There’s a moment in some conversations where everything gets uncomfortably simple. Not simplistic. Not motivational-poster simple. But truth simple.
That happened when John looked at the future of work—freelancers, contractors, fractional experts, AI, remote collaboration—and framed it in a way that left no room for corporate denial:
“If companies don’t reinvent themselves in a massive way, then they’re gonna be toast.”
No drama. No hype. Just the kind of clarity you get after decades of living through multiple waves of transformation—before transformation became a LinkedIn buzzword.
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In this episode of The Independent Workforce, we explored the now and the next of work through the lens of temporary employment—open talent, task-based work, AI-enabled productivity, and the uncomfortable truth that “job security” is often an illusion.
Here is what you can take from it whether you’re building a company or building a freelance career.
How John Accidentally Opened the Door to the Future (Back in 1985)
John didn’t start in “open talent.” He started with a simple observation that felt… oddly obvious.
In 1985, he bought a publishing company and acquired a larger magazine—Women’s Sports and Fitness. The editorial team had 40 full-time people: editors and writers. But something didn’t sit right.
John described a scenario that still happens in companies today:
A writer from New York is flown to Boulder, Colorado to interview a famous climber—John’s friend, Lynn Hill—then writes an article about rock climbing…without really knowing rock climbing.
The result?
Technically correct.
Professionally written.
Emotionally flat.
So John asked a “silly question” that became the first crack in the old model: “Why can’t we let Lynn write her own story and be really authentic—and then hire an editor to edit it?”
That decision wasn’t just editorial. It was philosophical. It was an early prototype of what we now call open talent: letting the people closest to the work create the value, and designing support systems around them.
And it worked.
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From Co-Creation to Crowdsourcing: “Brilliance Is Everywhere”
John’s thinking evolved from publishing into something bigger: co-creation.
Before “crowdsourcing” became a category, co-creation was the idea that customers (or communities) aren’t just consumers—they’re contributors.
John referenced classic thinking like Diffusion of Innovations and the concept of early adopters: if you work closely with people on the edge, you can often predict where the mainstream will go next.
But here’s the key twist John emphasized:
Not everyone is an innovator in the same way.
Some people are early adopters in tech.
Others are early adopters in… removing stains from clothing. (Yes, John used that example—and it landed perfectly.)
Everyone has zones of genius.
And if you build systems that discover those zones, you unlock something most organizations miss.
Then came the agency world—and that’s where John saw the future of work collide with corporate reality.
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The Breakthrough Moment: “We Didn’t Have Enough Creatives”
John helped grow an agency from 100 to 1,200 people in two years. Massive growth. Massive momentum.
And still—there was a problem:
They had around 60% turnover in the creative department. Then they won new business they couldn’t staff fast enough.
So they tried something radical for the time (2008/2009): Put work on a digital platform. Invite creative talent globally to contribute.
And suddenly, the talent they could never convince to relocate became available.
A brilliant creative in London who couldn’t move to Boulder.
A surfer in Sydney who wouldn’t leave the ocean.
People who were world-class… but geographically “out of reach”.
John loved the result. But he really loved one side effect:
“It really pissed off all the other agencies in the world.”
Because it challenged the ego of the traditional model. The message was basically: We’re not the most creative agency. The world is.
That ethos led to John launching Victors & Spoils, a crowdsourced agency that became one of the early seeds of how agencies now use freelance talent at scale.
And then John shared the line that might be the most important of the entire conversation:
“There’s brilliance everywhere… and opportunities are scarce.”
The Harley Davidson Story That Captures the Whole Thesis
John told a story that felt like a movie scene. Victors & Spoils wins the global business for Harley Davidson. And one contributor—a creative from Lexington, Kentucky—had spent years trying to get noticed by top agencies in New York, LA, London.
No replies. Not even the courtesy of a response.
But through the platform, he wins the Harley work, earns $150,000 in his first year, and two years later is named by Adweek as one of the top creatives in the world.
John’s takeaway wasn’t “freelancing is cool.”
It was deeper: Opportunity—not talent—is often the bottleneck.
And companies that rely only on credentialed pipelines systematically miss hidden excellence.
“Jobs Are Going Away.” What Replaces Them?
This is where the conversation moved from story into strategy. John’s view is clear:
Work is being unbundled. Jobs were the old container. Now, outcomes are the new container.
He explained it like this:
“The idea of jobs is going away… companies need outcomes. The best way to get to those outcomes is to taskify the work and apply the best humans.”
