Jack on The Algorithm vs The Artist: Inside a Creator’s Identity Crisis

There’s a moment every creator hits, and it’s not the beginning. Not the hesitation before posting. Not the “fuck it, I’ll try” phase. It’s what comes after. “The middle is way more interesting,” Jack tells us early in the conversation. “Once you’ve established yourself… you’re kind of an island. There’s no formula. No one really knows what the day-to-day looks like.” And that’s exactly where things start to shift.

From Writing in Isolation to Speaking to Millions

Before content, there was writing. Jack studied psychology and philosophy, only discovering his voice late, almost by accident.

“I didn’t think I was a good writer,” he says. “My sister was a published author at 16, so I just thought, ‘she’s the writer, I’ll do something else.’”

That changed when people started reacting. “I’d read my work out loud in class, and people would come up to me after and say, ‘keep writing.’ I’d never had that before.”

So he did something most people don’t, he committed. “I worked three jobs, dog walker, restaurant, teaching meditation, and I took all that money and invested it in super risky stuff. Like Dogecoin.” He laughs. It paid off, and it was enough to buy time. And time meant one thing: “I was like, I’m gonna write the book now. Not at 60.”

Eight Months, 15-Hour Days, and Nothing to Show for It

The first book consumed him. “I lived in this shitty apartment, worked like 15 hours a day, and lost my mind,” he says. “I wrote the most insane, incoherent book ever.”

No publisher wanted it, so he tried again. The second time was different, more structured, more refined. But the outcome didn’t change…

“I had multiple responses where they said, ‘this is good, but we don’t want stuff from people like you.’”

One publisher was blunt: “He literally told me, ‘you’re never gonna get published. The industry isn’t moving in the direction you’re writing.’ At that point, the question wasn’t just about talent. 

“I didn’t want to be that guy who’s like, ‘it’s the industry, they just don’t understand me,’” he says. “I was like… maybe I’m just shit.”

TikTok Was Never the Plan

The pivot didn’t come from ambition. It came from suggestion. “My girlfriend at the time kept telling me, ‘just post on TikTok.’ And I was like, ‘that’s so stupid, I’m never doing that.’” He laughs. “And then one day I was like… alright.” He didn’t announce it, didn’t overthink it.

“I just posted every day for like two months. I had maybe 600 followers. Nothing crazy. But it was enough to see, okay, this works.” Because for the first time, there were no gatekeepers.

“If your ideas are valid, they go straight to the consumer,” he says. “They don’t have to go through a literary agent, then a publisher… it just clicked.”

Learning the Algorithm, and Losing Yourself

At first, growth feels like clarity, you understand what works, you repeat it, you improve. But over time, that clarity becomes something else. “I got to a point, like two years in, where I knew how to make a well-performing video,” he explains. “Maybe not mega viral, but I knew the tone, the format… it would just go.”

Then he pauses. “But that format was diametrically opposed to everything I wanted to do when I started.” The shift wasn’t dramatic, it was subtle. “I went from being like, ‘I’ll say exactly what I want,’ to… ‘I’m gonna say this because it’ll get views today.’” And the worst part? “It happens so gradually. You never see it coming.”

The Pressure to Perform, Not to Be Right

One of the biggest tensions creators face isn’t talked about enough: The gap between truth and performance. “You’re forced to speak authoritatively,” Jack says.  “You can’t say anything nuanced.” Because nuance doesn’t work on short-form.  “If I start a video like, ‘this is probably not true,’ it kills the whole thing,” he explains. “But that’s what you should be saying.”

So the nuance gets cut. “I’ll film a video with nuance, and then I’m like, ‘this is too long,’” he says. “So I cut it out, post it, and then people are like, ‘that’s not true.’ And I’m like, yeah, I know.” It’s not dishonesty, it’s compression. But over time, it changes how you think, and how you show up.

Leaving New York to Make It Work

When content started gaining traction, another reality hit: Sustainability. “I was like, if I’m gonna do this full-time, I can’t live in New York,” he says. “I’d need like $70,000 a year just to live normally.” So he made a decision most people wouldn’t. “I just thought, I’m gonna go to the most efficient place possible to buy myself more time.” That place was Bangkok. “I didn’t wanna wait five years to make this work,” he says. “I wanted to do it now.” Two and a half years later, he’s still there. “And honestly, I’d probably stay here for the rest of my life if I could.”

Coming Full Circle, Back to Writing

Despite everything, the platform, the audience, the shift in medium, the goal hasn’t disappeared. “I think I have to write a book at this point,” he says. But this time, the intention is different. “When I was younger, it was like,  if I die now, I’ve done nothing,” he explains. “I’ve just consumed resources and given nothing back.” That pressure shaped the work.

“You can’t create art like that,” he says. “You just make this high-pressure piece of shit.” Now, the approach is slower. “I wanna do it from a place of patience and love. Not urgency.” Because people can feel the difference. “They can tell when you’re rushing.”

The Middle Is Where Creators Are Made, or Lost

What stood out in this conversation wasn’t how Jack started, it was what came after. Because the reality is, most creators don’t fail at the beginning. They fail in the middle. When:

• The algorithm is understood

• The pressure increases

• The identity starts to shift

It’s easy to start…. It’s hard to stay, hard to keep your voice when you know what performs. Hard to stay honest when performance is rewarded. And maybe that’s the real challenge of this industry. Not building an audience, but not losing yourself once you have one.  Because in the end, the algorithm can teach you how to grow, but it cannot tell you who to be.

Writer’s Note: Sophia

We’ve interviewed a lot of creators, and if I’m honest, the beginning of their stories is rarely the most interesting part. It’s usually the same: hesitation, a leap, a bit of luck. But the middle, that’s where things get complicated. That’s where things start to blur, where you realise there’s no formula, but at the same time, there kind of is. And once you see it, you can’t unsee it.

What struck me most during this conversation wasn’t how Jack started, it was how aware he is of that shift. There’s this quiet tension between playing the game and staying yourself. And the more you understand the game, the harder it becomes to ignore it. 

As someone building Roe from the ground up, I feel that tension constantly. you want to create something meaningful, but you’re also aware of what performs. You want to stay authentic, but you also want people to see it.

This conversation felt like a mirror in a lot of ways. The truth is, most people don’t lose themselves overnight. They adjust. Slowly. Strategically. Logically… Until one day, it doesn’t feel the same anymore.

And maybe that’s the part of the creator economy we don’t talk about enough. I am starting to think that the real challenge might not be ‘becoming a creator’, but it’s staying one without losing the reason you started in the first place.