Beyond the Hustle

10 Years of Marketing, Mindsets, and Entrepreneurs: Why We’re Scared to Be Us

Originally titled “Chasing Your Dreams” of 2015, I’ve updated it in March 2026 to provide some much-needed context.

We’re often told that “chasing your dreams” is a straight line. But after a decade in the marketing-entrepreneur trenches, from running a non-profit to building a full-service agency to teaching as a college professor, I’ve realized the path is anything but linear.

At the time the original was written, I was Ubering because my business needed cash.

Ever since my jump to be a YouTuber, I pulled back the curtain on what it actually takes to survive 10 years in this game. If you are a freelancer, a founder, or an intrapreneur working within a company, these are the (4) hard truths about the transition from consumer to producer.

DISCLAIMER: I’m a firm believer in education, but we’re born to do more than “work” for our lifetime. Even as a college adjunct professor, I love helping students break the box that they’ve been forced in. I’m a product of a broken system that let me fail because it had to “check specific boxes.”

1. The School of “Unlearning”

We are born innovators. As children, we solve complex problems naturally and color outside the lines. Then, something happens…  the indoctrination of school.

In school, failure is a letter grade that tells you you’re “bad.” In entrepreneurship, failure is the GPS that tells you where to go next. According to research on the Growth Mindset by Stanford psychologist Carol Dweck, the ability to view failure as an opportunity for growth is the single greatest predictor of long-term success. To succeed in marketing, my experience has taught me you have to unlearn the fear of being wrong. Failing leads you to success.

The Shift: In business, failure isn’t the opposite of success; it’s the data set required for it.

For example, it’s how I became a business owner: I never knew being an entrepreneur was my dream job, and that wasn’t one of the options available when I was a kid. Good thing nothing is permanent. Just like my employment status.

2. Relational vs. Transactional Marketing

I recently watched the documentary Buy Now, which explores how technology is used to manipulate consumerism. It’s a sobering look at the “Wild West” of modern marketing.

As a marketer in a small town (Vancouver, WA), I’ve learned that the most sustainable way to grow isn’t through transactional “button-pushing,” but through relational strategy.

• Transactional: High-pressure sales tactics that prioritize the “close” over the customer.

• Relational: Building Brand Equity by creating a message that builds comfort and solves a genuine problem.

Marketing is an investment in your brand’s “Satisfaction Experience.” If you aren’t sold on your own solution, your customers won’t be either.

3. The “Supporting Cast” Factor

You don’t have to be an entrepreneur to have an entrepreneurial mindset. Throughout my time as a professor, I’ve met students who don’t want the risk of owning the company, but they want to be around the fire.

Why aren’t more of us chasing our dreams and ready to conquer the world with our ideas, creativity, ingenuity, and passion? My personal belief is fear. At the point of fear, the mindset shouldn’t be a ‘chase’ but to ‘attract’ the right people, resources, and exposure into your life. Don’t be scared to push your boundaries and limits. Take one step at a time. This isn’t a sprint. It’s okay to fail forward. All the magic operates outside the comfort zone.

Every visionary founder needs a “Supporting Cast.” Research from the Small Business Administration (SBA) shows that 70% of small businesses that receive mentoring survive for five years or more- double the rate of those that do not. I’ll take a step further, and recommend it’s a paid coach or consultant. Whether you hire employees or work with a network of fellow business owners (my preferred model), your growth is capped by the quality of the people in your corner.

4. Overcoming “Scared to Be Me” Syndrome

I wrote my book, Scared to Be Me, because I realized that your personal demons eventually become your business obstacles.

Early in my career, I was intimidated by the $3,000 custom suits and the high-level boardrooms. I was scared people wouldn’t accept the authentic me. This is a common phenomenon known as Imposter Syndrome, which affects roughly 70% of high achievers at some point in their lives.

When you hide your authentic self, you create a “Brand Gap.” Your marketing feels hollow because it isn’t rooted in your “Why.” My work now focuses on helping clients bridge that gap—using their unique story as their greatest competitive advantage.

Key Takeaways for the Next 10 Years:

• Audit your “Insecurities”: Are they stopping you from pitching that big client?

• Invest in Relationships: Stop looking for a “sale” and start looking for a “solution.”

• Find Your “Red Rubber Ball”: Inspired by Kevin Carroll’s philosophy, find the one thing that keeps you creative and hungry.

In the meantime, here are some tips I’ll share with you that have helped me stay focused on my journey:

• remove any and all distractions that keep me comfortable
• do not listen to constructive criticism that isn’t helping your growth
• be careful of any advice who aren’t professionals in the field I’m seeking growth or knowledge
• not everyone is going to be a fan of your dream
• the work is very lonely
• guard yourself against immediate pleasures that allow procrastination

Are you struggling to find your authentic voice in your marketing? I’d love to help you bridge the gap between where you are and where you want to be. You can reach out to my team at or check out our Marketing Services to see how we can build your brand together.

Dream Big. Godspeed. And #beyou.

Nathan A. Webster, MBA