days, while another company is offering you $60,000 a year with 20 vacation days. PTO might make you think twice before taking a job that pays more money.
  • Remote work for work-from-home opportunities: since the COVID-19 pandemic, many companies have introduced fully 100% work-from-home positions. Being able to work from home may contribute to you deciding to join a company, as you don’t have to brave a daily hour-long commute into the city to get to work.

It’s important to know your worth when you’re applying for a position, so do your research and learn a bit more about how much you can expect to receive in your role. The sad truth is that most companies will pay you less than what you deserve. By knowing what you’re worth, you can clear up those feelings of fear with compensation.

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Do your research to know exactly what you should expect to be compensated for in a role that you’re in. You can do this by scouring through job applications and seeing what the average salary is for somebody in your position.

Assessing where you are at right now

As you work through the fear associated with switching a job, the best thing you can do is to assess where you are right now, and what skills you bring to the table, and start to think about where you want to end up in your career. Your goals and aspirations will drive the job search process. As mentioned above, tiny baby steps, incremental decisions that you make, can help you make decisions now to get you to where you want to be.

Ask yourself why you want to leave

The first thing you should do when you’re assessing whether you want to leave is ask yourself why. Why do you want to leave the current workplace that you’re at? Maybe your boss doesn’t understand you or you feel like the work that you’re doing isn’t meaningful and valuable.

Whatever the reason for you to leave your current job is, write it down somewhere. Whether it’s a napkin, journal, or a Word document, keep a note of why you left the company that you’re at. This can also help you form future goals and aspirations to find a job that suits you better.

Look at the job market right now

Discover if other companies are hiring right now at this moment. This takes a good deal of research to find the right position for you. The market is always changing, and there isn’t a crystal ball available to figure out which company is the best one. However, there are ways to assess whether a role is going to fit you.

Start scanning through job descriptions on job boards or company websites. This is brilliant advice for any jobseekers, as you can tailor your resume to a specific job description.

Look at your career aspirations

Don’t stress about finding a job that you’ll stay at for the rest of your career. It can be overwhelming when you think you need to find the perfect job, one that you’re going to be at until retirement. Instead, ask yourself this question: “Will the job I’m pursuing be one that will fit into my overall goals and expectations for my career?”

How you can do that is to write down a list of goals that you want to hit throughout your career. Some of these goals may include:

  • Skill development: Every single role you are involved with can help you gain skills and abilities that can allow you to progress in your career. Ask yourself this question, “Will this job allow me to gain the skills that I need to get to where I want to be?” For example, if you are a computer programmer with the aspirations of becoming a Chief Information Officer, you may look for positions that allow you to go beyond simple coding and website design, and allow you to develop management skills.
  • Networking: You may also choose a position that allows you to network with other professionals in your career. Having an established network of contacts can allow you to progress further in your career.
  • Career advancement: Larger companies that have been established for a longer period usually have a better system to promote candidates from within to management positions. If you’re looking to fast-track your career, you may look for a job at a company that could allow you to enter management sooner.
  • Entrepreneurial: Some companies will allow you to gain the knowledge that you need to be able to start your own company and create innovative products. If that’s one of your career aspirations, look for a company that can allow you to get to where you need to be.
  • Work/life balance: Maybe you’re tired of the “rat race”, of feeling tired because you have no work/life balance. If that’s you, look for a less stressful role that offers greater benefits like paid time off or working from home.
  • Being able to make a difference: Maybe the work that you've been doing at your company just doesn’t feel meaningful. Maybe you want to do something with your life where you can look back and say that you made a difference. This might be a major goal that you have in your life, and that affects your job search.

Get outside input

When you’re on the fence about leaving the company that you’re working at, it’s best to speak with someone that you trust. It should be someone objective, able to see the pros and cons of staying with your company or leaving.

This is why it’s important to have an extensive network of professionals who are in the same field. Best to speak with somebody outside of your current company, as they can provide you with a less biased view of whether you should move on. If you stay in contact with former colleagues or bosses, you can reach out to them and start to ‘test the waters’ to see if there are openings at other companies.

Also, speak with the people who care about you in your life, like your spouse, family members that you trust, and friends whose opinions you value. They may provide you with deeper insights Into your reasons for wanting to leave the company that you’re at. They may also allow you to look inside and check to see if it’s your ego that’s driving your decision or if you are making the right decision at the right time.

Organizing your affairs

There is never a great time to resign from a job, but there are some things that you can do to help lessen the chances of falling out with bosses and colleagues. Here are some tips to keep in mind to leave your current job on a pleasant note


  1. Write a resignation letter:A resignation letter isn’t just a document that shows that you’re leaving the company. Most HR departments will need you to put in writing that you are leaving the company and giving your two week’s notice. You may feel like having a simple conversation with your boss will be enough, but putting in writing that you want to leave the company is a professional thing to do.
  2. Leave on a positive note: Whether in your resignation letter or in person, convey to your boss how grateful you are for all the time and effort that he or she took to build into you. Make sure to not burn any bridges with your boss or coworkers by leaving on a sour note, like calling someone out on a past grievance.
  3. Prepare A resignation speech: When you hand in your resignation letter to your boss, you should be prepared with a couple of things that you want to say. Explain to your boss how grateful you are for the work that you’ve been able to do and for the mentorship that they have provided. Also, be ready and prepared for your employer to counter the offer.
  4. Pick the right time to leave: There is a right time and a wrong time to leave a company. For example, if your company just took on a major project which will last for the next month. If you leave right at the beginning of that, not only will it create a sour taste in the mouths of your colleagues, but it will also limit you from being able to put that project on your resume as an example of your achievements.

Example of a resignation email

If you’re scared to make the jump into a new career, speak with acareer counselor from Enhancv. They’ll point you in the right direction with how to ace your next interview and are also experts in resume writing and can help you to better understand the interview process.

Key takeaways

  • Don’t be afraid to address your fears head-on by assessing your skills and abilities and understanding the market better.
  • Be sure to get input from outside sources, including a network of colleagues who work outside of your company.
  • Take a serious look at the job market and learn about the other companies that are hiring for similar positions to the role that you fill now.
  • Be sure to leave your company on a positive note.
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Dave Van Kooten
Is a human resource expert that helps passionate jobseekers to put their best foot forward to prepare for an interview. He believes that success can be achieved through going out of your comfort zone.
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