9 Scary Thoughts About Leaving a Job


9 Scary Thoughts About Leaving a Job

Photo by Toni Blay

Deciding to quit a job is not easy. It requires going against the norm, facing the scrutiny of your peers, and then having enough faith to believe things will turn out okay.

Many people entertain the idea of leaving their job, much like the distant dream of winning the lottery. However, the closer you get to making it a reality, the more that your fears and doubts will begin to surface.

Your fear is an indication that something about the path strikes a chord with you. Fears are sometimes hard to articulate, but bringing them to light can help you face them. Here are some the thoughts I had when I was leaving my corporate 9-5 banking job to take a year off.

  1. Losing the security of a good steady income. Not only would I be spending my savings, I’d be giving up the professional salary I would have been making during my year off. That’s a lot of money if you think about it.
  2. Hurting future job prospects and a gap in my resume. Would a future employer want to hire someone who just finished taking off a a year from their last job? Would my old boss still give me a good recommendation if they’re called for a reference in the future? How would I explain my reasons for taking time off to future hiring managers? Taking a year off seemed like a huge taboo.
  3. Deferring financial goals. Building wealth and accummulating assets like a home and a retirement fund were goals I had started working towards. I was at the crossroad between continuing to work and putting a downpayment on a home, or using a substantial amount of savings to fund my extended time off. Indeed, just about everyone I talked to told me buying a home was a more sound investment.
  4. Feeling like alone in my journey. It was difficult to talk about my unsettled feelings towards my career and what the options were, particulary since others around me continued to assure me that it was normal to not fully love your job or that it’s common to wake up on mornings wishing you didn’t have to work. Deep inside I knew it would eventually come down to me leaving my job, but taking a direction different from everyone else raised a lot of self-doubt.
  5. Uncertainty about what I’d do when my year off was over. Would I have to return to a similar job as before, thus ending up where I started? Would my year off have been in vain with tens of thousands of dollars down the drain? The worse case was disturbing, but I didn’t know what the best case scenario was either. Would it be finding a job that paid just as well but where I could wear jeans, a totally different job that I loved but was getting paid less, or would I want to try freelancing? I had no idea.
  6. Telling people my decision. I’d have to explain my seemingly-crazy choice to my boss and colleagues. Friends would also eventually find out, along with people who I suspect secretly liked to compete with me in the race for better job titles and salaries.
  7. Articulating my plans (or lack of) when people ask what I’ll do with my time off. The idea of having to explain my plans to potential critics was intimidating. I imagined all the unconstructive feedback I would get (which I did get a bit of), but I also knew I had an internal critic to face as well.
  8. Taking an active stance and going against convention. I was scared about going against the norm for my job, but if I had the power to take control and go against the norm for my job, what does that mean for other areas of my life? The idea that I had the control to also follow an unconventional path in other areas in my life also opens the door to possibilities that scared me.
  9. Facing the truth that I wasn’t fulfilled where I was. I have almost always felt that there was something slightly off about the 9-5 lifestyle that I couldn’t put my finger on. It took me a long time to recognize and acknowledge it, but the scariest was facing the idea that I could take action and couldn’t play the victim role anymore.

    These were all big fears to face – big enough that they may cause you to cry in frustration or secretly wish you could be a ‘regular’ person who accepted their 9-5 fate without so much question.

    If you feel alone, know there are many people going through the same experience as you and the further you continue on your journey, the more people you’ll meet who are going through the same process.

    If taking the leap is right for you, and when you’re ready, you’ll find that courage will magically appear by your side to help face your fears and do what’s right for you.

    Before you know it, you’ll find yourself happier, lighter and seeing more incredible things flow in your life than you would’ve imagined before.

    >> What scares you the most about leaving your day job? Or, if you’ve already quit your job, what tips do you have for people preparing to leave?

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    • njn

      Great post! In 1982, I walked away from what would now be a $90,000 a year job. Lots of triggering experiences but my bosses did understand. I had been a good worker and had been thrown in to a few jobs and made them work.

      I went back to school. First class, at my alma mater, was Organic Chemistry, an entire year, with lab, in seven weeks in the summer. After 8 years away from school, I still got second highest grade. Prof said something about sacrifices. Tell me about it.

      The whole thing didn’t work out the way I’d hoped, but it worked out okay. I have no regrets.

    • Wrabbit007

      I would love to take a year off and travel, simply because traveling is when I am the happiest and, I think, at peace with myself.  However, I ADORE my job and don’t want to lose it!  I love the home I’ve built with my husband and don’t want to sell it, either.  The thought of renting it to others who won’t take care of it horrifies me. Hm, makes taking a year off a bit of a challenge. 

