Questions To Ask If You’re Unhappy At Your Job
What I discovered when I got real with myself

I had been unhappy at my job for a while before I realized that I had long ago passed the marker with a glaring sign reading “It’s time to quit.”
Of course, there were several pragmatic reasons that I chose to stick around.
One: My job offered a solid, stable paycheck that granted me the ability to live comfortably in the outrageously expensive city of San Francisco.
Two: I had climbed the professional ladder to get this position in the general realm that I was interested in: using technology to improve our very broken healthcare system. This is what I had wanted to do for a long time.
Three: The two people to whom I directly reported were both amazing human beings and personalities highly compatible with my own. I felt so much empathy and support from them that I didn’t want to leave anyone in a lurch.
Eventually, however, I began noticing that it took increasing amounts of energy for me to get the smallest tasks done. I would come home tired and depressed.
My eating habits, exercise habits, and relationships were beginning to suffer. Getting through the workday seemed next to impossible, and doing any extra work put me on the verge of another breakdown.
I felt trapped.
I tried to figure out exactly why I was having such a hard time committing to the career I had chosen for myself. After some hard reflection, I understood the problem.
While I was in the field of my interest, my role responsibilities did not fulfill me. I wasn’t getting what I needed out of my job.
While my job title and scope of work looked excellent on paper, it wasn’t what I wanted to spend 40 hours a week doing. It wasn’t enough that I was in my industry of choice. I wanted to enjoy my role within that sphere.
Once I came to this conclusion, I began asking myself some other questions.
What were the parts of my job that I really couldn’t stand doing?
I don’t like work that consists of hundreds of small tasks that involve very little problem-solving skills.
I don’t want to edit endless word documents, and I am not at all interested in choosing the right font and color for headers. Spending hours engaging in this tedium is enough to make me bury my head in my hands.
It hurts my soul to fill in multiple tracking spreadsheets, and I loathe going through hundreds of emails. However, the email-related issue might be something I just need to come to terms with.
Furthermore, wasting time in hour-long meetings that have about a five to ten-minute amount of relevance to me is not my cup of tea. I like to know what I need to do in a straightforward manner and get on with it.
Were there any tasks that I enjoyed?
I loved solving problems that required critical thinking skills. I enjoyed collaborating with and learning from the technical team.
The answer to the question is short, which is another testament to what a bad fit there was between my interests and my job.
What would I need in order to be happy at my job?
For me, this question was about a future job. I knew that this position wouldn’t be able to provide what I needed. That may not be the case for others.
My needs may change in the future, and I’ll be open to that when the time arrives.
For now, I want a work environment where I can develop my analytical skills independently. I’d like to avoid unnecessary meetings, and I want to work from home.
While this may seem difficult to find, freelance writing is giving me the kind of work lifestyle that I desire for the time being.
Of course, there are compromises. Changing careers has come with lower financial resources. Still, I would rather make less money for now and spend my time invested in my work than dread each weekday and feel my mental health suffer at my job.
Being tremendously unhappy at my last job taught me a lot of things. For example, good managers can make you want to stick around.
I now understand that my path can change, and that’s okay. As I learn more about myself, I will hone in on exactly what I’d like to do professionally.
When everything’s said and done, it’s important to consistently check in with yourself. I’ve made this a goal in my own life.