Am I an Entrepreneur? 6 Telltale Signs You Have the Mindset

It’s a question discussed in bustling Seattle cafes, debated over late-night phone calls, and considered seriously during career transitions:

Am I an entrepreneur?

The answer isn’t always clear.

Entrepreneurship isn’t just about owning a business, wearing a hoodie to work, or pitching to investors in Silicon Valley. It’s not reserved for people with a Shark Tank–ready idea or those chasing venture capital. At its core, entrepreneurship is as much about how you think and act as it is about what you build. How do I know? Well, aside from wearing a hoody to work, I have owned businesses, pitched to Venture Capitalists, and facilitated Shark Tank like events to evaluate next generation leaders and their ideas.

Here are some signs—obvious and subtle—that might help you recognize the entrepreneurial mindset in yourself.

1. You See Problems as Opportunities

Most people encounter a problem and feel frustration. Entrepreneurs encounter the same situation and see potential.

They ask: “What if this gap could be filled?” and “Could I be the one to solve it?”

From new twists on existing products to better ways of delivering services, entrepreneurs turn roadblocks into runways. Check out this Forbes article on, “The Opportunity Mindset.”

2. You’re Restless With “The Way It’s Always Been Done”

If you’ve ever suggested a change and been met with, “That’s not how we do things,” only to feel your stomach tighten—that’s a clue.

Entrepreneurs aren’t rebels for rebellion’s sake. They simply believe there’s always a better way. They thrive on questioning assumptions and imagining alternatives. I have been involved in several organizations that did not have adaptive ability to pivot toward new ideas or market realities which caused me to leave to start new ventures.

3. Risk Doesn’t Scare You—It Motivates You

Entrepreneurs don’t leap blindly. They embrace calculated risk: researching, weighing trade-offs, and then taking action when others hesitate.

If you’ve ever thought, “I don’t know exactly how this will turn out, but I’m going to try anyway,” you’ve already spoken the entrepreneur’s language.

4. You Create Before You’re Asked

Some people need assignments. Entrepreneurs create without permission.

Maybe you started a side hustle on weekends, designed a prototype after work, or taught yourself a skill just because the idea wouldn’t leave you alone. That proactive drive is entrepreneurial DNA.

5. You Care About Impact, Not Just Income

Yes, revenue matters. But ask a true entrepreneur what keeps them up at night, and you’ll hear words like freedom, purpose, legacy, and impact.

Money is important—it fuels the journey—but it’s rarely the ultimate destination. The best start-ups I’ve been engaged with also highly protect culture and strive to keep the “start-up energy” alive even long after the initial phases or an acquisition or IPO event. Keep in mind that founders’ personality traits are strongly linked to an organization's success and sustainability.

6. You’re Resilient When Things Go Wrong (and They Will)

Every entrepreneur has a story of setbacks: partnerships that collapsed, products that failed, funding that never came through.

The difference is how they respond. Startup founders treat setbacks as tuition in the school of experience. They pivot, adapt, and keep moving forward. This happened to me after 9/11. Our well-funded start-up got amassed in the dot com bubble and quickly failed after the Twin Tower attacks. Within a year, I was working on a new security infrastructure hardware and software solution based on the market shifts post 9/11.

So… Are You One?

Here’s the truth: you don’t need permission to call yourself an entrepreneur. You don’t need employees, an LLC, or six figures in revenue.

If you see opportunities where others see problems, question the status quo, embrace calculated risks, and get back up when life knocks you down—you’re already on the entrepreneurial path.

Maybe you still have a day job. Maybe your idea is still on a napkin. That’s okay. The mindset comes first. The business follows.​​ The best entrepreneurs and emerging leaders are coachable and seek guidance.

The real question isn’t “Am I an entrepreneur?”—it’s “What will I do about it?”

Ready to take the next step in your leadership or entrepreneurial journey? Connect with us to explore coaching and collaboration designed for values-driven leaders across the West Coast.