What if your Sunday Scaries aren’t caused by the 4 meeting you have Monday morning, before you will even get to your email, the 47 Slack messages that are waiting in your inbox, or the PowerPoint you have to finish by the end of the week, and you are still waiting on the “new format”? What if they are the direct result of a fantasy you believe about work?

We even recognize that our view is wrong or missing things, and yet we still continue to act as if it is true because we can’t imagine another way. That way of seeing things is our fantasy.

Fantasy is how we learn what we desire. Let’s look at a fairly common example: “If I just get promoted, I will feel respected at work and will be confident.” This fantasy is that the promotion will make me feel confident. This is based on another person, likely your boss, showing respect for you based on what you think they want. These fantasies are what cause us to want what we think we want. We want the promotion because of what we think it will mean and what it will give us.

It is also important to note that fantasies aren’t some illusion that we see; rather, it is the distortion that allows our world to make sense. These fantasies structure how we see the world and how we function. And that includes at work.

My Fantasy: The “Outside” Manager

As we talked about last week, part of my desire to manage was based on the idea that I could occupy a hierarchical role while remaining outside the forces of hierarchy. I could somehow be a manager and be outside of the pressures that the role created. I could magically make things better for my employees. And so I desired happy employees, meaningful one-on-ones, and giving up my power to the team so they could be empowered.

The problem with the fantasy was that all of these things that I wanted, and then everything I did, only hid the reality of my authority and power. It was still me at the end of the review period with the spreadsheet determining how to spread out our budget for raises across the team.

I remember when the fantasy broke. I had been working hard with someone who had recently transferred onto my team and was adjusting to new leadership expectations. They were doing everything right: learning new skills, working hard, shifting patterns. And then layoffs came, and their name was on the list.

I realized that everything they did didn’t matter to the organization. The work I put into helping them achieve in that structure didn’t matter because I couldn’t control it. I now had to tell this person, who had done everything that I had asked, that they no longer had a role. I was no longer the helper, getting them to shift to support the new expectations; I was now the authority figure explaining severance.

But here is the thing, it wasn’t really a surprise. Not that I knew it was coming exactly, but I knew layoffs were likely. But more importantly, I knew I was in that position of power despite how much I disavowed it. I knew that I wasn’t just supporting this employee’s growth; I would also be one of the people to judge it, and if leadership said so, I could have to lay off anyone on my team. My fantasy allowed me to pretend that what I knew to be true wasn’t.

What broke the fantasy wasn’t that I learned something new; it was having to follow through with the act that showed what I had tried to disavow. That I was the one who had to execute the organizational power.

Finding Your Fantasy

Your fantasy could be different. Maybe it isn’t about protecting or supporting your team. But more than likely, what frustrates you most about work isn’t the work. It’s the gap between what your fantasy promises and what reality forces you to confront.

Here are some common fantasies that I have heard from leaders, some of which you might recognize as your own:

The Apolitical Craftsman:

• Fantasy: I’m just here for the tech; I don’t do ‘politics’.
• Desire: Focus on and optimize the technology.
• How it breaks: “Neutral” tech choices are deeply political.
  

The Future Leader:

• Fantasy: Once I have the title or own the budget, THEN I’ll be able to do things my way.
• Desire: Get the next role, the bigger team, or specific ownership.
• How it breaks: The conditions for agency never arrive; each new level brings new constraints that weren’t visible before.
  

The Misunderstood Genius:

• Fantasy: Once people really understand my work/ideas, they’ll naturally see the value and give me the influence I deserve.
• Desire: Recognition by getting your idea or work just right.
• How it breaks: The value of work is never self-evident; it’s always mediated through organizational politics.
  

The Culture Fixer:

• Fantasy: Once we fix the culture/get the right leaders/change the processes, work will finally feel natural and aligned.
• Desire: Hiring a new leader, buying a new tool, or creating a new process.
• How it breaks: Challenges are structural. Every culture filters what can be said, and any process creates new frictions.
  