      That’s why I squeeze travel into every holiday I get: kind of a compromise.  A lot of people can focus on traveling that way too – sometimes it doesn’t have to be “go hard or go home”.   The trend lately in the world of travel blogging is to leave your life and go for a RTW trip, which is beyond what a lot of people can do.  I love this post, but I just want to remind people that it doesn’t mean you don’t get to explore the world if you don’t take a gap year.  bit.ly/MyPGrl

      • You make a really good point about taking short vacations rather than a year-long one, particularly if you love your job and your day-to-day life. I think many people who have the desire to take an extended trip need it for finding clarity if they’re uncertain about the direction of everyday life, for example if they’re contemplating their careers or life purpose, or maybe they need the extended time for rejuvenation or personal growth. 

        Thanks for stopping by!
        – Lily

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    • Hi Lily,

      Been reading your blog for quite some time now. And I find it very inspiring. I just filed my resignation letter two weeks ago and I’ll also be going on a trip for the next few months. Deciding to finally do it last year and prepare for it seemed like a relatively easy decision. But during the week that I filed it, it was pretty nerve-wracking. I was able to finally comprehend the gravity of the decision I made. And this blog post summarizes all my fears and concerns. But I knew that I had to do it and backing out was not an option. I just had to remind myself again of the reasons why I made this decision.

      And after doing it, I felt lighter. I just knew that I had to change something in my life and pursue the things that make me happy.

      And reading your realizations and experiences remind me that it’s going to be worth it. Thanks again for sharing to us your story. Keep inspiring people! :)

    • Hey Lily,

      It’s so true, there are so many reasons that quitting a job can be scary but what I’ve learned is everything will work out some way or another. I haven’t worked a traditional job for the last 3 years and I’ve been making it, both my daughter and I. Now I may not have the picturesque lifestyle many dream of, but I’m happy that I get to make my own choices and do the things I want. We all have to give up something in order to have something else, and many are giving up their happiness for a “secure” job. I’d rather be happy and fulfilled knowing I love what my life is made up of. Hey to your courage and believing in yourself. Best of wishes, and don’t forget one of these days we’re going to have to meet.


      • “What I’ve learned is everything will work out some way or another. I haven’t worked a traditional job for the last 3 years and I’ve been making it, both my daughter and I.”

        Alyx, you’ve made a really an inspirational point. It took time for me to let go of what I believed “security” meant. Knowing how challenging it was for me, a single 20-something year old, I have so much admiration for others with families to support and still able to find the courage to think outside what is traditionally considered “secure” or “normal”.

        And yes, we will meet one of these days… perhaps over coffee and working on our Macs! :)
        – Lily

    • Your post is definitely something I needed to read today. Although my quitting day is many months down the line, I’m faced with the fear that when I come back from my trip I will feel alone, and I won’t have a stable income. But something inside tells me that my trip is worth it and everything will work out in the end. It always works out. Always.

      • Hi Sheryll,

        I was scared before I started my trip – scared of being lonely, uncertainty, not having income – but none of those feelings surfaced while I travelled and now that I’ve travelled for a few months, I can’t think of having made a different decision. I do believe that “will work out in the end” as you mentioned.

        – Lily

    • Hi Lily, I remember when I quit my job to start my own business. It was scary at the time, but I was also motivated by the fact that I hated my job and didn’t have much hope of finding a better one. I didn’t end up traveling for a year, although I did make it to South America.

      This year is definitely going to be one of transition, and more travel too! I don’t have all my plans lined up, but I’m mostly okay with that. :) For me, the worst part is before I make a decision. Once I decide to make a change, I feel so relieved.

    • Kim

      No health insurance scares me! I know we can get travelers insurance on the road but when we come back… nothing.

      #8 really stood out to me. It’s what I’m finding out about myself right now- which is that it is thrilling and scary to realize you have all the power and control over your life. It’s like a famous quote that says that our greatest fear is not that we are inadequate, our greatest fear is that we are powerful beyond measure. True!

      • Hi Kim,

        I love that quote – it’s intimidating to consider, yet very simple and true.

