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How I Knew it was Time to Quit My Job (10 Big Questions I Asked Myself)

Almost one year ago, after a long period of questioning and floundering, I made the difficult decision to quit my job just a few years short of retirement. Since making that decision, I am often asked by others going through the same struggle, “How did you know it was time?”

I am always hesitant to give advice to anyone in the same situation, as I believe a decision of that magnitude is incredibly personal. Reasons for leaving or staying will be different for everyone and my questions and struggles may be vastly different from yours. However, there were several big questions I had to ask and answer for myself that helped me make my final decision. Looking over them, I believe these could be helpful for others wondering whether it’s time for a big change. So, with that being said…here are “10 Big Questions I Had to Answer Before I Quit My Job”.

1) How long have you been discontent? This was one of the biggest factors for me when deciding I just could not stay in a situation that left me feeling so unfulfilled every day. Because I was in education, I was blessed to have long breaks for holidays and summer. For several years, those breaks gave me the time I needed to recharge and to get me through nine weeks at a time. But, once that was no longer the case and when I became so anxious that I began feeling true panic as I drove into the school parking lot each day, I realized that this was more than just a season of not liking my job. This discontentment ebbed and flowed for more than two years before it finally came on and stayed for several months. As I realized that I no longer felt any passion for what I had loved for most of 25 years, I knew that it was time to make a significant change and I did not think I could “just hang on” for several more years.

2) Do you need a change of environment/people? I was blessed to work with incredible people who I loved dearly. In fact, that is the part I miss terribly…the people. But, as a last resort to be certain of my decision, I requested a change of schools to help determine if I just needed something new. Once again, I landed in a situation with amazing people who I greatly enjoyed working with, but the job continued to leave me anxious, frustrated and to be honest…miserable. I was really glad to have been given the opportunity to at least try that change before making my final decision and it definitely helped me to know for sure that it wasn’t just one environment.

3) Is it your personality? Why are other people happy doing the same job? This was really hard for me because many of my dearest friends work in this field and they seemed to be doing just fine. So, I often asked “Am I just too weak? Too sensitive? Lazy? Selfish?” I could not figure out for the life of me why I couldn’t just “suck it up” and make it work for me. After all, like I mentioned earlier, the schedule in education is a dream. Holidays and summers off. Not crazy long work days (which actually is a myth…the days in the buildings may not appear long…but the work that comes home is intense). Good benefits, decent pay (at least after 25 years). What I finally realized was that even if the answer was “yes, it IS just my personality”…it IS MY personality and I wasn’t going to be able to change it enough to feel better about what I was doing.

4) Can you change your perspective and find contentment in the mundane things or the things that bring you joy outside of work? What I found was the answer to this question was “yes” and “no”. I tried incredibly hard to compartmentalize and to leave work at work, but the success of those endeavors was short-lived and before long the opposite was occurring. My work life was seeping into every other aspect of my life and I was feeling overwhelmed and unhappy almost all of the time.

5) Is the fear of regret greater than the fear of failure? I knew in my heart that I was being called to something new vocationally – but it was scary. Even though I was miserable…it was a misery that had become predictable. I knew what to expect and there was very little unknown at this point. To leave the familiar to do something completely new felt terrifying. But I also knew that if I didn’t at least try that I would spend the rest of my life regretting playing it safe. I often think of the Biblical account of Peter walking on the water…if he never left the boat, he never would have known what God had made him capable of doing.

6) What are you willing to sacrifice? There was a big financial cost to leaving my job…but there was also a bit of an identity crisis. I had gone to college almost 8 years to carry a title I was proud of and I had established a name for myself through longevity in a career I was pretty good at. What if I boldly followed this new path only to fall flat on my face or to never make any money doing it? What if it was a huge mistake? These were all questions that I had to wrestle…and I had to weigh the costs. What was I willing to give up both materially and emotionally?

7) Is this just a season? After all, I am almost 52. Is this just my mid-life crisis? Am I making a bigger deal of this than it really is? If I hang on a little longer, will the feeling pass? (See question #1). I prayed for almost two years, “Lord change my heart or change my circumstances” before making the move. I wanted to be 100% certain I was not just “going through a phase”.

8) Whose permission are you waiting for? I will never forget the day I realized I am a grown woman who doesn’t need anyone’s permission to live my own life. Obviously, I am not going to make decisions that greatly impact my family without discussing those with them, but outside of that, I have choices. In fact, I remember reading somewhere “You are not a tree, you can move” and thinking, “But can I?” We do have to live with the consequences of our choices, but they are OUR choices. You get to decide what you want to do. (And trust me, there will be PLENTY of opinions about what you should do. Limit who you let speak into your life…especially if they have no skin in the game).

9) Can you go back if you choose to? For a lot of the time, I was thinking that my decision would be a permanent one. What if I got “out” and found the grass isn’t as green on the other side as I might have thought it was. Fortunately, I felt pretty certain that even if my exact position might not always be available to me, there would be something in the field of education I could return to if/when I chose to. So, although it was a big jump, I wasn’t doing it without a parachute and a soft place to land if needed.

10) Do you have faith? I spent months praying and journaling before I made the decision to leave. I read books by Christian authors and listened to podcasts about faith over fear. I knew in my heart that I felt God calling me into a new chapter, but it wasn’t until my husband told me that he also sensed that God’s will was for me to do something new that I knew I had to trust God’s plan for me. I wasn’t able to say I had faith that He would always take care of me or that His plan for me was bigger than mine and then cower when the cost felt greater than I wanted it to. So ultimately, it was a leap of faith and surrender. And once I realized that…I felt an incredible amount of peace and knew I had made the right decision.

Again, I can’t tell you how to decide in your own situation, nor would I…but maybe by walking through some or all of these questions, you will reach your own conclusion and find your own peace. And please don’t hear me say that the field of education is a terrible one. I love education and educators with all of my heart. This is just MY story…and for me, it was no longer where I needed to be. One can feel stuck in a career in any field, at any time and every story will be different.

I would also caution against making an impulse decision on a really bad day. Rarely are our snap decisions the best ones and the last thing you want is to regret doing or saying something that could burn bridges forever.

If you are struggling and need someone to walk alongside you for encouragement and accountability, consider On Purpose Coaching. I would love to help you with your journey. To schedule a FREE consultation session with no strings attached, e-mail me at and let’s connect. Believe me, I know exactly what you are going through and it helps to have someone to talk through the big questions. I’d like nothing more than to do that with you.


Stephani Cook is a life coach, speaker, writer, podcast host and the creator of On Purpose Coaching. Through On Purpose Coaching she helps others to improve relationships and to discover intentional abundant living. She does that through group and/or individual coaching, live event speaking or Enneagram workshops in private and corporate settings.

To connect with Stephani about the possibility of coaching or speaking to your group or organization, visit her website

1 Comment

Stacy Fye
Stacy Fye
Jun 12, 2021

Thanks for posting! Things to consider…

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