Are You Ready?
Adapting to the future of work and how changemakers can prepare for the rise of the freelance economy.
Maybe you’ve noticed it, too: more friends, colleagues, and collaborators are freelancing or contracting than ever before. Right now, about 59 million Americans are working independently — and by 2027, more than half of the U.S. workforce will be freelancing.
The structure of the workforce is rapidly changing; and it’s a massive shift happening under our feet.
Massive change like this can feel unsettling, and there are implications for leaders and employees alike. But like with any change, there are opportunities too.
The changing landscape is also an invitation to rethink how we work, restructure support, and create thriving, flexible teams in a world where the traditional W2 model no longer fits for everyone.
This month, I’m highlighting three areas changemakers must be focusing on to build future-proofed, effective teams: skills, benefits, and culture.
Teams today are increasingly blended — a mix of full-time employees, freelancers, and contractors. But most leadership models were designed for a different era: one where everyone sat under the same roof, on the same schedule, in a uniform structure.
Here’s where to start when it comes to imagining teams in this new model of work:
Think carefully about what skills you need in different team members. Full-time Employees anchor the team with vision, strategy, and strong relationships. Freelancers bring specialized expertise and flexibility, allowing organizations to scale and adapt as challenges and opportunities arise.
Adapt your systems for a hybrid team. Are your processes designed for a world where everyone is on payroll — or one where teams are increasingly fluid? Rethink workflows, reporting structures, and expectations so they work for diverse team setups.
Lead with flexibility. Managing distributed, project-based teams means setting clear expectations, establishing open lines of accountability, and creating a system of autonomy and trust. This must be created at every level of the organization and within every role.
The bottom line: Build teams with skills specific to their full-time or freelancer role, and ensure your systems and policies support a blended team.
The reality is that our systems were built on the assumption that healthcare, benefits, and security come from one employer. But in a workforce where freelancing and contracting are growing fast, that model no longer works.
So what do we do?
This is the question I keep coming back to — both as a consultant and as someone who hires freelancers myself. Employee well-being can’t stop at employees anymore. It has to become team well-being.
In action, this means:
Reimagining benefits. Some organizations now offer stipends that allow freelancers to secure their own healthcare plans.
Building partnerships. Collaborate with organizations that bundle benefits for independent workers.
Advocating for policy change. System-wide reform is needed — and leaders can play a role by supporting policies that expand affordable coverage and protections for everyone contributing to the work.
The bottom line: We simply must redesignbenefits in ways that create healthier, more equitable teams — no matter what someone’s employment status looks like.
In any team, connection is everything.
When contributors flow in and out of projects, building culture takes more than water cooler chats and team lunches. It requires intentionality.
Here’s where to start:
Create a Shared Vision. Make sure every contributor — whether W2, contractor, or consultant — connects to your mission and understands how their role helps to advance it.
Ensure Clarity of Roles. Clearly define responsibilities and reporting lines so freelancers and employees alike know exactly where they fit.
Invest in Relationships. Create rituals, shared practices, and opportunities for collaboration that make people feel seen and valued, no matter how long they’re with you.
The bottom line: When we design culture with everyone in mind, we stop managing freelancers as “outsiders” — and start creating teams that move together toward the same goals.
The workforce is shifting faster than policies and systems can keep up. That can feel daunting — but it also opens the door to create something better.
This isn’t just about keeping pace with change. It’s about shaping it.
Leaders who adapt early — who rethink their systems, rebuild their structures, and invest in supporting diverse team models — will create stronger, healthier, and more resilient changemaking organizations in the years ahead.