Phil Pallen on Designing a Business That Gives You Freedom

1 Aug

In this episode of Looks Good From Here, Hannah chats with Phil Pallen, a brand strategist, AI expert, and keynote speaker who helps businesses build standout brands. Phil shares his journey from brand strategist to content creator, his approach to AI for small businesses, and how he's designed a business that allows him to travel the world. Watch the video or continue reading below.

The Business Pivot That Changed Everything

Phil's story began like many designers: fresh out of school, moving to LA, and struggling to land an agency job. Instead of waiting for someone else to hire him, he decided to help small business owners navigate the emerging world of social media. His first three clients? A makeup artist, a real estate agent, and a jewelry designer.

"I never intended to be an entrepreneur ever," Phil reflects. "It just kind of happened, born from the fact that I had passion and tangible skills that I could sell."

Fast-forward 14 years, and Phil made a dramatic shift. From 2023 to 2024, he reduced his client work by 50%. By early 2025, that reduction reached 76%. The reason? Content creation and AI education now generate more income while allowing him to impact more people.

YouTube Success

The turning point came from an unexpected source—a client's feedback on a simple screen recording. After Phil sent a quick tutorial on updating a Squarespace website, the client responded: "Why don't you post videos like this on YouTube? This was so helpful for me."

That single comment launched Phil's YouTube career. His breakthrough video, "Three free apps for content creation," hit half a million views and attracted brand partnerships that started small but grew into his primary income source.

"I make more money as a content creator, and more importantly than money, I get to affect more change and I get to work on projects that I'm more passionate about," Phil explains.

AI as Your Thinking Partner

One of Phil's most powerful contributions to the design community is reframing how we think about AI. Instead of viewing it as a replacement for human creativity, he positions it as the ultimate thinking partner.

"I want to respect my team's time, and I'd like to bring ideas to them as 80% baked instead of 50% baked," Phil shares. "AI helps me get to that point."

Practical AI Workflows for Designers

Phil's approach to AI focuses on enhancing human expertise rather than replacing it. Here are some of his proven workflows:

Client Strategy Sessions: Phil uses AI note-takers for every client call, then uploads transcriptions to ChatGPT. Months later, he can reference specific conversations to inform copy writing or strategy decisions.

Content Creation: When developing YouTube scripts, Phil provides AI with the client brief, homepage copy, three high-performing video examples, and even competitor analysis. The result? A 95% complete script that just needs human refinement.

Email Management: Tools like SaneBox automatically organize emails into preset folders, reducing Phil's daily inbox to just 2-3 priority messages.

The key insight? "AI is computing a lot of information quickly. We still need the human—we still need personality and how you say things. But you can be the conductor of this orchestra."

Building a Business That Travels

Phil's current lifestyle—working from anywhere while maintaining a profitable business—didn't happen by accident. It required intentional decisions about what to keep and what to eliminate.

His strategy includes:

Reducing client roster from 15-20 to just 5 carefully selected projects
Grouping all calls into specific days (Tuesdays and Thursdays only)
Staying in locations for a month rather than rushing through tourist destinations
Being mindful of time zones to avoid creating stress for collaborators

"You just have to think: what's keeping me here? Then be intentional about designing a life that has as few things as possible keeping you in one place."

The Evergreen Approach to AI Education

Despite writing a book about AI—a topic that changes daily—Phil focused on evergreen principles that transcend specific tools or trends. His book includes 185 tool recommendations, real-world examples, and proven prompts based on years of hands-on testing.

"Don't let AI derail you from your business objectives," Phil advises. "AI is not as important as it seems. Hitting your business KPIs is more important. Making sure your business fulfills you and your team is more important."

Staying Creative in a Digital World

Managing the intensity of content creation and client work requires intentional breaks. Phil schedules two complete disconnections per year—April and November—when he does minimal work and focuses on recharging.

"I find that after the marathon and sprint combination, I need to just take two weeks or three weeks off and do the minimal amount of work to keep the business going."

Key Takeaways for Designers

Phil's journey offers several actionable insights for designers looking to evolve their careers:

Start with your existing skills: Phil began by packaging knowledge he already had into helpful content
Use AI to enhance, not replace: Focus on tools that make you more efficient at what you already do well
Design your business intentionally: Consider what kind of lifestyle you want, then build systems to support it
Test and iterate: Phil's approach to both AI and business development involves constant experimentation
Balance is essential: Plan downtime into your calendar before you need it

The Future of Design Business

Phil's transformation from traditional service provider to content creator and AI educator represents a broader shift in the creative industry. As AI tools become more sophisticated, the most successful designers will be those who learn to leverage technology while maintaining their human creativity and strategic thinking.

The question isn't whether AI will change design—it's how you'll adapt to create more impact, more income, and more freedom in your work.

Ready to explore how AI can enhance your design workflow? Phil's book "AI for Small Business" provides practical tools and strategies for getting started, while his upcoming Brand Masters membership will offer ongoing support for designers ready to systematize their approach to client work.

Your design career doesn't have to follow the traditional path. As Phil proves, with the right tools, mindset, and strategic thinking, you can build a business that works for your life—not the other way around.