The Uplifting Connector

Client Snapshot	Evan: The “Meaning Maker”
Who:	28-year-old data analyst convinced he had to choose between corporate stability and becoming a writer.
Stuck Point:	Successful but restless, torn between “Builder” (data, code) and “Heart Maker” (narrative, connection).
Handbrake:	“The Binary Trap”: Paralyzed by zero-sum thinking, functioning as the “Invisible Architect” who got little credit for his impact.
Insight:	He is a Uplifting Connector. His strength isn’t coding or writing—it’s using both to build bridges and translate abstract ideas into tangible purpose.
First Step:	Instead of quitting, he turned his workplace into a sandbox. Built Massimo (an AI tool connecting data to people) and launched The Drip (a newsletter spotlighting colleagues)—proving his assist-giving nature was his highest-value asset.

There’s a guy wailing on a beach in Hawaii.

Not crying—wailing. Face in his hands, body shaking. Tourists walk past. Couples avert their eyes.

Evan Tesei sits down next to him.

He doesn’t have a plan. Just knows he can’t walk past. They sit there until the wailing subsides. Eventually, the guy thanks him. Evan doesn’t remember what they talked about. Just remembers the sitting.

“I don’t know, man,” Evan would say later. “I just couldn’t keep walking.”

That’s been the pattern his whole life. His earliest memory: making friends with Greek kids on a dock during a family vacation, then feeling devastated when the trip ended. Not because he lost the fun. Because he lost the connection.

The Question He Couldn’t Name

By late 2024, Evan had a problem he couldn’t articulate.

He was 28, working in analytics at Rinsed—a car wash SaaS company in New York. Good job. Great work-life balance. He’d moved back East to be closer to family. Had friends, adventures, wrote stories in his spare time.

On paper, it all worked.

“Sometimes work can be a suck,” he wrote in December. “My company’s product doesn’t bring inherent joy to me. Sometimes this spirals into a more general inquiry into whether my career is maximizing my potential.”

The real question underneath: Should I just quit and become a writer?

He’d been circling this for years. Corporate felt misaligned. Writing felt alive but impractical. He couldn’t figure out which version of himself was real—the data guy who built internal tools, or the storyteller who crafted profiles of friends as gifts.

The First Clue

Back at Novantas, his first job out of college, there was this Excel process everyone hated. Manual, tedious, soul-crushing.

Evan asked his manager if he could try to automate it.

He didn’t know how to code. But he taught himself. Stayed late, googled endlessly, broke things, fixed them. Eventually got it working.

The victory wasn’t about solving a technical puzzle. It was watching his coworkers’ faces when they realized they’d never have to do that process manually again.

That feeling—making other people’s work less miserable—felt better than anything else in the job.

The Test

His junior year at Northwestern, things came to a head.

Evan had found his people in Project Wildcat—a pre-orientation backpacking program. He’d gone as a student, fallen in love with it, become a counselor, then joined the committee running the whole thing. His junior year, he was in charge of curriculum.

Then an anonymous misconduct report came in. University administrators descended. Threatened the program. Threatened the students running it.

“It was truly horrible,” Evan wrote later. “I broke up with my girlfriend and began to get migraines.”

He could have quit. Instead, he fought the administration. Kept motivations high. Endured a semester of hell because he believed in what PWild offered students—authentic connection through shared adversity.

His senior year, they had the safest, best trip on record. The university killed the program anyway the year after he graduated.

But Evan had learned something. His warmth wasn’t weakness. His optimism wasn’t naïveté. When he believed in the integrity of a human system, he’d endure personal hell to protect it.

The Shift

“You’re still siloing these two things,” Chris told him in one of their early sessions. “I think there’s a place where they come together.”

Evan bristled. It felt like one of those annoying coaching moments where the answer is supposed to be obvious but isn’t.

“You have to dig below the bottom of the silos,” Chris pushed. “Find where the root is.”

The work they did together started giving Evan language for something he’d always felt but couldn’t name. A framework for understanding why he’d sat with the wailing man, why he’d fought for PWild, why he’d taught himself to code just to free his coworkers from misery.

Armed with that clarity, he started making different choices at Rinsed. Instead of treating “data Evan” and “writer Evan” as rivals, he started asking: how could they gang up together on the same problem?

He built an AI tool called Massimo. Technically complex—an interface connecting to their database, writing SQL queries in natural language for customer success managers who didn’t know SQL. He built it from scratch. Got it working so well the company considered productionalizing it.

“I wanted to meet each team where they were at.” The customer success managers were drowning in data requests. Massimo was a bridge.

He organized an internal newsletter called The Drip. Not to showcase his own work—to give colleagues a spotlight. When his friend Avery pulled off an audacious climbing feat, Evan wrote her a profile. Not for a magazine. Just as a gift.

“I love a sick assist,” he’d tell people.

His teammates noticed. When asked to describe Evan for a feedback exercise, the responses confirmed what he was starting to understand about himself: “Guardian of Wonder.” “Catalyst for connection and positive change.” One person called him a “boat floater”—someone who gets more fulfillment from the assist than scoring the goal.

The Pattern

That September, his performance review hit different. He got recognized not for his SQL skills or dashboard design—but for connecting dots between teams. Translating data insights into stories that motivated action. Helping others see their work as part of something meaningful.

“I feel like as I just started doing more and more of that,” Evan said, “I just started getting such positive feedback at work.”

His new head of data science pulled him aside. Told him he’d get bored if he focused on narrow technical problems. That his strength was his multithreaded nature—understanding different teams, building bridges.

“You’re getting experience to learn how to be a founder,” the guy told him.

By October, Evan was facilitating a personality assessment session for his data team at Rinsed—using a framework he’d tested through ARC.

“My superpower name is the Uplifting Connector,” he told them. “Though Gav called me The Guardian of Wonder, which I liked even more.”

He was supposed to be a data analyst. But here he was, facilitating a conversation about how people work best together. Using his project management skills to organize it. His narrative skills to help people articulate their strengths. His empathetic sensing to create safety for vulnerability.

The hour flew by. People opened up. Shared things they didn’t usually talk about at work.

Something clicked. He wasn’t facilitating team dynamics instead of doing data work. He was using data-thinking to architect human connection.

Massimo wasn’t a coding project. It was infrastructure for uplifting customer success managers.

The Excel automation wasn’t about efficiency. It was about freeing coworkers from misery.

Fighting for PWild wasn’t about outdoor adventure. It was about protecting a system that helped freshmen connect authentically.

Sitting with the crying guy on the beach wasn’t about being nice. It was about creating space for someone to be seen.

It was all the same thing.

The Questions Now

Evan’s still at Rinsed. Still writing. Still wondering about next steps—maybe an MBA, maybe starting something.

He’s not asking which Evan to be anymore. He’s asking different questions now.

Not “writer or corporate?” but “Does this let me uplift at larger scale?”

That question connects Massimo and blog posts and team offsites and sitting with strangers on beaches. It makes NYC and the mountains, corporate trajectory and creative freedom, all tributaries from the same source.

Not perfectly resolved. Not without ongoing doubt. But clearer now.

The pattern’s there. He can see it.

What This Reveals

Evan’s journey illustrates the trap of divorcing our “creative self” from our “work self” to survive. The breakthrough came when he stopped asking “which career should I choose?” and started testing where his skills could converge—ultimately facing the question: “Are you doing it for yourself with the same intentionality you bring to others?” If you feel torn between two identities, the answer is rarely to pick one—it’s to find the specific context where they must combine to solve a bigger problem.