Too Good to Leave, Too Bad to Stay: 7 Questions to Ask Yourself About that Job You Feel Stuck In

Last year, I made the hardest decision of my professional career. I left a job I had been working at for three years. It was a job I called, at one point, my dream job.  

I built the team, hired amazingly talented passionate people, handled great content and got to use both my creative and strategic skills. I loved every minute of my time there.

Except not every minute, because I left it. In my three years managing that team, I had five different direct managers and my team had been affected by three different reorganizations, resulting in a complete change of three different executive leadership teams and consistent culture shocks.  

Throughout all those organizational changes, I was working as a temporary hire. Every six months, I’d wonder whether or not I’d still have a job in a week’s time. I was working seven days a week, taking calls on vacations and sick days. I was constantly having to prove the value of myself and my team for three consecutive years to decision makers who did not understand my business at all, let alone comprehend how my team was leading the way in the industry.

It was exhausting.

But I loved my team. I worked with great partners in other lines of business, and my direct reports remain to this day some of the greatest people I worked with. I liked my job enough. So I stayed, weighing all the pros and cons of this job that was, by all accounts, too good to leave and too bad to stay.

If you find yourself in a position of evaluating your current job, you’re probably doing what I did: listing all the pros and cons of staying versus leaving. The problem being that the more you evaluate pros and cons, the more they stack up on each end and one side does not balance out the other.

You can have a really, really bad day at the office and look at your pros and cons lists with one foot out your door. But then, you can have a really great day. You could have a great presentation, be celebrated for your success, meet new people, and you see the scale begins to balance back out.

This is called The Ambivalence Trap.

  • The more we try to weigh the mountain of facts and feelings we have about our jobs, the more confused we get.

  • The more confused we feel, the less we trust ourselves.

  • The less we trust ourselves, the more we feel like we need to wait, which allows us to collect more facts and feelings that confuse us.  

It’s a never-ending cycle that will not go away until you stop looking just at pros and cons.

Ultimately, I made the decision to leave in October. There were a lot of things that went into making that decision and plenty of other complex emotions I sorted through after I had left.

But about a month ago, I was reading a book about relationships that talks about those relationships that, like my old job, are too good to leave and too bad to stay in. The book outlines diagnostic questions that I wish I had at my disposal when I was thinking about leaving my job this time last year.

Thinking about these questions in the context of my relationship with my job made me realize how right of a decision I had made in leaving it behind. 

I know making the decision to leave a job is not an easy one. But if you’re really on the fence and trapped in ambivalence, here are seven questions to ask yourself.  

Question 1

Will you face any physical, emotional or sexual harm or harassment if you stay in your current job?

This one seems like a no brainer. If your current job is a potentially dangerous situation for you, outside of any on-the-job hazards you are fully aware of and come with your career of choice, you need to leave it. 

Absolutely go through the process of reporting those things to your Human Resource department or senior leadership, but if it’s been reported, it has not helped, and you fear for your health and/or safety, you will find peace of mind when you leave.

There is absolutely no job on earth worth you risking your personal safety.

Question 2

Think of a time when you felt totally optimistic about your job; your best memory of being in this role. Looking back at that time, can you honestly say you were really happy then?

When I think about some of my favorite creative projects I got to work on at my old job, I still feel so proud of the completed results. But, lurking in the background of those projects were my challenges getting senior leadership to understand and value the work my team did. I thought about so many times creative projects went so well, but months of work for other more strategic and tactical projects were in the trash because of red tape or a pulled plug.  

I overlooked those issues then because I loved my team, and because those one or two awesome projects fueled me enough to forget the other nonsense I was dealing with. But the nonsense was always there.

If you answered “No” to Question 2, it’s likely that you’ll feel good about leaving. A job exists for you where you can and will be happy about all everything. You don’t need to settle.  

Question 3

Have you made a concrete commitment to pursue an action or lifestyle that definitely excludes you from your current job?

My last year working for my old company, I did something way out of my comfort zone. I auditioned to be a peer trainer for employees on their first day of work. The job involved rigorous auditions, speech preparation, script memorization, networking – the works.

I worked and studied for weeks going through the audition process before hearing I was accepted. Being on this team meant that as often as three or four times a month, I wouldn’t have to go work my regular job, I went to a new building on property and trained these new employees.  