That word—taskify—matters. Because it reflects the shift from employment as identity to work as modular outcomes.
And it doesn’t mean everyone becomes a freelancer overnight. It means companies increasingly pull talent in based on what needs to be done, for however long it takes:
an hour
a day
a month
a year
Work becomes fluid.
AI Won’t Kill Freelancers. But It Will Expose Them
When we moved into AI, John didn’t go into sci-fi. He went into survival.
“If freelancers aren’t building AI workflows into their systems… they’re gonna be toast.”
And he quickly added:
Same goes for companies. The point wasn’t fear. It was realism. AI is not simply “automation.” It’s a democratization of capability.
A strong freelancer with good judgment + AI tools can now operate at a level that used to require teams.
John also laid out what remains uniquely human in the age of AI:
- Judgment (built through experience and failure)
- Trust (human-to-human credibility)
- Tool integration (turning AI into real workflows)
- Brand (how you show up and what you represent)
And that leads to a powerful reframing: Even if AI makes production easier, trust becomes the true premium.
A Big Idea: “Assessment Is the Atomic Unit of Work”
This was one of the most provocative moments. John said we’ve been using the wrong “smallest unit” of work. Historically, we treated the human as the atomic unit:
Hire the person → control the person → get the output.
But John argues that in the AI era, the atomic unit is: assessment.
Meaning: Real-time signals of what someone can actually do now—not what their title says, not what their resume claims.
He described a future where freelancers are continuously assessed and supported by AI “coaches,” so clients can see credible proof of capability without months of interviewing and bureaucracy.
Whether or not that exact system becomes mainstream, the underlying point is powerful:
- Trust has to scale
- And traditional hiring doesn’t scale trust fast enough
Why Companies Resist (And Why That Might Not Matter)
When we asked John how to convince companies still living in the “past of work”—the ones who believe full-time in-office employment is the only serious model. John’s answer was blunt:
“I don’t know if we’ll be able to convince the current historical clients.”
He compared it to buggy whip companies facing cars. If you don’t reinvent yourself, you don’t “lose a little.” You become irrelevant.
And then he dropped a quote that should be printed on a wall in every boardroom:
“If you don’t like change, you’d like irrelevance even more.”
Who Owns the Change Inside a Company?
When we talked about who should lead transformation, John made it clear: It starts with the CEO.
Not the HR team.
Not procurement.
Not a “future of work committee.”
“You can’t just say the words—you’ve gotta actually change.”
John also emphasized something many corporates avoid: You need a learning function inside the organization—a Center of Excellence that experiments, breaks things, and learns fast. Because in this new world, failure isn’t an accident.
It’s the tuition.
“Go and fail at everything. Expect that you’re going to fail… you don’t know until you know.”
That’s not chaos. That’s adaptation.
John’s Advice to Freelancers: “You’re the CEO.”
John’s advice for people entering freelancing was refreshingly direct:
“Freelancers have to have the mentality that they’re a CEO… not just do the work, but sell the work.”
This is the shift a lot of new independents underestimate: Being great at delivery is necessary.
But in the independent world, you also need:
- positioning
- communication
- relationships
- a point of view
- consistent learning
Because the market doesn’t “assign” you work. You have to create the conditions for trust and opportunity.
The Real Takeaway: It’s Not Negotiable
Working with freelancers isn’t a “nice-to-have.” It’s becoming non-negotiable.
Because once you accept the premise that speed is strategic advantage—and work is modular—and AI accelerates everything—then the conclusion becomes inevitable.
“When you’re pushed up against the wall, your choices are limited. It’s easy to make a decision.”
Practical Takeaways (Steal These)
For companies:
- Design work around outcomes, not titles.
- Build trust systems faster than you build control systems.
- Expect failure early—that’s how capability is built.
- Reduce hiring friction so teams can pull in talent quickly.
- Treat freelancers as a strategic capability, not a last resort.
For freelancers:
- Think like a CEO: you sell, deliver, learn, and build relationships.
- Integrate AI into workflows now—don’t wait.
- Build a clear brand: how you show up is part of the product.
- Turn proof of work into trust (case studies, outcomes, references).
- Stay close to the future: your edge is learning speed.
Closing Thought
This conversation wasn’t really about freelancing. It was about evolution, and about how the companies—and individuals—who win next won’t be the ones with the perfect plan. They’ll be the ones willing to admit: “I don’t know.”
…and then learn faster than everyone else.
Because the future of work isn’t coming. As John made clear: It’s already here 
