The Hectic Podcast with Anthony Sills: Power of why

Hear how Anthony Sills, founder of Professional Pen, talks about his 13 years of experience as a freelancer, and why there should be more POC freelancing.

The Hectic Podcast with Anthony Sills: Power of why

While you might not know his name, you’ve likely had at least a taste of Anthony Sill’s work. A 13-year freelancing veteran and power content marketer, he has achieved great success with his business, Professional Pen. His clients include American Express, IBM, SEMrush, and Infusionsoft, among others.

When he founded the company in the middle of the 2008 recession, he was tired of dealing with the ridiculously extensive job-seeking process. Attending interview after interview for just the chance to get hired pushed him to consider self-employment.

“I kinda started it out of necessity,” he says. “I’m not going to beg you to work, to exist, to provide for myself. So I started freelancing.”


Thirteen years later, Anthony’s seen the number of freelancers boom. As he recently learned while writing an article on freelancing, however, self-employment isn’t as popular among people of color. In fact, people of color make up less than 40% of all freelancers in the U.S.

“It’s really really skewed as far as who is doing freelancing. And I don’t have a handle on why more people of color don’t freelance,” he says. “I just think it’s really interesting that freelancing is kind of having this moment in the spotlight, if you will, and you don’t see too many people of color looking at it as a viable work situation.”

This is true statistically and in Anthony’s own experience. Despite his years in the field, he hasn’t seen many other people of color working independently.

“You don’t see many people of color, you don’t see as many robust forums talking about freelancing, and I really have a big question mark as to why that is,” he says.

As a fellow black man and freelancer, I shared that my work as a freelance photographer was always seen as just a hobby, not a business or career, by my community. Entrepreneurship and freelancing were never pushed as an option, which can condition young people of color to continue missing out on the opportunity. 

Instead, we were told to get a government job that would offer a pension and retirement. But, as 2020 showed, no job is safe today. And if you lose the great career you have, you lose everything you rely on.

“Freelancing may not be for everybody,” Anthony says. “But who can tell you that you can’t do something on the side so that if your job does go out of business, you can scale that up rather than being there with your hat in your hands? And I think that’s a conversation that needs to be had. It’s not an either/or thing.”

Changing this mindset starts with the people who are succeeding on their own, he says. Rather than qualifying or belittling their work, communities should point to their example.

“We need to look to people who are successful and model that,” he says. “And maybe be a little more vocal when we are succeeding so that people in our neighborhoods, in our communities can say, ‘Oh, if Darryl does that, I can do that when I grow up.’ And so maybe they won’t spend ten years at a job they don’t like because they don’t know they have another option.”

People also need to realize that success doesn’t mean making six figures. It’s having the flexibility to live the life that you need or want to create.

“There’s more to it than money,” he says. “It’s not just a money play, it’s a time play. And when you’re in control of your time, it makes it easier to make money. That’s part of the conversation I don’t see people making a lot.”

Another part of the conversation is the tendency to dismiss freelancing as a real job. Instead, Anthony says, he wants to see freelancers at career day and in documentaries.

“I think we need to dispel the whole ‘people are freelancing because they don’t have other options,’” he says. “And I think we need to somehow make successful freelancers, especially people of color, more visible to their neighborhoods and communities.”

Rather than shaming people for their independent careers, we should have conversations in public to give people the inspiration and drive they need to try going out on their own.

“I’m able to help more people and reach more people in marketing as a freelancer than I would if I was in-house at an agency,” he says. “So I think it’s defining what you want out of life and for some people, for a subset of the population, freelancing is a way to go about getting it.”

It’s all about determining why you are doing what you’re doing, he says. Your why, not anybody else’s.

“If you’ve identified your why, for some people, traditional employment is a barrier to achieving the things that you want,” he says. “Maybe we need to not just change the conversation, but to some degree change the company we keep so that people feel inspired and know that it’s possible.”

Hear the full conversation here, joining us as we discuss the best ways to bring value to clients as you grow your freelancing career. You’ll also get a sneak preview of Anthony’s new book, “Content Clarity: How you can compete with bigger, more established companies even if you’re a one-person content team.

You can connect with Anthony on Twitter at @professionalpen or on LinkedIn.

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