How to Stand Out as a Creative Entrepreneur: Point of View, Values, and Knowing When to Change Your Mind

I recently re-listened to a podcast conversation between Trevor Noah and Malcolm Gladwell, and it was so energizing I basically wanted to call someone and talk about it immediately. Already a huge fan of Trevor Noah’s intelligence, curiosity, and humor, I was pleasantly surprised to find I loved Gladwell just as much by the end.

In their freewheeling, completely captivating conversation, they discussed Gladwell’s decision to fully rewrite—not merely update—his phenomenally successful 2000 book The Tipping Point for its 25th anniversary. His publisher had suggested an update. Gladwell said no, and rewrote the whole thing.

Why? Because his ideas had changed significantly since 2000. When he cheerfully referred to the original chapter on NYC crime in the 1990s and then-Mayor Giuliani’s Broken Windows campaign as “an appalling chapter,” he won a permanent place in my heart.

It was so refreshing to hear someone of his stature openly acknowledge that a groundbreaking book had real problems when viewed through the lens of his current experience and understanding. Gladwell’s core premise—that a tipping point is the moment an idea, behavior, or trend crosses a critical threshold and spreads rapidly—stays the same. What changed were the examples, the research, essentially the entire book.

It got me thinking: why don’t we change our positions more often? Are we afraid that changing our mind means admitting we were wrong? Do we worry about losing credibility, or being seen as a flip-flopper?

“Values you hold tightly, but ideas you hold loosely — because stuff changes.” — Malcolm Gladwell

Your ideas are not your values. They’re not your identity. They’re just ideas. What if we held them more loosely—would better ones emerge? I think so.

If you’re picking up what I’m putting down but wondering exactly how to do this, read on for 3 ideas.

1) Identify your values

Creative entrepreneurs and freelancers often skip this step because—when marketing and sales are top of mind—thinking about values can feel ephemeral, or like it lacks ROI. I don’t totally disagree. But spending a couple of hours one Sunday afternoon getting clear on your professional values and what they look like in action will serve you well as you build your business. If you’d like to go deeper on this, check out this post: Leaning into Your Values During Times of Crisis.

2) Develop a unique point of view

Whether you’re a graphic designer, copywriter, branding agency, or strategist, there are countless other professionals who do what you do. We’re all painfully aware of this—and it can trip us up to varying degrees depending on the day.

So what separates the creative entrepreneur who consistently gets clients from the one who doesn’t?

Having worked with hundreds of creative professionals and business owners—first as an agent, then as a business coach—my observation is that success isn’t just about talent. It’s about having a distinctive point of view: something that drives the way you create, an opinion strong enough to be memorable, yet flexible enough to be collaborative.

Counter-intuitively, when creative professionals are in a scarcity headspace, they tend to dial down that differentiation—believing that the more palatable they are, the more hireable they’ll be. As tempting as that is, don’t do it.

Action step: Use these prompts to define and lean into your uniqueness:

  • What gets you fired up?
  • What makes you mad?
  • What life experience or challenge have you navigated that might benefit someone else?
  • Where do you see patterns or connections that others miss?
  • What topics excite you? What bores you to tears?

A heads up: your inner critic and imposter syndrome will make themselves very known as you do this work. Need a little extra juice to kick that voice to the curb? Check out my post: How to Build Confidence and Reduce Imposter Syndrome in Your Creative Career.

3) Ask your trusted network for feedback

Your idea is just the starting point. Now you need to find out if it lands with the people it’s meant for.

This step is about having a handful of targeted conversations that help you refine and sharpen your thinking. For example, I recently created a new service for creative companies, agencies, and in-house teams looking to connect vision, values, and goals to people, process, and outcomes. Each time I’ve run it, I’ve learned more about the actual need I can fill. Interviewing people in the spaces where I want to work has been one of the fastest ways to gain real insight.

Fair warning: if your imposter syndrome wasn’t showing up before, it likely will here.

Saying “I believe there’s something to this—do you see it too?” is genuinely vulnerable. You’re inviting people to tell you where the gaps are just as much as where the promise is. That takes guts.

Which you have. Obviously.

Action steps:

  • Email 3–5 people asking for 20 minutes to get feedback on your idea
  • Draft your questions in advance so you get the most from the conversation
  • Take good notes
  • Write challenges and opportunities on Post-its
  • Look for themes, patterns, and areas of interest

If any of this resonates—the values work, the point of view, the vulnerability of putting your ideas out there—and you’re wondering what it might look like to have support as you navigate it, I’d love to talk. Sometimes all it takes is one good conversation to get clear on where you are, where you want to go, and what’s getting in the way.

If that sounds like something you’d find useful, you can book a complimentary intro call with me here.

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