I know work is a four-letter word, but does it really have to be this painful?

During my years of coaching, I’ve heard many clients express this sentiment. And that’s a shame. I believe work should be joyful and fulfilling. When a client is unhappy at work I want to get to the root of the problem right away, before she or he does something rash, like telling the boss to “take this job and . . .” well, you know the rest.

In diving deeper to find out why a client is unhappy, I often find our discussions revolve around “fit.” Is the job not a good fit for my client, or is my client not a good fit the job? Three recent clients—all unhappy at work—presented three different issues around job fit.

Julie is an exceptional program analyst and her boss knows she has much to contribute. He wants her to be more visible and speak up in meetings. But Julie is an introvert who prefers to think before she speaks. Unfortunately, by the time she knows what she wants to say the conversation has moved on. She’s tried talking while she thinks, but her ideas are disjointed and she rambles too much before arriving at her conclusion.

Another client, Tim, loves to drive change and is eager to improve his organization. Yet he has been told to slow down and not push so hard to change things right away. But to Tim’s way of thinking he isn’t doing a good job if he isn’t aggressively pursuing a goal. It’s like he only has two speeds: fast and very fast.

Terry, a strategy consultant, can be too direct. In fact, he’s gotten feedback that his interactions border on being inconsiderate at best and insulting at worst. But Terry doesn’t think there’s anything wrong about his behavior or communication style. He feels that the organization should take him as he is; after all, he does a good job and the clients love him.

How much should you have to change to fit your job or your organization’s culture? I look at that question from two aspects. Would developing the skill you need to fit in better make you more successful in your career, regardless of where you work? Would changing your behavior violate something you consider an intrinsic part of yourself?

If fitting in requires you to become adept at a skill that is transferable to other workplaces, I’d suggest the struggle may be well worth it. Were you to quit because you didn’t want to make the change, it is entirely possible that your new job will be no different in requiring that skill.

But if you are being asked to go against something that is at the very core of who you are, I would help you find a position at another company.

For Julie, the ability to think on her feet and speak succinctly in meetings would serve her well no matter where she worked. I helped her develop a framework for anticipating what topics might come up in meetings, thinking through her perspectives on those topics, and imagining what question she might be asked. I also provided tips on how to confidently defer commenting by requesting time to make an adequate assessment and specifying when she’d respond. Giving Julie permission to use the words “Let me get back to you” was like throwing a life preserver to a drowning woman.

To understand why Tim was being told to put the brakes on his drive for change, I gathered 360-degree feedback from his bosses, peers, and direct reports. I wondered if the response he was getting had to do with the changes he wanted to make to improve the organization or with how he was going about it. After the fifth interview, I had heard the same chorus over and over: “We are doing fine as we are. Why do we need to change?” People sincerely liked Tim, but they wanted him to allow change to happen more gradually. Upon hearing this feedback, Tim decided to update his resume and look for another position. He knew he needed to work in an organization that was nimble and unafraid of disrupting the status quo. And he knew what questions he should ask of interviewers to determine whether a prospective position would be a good fit for him.

Terry was a tougher nut to crack. He knew how to behave professionally; he got along fine with the organization’s clients, who thought very highly of him. Terry’s unacceptable behavior was all focused on his colleagues. He had lost respect for his leadership team and was “acting out” like a moody teenager. It was almost as if he were daring his boss to fire him. When I asked him if that was his goal, he realized he didn’t want to be fired but he could see his behavior was leading his boss in that direction. I helped him understand what was really bothering him about the organization and how to have productive conversations with his leaders. If he could work through the things that bothered him, he would feel better at work. If not, he could always resign. But why leave a job with people happy to see you go, especially when you might meet them again in your career? After resolving his concerns, Terry chose to stay and be as respectful to coworkers as he is to clients.

If you feel like a square peg being pounded into a round hole at your job and you’re wondering whether you ought to quit, do some self assessment and collect feedback (or ask your coach to gather it). That will help you determine whether you need to smooth your sharp corners or look for a situation more conducive to right angles.