Why Companies Must Rethink How They Work with Freelancers – Episode 10 with Matthew Dowling

Freelancers have always been part of the workforce — but what’s happening now is different. We are entering a new era shaped by agility, global talent, AI, and the ability for individuals to build careers outside traditional employment.

In this evolving landscape, few voices are as influential as Matthew Dowling, Founder of Freelancer Club, leader of the #NoFreeWork movement, and architect of initiatives to empower one million freelancers by 2026.

In our conversation on The Independent Workforce, Matthew opened up about his accidental journey into freelancing, the systemic problems he’s spent a decade solving, and what companies must understand if they want to thrive in a blended workforce future.

From Accidental Freelancer to Reluctant Advocate

Like many who eventually dedicate their lives to a mission, Matthew didn’t choose freelancing — freelancing chose him.

I fell out of university and straight into freelancing by accident. I had no clue what I was doing. I stumbled around in the dark for two years.

His photography work picked up unexpectedly — but so did the risks. The turning point came when a company he worked with for a year suddenly stopped paying him. After months of silence, Matthew finally walked into their office… and found they had gone bankrupt.

No contract. No rights. No payment.

A journalist heard the story, and suddenly it was national press. Embarrassing — yes. But it became the seed of Matthew’s life’s work: making sure this never happens to another freelancer again.

This moment became the origin story of Freelancer Club, a platform now supporting over 300,000 freelancers with education, training, and community.

Fighting for Fairness: How #NoFreeWork Changed the Conversation

When Freelancer Club launched, Matthew made a decision that would define their identity: No unpaid work. Ever.

He started the #NoFreeWork hashtag — and it exploded: “We trended number one on Twitter more than once. It became clear freelancers were pissed off — exploitation through unpaid work was everywhere.”

The campaign led Matthew directly into advocacy, including long-term collaborations with the UK government and eventually his current leadership role as Chairman of the Good Work Review Working Group for Self-Employed Creators.

And for the first time in UK history, a “Freelance Champion” role is being established in government.
A decade of relentless work — finally paying off.

Why Freelancer Education Needs a Complete Rethink

Universities prepare students to become full-time employees — not business owners. But freelancers are business owners. That’s where the education gap begins.

You can be top of your class in your craft, but without business essentials, mindset, and core skills, freelancing becomes unsustainable.

Matthew’s training programs help students learn everything traditional education misses:

• How to price work
• How to negotiate
• How to manage client relationships
• How to run a brand
• How to protect IP
• How to build confidence
• How to create a long-term freelance career

It’s not just skill-building — it’s identity-building.

Where Companies Get It Wrong (And Freelancers Feel It)

Matthew sees both sides: freelancers struggling to navigate corporate systems, and companies struggling to adapt to modern talent models.

The issues usually start early:

1. Bad briefs and mystery budgets – “I showed a group three real job posts. They guessed budgets from £150 to £6,000. For the same job. That’s the problem.” Companies underestimate how damaging vague job descriptions can be.
2. Delegating hiring to the wrong people – Often, an intern or assistant ends up hiring a highly skilled freelancer. “You wouldn’t hire a full-time senior person that way — so why treat freelancers with less care?”
3. Isolation inside the company – Freelancers are brought in to contribute, yet feel like outsiders.“If you want to know who the freelancer is, look in the corner — the one alone with a laptop.”
4. Late payments (sometimes 90+ days!) – This one hurts the most.“Companies think it’s just a few thousand. For freelancers, that’s survival money.”
5.  Scope creep without conversation – Freelancers fear pushing back because companies have more power. Result: burnout, resentment, and mistrust.

Ethical Hiring: The Missing Framework

The concept Matthew pushes forward is simple — but transformative: Treat freelancers with the same respect as employees.

Not legally. Not contractually. But culturally.

He calls it ethical hiring, which includes:

• Clear briefs
• Fair compensation
• Prompt payments
• Inclusion in communication
• Proper onboarding
• Respect for their expertise
• Transparency and trust

You’re not hiring hours — you’re buying years of experience across industries.

The Blended Workforce: Employees + Freelancers + AI

One of the most important insights Matthew shared is the framework used by top tech companies today:
The three pillars of the future workforce:

• Flexible work (legacy of the pandemic)
• Freelancers / agile talent
• AI agents

This combination creates adaptability no traditional team can match: “The world is unpredictable. Companies must be able to shift direction fast. Freelancers enable that.”

Businesses still relying purely on full-time staff are already facing operational drag.

Companies that embrace freelancers gain:

• access to top expertise they couldn’t afford full-time
• faster iteration
• external perspectives
• innovation at lower risk
• anti-fragility (as Matthew called it)

Companies that avoid freelancers?

“They get slower. More rigid. And they miss opportunities. It’s that simple.”

 So… How Should a Company Start?

Matthew’s advice was crystal clear — and practical:

1. Give context, not just tasks: Freelancers work better when they see the bigger picture.
2. Talk to them: “A 10-minute conversation can solve months of future friction.”
3. Build trust early: Freelancers can solve more problems than you assume.
4. Treat them like humans: Respect is a multiplier of performance.
5. Pay fairly — and on time: Freelancers shouldn’t be financing corporate cash-flow cycles.

As the conversation came to a close, one message stood out:

The best time to start working with freelancers was yesterday. The next best time is today.

Freelancers aren’t an optional add-on anymore.

They’re a strategic advantage. They’re a source of speed, innovation, resilience, and agility. And companies that embrace them will shape the next decade of work.

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