This isn’t exhaustive. Your fantasy will have its own specific coordinates, and it will be messier than this clean three-part list implies. But we all experience work through fantasy. It’s not pathological; it’s how we make sense of impossible positions. These fantasies constitute the role through you, shaped by your history, your organization, and your structural position. Recognizing this doesn’t let you off the hook; it shows you where you actually have leverage to act.

Why it matters and why we fail

It might be tempting to see these fantasies as mere beliefs we cling to, but they are far more than that. They are how we structure who we are. And so when people run into the problems the fantasy introduces, it isn’t just a minor disruption. It is a shock to their very identity. And so what do people do?

1. Attempting to “see reality clearly” / “be more realistic.” People try to twist the shock into their beliefs and make it fit their narrative.
2. Job-hopping to find the “right fit.” They try to change jobs, thinking that a different environment will change how things are and that their fantasy will come true.
3. Doubling down on the fantasy (working harder at the same strategy). They see the issue as a personal failing and not trying hard enough.
4. They amend the fantasy to slide to a new target. The object of desire is something that can’t ever be reached, and so when making Director doesn’t change the dynamic, they set their sights on VP.
   

Each of these approaches continues to fail. Attempting to see reality only creates a new fantasy that they can see reality clearly, and that it will all make sense. Job hopping only changes the details, but the structural challenges remain. Working harder only leads to more frustration, as they continue to run into the same issues. And finding a new target only shows that the object of desire will never really give them what they want.

The problem isn’t that these approaches are wrong-headed. It’s that they try to resolve the contradiction rather than work with it.

Traversing: Identifying with the Symptom

Now the solution isn’t to see that the fantasy isn’t real or to finally see the reality behind it. How we see things will always be structured by some sort of fantasy. Rather, the way to navigate the fantasy is by seeing the symptoms, the things that don’t fit, and identifying with that symptom.

This shifts where you find satisfaction. It can no longer be in the fantasy’s promise (that is impossible), but in working directly at the point where that promise breaks down. The symptom isn’t the problem to eliminate; it’s where your actual work begins. You need to figure out what is possible in dealing with that symptom.

The Apolitical Craftsman: Identifying with the symptom means owning that the technical decisions are political. You stop claiming neutrality. You identify as a political actor whose “clean code” is, in fact, a specific distribution of power. You find satisfaction in making explicit political choices rather than pretending they don’t exist.

The Future Leader: Identifying with the symptom means identifying with someone who is always above you and holds more power. You realize that the higher you go, the more you are a servant of a different force: the CEO, the board, the market. You take the role but recognize you can’t “change it from the inside.” Instead, you find satisfaction in using your position to surface contradictions upward, making the impossibility visible rather than trying to resolve it.

The Misunderstood Genius: Identifying with the symptom means accepting that your ideas require political mediation. You stop waiting for merit to be recognized and start actively building the coalitions, alliances, and translations needed. You find satisfaction not in being understood but in the work of making yourself understood through organizational terrain.

The Culture Fixer: Identifying with the symptom means accepting that misalignment is structural; there’s no configuration in which everyone’s naturally aligned. You stop searching for the perfect culture and start working with the friction itself. You find satisfaction in the micro-interventions, the specific conversations, the small process changes, not because they’ll ‘fix’ culture but because navigating structural tension is the work.

In all of these cases, a big part of the work is seeing that you aren’t a “hero” or a “failure”; you are the site where these structural forces meet. And there is an ethical obligation to stay with that symptom and not let it go. It is one that commits to acting from the constraint itself; not trying to eliminate it or pretend it doesn’t exist, but figuring out what becomes possible when you stop waiting for conditions that will never arrive.

Finding Your Drive on Monday Morning

How can this change your Sunday Scaries? It certainly won’t fix whatever symptom is showing up, but it will tear your fantasy apart. That’s where your actual leverage lives. Not in fixing the contradiction, but in acting from within it.

This Monday, instead of asking “How do I fix this?” try asking: “What does this breakdown reveal about the constraints I’m actually in? What becomes possible when I stop waiting for those constraints to lift?” That’s where your leverage is.

This is tough work, and it helps to have support. If you’re hitting struggles in your work (symptoms) and would like support in identifying the fantasy that is driving your desire, let’s set up a free call and talk. (Click Here)