As the year went on and my ambivalence about my job grew, I found myself picking up more of these training shifts. I went to more networking events. I was strategically volunteering for shifts on days when I met with my leader or our leadership team – things I dreaded.

I was making a commitment to something that kept me away from my current job. If this sounds familiar to you, you’ll probably feel pretty good about leaving your job. You might even want to explore if that side project or lifestyle you’re pursuing is a better course of action for your career!

Question 4

If a mentor, team member or leader you admire gave you permission to leave, would you feel relieved?

Think about it. If today, a professional connection whose opinions you value above all others, walked into your office today looked you in the eyes and said “I can tell you’re unhappy here, and I want you to know that I completely will understand if you want to find something new. You have my permission to leave this job.” How would that make you feel? 

Maybe it’s not a professional person you respect, maybe it’s God or your parents or your kids. If one of them looked at you and said “We know you’re unhappy, it’s okay with us if you leave.” Would you feel like a huge weight lifted off your shoulders?

As the manager of my old team, I loved my direct reports. I saw them as my work babies, and I did so much to make their work experience the best it could be. I fought for their work-life balance, I pushed to open new doors and give them great exposure. I loved each of them so much (still do) that I stayed as long as I did for them.  

Looking back, if just one or all of them had said to me that I had their permission to find something new, I would have felt such immense relief. That’s a sign that I wanted to leave.

Question 5

In spite of its problems, would you said there is an aspect of your job (besides people – your team, your leader, etc.) that you LOVE and will continue to be passionate about for years to come?

Here’s another way to think of this.

Pretend your job is your significant other. You and your S.O. are happy enough but you’re not completely satisfied with the relationship, but together you have a sweet baby. The three of you love spending time together as a family but outside of raising your kid, you don’t have anything in common with your S.O. You don’t like the same movies, you don’t like the same activities, you just have your kids.

Relating this back to your job, your kids in this scenario is the people you work with, your team. If the best thing about your job, the thing you LOVE about coming to work every day, is the people you work with, it might be best to leave.  

Look, some people work in Dunder Mifflin offices where they sit across from the same people for years on end and never want to leave. But that’s not realistic for everyone.  

You can’t base your happiness for your job on people. People will leave, they’ll get new opportunities, get promoted, chase a dream, move home. Their priorities will shift and adjust as the years go on, and if the only reason you’re staying in a job you don’t really like is because of the people you work with, it’s not a sustainable long-term solution for yourself.

Leaders, if this is your situation, don’t make yourself a victim of “I don’t want to be a bad person” Syndrome. Don’t stay in a job you don’t completely love because of the belief that in order to be a good person, you need to stay and work hard to make things better for the people who work for you. You need to do what’s best for you.  

On the other hand, if you look at your job and can definitively say that while you love the people around you, you love pulling your weekly report, or designing the Town Hall decks, or finalizing creative, that’s something you might be happy to stick around for. 

Question 6

Would you say that your leader or the brand you work for is basically nice, reasonably intelligent, not to neurotic, and most of the time smells alright?

That’s a lot to think about so let’s break it down.  

Nice: Do you feel your boss or leader is a nice person? Do you feel they care about you and the work you do? Do you feel they understand your needs? Do you feel they value the things that matter the most to you, like work-life balance?

Everybody has off days or their own quirks that are hard to deal with. You need to ask yourself if your leader on their own is generally “nice”.

Intelligent: If your leader is your leader, they need to be able to provide some sort of wisdom. Industry knowledge, development skills, general insight and able to provide great advice. They need to be intelligent in the sense of their role as YOUR leader for YOUR role. 

If you have a manager who does not, truly, does not know a thing about what you do; if they don’t have any prior experience in the industry; if they don’t seem to be able to provide any insights or direction to tactical questions you ask them – that is what we’re talking about here in regards to Intelligence.

Not Neurotic: Is your boss crazy? Erratic? Does their mood change at the drop of a hat? Are they absolutely obsessive about having projects and reports delivered a specific way? Are they racist? Misogynistic? Sexist? Politically incorrect? Are they just off?

I once worked for an executive. After weeks of working with her admin support to find a free hour and staying late to perfect a deck, I arrived to the meeting on-time and ready to pitch. She rolled in 15 minutes late and proceeds to tell me about how she’s moving slow because she’s worried about her cat. She said she came home from work the day before, looked into her cat’s eyes and knew something was wrong. The cat communicated to her without meowing or acting lethargic. She said she “heard her in her mind and on her heart.” My executive goes on to say her “sick” cat had her so worried she hired a pet psychic. The pet psychic said she believed the cat was anxious and my executive needed to calm her, so my executive brought in a cat acupuncturist to relax her. Her cat still got sick on her rug.

