What Jerry Maguire Can Teach Us About Freelancing

As a freelancer, it can be difficult to find balance between the things that you believe in and your genuine need to keep income rolling in. Without a clear-cut personal mission statement, burnout and disillusionment can set in quickly. But if you look around, you’ll find many examples of how to make your freelancing life not just financially successful, but also deeply fulfilling and something you can be proud of.

Tom Cruise as Jerry Maguire

One seemingly unlikely (not to mention entertaining!) place to find inspiration is from the movie Jerry Maguire. The main character, Maguire, embodies some of the traits that make for a successful, ethical, and satisfied freelancer—but he wasn’t always like that. The great thing about this movie is that we get to see his journey of how he came to be an effective freelancer.

When it comes to the phrase “Show me the money,” here are a few things that Jerry Maguire can teach us about freelancing (warning: spoilers ahead):

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Seeking Wealth Alone is Unsatisfying

At the beginning of the movie, Maguire is at the top of his field as a sports agent. He’s making great money, he’s surrounded by sports celebrities, and he’s living the good life. But simply accumulating these material achievements leaves him feeling unsatisfied, which propels him into making a change. This is not to say that having an abundant lifestyle is a bad thing; it’s just that for true happiness it can’t be the only thing.

When it comes to a fulfilling career, money is just part of the picture. Surveys say that other factors matter as much or more, such as being able to use one’s skills (63 percent) and a supportive relationship with those you work with (54 percent). Decide what’s truly important to you as a person and a business, and then never veer away from that.

Authenticity Pays Off, But It Takes Time

When Maguire writes and sends out his values-oriented mission statement, the immediate fallout looks pretty grim. He loses his job, his girlfriend dumps him, and almost all his clients choose not to stick with an agent who seems to be a loose cannon as he forges out on his own.

But he does manage to convince one athlete, Rod Tidwell, to stay with him. Rod is unhappy with the agency and, more importantly, he likes Maguire. They forge a relationship that is built on authentic affection for one another. They aren’t just clients or numbers on a spreadsheet; they are friends who genuinely care about one another’s well-being.

Jerry Maguire and Rod Tidwell

Besides his talent for what he does, it is his authentic concern for Rod’s well-being that pays off for both of them. By the film’s end, he has scored an $11.2 million contract for the player—and the industry (including some disgruntled athletes at the agency) takes notice of the fact that Maguire honestly cares for his client.

Perseverance Counts

When you read the stories of successful freelancers and entrepreneurs, there’s one trait that you’ll almost always see: they didn’t give up when things got tough.

When you are building a freelance business, it can take weeks for your first social media follows to come along. It can be months before you have a stable of clients large enough to support you full-time. And sometimes it takes years of effort before you get out of the feast or famine cycle that is so common in the freelance lifestyle. According to Entrepreneur Magazine, a new product can take up to three years to become profitable. So if you expect to match or exceed your old salary right away, you will be disappointed.

Maguire’s freelance business looks like a flop at first. Only one employee, Dorothy, believes in him enough to leave the agency and join him. And his sole client, Rod, expects and demands a lot from him. Had Maguire taken this initial lukewarm reception as a sign of what he could expect long term, he would have given up before Act Two. But by persisting in his dream and believing in himself (most of the time), he eventually landed a contract that made his dream sustainable.

Have a Hook

As a film, Jerry Maguire’s greatest strength is its quotability. Phrases like “Help me help you,” “Show me the money!” and “You had me at hello” still show up in pop culture almost 20 years after the movie’s release.

While you don’t necessarily need a catchphrase, you do need some quality that makes you stick and out and stick in people’s minds. Think about what makes you unique and valuable. If you are a freelance writer, do you bring a fresh perspective to a new industry? Are you a web designer who has won numerous awards? If you’re a photographer, have your pictures gone viral? Make sure that you are able to convey why you are the one that your prospects should hire. If you were a hit movie, what would your favorite quotable line be?

Freelancing isn’t always easy. It takes dedication, confidence, and creativity. On the other hand, it can be some of the most rewarding work of your life. As long as you are authentic, truly care about your clients, maintain a standard of excellence in all that you do, and don’t give up, over time clients will be more than happy to show you the money.

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