        – Lily

    • To help ease the feeling of being alone I wanted to address all 9 points:

      1) Once you are gone you won’t regret passing up the income. I made 80K at my job and I don’t miss it a bit.
      2) There isn’t a gap at all. Employers are human too and they will value your experience. I once got a job in technology (10 years ago) because I could talk about how many places in Asia were skipping cable internet and going straight to wifi. You do learn things on the road.
      3) Instead of investing in retiring you are investing in your happiness. I also could have bought a home instead, and sat in a beige room wishing I could travel instead of having a mortgage.
      4) You aren’t alone in your journey, there are hundreds of travelers on my twitter lists that are going through the same thing. When you open your mind to alternative views you start to realize that there’s a big group of us doing this even if our friends are not,
      5) It’s okay to be uncertain now, you may find with fresh eyes that you find a passion you want to pursue. I did.
      6) When I told people I was shocked at how many said, I wish I could do that. But they have a mortgage…see point 3 :)
      7) You don’t have to justify what you are going to do when you travel because the reality is it all changes.
      8) Challenging convention should be welcomed not opposed, it’s how we change the world.
      9) I wasn’t completely happy either but made the tough decision to leave. You should pity the rest of the people who aren’t happy but doing nothing about it.

      On the road you start to meet so many people from different backgrounds and you start to realize that money and career aren’t anything, happiness should be number one and you’re on the road to it.

      • Hi Ayngelina,

        You just gave me, and probably many others too, a huge reminder of how and why you should follow your heart and that things will work out just fine, even if one is initially afraid. Thank you.

        – Lily

    • Unfortunately I didn’t get the choice to quit; I was laid off. But I’m taking it as a huge opportunity to take this time to finally do what I want to do: work from wherever the heck I want via an online business. I’m determined!

      • Hi Briana,

        Having a fresh start is sometimes one of the best privileges! Best of luck with your pursuits and keep us updated :)

        – Lily

    • I guess I was scared simply because it was something nobody around was doing. It’s human nature to follow the majority and we don’t feel comfortable making unpopular choices. But leaving my job and traveling was the best decision of the lifetime. It’s not only because traveling is great, but also because being away from 9-5 job for long does widen the perspective. I discovered lots of things about myself and how I want to live my life. Priceless experience.

      • Hi Magda,

        I couldn’t agree with you more about how much growth one experiences through travel and being away from the 9-5 norm. I was nervous when I quit my job, and even for months after, but now that I’m 9 months into it, I realize I haven’t once wished that I was back at the office. Looking back, I can’t think of having made a different decision!

        – Lily

    • Ugh, we still have to do this and it is a dreadful prospect. For pretty much the reasons you listed above. I’m more scared that they hate me for abandoning them as I’ll be leaving in the middle of a project.

      • Hi Jill,

        I know how you feel leaving during a work project or at time when the company is short-staffed. I tried to compensate by giving many weeks of notice, although thinking back, there probably wouldn’t have ever been a “good” time for me to leave the company’s perspective (unless they were about to lay you off) :)

        – Lily

    • We’re having the exact same thoughts now – sometimes we think about it and think it’s crazy we’re leaving such good jobs, but then we really think about it and it’s more crazy not to chase our dreams while we still can.

      Even though one door might close, we’re sure that another (if not several more) will open as a result of our RTW!

      • Hi Amy & Kieron,

        I completely agree with you – it’s scary, but “if not now, then when”? I also believe that following the path you feel most connected to will naturally help you see new opportunities along your journey as well.

        – Lily

    • I’ve met many people on my previous travels who struggled with number 5 – a lot. Some ended up back doing what they were doing before, but with a store of goodly memories, and a depleted bank account. Others have changed their lives dramatically, although they had no idea what would happen to them when they set out on their journeys. I guess it’s about having the courage to cross the Rubicon, and letting fate test you. I remember once I left a job I didn’t like, with enough money for a few months off, and no idea of what I’d do, and a lot of fear about whether I’d ever be able to find a job again. I had a great 3 months, and then got a better job, with more flexibility, and more money. Not a revolutionary change, but on the other hand not a disaster either. One of the most practical tips is learn how to reduce your expenses. Once you really get a handle on keeping your costs down, and saving more, it makes quitting your job, or taking a year out, a lot less stressful. The other piece of advice I’d give to people is believe in yourself. We are often far stronger and more capable than we think we are.

      • Hi Tony,

        Your tip on managing your expenses is a great one, I don’t think I could have gone on my year off if I had saved aggressively in the previous years. I travelling through South East Asia will give me even more motivation to save in the future because I know even $4 saved on a Starbucks coffee can buy me an entire meal here or almost the cost of a guesthouse for the night.

        #5 is probably the only one that still makes me anxious, mostly because I’m approaching my 10th month of my year off and still don’t know what I’ll do afterwards. For now I’m keeping the faith that things will work out and start thinking about the question thoughtfully.

        – Lily