@ilyaonthefly was a Tennessee-raised freelance filmmaker and editor who had gone full-time in high school and built his client base almost entirely through Instagram outreach and community. Isaac had been connected with him online for years before they ever actually spoke, and the episode opened exactly the way those conversations do when two people finally get on — honestly, with Ilya talking through creative ruts, mental health lows, and the gap between what he wanted to make and what paid the bills. They covered the tension between passion projects and freelance work, what a lost retainer taught him about structuring recurring income, and why the DM habit had driven everything he’d built.
@ilyaonthefly on Mental Health and the Creative Ceiling
The episode opened with Ilya being honest about where he was: a rough stretch. Creative ruts, mental health lows, a forced kind of reckoning with himself. He wasn’t making a spectacle of it — he just called it what it was and talked through it.
What stood out wasn’t the struggle itself but how much it had spilled into his output. Not just the will to edit or take on projects, but everything downstream — the quality of his thinking, how he dealt with clients, whether he could show up the way he wanted to.
“You focus so much on the skill side of it, on getting better as an editor, getting better as a filmmaker — and you’re like that’s all you’re focused on. And then you reach a certain ceiling, and until you like work on your foundation as a person and how you actually treat people and like what your whole stick is, you can’t really go further.”
Isaac related. The work costs something real. The level it takes to make something people actually stop for has gotten genuinely demanding, and that cost shows up somewhere — whether you’re tracking it or not.
The conversation landed on a frame that held up: almost every figure worth studying had some version of imbalance at the center of what made them great. Arnold Schwarzenegger’s boring, singular obsession with the gym. Mike Tyson crying before fights because he didn’t recognize who he became in the ring. Caitlin Clark getting kicked out of PE in elementary school for being too competitive. Ilya’s mom had put it to him directly.
“There’s not a single legendary musician or artist or famous whatever that wasn’t like to an extent a little messed up in the head — every single famous whoever, inventor, musician, athlete, all the greats — to an extent, most of them to a very high extent, pretty imbalanced as far as all they’re focused on is like the thing they want to be great at.”
Passion Projects vs. Freelance
This was the core tension. There were the things Ilya would make regardless of money — projects that genuinely lit him up — and then there was the freelance work that kept the lights on. In theory, the second funds the first. In practice, creative energy isn’t infinite.
“The more I work on the passion projects, the less mental health stuff and the less stuff all around — when I’m working on what I really want to work on.”
Freelance wasn’t the problem in isolation. The problem was that it spent something. By the time a client job was through — the revisions, the follow-ups, the waiting on feedback — there was less left for the work that actually mattered to him.
He was honest about what that meant for the quality of what he delivered on the freelance side:
“You’d have to pay me an insane amount of money to actually put in the effort that I put into my passion stuff into my freelance stuff — it’s just not like I just don’t care about it that much, it’s just there for money.”
Isaac’s take from his own path: the fix wasn’t finding only passion-aligned clients — it was finding freelance work that didn’t drain the creative tank. Consistent, predictable, not particularly taxing. The retainer model had been part of that answer for him.
Going All In From High School
Ilya had been shooting since he was around nine or ten — already locked in, making stop-motion Lego videos in his room, already on YouTube. By 13 or 14, in middle school, he’d decided he wasn’t going to college. His dad was a college math professor.
He was on board.
“I got so lucky — my parents were like pretty much like 95% support.”
Part of what made that work was evidence. Ilya wasn’t asking to skip college on a vague hope — he’d been doing the work for four or five years already. And his parents, rather than pushing back, became something closer to business advisors. They flagged bad situations. They could see through people he was too young and naive to read yet — and nine times out of ten, they were right.
He’d had one job outside of freelance: Subway, for a couple months in high school, just long enough to save up for something he needed. After that, everything had been freelance — building from high school rates toward something that actually covered life.
The Retainer Lesson
Isaac had found his way out of the feast-or-famine freelance cycle through retainers — consistent monthly work that was reliable enough to level out the swings without draining the creative tank. He walked Ilya through it: find the low-tax work, stack two or three of those, and the rest of the time is yours to spend how you want.
