The Lonely Side of Always Being “The Contractor”

There’s a quiet truth behind the freelance and contract life that rarely makes the highlight reel. While we often get praised for our flexibility, our ability to set our own schedules, and the potential to earn more than some full-time employees—we don’t talk enough about what it costs to live on the outside looking in.

Never Part of the Group Photo

You show up, you deliver, you shake hands, maybe even get a round of applause for your work. But then you pack up and leave. The hugs and inside jokes? They’re for the folks who work together every day. You’re the vendor. The service provider. The reliable extra.

You’re the one who captures the moments and the memories… but rarely gets to be in them.

This isn’t about wanting attention. It’s about connection. And in a world where teams bond over lunches, team-building events, and shared daily challenges, the contractor often operates in solitude—swinging in just long enough to execute, but not long enough to truly integrate.

Isolation in a Crowd

There’s a unique kind of disconnection that comes from working with teams but never really in them. You’re looped into email threads, asked to contribute to important moments, and relied on for critical deliverables. But when the Slack channels close, or the happy hour starts—you’re already gone.

Even for those of us who hire our own teams, it’s different. We may lead crews on projects, but it’s rare that we operate day-to-day with the same people, week in and week out. There’s no water cooler, no “you won’t believe what just happened” convos between tasks. It’s a revolving door of faces, locations, and workflows.

You’re Never “Safe”

One of the hardest parts? You’re always chasing. Always scanning the horizon. There’s no two-week notice when a regular client stops calling. There’s just silence—and the creeping realization that your services might no longer be needed.

You can have a great year. Land big projects. Feel like you’re in high demand. But it only takes a few quiet weeks to remind you: everything you have, you’re constantly re-earning. There’s no resting on past work. No guaranteed paycheck. No internal pipeline.

Even with long-standing relationships, there’s often no real closure—just a ghosted inbox or a polite “we’re moving in a different direction” months later. That ambiguity eats at you in ways few people understand.

Camaraderie vs. Connection

You can build systems, you can hire contractors and collaborators, you can have amazing clients—but it’s not the same as seeing the same people every day, building inside jokes, witnessing someone’s life change over a morning coffee. That kind of connection isn’t easy to come by when every job is a new room, a new team, a new goodbye.

Not Just a Videographer, But Still Running Solo

I’m not a lone videographer lugging around a camera bag from gig to gig. I run a small business with a core team, a trusted network of contractors, and established systems that keep projects moving at a high level. This is a real operation. We deliver for commercial clients, multi-day events, livestreams, marketing campaigns—the works.

But here's the thing: even with a team behind me, we're rarely in the same room together. Most of our coordination happens through group chats, project boards, and voice notes while driving to separate gigs. Everyone's hardworking, reliable, and sharp—but it's not the same as walking into a space where everyone shares the same mission, culture, and rhythm.

That sense of “team” in the traditional sense—daily connection, shared momentum, real-time support—is something that doesn’t naturally exist in this model. And it’s a void that shows up quietly… until a moment reminds you just how separate you really are.

Why This Isn’t a Complaint

Let’s be clear: this isn’t a pity party. Many of us choose this life—for the autonomy, the creativity, the ability to build something that’s ours. And there’s a strength in that. But strength doesn’t mean we don’t feel the weight of it.

This post is for the contractors, freelancers, and solo operators who show up, give 100%, and go home to their families or alone —who carry the mental load of running a business while still trying to feel human in a world built for teams.

It’s also for the folks on the inside—to say: if you’ve got people in your ecosystem who show up consistently, even if they’re “just vendors,” know that they’re giving more than a service. They’re giving themselves—and they feel the gap just like anyone else.

Let’s Talk About It

If this resonates with you, I’d love to hear from you. Whether you’re a full-time creative who’s found ways to stay connected, a contractor who’s felt this same ache, or someone in a hybrid role navigating both worlds—drop a comment or message me.

And if you’ve never felt this way, that’s okay too. Maybe this gives a little insight into what the other side of the curtain can look like.

Either way, thanks for reading. We don’t always talk about this part of the journey—but maybe we should.