Running an Agency That Serves Your Life: Phil Bennett on Creative Freedom, Boundaries, and the Power of Staying Small

When Phil Bennett launched Pip, he wasn’t chasing an exit strategy or a seven-figure turnover. He was chasing something simpler, a business that gave him time, freedom, and the joy of doing great creative work.

“If you get too big, you’re just constantly treading water to feed the beast. And that’s not what I want.”

For the past decade, Phil has built a profitable, purpose-driven branding studio in London that’s intentionally small. Pip runs on a four-day work week, operates a trust-based culture, and has profit share incentives, proof that a creative agency can thrive without scaling endlessly.

From Burnout to Balance

Phil’s journey began in frustration. After years of working in an agency where late nights and lack of care were the norm, he hit burnout… twice.

“I went through burnout twice because I didn’t learn my lesson the first time. I was working every hour God sent. I loved what I did, but it was toxic.”

That experience shaped everything about how he runs Pip today. When he went freelance, he vowed never to replicate the culture that broke him. Instead, he built an agency that values autonomy, trust, and well-being for himself and his small team.

“I’m a leader, not a boss. I’m there as a support mechanism - to teach, to guide, to back people up, not to micromanage.”

The Power of Staying Small

Pip isn’t small by accident; it’s small by design. With three core team members and a trusted freelance network, Phil can scale project capacity without scaling the business itself.

That model has its perks. “We’re not chasing the masses,” Phil says. “The clients we want aren’t on social media looking for agencies, they’re larger organisations that value personal service and creativity. Our referrals and partnerships bring in exactly the right kind of work.”

While he has no desire to grow beyond 10 people, he’s open to what he calls “considered growth” expanding the team slightly to support bigger, more strategic projects. But the focus remains the same: work that matters, people who care, and freedom to live.

The Four-Day Work Week: A Game-Changer

In 2022, Phil introduced a four-day work week. The goal wasn’t productivity metrics; it was sustainability.

“Nothing gets reviewed on a Friday. No print deadlines, no client calls. If it’s not done by Thursday, it can wait till Monday.”

The results? His team came back more refreshed, creative, and loyal. Clients noticed the difference, and one of them even decided to trial their own condensed week after seeing how well Pip made it work.

While the team doesn’t work on a Friday, Phil will often use it as a ringfenced time to work on the business rather than in it. Precious time that many Freestyle and Stepping Up founders find it hard to secure for themselves. 

The policy stuck. “We’re still hitting deadlines, the quality is high, and everyone’s happier,” Phil says. “I could sustain this well into my 70s.”

Making Data Simple

Despite scoring high on the Checkpoints and Fitness pillars in The Agency Adventure Diagnostic, Phil’s approach to systems and data is refreshingly simple.

“A Google Sheet and Monday.com -  that’s it. I know it sounds basic, but it works. I just need to know: do we have enough in the pot to pay people and invest back into the business?”

He uses external specialists like accountants and freelancers to fill any gaps he and his core team don’t possess. “I’m a creative, not a finance director,” he laughs. “So I rely on people around me for the oversight I need.” It is a strategic decision to rely on external experts to aid my decision-making. 

Freedom, Focus, and a Long Game

Phil’s clarity about what success looks like is one of his defining traits. While many founders are lured by the pressure to grow or sell, he’s confident in his lane. 

“There’s a lot of noise about growing, selling, exiting. But that’s not for me. I know what I want from this business, it serves my life, not the other way around.”

Three standout lessons from Phil for other Freestyle founders:

1. Boundaries create freedom. Protect your time. Structure your business around your energy and values.

2. Small doesn’t mean static. You can grow selectively, not exponentially.

3. Culture scales faster than headcount. Empower people, trust them, and they’ll deliver.

   
   

You can find out more about the culture at Pip and the way they work by contacting Phil and checking out the clients that sustain their practice here: www.pip-creative.com 

If you’re a Freestyle founder and need support to build a business that works for you and not the other way around, get in touch with claire@agency-adventure.com

Of course, Phil’s journey may not resonate with you at all, and that’s OK! Discover your Founder Profile with our Your Agency of the Future assessment and follow along for more agency owner stories soon.