Ilya had gotten close. A recent retainer had just fizzled — decent money, minimal work, and then gone. Looking back, he could see what went wrong.
“I was trying to treat my retainer like a passive income thing, and that’s just like doesn’t work.”
He’d set it up loosely. Didn’t think deeply about the structure, just hoped the client would stay happy and the money would keep coming in. Now he understood what had been missing.
“I understand now that more has to come from my end — not just the filming and the editing and delivering high quality stuff fast — like actually structuring the retainer to where it makes sense for me and them and like they know the reasoning for why it’s structured that way.”
The retainer didn’t fail because the model was wrong. It failed because he’d treated it like something that runs itself.
Building a Network Through DMs and Engagement
Almost everything Ilya had built — every gig, every connection, every client — traced back, directly or indirectly, to Instagram. He’d taken the Gary Vee 100-DMs-a-day concept seriously as a kid sitting in class in high school and started doing it.
“I literally 100% of my income, for over the last however many years, has come either directly or indirectly from that — I remember sitting in class sophomore year, junior year, and I would literally be DMing like a hundred people.”
Instagram wasn’t just a portfolio — it was a digital business card, an outreach tool, and a credibility signal all at once. When a mutual follower connected two people who’d never spoken, that was the system paying off. The engagement wasn’t about vanity.
“It’s like a video game — it’s like how many comments can I get, how many followers can I… build up this avatar that is my Instagram profile.”
What had grown out of years of that habit was a group chat that had been running for six or seven years — a core community of creatives who’d gone from sharing rough early work to being called up for real gigs. Isaac had recorded with Henry Smisek while Henry was on the road with Logic. That was what the group chat had become for the people in it.
“The people in those group chats are going to run the world here soon — it’s just funny how they’re calling out gigs and like we need to go here and do this.”
The tiers of connection that Ben Skaar had laid out in his episode was the articulation of something both Isaac and Ilya had been doing intuitively: a like at the bottom, then a comment, then a DM, then a space or group call, then a personal call, then in-person at the top. The closer to the top, the more real the relationship.
“Me and you have been exercising these bottom-tier ones for a while — what’s stopping us from hosting a space once a week, creatives tap in, kind of a thing?”
What’s Next
Ilya had passion projects in motion — outdoor, high-energy cinematic work in the country music space, the kind of short-form content that felt genuinely like his lane. There was also a snowboarding project in the queue, a combination of two things he’d been doing separately for years finally brought together.
What he kept coming back to was the relationship between his internal state and what he was able to take on. The ceiling he’d hit wasn’t a skill ceiling. It was a capacity ceiling — and the only path through it was working on himself, not just grinding harder.
“The more I work on mental health and the more I get myself balanced, the more I’m able to hold space for the bigger projects, for the cooler opportunities.”
Isaac had been in a version of that same place — where the external variables only started to stabilize after the internal ones did. There wasn’t a clean timeline on it. But both of them had reached the point where the direction was clear, even when the details weren’t.
“You don’t know exactly where it’s going to lead, you don’t know exactly the people, the projects, the details of it — but you do know that you have to do it. Like there’s no question about it.”
Key Takeaways
- The skill ceiling is a people ceiling. Past a certain point, progress requires working on yourself — your reliability, your relationships, your foundation — not just getting technically better.
- Passion projects protect your mental health. The more time spent on work that actually matters to you, the less friction everything else generates.
- Freelance energy isn’t unlimited. Some client work drains more than others — finding low-creative-tax work is what makes space for everything else.
- Retainers aren’t passive income. They require structure, clear expectations, and active relationship management — they fizzle out when treated like a set-and-forget arrangement.
- Consistent outreach compounds over years. Treating Instagram engagement like a daily habit — not a campaign — built an entire income stream and creative community slowly and reliably.
- Move up the tiers of connection. Likes and comments are the floor. Phone calls and in-person meetings are where relationships actually become relationships.
Follow @ilyaonthefly on Instagram. Connect with Isaac at isaacjarnagin.com.
