The Job vs Personal Freedom Dilemma: The Surprising Modernity of George Cusack’s 1938 Holiday

Some spoilers ahead.

“I want to know who I am, what’s going on… now that I’m young.”

This feels like something a young person would say today.

Well, this line was written in the 1930s. It is said by Cary Grant in one of my favourite comedies: Holiday. This film navigates the not-so-light journey of finding your path in life and making a choice between freedom and financial security, a few years after the Great Depression of 1929.

Here is why Holidays’ central question of understanding yourself to make the right choices still rings true for every young talent affected by the current crisis.

A Comedy Posing an Existential Question

The scene is set in 1938 New York. The Great Depression of 1929 still lingers in the minds of many Americans as the economy struggles to recover. The story of Holiday starts on a whimsical note, kicking things off with Johnny, who is played by an ever charming Cary Grant. This delightful main character falls head over heels for Julia, a spontaneous girl he met on vacation just two weeks before. Things get serious at lightning speed, and a smitten Johnny is (all too) quick to be convinced that she is the one.

As he visits her at her house to ask for her hand in marriage, he discovers she is the mega-rich daughter of a banker. I mean, there are butlers everywhere and an elevator inside the mansion (how lazy do you have to be). Surprised by this absurd amount of wealth, our main protagonist starts to worry that the father will reject him. While feeling preoccupied, he meets the sister of his fiancé, Linda. Quirky and free-spirited, she craves independence from this very conformist rich family. This refreshing character is played by Katharine Hepburn, and it’s no coincidence — as she was often type-casted to play unconventional roles, such as in Little Women.

When Linda gets in the picture, the real plot of the movie unravels. Johnny, a playful and amusing character, is also pretty good at finance and holds a steady job — a true self-made man from a modest background. The rich father is swiftly impressed and says yes to the wedding, suggesting even he might make Johnny his heir so he can take the reins of the family business. This means he will snub his son, Ned, a musician turned banker against his will, resulting in some shameless Frank-Gallagher level of drunkenness with more class.

However, Johnny is anything but conventional, especially for his time. If he conformed to society’s rules — working hard to become financially stable — it is to achieve one goal: to have some free time to think about the purpose of his life. He is a man with a plan. Now that he has enough money saved, he wants a holiday, as the film indicates, to figure himself out. And he is not talking about 2 weeks under the sun taking yoga classes. He wants to access the truth of who he is, and what his mission in life is. Of course, this clashes with the daughter-father combo, who are shocked and outraged by Johnny’s true aspirations — “Why would you not want to make money?” They simply cannot understand why you would want to stop everything to think things over. But to Johnny, it’s the most important question there could be.

The “Purpose Dilemma” We Are Also Facing Now

Here is how Johnny expresses his point of view in the movie to Linda, the sister of his fiancée:

“I don’t call what I’ve been doing living.

“And what do you recommend for yourself, doctor?

“A holiday.

“For how long?

“For as long as I need.

“You mean just to play?

“No. I’ve been working since I was ten, I want to find out why I’m working. The answer can’t be just to pay bills and pile up more money. Even if you do, the government is going to take most of it.

“Yes, but what is the answer?

“I don’t know, that’s what I intend to find out. The world is changing out there, some new exciting ideas are running around. Some might be right, some might be wrong, but they are affecting all our lives. I want to know how I stand, where I fit into the picture, what it’s all gonna mean to me. And I can’t find that out sitting behind some desk in an office, as soon as I get enough money, I’m gonna knock off for a while.


“Quit! I wanna save a part of my life for myself. There is a catch to it though. It’s gotta be part of the young part. You know, retire young, work old. Come back to work when I know what I’m working for. Does that make sense to you?”

Choosing one linear direction — or taking the time to think about your purpose and life’s mission — is especially relevant today. Technology has transformed the economic landscape starting in the ’80s. Meanwhile, the current crisis has shattered work perspectives, bringing back the question of jobs’ usefulness to the centre after years of impactful publications on the topic. For those who are not experiencing financial distress — and have other things to think about — the existential threat of COVID-19 has spurred questions about our sense of self, our happiness, our well-being and our mental health. Like many pandemics before, it has created a sense of urgency for us to think about where we stand and where we want to be. At the same time, the economic recession created a daunting financial uncertainty — prompting for some short term answers in order to achieve economic security.

