Building Up The Courage to Leave Your Job

Even if you know you’re not happy at work, it can be challenging to leave the security and known challenges of your job for the freedom and unknown challenges of unemployment. Leaving your job can raise lots of uncomfortable questions:

  • What will I do if I run out of money?
  • What happens if I can't find another job?
  • How will I fill my time?
  • What will my friends and family think about me?
  • What will I think about myself? 

Luckily, there are a few useful techniques to bridge the gap between your desire to leave and your belief in being able to do so successfully. This post will walk you through the process I used to overcome my fears about leaving my job, as well as tips and tricks other people have used to successfully manage the transition.

Like most of my writing, this post focuses on extended time away from full-time employment, although I hope it’s useful for people leaving jobs for other reasons too.

My Experience Preparing to Leave My Job

Even after I was financially prepared to leave my job, it took me a while to become emotionally prepared. I thought that walking away would be easy; I knew that I wanted to leave, and it felt silly to have the resources to take a break yet find yourself unable to. 

After talking with other people about their experience, I found that I wasn’t alone. People consistently underrate the importance of psychological issues when it comes to leaving their jobs. Even the more “logical” aspects of planning (such as your financial plan) carry some important and deep-rooted psychological ties.

Why It’s So Hard To Leave Your Job, Even When You Think You Want To

Part of why it can be difficult to get past the mental hurdles of leaving your job is because a job meets a lot of personal needs—we get more from jobs than just a paycheck. Here are some of the needs that jobs meet:

  1. Money; financial security.
  2. Meaning; a sense of identity.
  3. Social network; friendship and human connection.
  4. Power; seeing an impact in the world from your work.
  5. Schedule and routine.

This part of taking a sabbatical is very similar to the transition that people make when they leave the workforce permanently–retirement. Because of this, we can use research and stories from retirement to inform how we can manage the transition to a sabbatical in a healthy and productive way. You’ll see a few ideas from retirement researchers in the list below.

The exercises and perspectives below will help you explore the emotions around your decision to leave your job; they helped me solidify my decision to leave and gave me the confidence that taking a sabbatical was the right choice. I hope they help you out as well!

11 Ways to Psychologically Prepare for Leaving Your Job

  1. Recognize and appreciate your fear as a self-protective impulse.
  2. Realize that your job is not guaranteed either—you could be laid off, need to take extended sick time, or be otherwise unable to work out of choice or not.
  3. Create a job leave checklist so that you have a plan for transitioning out of work and into your sabbatical.
  4. Create a sabbatical budget to build confidence in your savings and spending plans.
  5. Reviewing your plan with your significant other, a trusted friend, or sabbatical community can help vet your plan and point out things you might have missed.
  6. Complete this short journaling exercise to reflect on your experience and feelings:
    • Write down all the things that you are unhappy with in your current position to get them down on paper and make them more tangible.
    • Write down all the things you are excited for, to change your mindset from "I hate my job and should have quit a year ago" to "I'm excited to have the time and space to do the things I want to".
    • Write down all the things you have achieved at work in a way that makes it feel like a complete project that you can feel good leaving.
    • Review the non-monetary needs your job fulfills (social network, work impact, etc.) and sketch out how you can meet those needs during your break. This is closely related to the identity bridge exercise below!
  7. Go through a fear setting exercise to get more comfortable with the risks of leaving your job.
  8. Prepare to build an identity bridge during your sabbatical. There’s a lot to this, but you could start by figuring out what projects or hobbies you’d like to spend time on during your sabbatical.
  9. Set a deadline for yourself with personal or professional meaning. I gave myself an artificial deadline of leaving around my 10 year anniversary, for no reason other than it was a nice round number. You might use something like a certain amount of time at a particular job, an age milestone, or every 7 years (the traditional timing of a sabbatical).
  10. If you know people who have left their jobs to take a sabbatical, reach out to them to chat and learn from their experience!
  11. Read other people’s sabbatical stories. Everyone’s situation is different, but finding common challenges, solutions, and outcomes can help you learn how to approach and benefit from the transition of a sabbatical.

I hope that these exercises give you some new ways of thinking about leaving work and getting the most from your sabbatical.


Do any of these techniques resonate with you? Try it yourself and see what you come up with!

Further Reading & Resources

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