45 minutes into my hour meeting, I was still sitting on the title slide of my presentation and she was talking about the life force she felt within her rug.

That should have been a red flag but I worked for that woman for a year more.

Smells Nice: Use your imagination on this one, when you walk into work every day, when you interact with your manager does something smell fishy? Do you feel like you can trust them? Do you feel like they are always hiding something from you? Do you feel like they have your back and wont throw you under the bus?

You know the saying, if it smells like a rat and it looks like a rat, it’s a rat. 

If you don’t feel your manager, or the company you work for even, is nice, intelligent, not neurotic or smells nice – you’ll probably feel much better if you get yourself out.

Question 7

Does your leader make it as difficult as possible to get the things you ask for? Does any need you have get obliterated? When you finally do get what you want, was getting it such a hassle that you feel it was not worth it at all?

When you approach your leader and say, “I need time off,” do you get the time you need, or are you made to feel guilty for requesting the time off (within reason)?

When you ask for help or resources or approval, are you constantly met with red tape or “let’s table this” or excuses?

Are there approval processes or operating procedures in place that make it incredibly difficult for you to do your job?

This is a question of power and development. Do you feel completely powerless in your current position that you do not believe any amount of work you put into something, it will never get approved?

Let me tell you about the moment when I decided to leave my job. In a 1:1 with my leader, I asked about the extension of my contracted role. My end date had passed a week prior, and I had not yet been told I was extended.

“Just keep coming to work,” she said. And I didn’t like that answer. My job technically ended two weeks ago, how can I be guaranteed benefits or pay if my contract hadn’t been extended?

I asked “Is it possible to expect to get my new end-date by the end of the month? Or, since I’ve been in the position for almost three years, is it safe to assume I will be offered full-time employment in this position soon?”

My manager sighed, “Look, we’re not firing you. Just keep coming to work and it’ll be fine. It’s a lot of paper work to file to get your end date extended and I’ve been busy with much more important projects that I haven’t gotten to it yet, but it’s coming. It takes a really long time for these requests to come to be. Statused positions are not in the cards at this time, though.” (Not her exact words but pretty damn close.)

The conversation moved to discussing Christmas. It was October, but we were already planning for Holiday coverage. I stated, “I am happy to work Christmas Eve and Christmas Day, but I only ask that I can either leave a few hours early on Christmas Eve, and I’m happy to start my day earlier, OR start late on Christmas Day, and I’ll work later. I would just like to have Christmas Eve dinner or open gifts Christmas Morning with my kids.”

Did you hear that? I said:

  1. I would work a full shift on Christmas Eve and Christmas Day, despite working on a team of peer leaders who could also cover for the day.

  2. I asked for a 2-hour shift in my schedule on either day so I could spend time with my family on a significant holiday.

“How old are your kids?” She asked me.

“I have a five-year old and a two-year old.” I responded.

“OH.” She said, rolling her eyes and sitting back in her seat, “So they wont even KNOW you’re not there. If you’re going to work, you can’t just work when it’s convenient for you.”

Those WERE her exact words. That was when I made the decision to quit, and a much angrier version of me made a comment to her that I would be looking for jobs outside of my current company.  

The next day, in a grand ceremony in front of my direct reports and our leadership team, she statused me. The thing that took so much time, was too difficult to get done, that wasn’t in the cards, happened over night. I realized that they had the power to make that happen the entire time, and instead chose to drag me along for three years because they knew I wouldn’t stand up for myself. They underestimated me, and I underestimated myself.

Deciding to leave a job can be as difficult as deciding to leave a long-term relationship. It’s okay to be confused. It’s also okay to feel hurt and sad after it’s over, I know I did.

If you read through all seven of these questions, and you found within yourself proof that you are unhappy where you are at - stop settling. You spend at least 40 hours a week doing this job. For some, that’s more time than you’ll spend 1:1 with your families, with some friends or even to yourself. You deserve to be more than happy enough.

You can and will find a job that suits all your talents, challenges you and understands your value. And when you do, you wont be ambivalent about it.

You deserve it, lady.