For Holiday, the answer is unequivocal: to free yourself from social pressures and expectations, you have to declare your independence and embark on the risky, adventurous journey of finding out what is your life’s mission. For that, you need three things: enough money to support your work hiatus, time, and the courage to ask yourself the most important questions.

The movie highlights an interesting point: you have to do so before the traditional midlife crisis hits you when you’re in your 40s, at which point you might have more emotional baggage and too much cynicism to rethink your life’s mission.

Broken Dreams, Cartwheels, and Social Conventions

Holiday presents three different portraits of children from a wealthy family, expressing opposite views on how to approach the meaning of life, and careers.

Let’s start with Julia (Johnny’s fiancée at the beginning). She seems sweet and soft-spoken, only to reveal herself to be very assertive, traditional, stiff, and unwilling to rethink the cost of her position of privilege. She goes as far as pushing Johnny to become his father’s successor despite his wishes, using heavy emotional blackmail. Through her attitude, she represents the status quo and the reluctance to change, dismissing the idea of thinking things over as crazy, finding comfort in perpetuating the tradition. She even has one of the funniest lines in the movie when she mistakes Johnny’s idea of a holiday for a request to relax, suggesting he take a short break — “And if, when he comes back, he wants to sell peanuts, oh, how I’ll believe in those peanuts!” Sure, Julia.

Her opposite is Linda, suffocating in this artificial environment and wishing to be free and independent. She mirrors Johnny’s own doubts and questions, refusing the role society and her family have designed for her. But, unlike Johnny who is very much free to act on his desire to escape, Linda is still in the rebellion phase, mostly due to her gender and the restrictions associated with it. Even though she is acknowledging her unhappiness, she hasn’t acted upon her desires for freedom, bearing the weight of her rich traditional family. Every time she points out the hypocrisy and shallowness of her family, she is treated like an ungrateful child. A sign of her inability to claim her freedom is her hiding in a nursery playroom, which she uses as a retreat from her social obligations. She often escapes there, as a teenager would take refuge in a video game to escape a dim reality.

Playing with her old childhood toys, laughing it out, she brings Johnny to her retreat and performs several cartwheels with him. Her character represents that free-spirited part of us that is brought down by circumstances. Her encounter with Johnny changes that, as the two reaffirm their desire for freedom in the other. As Johnny hesitates to give up on his “Holiday dream”, Linda is here to put him back on track, telling him to follow his plan :

Johnny: “Of course, they may be right.”

Linda: “Don’t you believe it.”

Johnny: “I don’t know, they seem so sure.”

Linda: “It’s still your ride, isn’t it? You know where you want to go, don’t you?”

Johnny: “I thought I did.”

And then, last but not least, there is the cautionary tale of Ned, the brother of Linda and Julia.

In a perpetual state of inebriation, this musician-turned-banker-against-his-will is deeply unhappy. He too spends a lot of time in the old nursery, where his instruments are — as if he wallowed in the graveyard of his dreams.

He represents the broken man, acting as a possible future version of Johnny who struggles to make his decision for most of the movie.

Risking It All?

In the movie, Cary Grant aka Johnny finally decides on sticking to his values after trying to accommodate the family. He dumps Julia and flees to a life of adventure and self-discovery, only to be joined by Linda at the very last minute. He performs a final cartwheel, as a true expression of his freedom.

Although the movie received a positive response from critics, it was not a commercial box office hit. In the late ’30s when the film hit the theatres, the Great Depression was not far behind and people were struggling to find jobs. The idea of leaving all behind to find your life’s mission might have seemed childish and out of place at the time, eluding any money considerations (in some cases a life-and-death issue) by setting the plot in a wealthy environment. Like many films from the ’30s, its escapism over-simplifies the job VS freedom dilemma.

But, however simple the plot of the movie might be, it does point out some valid, essential questions that still resonate today. To know yourself, you need to take the time to do so, instead of burying the questions under too much work and social pressure. Is pushing back self-discovery to a later time such a good plan? Essentially, the movie Holiday confronts two types of risks: the risk of the unknown and the risk of regret. Taking into account the financial constraints and distractions we might have, it’s worth challenging the meaning we want to give to our lives.

Like Johnny, we can at least imagine a plan to take back the time we need in order to do so.

I am a content manager at a French startup. Illustrator whenever I can :)

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