If you’re drowning in client work but hesitant to bring someone else on board, you’re not alone. The leap from solo freelancer to team leader is one of the most significant—and nerve-wracking—transitions you’ll make in your business journey.
Jordan Reyes, founder of Pixelflow Studio, recently asked us this exact question: After six years of freelancing in web design with more work than they can handle, how do they know when it’s the right time to hire their first contractor?
Key Takeaways from this Episode:
Start by clarifying your ultimate business objective—scaling to sell requires different hiring strategies than pursuing work-life balance.
Look for skill gaps rather than just overflow work. Hire people who complement your expertise or can handle business operations you’re weak at.
Consider “business hires” (operations, finance, growth) before redundancy hires. Build different functions first, then add backup for your core skills later.
Start With Your End Goal
Before making any hiring decisions, Christine Olivas—founder and CEO of No Single Individual—recommends taking a crucial step back: What’s your ultimate objective?
This might seem obvious, but the answer fundamentally changes your approach to building a team.
If your goal is to scale and eventually sell your business, there’s no better time than now to start bringing on help. Even if your margins temporarily decrease, you literally cannot build something viable and scalable without delegating work to others.
But if your primary goal is work-life balance and financial flexibility, Christine suggests a different approach: Handle as much as you can yourself, maximize your earnings, and give yourself the freedom to take extended time off when you need it.
Why? Because the moment you bring someone onto your team—even as an as-needed contractor—you transition from being solely responsible for yourself to being responsible for someone else’s wellbeing. That’s a significant shift that changes your day-to-day reality.
It’s Not Just About Overflow
Here’s a critical insight: Volume of work alone shouldn’t be your only reason to hire.
Yes, Jordan has more client work than they can handle. That sounds like a clear signal to bring someone on. But as Christine points out, client work is cyclical. You could hire a contractor to handle overflow today, only to have work return to normal levels in two months.
Instead, think about hiring as a way to address skill gaps and deepen your expertise.
Christine isn’t great at social strategy or influencer work—she knows this about herself. But when she pairs herself with someone who truly understands speed-of-culture work and modern platforms, they become far more powerful together than either would be alone.
This is the “rising tide lifts all boats” approach to team building.
Ask yourself: What areas am I less equipped to handle in the long term? What skills would complement mine and make our combined offering stronger than what I can provide alone?
Two Types of Hires: Deliverable vs. Business
When you’re ready to bring someone on, you essentially have two options for your first hire.
**Deliverable hires** are people who execute the work you deliver to clients. If you’re a graphic designer, this means hiring another graphic designer. These are the people who help you fulfill client projects and scale your service delivery.
**Business hires** are people who work on growing and running your business itself—operations, finance, sales, marketing strategy. These are the people who free you up to focus on either client work or strategic growth.
Most freelancers instinctively think about deliverable hires first. It’s the natural freelancer mindset: Who can help me with this next project?
But the founder mindset asks: Who can help me grow this business?
Christine’s first employee hire was someone to run finance and operations. She readily admits these aren’t her strengths, especially future forecasting and financial modeling. And hands down, she says it was the smartest decision she made in five years of business.
There’s no universally “right” choice between these two types of hires. It depends entirely on what you want to keep on your plate. If you love client work and want to stay involved in deliverables, hire someone to handle your business operations. If you’re energized by growth strategy and business development, hire someone to execute the client work.
Just avoid the trap of hiring a mini-me without thinking strategically about what your business actually needs.
Build Functions First, Redundancy Later
Christine shared an interesting evolution in her hiring approach: She started by building out complementary skill sets and different functions first, then added redundancy layers later.
First, she brought on people with expertise she didn’t have—different strategy specializations, operational capabilities, financial acumen. This made the overall pie bigger and created a more robust offering.
Later, as the business grew, she added redundancy—other people who could handle sales calls, represent the company at speaking engagements, or manage client relationships the way she does.
That’s when the real freedom began.
This mirrors how many startups grow: First you build out your different functions (engineering, sales, marketing, operations). Then, once you hit that next level of scale, you create redundancy and deepen each individual area so people can take vacations and the business can operate smoothly without any single person.
If you’re seeking freedom right now, it’s tempting to jump straight to hiring someone who does exactly what you do. But if you can hang on a little longer, it often makes more sense to first bring on people who can help you grow the business or fill critical skill gaps. The redundancy hires—the ones that truly give you time off—come after you’ve built that foundation.
The Mindset Shift You Must Make
Perhaps the most important thing Christine shared is this: The moment you bring someone else onto your team, you can never really go back.
It’s less about tactics and more about mentality. You go from “the me show” to “the us show.” You become responsible for training someone else, getting them up to speed, articulating what’s been in your head, and ultimately letting go of some control.
For some people, this transition is energizing and exciting. For others, it’s uncomfortable. Not everyone thrives in a management role—and that’s okay. The skills that made you an exceptional freelancer aren’t necessarily the same skills you need to be a great founder or manager.
Think about your own working style. Do you enjoy training people? Are you comfortable delegating? Can you articulate your processes clearly to someone else?
If management doesn’t appeal to you, that’s valuable information. You might be better suited to staying solo and optimizing for maximum earnings and flexibility, rather than building a team.
When Is the Right Time?
So when should Jordan—or anyone in a similar position—actually pull the trigger on their first hire?
The right time isn’t just when you’re busy. It’s when you’ve identified either a critical skill gap that’s holding your business back, or when you’ve decided you want to build something that can eventually run without you at the center.
It’s when you’re willing to make that mindset shift from independent contractor to team leader. When you’re ready to let go of some control and invest time in training and managing someone else.
And it’s when you’re clear on what you’re building toward—not just reacting to being busy this month.
Start small. Bring someone on for a specific project or in an as-needed capacity. See how it feels to delegate and manage. Learn what you’re good at and what you struggle with as a team leader.
Then adjust from there. Some freelancers will discover they love building teams and scale dramatically. Others will find they prefer staying lean with just one or two key people. Neither path is wrong—they’re just different routes to different destinations.
The most important thing is to move forward with intention, knowing what you’re building and why.
