When you want to leave your job: 8 questions to ask yourself first

We all are reading about “The Great Resignation”. I can’t open LinkedIn without seeing someone in my network to be congratulated on starting a new job. I get it. This last year plus was rough. Some companies shifted to support their workers; others did not. Some companies are forcing people to come back to an office while others are extending the flexibility. Some people have decided life is too short to spend their days in a meaningless job with no future or to be toiling away for a less than reasonable wage.

I always encourage people to find a job or career that aligns to their values and meets their needs. Life is too short to spend a lot of our days doing something we can’t stand. No one should wake up with dread every day. We should rest our heads at night feeling we did our best and wake up with some energy and excitement to take on what is ahead for us.

The job market has also changed. For those organizations who allow flexibility, they extend their talent pool greatly. They can hire from all over the country or the world depending on their reach. For job seekers, this also opens up opportunities to move into new industries or find a better-fit job.

To make a job change is a very personal decision. Only you can know when it is time to move on. Maybe there are some dealbreakers you can’t stomach anymore. Maybe you aren’t able to accomplish what you’d like at your current organization. 

A question at the crux of deciding to leave can be: Are you running away from your current situation or running to something that is a better fit for you, your life, your family. Or, is it a little bit of both. Obviously, you wouldn’t be leaving a job if it was a good match. However, I have also known people who left jobs they held for a long time just to try something else or somewhere else. 

No situation is perfect; leave perfect at the front door. It is a myth. There will always be processes that don’t make sense, politics you can’t understand, and personalities that can be challenging. This is part of being human working alongside other humans. I suppose if you work with robots, you may not have these challenges.

Before you decide to launch a job search or entertain a new job, ask yourself these questions.

1. Are you living in sync with your values?

The most important question to ask yourself is are you living in sync with your values. When you are out of sync, you will know it. You will feel stressed, anxious, edgy and maybe have insomnia. You wake up with that dread feeling or the feeling that everything is just too darn hard. You feel very much like a square peg being shoved into a round hole. Things are uncomfortable and not quite right. Being in a position where you can live your values, whatever those are, is critical to being happy and fulfilled. If you don’t know your values, spend some time to think about it. What matters to you? For me, it is autonomy, being valued for my expertise, being inclusive and fair. These are at the core of my being. When something isn’t fair, I really feel pinched. When I am hovered over or micro-managed, I almost get angry. Know thyself. This is always the first question to ask.

2. Do you feel connected to the organization’s vision/mission?

For some, being connected to the bigger picture may not matter. For others, the industry matters or how involved your organization is in their communities or charities matters. For me, the industry has mattered a little less than the role and my ability to make a difference in employees’ lives. I have worked in real estate, professional services, technology and finance. My skills are transferable and my focus is people. For others, being with a chemical company that disposes of waste ethically matters. You might be committed to consulting and want to work for a consulting firm. You might want to be with a non-profit that helps kids or the environment. You might just want to work with a company who helps there homeless. Think about how much this matters to you and if you current organization fills the bill.

3. Do you like the people you work with?

Equally as important as the organization’s mission is who you work with. I have had colleagues say that the company wasn’t the best but the people they worked with were outstanding, which makes it all worth doing. Your manager, your leader, your peers, your team (if you have one) can make or break your day. Are we cooperative and collaborative? Are we competitive or back-stabbing? Drama can ruin a day. How much drama is there in your day-to-day? If your job scores low on the drama-meter, it may be worth staying. For me, drama is a time and energy suck. I have left jobs because of drama and leaders’ inability to manage or prevent it. Think about the people you interact with. The answer could help you think about staying or going.

4. Can you still grow?

Not everyone is looking for growth but, outside of compensation, career growth, is cited as the number two reason people leave jobs today. (This could be unseated by where we work/flexibility shortly!) For many, leaving a job results from hitting a ceiling. There is no chance to move up or expand out anymore. I know several colleagues who have stayed with their organization a long time because there has always been opportunities to grow and try new things. This didn’t necessarily result in a promotion or high-level job but growth in terms of added responsibility or even diverse roles. If you have reached a point of no growth or opportunity to do something new, it could be time to go.

5. Have you not had a raise in a while?

This is a tough question now because many organizations not only did not hand out raises but cut jobs. Ask yourself this question over the last few years not just 2020. Last year was very atypical. How important is money to you? Do you make enough? Are you making market value for your job? I know most of us feel underpaid but try and take an objective look at this. Take a look at other tangibles or intangibles? Do you have a pension? Do you have awesome benefits? Do you get a lot of time off or even a sabbatical (which is totally cool)? Do you get to be highly flexible? Can you cut the cord at 3 pm on a given day to work out without any implications? There are many benefits of working for an organization that may not be money-related. Ask yourself how important those are in conjunction with money.

6. Does the job fit your life?

As I referenced above, how flexible is your day and does the job fit your life? Are you working 70 hours a week or can you work 45 and fit in all the other things that fill your cup — family, exercise, gardening, writing, reading, Netflix. Can you set your hours or are you expected to be on call around the clock? Don’t underestimate the value of flexible work schedules. We are all dedicated to our careers but career should not equal life. If you can do all those things you want to do and do well at your job, that is important! Don’t throw that away for a small bump in pay.

7. Are there other dealbreakers that exist now?

Your values are (or should be) dealbreakers. What are the other ones? Maybe there is something so wrong about your current situation, you need to leave. Or, maybe there is something you want to pursue that just doesn’t exist at your current job. If this is the case, then you should consider looking. Again, you can be running away or running to something. You have to determine if that “thing” is worth making a huge change for. In my life, I have several situations where I left. One was overly competitive and cut-throat; that did not fit my paradigm. One was moving in the wrong direction for me…away from what I loved. One time I had a unique opportunity I wanted to try, so I took a risk. Sometimes, it is the right time to take a risk. Only you can answer that question. I do think taking risks can be good even if they don’t work out. The lessons and self-discovery that comes from taking risks can be invaluable.

8. Is the grass really greener?

A tough one to answer. Is the grass greener or just a different shade of green? Unfortunately, sometimes you trade bad problems for just different problems. It can be very difficult to ascertain a good fit through the process of interviewing. It is okay to ask provocative questions if you are professional. I have asked about how decisions are made, how teams interact with one another, and how people are rewarded. This helps to see how competitive a culture might be. That was something I did not like so I make sure those concerns are addressed. I once left a job that I regretted leaving. I left because I thought something was unbearable where I was. Turns out, the new job was new and shiny (and therefore exciting) but full of worse problems. I stayed for 6 months and moved on. This became a huge lesson for me and I carry this with me so I don’t make similar mistakes in the future.

There are many situations and times in our lives when we should make a change. Running from something can be a motivation if our present situation is out of alignment with us. Running to something new and better can also be a reason. Do some self-reflection to learn what is unlivable in your current environment. Do your homework to make sure what you’re running to is everything you want it to be. Good luck!