Why Freelancers and Business Executives Are Afraid to Be Original – and How We Can Help Each Other

I don’t know about you, but I want my work to be described as being “in a class of its own.” I want to be different than the billion other copywriters and content strategists out there. No doubt you want the same for your business or brand.

Lots of people want this (or rather, they want the results it brings), but not all of them are willing to make it happen. Because being original – going against the grain and creating something different – is hard.

Ed Catmull, co-founder and President of Pixar, shares just how hard it was to create completely original movies in his book Creativity, Inc. He devotes an entire chapter to the concept of creating something brand new and protecting your infant ideas, in which he says:

“Part of our job is to protect the new from people who don’t understand that in order for greatness to emerge, there must be a phase of not-so-greatness.”


“The system is tilted to favor the incumbent. The challenger needs support to find its footing.”

Image by Web Summit

While there are benefits to learning from what’s worked before and using proven strategies, there’s also benefits to experimenting and trying new approaches.

For your brand to innovate and stay miles ahead of the competition, you MUST be willing to stray from the safety net of what’s worked before and try new ideas. This is true in product development, in marketing, in customer service, and in all branches of your brand.

Past success can make us complacent. We think that we’ve got it figured out and can just rinse and repeat.

The problem is that success isn’t always repeatable. There’s too many other random factors outside your control, especially in this world of shifting technological landscapes and 24-hour trending cycles.

All it takes is ONE competitor who’s willing to push the envelope to leave you and your “proven success” in the dust. The music album retail industry learned this the hard way with iTunes, as did Blockbuster with Netflix.

There are times for us to stick with what’s worked and time for us to try something new. If we wait until our current systems break to begin experimenting with new ideas, we set our business or brand up for failure. Playing catch up will ultimately cost us more customers, loyalty, and money than experimenting ahead of the curve will.

So What’s Stopping Us?

What prevents so many people – freelancers and business executives alike – from trying new approaches is innovation’s inherent risk of failure.

Starting something new or taking an original stance on something is rarely easy. Anyone who has invented a new approach or standard was viewed as a little crazy or obsessive. . . until it became the trend and eventually the norm. Then everyone wants on board, and suddenly those first original few are geniuses, icons even. All because they embraced the hard work of doing something new in the face of potential failure.

The irony is that failure is often a necessary part of progress. During his attempt to invent the electric light bulb, Thomas Edison famously said, “I have not failed. I’ve just found 10,000 ways that won’t work.” Trying to avoid failure altogether is unrealistic and creates an unhealthy culture.

To go back to our Pixar example, Pixar’s leaders believe in the inevitability, even the necessity of failure, so they’re willing to experiment – even though they know that not every experiment will work on the first try. . . and that some won’t ever work. For example, while creating the incredibly original movie Up, the storyline alone underwent four separate overhauls before it became the story we know and love today. In his book, Ed says:

While experimentation is scary to many, I would argue that we should be far more terrified of the opposite approach. Being too risk-averse causes many companies to stop innovating and to reject new ideas, which is the first step on the path to irrelevance.

Failure isn’t the enemy. Complacency is.

When trying to blaze a new trail, sometimes we must try 10 wrong paths (read: product iterations, marketing strategies, headlines, etc.) before we find the right one. But those 10 wrong paths were not a waste of time. Rather, they are part of the reason we find the right one.

When we create a culture that has this positive, healthy view of failure, rather than a fear-soaked one, we free ourselves and others to truly innovate.

How Can Freelancers and Business Execs Work Together to Create Something New?

When freelancers and business executives who understand these concepts partner together, they’re able to have bigger discussions and reach for higher possibilities. But this scenario is only possible if you work with the right people. This means we have to do our research on the client/freelancer we’re considering and ask pointed questions in our get-to-know-you calls. It means we must listen not only to what they are saying but also to what they aren’t.

When we connect with like-minded people, we can create space for the new. We’re able to suggest radical ideas without fear of being scolded, laughed at, or brushed off. We’re able to discuss changing old processes without either of us becoming defensive. We’re able to accelerate new marketing strategies or branding approaches, rather than doing it halfway, with each of us afraid of screwing up. (By the way, this anxiety and timidity often becomes a self-fulfilling prophecy.)

If our new approach does fall flat on its face, we have a long-term vision and proper understanding of failure that enables us to not place blame on each other or beat ourselves up but to instead brush ourselves off and adapt – whether that means revising the idea for the first time or the third time or knowing when to ditch it altogether.

To arrive at this healthy place, freelancers and executives need to:

Find a like-minded person to partner with

As an executive, you want a freelancer who isn’t afraid to challenge the way things have always been in your company and who will suggest new ways of doing things. As a freelancer, you want to find a client who is open to new possibilities, who respects your expertise, and who is willing to listen to your ideas.

View this working relationship as a partnership

This isn’t your typical employer/employee or even company/contractor relationship.

Executives, you need a freelancer who truly cares about your business’s success beyond how it affects their paycheck, who looks at the big picture and not just the role they play in it, and who wants to see the results of their work and then improve on them. Freelancers, you need to work with executives who ask for your insight, who invite you into the strategic conversations, and who want to talk with you and not at you.

Be open with each other

Communication and transparency are critical to a successful partnership of any kind. Each party has to be willing to share their concerns, their past experiences, their knowledge, and their opinions with the other. Being completely open and honest with one another, even when it’s embarrassing or unpleasant, sets your relationship up for success.

When the freelancer and executive already have a mutual respect for each other, they’ll want to hear what the other has to say, and they’ll find ways to work through it. And just like every other kind of relationship, this openness will foster an even greater mutual respect.


Doing something differently or trying to create something new will always come with growing pains (or maybe it’s birthing pains?). But that’s not an excuse for not trying.

To quote Ed Catmull one more time, “To be a truly creative company, you must start things that fail.”

We can’t know ahead of time which ideas will work and which will flop. But we do know this: we’ll never hit a home run if we never swing the bat.


Are you looking for a freelance partner who isn’t just there for the paycheck but who will value your business like you do and collaborate with you to make it skyrocket?

If this sounds like you, contact Jessica here and request a complimentary phone call to talk about your business.

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