Our Biggest Lessons Learned as Freelancers

Freelancing promises freedom, flexibility, and the chance to build something uniquely yours. But the journey is rarely as straightforward as most people imagine. Behind the glossy Instagram posts of laptop lifestyle and flexible work hours lies a complex landscape of personal growth, self-management, and continuous adaptation.

Key Takeaways from this Episode:


• Entrepreneurship is a dynamic journey that requires consistent personal development
• Successful freelancers master time management and self-discipline
• Flexibility and curiosity are just as important as technical skills

When you first step into freelancing, you’re likely armed with a skill set, some professional experience, and a dream of working on your own terms. What you might not realize is that the most significant challenges won’t be about your technical abilities, but about managing yourself, your time, and your evolving business.

One of the most profound realizations for many freelancers is that the business you start is rarely the business you’ll end up with. Meredith Cooley, a copywriter for educational companies, emphasizes that entrepreneurship is fundamentally a journey of personal growth. It requires being consistently curious, willing to adapt, and open to unexpected opportunities.

Time management emerges as a critical skill that many freelancers struggle with. Unlike a traditional job with set hours and external accountability, freelancers must become their own managers. This means creating systems that keep you focused, productive, and balanced. Techniques like the Pomodoro method—working in focused, time-boxed intervals with strategic breaks—can help maintain productivity and prevent burnout.

Setting boundaries is another crucial lesson. In the beginning, many freelancers feel pressured to say yes to every opportunity, to be available at all hours, and to bend over backwards for clients. However, sustainable success comes from learning to say no, establishing clear communication protocols, and protecting your time and energy.

The most successful freelancers find a delicate balance between discipline and creativity. They’re committed to their core business while allowing a small percentage of time for exploration and innovation. Think of it like Google’s famous 15% rule, where employees can dedicate a portion of their time to creative side projects—but with the crucial caveat of returning to core work when that time is up.

Ultimately, freelancing is less about having a perfect plan and more about being adaptable, consistent, and intentional. It’s about showing up for the boring administrative tasks, tracking your metrics, and remaining open to pivot when something isn’t working.

For those just starting or considering the freelance path, remember: your business is a living, breathing entity. Nurture it with consistency, feed it with curiosity, and be patient with yourself as you learn and grow.

The road to becoming a successful freelancer is paved with lessons, not just skills. Embrace the journey, stay flexible, and keep learning.

Preston Lee

Preston Lee

Preston Lee is the founder of Millo.co and host of Freelance to Founder, a podcast that helps solo freelancers scale into thriving agencies. Having started, grown, and sold multiple six-figure businesses of his own, Preston now shares proven strategies for landing bigger clients, building small teams, and making the leap from solo work to sustainable agency growth.