top of page
  • Writer's pictureBrendan Stec

That's a hassle

Lumbergh: Hi, Milton. What's happening? Milton: Nothing. Lumbergh: I'm going to have to ask you to go ahead...and move your desk again, so... if you could go ahead and get it as far back...against that wall as possible...that would be great. Milton: No, because I was... Lumbergh: That way, we'll have some room for some of these...boxes and things we need to put in here. And...Oh, there it is. Here, let me just go ahead and get that from you. [Grabs stapler from Milton] Great. So if you could just get to that as soon as possible...that would be terrific, okay? Thanks a bunch, Milton. Goodbye.

Office Space (1999)


In Office Space, Milton Waddams is the office punching bag. The VP takes his favorite red stapler. As cake gets passed around for a corporate birthday party, everyone gets a slice but him. His desk is inexplicably moved to the basement. Then the consultants decide to stop paying him altogether until “things work out naturally.” In the end, Milton takes some extreme action as revenge, which I won’t discuss to avoid spoiling the film. Besides this last action, I'd bet you can mostly relate to Milton’s situation and what you also go through each day. The common theme is… BS. Hassle. Minor injustices. Inexplicable problems. People saying things you disagree with or doing things that interfere with your goals. Sometimes things legitimately go wrong. But even when things do go right, there is almost always some hassle along the way. There is simply no getting around it. Hassle is the natural friction that exists in the complex machine we call society. When it comes to dealing with inevitable hassle, often people fall into one of two extremes. Let's call the first extreme the Miltons. Miltons tend to be more timid. Hassle certainly bothers them, but they have trouble standing-up for themselves and eliminating its root cause. The injustices and frustrations pile up until their resentment can't be contained any longer. Many people have Milton-esque qualities, but more commonly people fall into the second extreme. Let's call them the Control Freaks. The Control Freaks have absolutely no tolerance for hassle. Minor inconveniences become major obstacles. A DMV employee's apathy is interpreted as personal disrespect. Being a Control Freak is often worse than being a Milton because perpetually expecting a hassle-free world can drive you crazy. The author Steven Pressfield noticed this while living in a halfway house to save money on rent. After interacting with the other residents for a time, he was surprised at how funny and intelligent many of them seemed to be. How did they end up there? As Pressfield recounts:

“[W]hat I concluded from hanging out with them and from others in a similar situation was that they weren’t crazy at all. They were actually the smart people who had seen through the bullsh*t. And because of that, they couldn’t function in the world. They couldn’t hold a job because they just couldn’t take the bulls*t, and that was how they wound up in institutions.”

This story is what led author Morgan Housel to conclude that there is an “optimal level of hassle” you should be ready to accept at any given time. In other words, you want to be somewhere in between a Control Freak and a Milton. Moving from away from Milton territory is more straightforward. It mostly involves becoming more assertive and less agreeable. Psychologists often work with people on improving their ability to stand-up for themselves—and it's a fairly learn-able thing to do. Moving away from Control Freak territory is a little different. It mostly involves acceptance of what's beyond your control...and accepting hassle is certainly easier said (or written about) than done. Today, as I write this and you read it, we both may intellectually accept hassle as an inevitability. Tomorrow, though, we’ll likely still expect a hassle-free experience on the highway, in a meeting, or at the doctor’s office. But this too can be practiced. The Stoics often remind us that small inconveniences are opportunities to practice handling the big ones. The good news is that there is almost always enough practice. FDR was reminded of this frequently, as he once said:

“If you can’t use your legs and they bring you milk when you wanted orange juice, you learn to say ‘that’s all right,’ and drink it.”


bottom of page