Why is it so hard to tell what is making work miserable?
It’s so hard to tell what’s truly making work miserable because there are a lot of parts about work that interact with each other that create confusing environments. In the world of human and systems thinking, the context can drastically change everything. In one environment you might hate a project because of the people you work with, but in another environment you might struggle with the people because of the project you have to do.
You might dislike a project because the work itself does not interest you, or maybe it’s not aligned to what you think the company should do, or even what personally energizes you. You might enjoy the work but hate the conditions you have to do it in - maybe the process is annoying, the people are difficult, budgets are constrained, or the time crunch is too tight. Sometimes both are miserable and sometimes one makes the other harder to tolerate.
A difficult working environment can drain the enjoyment out of something you normally love. Work you dislike can also make the processes and interactions around it feel more frustrating.
It can become a chicken-and-egg problem. Which one is causing the real problem, or are they feeding off of each other in a downward spiral?
The real answer as with anything involving humans… context is critical and humans are complex.
Before deciding what to do, it helps to make that tangled experience more visible.
How can I figure out what is actually bothering me?
As with anything that is difficult to understand in our brains or intuitively, the best skill is to externalize it. Get it down on paper.
Choose an activity or project you are not enjoying right now. Give yourself two columns with ample writing space. Write down the things you like, or that feel okay, alongside the things you hate or that feel unacceptable. Leave extra room between each item.
Then look at what each item concerns. Is it about the work itself? The process or system around it? Your manager, coworkers, or other people involved?
For every item, then ask why.
Why is that part interesting? Why does that interaction drain you? Why does that process bother you so much?
The why is the most important part. “I hate this project” gives you very little to work with. “I keep redoing the work because nobody will agree on what we are trying to achieve” gives you something more specific to examine.
Writing it down gets the experience out of your head and gives you something to reflect on. Sometimes that alone creates enough space to see a possible next step.
Would different work or different conditions change how I feel?
Once you have explored the reasons, try two thought experiments.
Different work, same conditions: Imagine working on another project while keeping the same people, budget, limits, and ways of working. Would you still feel miserable, or would it feel much better?
If changing the project seems likely to make a substantial difference, the work itself may be an important part of the problem.
Same work, different conditions: Imagine doing the current project with a team, system, or working environment you previously enjoyed. Would the project feel more appealing there?
If so, the conditions may be contributing more than you first realized.
These are clues to investigate. The thought experiment cannot establish exactly what would happen, but it can help you identify what to explore next. You may also discover that both the work and its conditions need attention.
What if I cannot change the work or the conditions right now?
In many situations it’s far too big of a task to change the conditions or the project itself. So there’s only one thing left to do (well, technically 2, but just continuing to suffer through it isn’t a lot of fun).
Sometimes the immediate opportunity is to change your relationship with the work. This is where knowing your identity (specifically your values) can help.
In my experience, work often becomes more distressing when it pulls us further away from what matters to us. Looking at those points of tension can reveal small ways to bring more of ourselves into the work.
If you are unsure what your values are, try the free values card sort I built. It gives you a starting point for this reflection.
Take the project, activity, or working relationship you want to assess. For each of your values, ask: How much does this situation allow me to live out this value, and where does it push me to compromise it?
You can score each one from 1 to 5: 1 means it strongly conflicts with that value; 5 means it gives you plenty of room to express it. The numbers are simply a way to make your own assessment visible.
Then choose one value to work with. It does not have to be the lowest or highest score. Choose one where a small change seems possible.
Could you adjust how you plan the work? How you approach a task? How you interact with someone? If learning matters to you, is there something you could learn through this project and intentionally make room for?
Sometimes the adjustment is something practical you can actually execute and do, and sometimes it is a different way of understanding your contribution and role.
This can take some time to try different things. And while you may still need changes to the work or its conditions, I have found that getting grounded again in who you are and what matters to you can sometimes make an unchanged situation feel a little less distressing. That little bit of space can help you decide what to do next.
