Why I Decided To Quit My Job… All Five of Them

In eight years I’ve had five very different jobs. Some of them overlapped and some lasted longer than others. The consistent thread among the five of them is that I’ve left them all on my own terms and felt very good about that decision each time. 

However, deciding whether or not to leave a job is not something to take lightly.

I carefully thought it through each time and there were different reasons based on each job and that time of my life. 

The job I left because I hated it

My first full-time job was a poor fit from early on. Unfortunately, the manager who hired me left very soon after I started and the position morphed into something different from that for which I was originally hired.

However, I was committed to staying there for at least one year because I was gaining necessary training related to my career and trying to provide some consistency for clients under my care. 

There were good and bad moments with that job.

  • I formed some wonderful friendships and felt very supported by my colleagues.

  • I learned priceless strategies for managing my time in a busy environment.

  • I was exposed to clinical experiences I would not have chosen to put myself in, but those experiences have proven valuable throughout many points in my career to date. 

However, I knew the job was not what I wanted and I was not paid well for the stressful work.

I began to resent the company and dreaded going in to work each day. I came home feeling exhausted because it was emotionally taxing to be there knowing it was not a good fit. I stopped working out, didn’t eat as well and gained weight. I wasn’t always fun to be around. 

Basically, the negativity surrounding my work was permeating every other area of my life.

I pulled through for exactly one year and left on good terms. Thankfully, I was also working just two days a week as a contractor for another company and when I left this job I was able to obtain more hours there. Which brings me to that position…

The job I left because I wasn’t growing

I originally started this job to make some extra money while working in my previous position, and because it was work I truly loved. As I started to work more hours I was able to learn some new skills and take on additional responsibilities. My coworkers were fun (for the most part) and the schedule was flexible.

This was the good life!

However, three years later, I was still doing exactly the same work. The job was very specific and the company was a small business so there was no room for advancement or expanding my position.

It was difficult to leave this position because of the many perks, but I realized that I wanted to grow in my clinical skills and it wasn’t going to happen staying there. 

I looked around for other jobs and had the good fortune of finding something that would be a good transition fairly quickly. It seemed like something that would provide me a lot of opportunities in a new area of my industry so I took it. 

The job I left because I had a new opportunity

This next job was also a really great fit for me and I learned soooo many things. I found out that training was a skill of mine and was given opportunities to pursue this more. I worked with a supportive, hardworking and intelligent team of people. My boss was the best I’d ever had (and still have ever had). 

Every job has its ups and downs so things weren’t perfect but as far as jobs go, it was a pretty great deal.

I knew going in that this wouldn’t be a long-term position and my boss knew this, as well. She offered me opportunities to grow as much as possible but some point it became clear it was time for me to look into entry-level management (since my ultimate goal was to manage my own business). 

I used the fact that I had a good job to take my time and select what would be a good stepping stone for me.

I talked to my boss about it. I spent time asking lots of questions during interviews, and then identified what was a good chance for me to gain some management experience and new responsibilities. 

The job I left because I needed flexibility

This new management position was for a much smaller company so I ended up doing some things that were well beyond what I had done before, but also things that our program assistant in our previous company had done. I learned about management, represented the company at district meetings and was given the opportunity to pursue a lot of my training interests.

However, at this time I had also started my own business on the side and it was begging for more of my free time.

My commute was one hour each way to and from work. I struggled to manage things at home while also starting a business. I needed some flexibility.

Again, I took the opportunity to look for other positions while I still had a good job. I looked for jobs that would be closer to home or provide telecommuting options.

I also approached my boss about flexible work options, something that was really hard for me to do. He was very understanding and didn’t say “no” but he said “not yet.” 

That kept me looking until I found the perfect solution… a job that would allow me to telecommute two days a week and also gave me a large pay increase.

My future boss seemed great and it was something totally new where I could learn more skills. I dove in head first. 

The job I left because the company was poorly managed

My next (and last) job was honestly a train wreck from week one.

Some things were amazing:

  • My boss was really great and she was teaching me so much.
  • I was now managing a larger team and had the opportunity to impact program policies because we were starting this from the ground up.
  • I was learning new clinical skills.

However, the upper management of the company was working from a traditional management mindset that suits factory employees rather than a motivated team of highly educated people.

There was inconsistency and the company espoused values that were no where near the actions or policies enacted. 

Due to poor communication, lack of planning, and short-sighted and abrupt decisions, the program began to struggle very early on. That put pressure on everyone involved. I was required to relay bad news to my employees on a regular basis.

Morale was low and things continued to go from bad to worse. 

Thankfully, I was able to turn lemons into lemonade and use one of these unfortunate circumstances in my favor. I finally decided it was time to focus on my business full-time. The timing was perfect because moral dilemmas in management were becoming more common and I could no longer support what was happening in the company or the program. 

My personal values were out of alignment with the values expressed by the company.

I was no longer growing as a professional and I had the opportunity to pursue my own business. It was time to call it quits for the last time. 

Life Lessons

So what have I learned from all these career moves?

Your work impacts your life in a multitude of ways that include so much more than just money. Finding a good fit is priceless, but the job that is a good fit for you now may not be a great fit two years from now.

If you’re trying to decide whether or not it’s time to leave your job, ask yourself the following questions:

  • Does my boss provide me the support I need?
  • Am I growing professionally (learning new skills, exposed to opportunities, etc.)?
  • How do I feel when I arrive home from work each day?
  • How does this job fit in to my long-term career goals?
  • Are there things I can adjust now to make my job better?

It’s important to identify how much of a conflict it is for you to work in your position at your company.

If the company’s values aren’t in alignment with your values, that is when conflict and discomfort is likely to arise. Or perhaps your skills and goals are not a good fit for the needs of the position (e.g. being over or under-qualified). 

Evaluating the situation as objectively as possible and identifying the potential mismatch can help you decide what action to take next.

That may be looking for other jobs, asking your boss for training, or deciding on a timeline for advancement so that you feel motivated to stay where you are and gain all the experience you can. 

If you’re still not sure where you fit in to the working world, a strategy session can provide you guidance that is based on your interests, skills and potential for growth.

Don't let doubt or worry keep you from achieving a more fulfilling life.