The Apartment

5 Things Billy Wilder's "The Apartment" Taught Me About the Freelance Life


The other night I watched Billy Wilder’s subversive 1960 film, The Apartment, and it got me—a freelancer—thinking about the trade-offs we all make in the business world. The movie tells the story of a devoted organization man played by Jack Lemmon, who loans his Manhattan apartment to a group of men of power and wealth, who use his pad for their liaisons with various mistresses.

Lemmon’s character doesn’t admire their dalliances but goes along with the charade because he believes it will advance his career. He is a man accustomed to disappointment; his job is crushingly dull, and he could easily waste his life as a spiritless drone in the corporate machine.

So he sets his sights on bigger things, but his bosses’ promises to him are about as the good as the promises they make to the women they squire.

Shirley Maclaine is one of them. A slick Fred MacMurray strings her along with promises to someday divorce his wife. Despairing, she swallows pills to off herself, only to be rescued by Lemmon. Director Billy Wilder pulls all of this together as a brilliant piece of black comedy. Forty-eight years later, the film offers fine lessons for the employed and self-employed alike:

  • Accept that life is all about trade-offs. It’s easy to mock the corporate world. Cliches abound: For 11 holidays a year and a poorly managed 401k, it sucks your soul dry. Ah, but the freelance life has its trade-offs, too. In exchange for your freedom, you’ve got to got to make your peace with the beast of insecurity gnawing at your guts.

  • Be aware that freelancer can also be manipulated and used. Clients who want something for nothing, who crave ceaseless hand-holding, and who never know when the project is over feast on your soul just as much as the bosses on the 27th floor.

  • Be prepared to confront your morality every day. Just how far are you willing to go for a client? What will you, or won’t you, do? The Apartment dances around the issue of sex, but I’m talking about business ethics. Your code. What you stand for. Consider: the 2008 housing crash happened in part because far too many people—realtors, bankers, mortgage brokers, appraisers, and yes, buyers and sellers—routinely gamed a system that was bound to fail. When they should have acted honorably, they looked the other way. Learn to say no. Say it early and often.

  • Know that redemption comes at a price. Call quits on the game, and you risk loss of work, respect, and whatever power you may have seized for yourself. But if you can accept the consequences of your actions, you will always be free.

  • Remember that some things are worth more than the gig. If you don’t have work now, and you turn down a potential client because you know working for him or her will be more trouble than it’s worth, resist the impulse to look at the experience negatively. Yes, you may have lost a paycheck. But you have gained peace of mind and perhaps the knowledge that you were right. Try pricing those out sometime.

* This post first appeared in slightly different form on my old blog, Feb. 13, 2008.

Yes, I am trying to post here more often. Thank you for noticing. If you want to sign up for my newsletter and claim your free ebook, go here. Thanks — Joseph D’Agnese