Late one night, long after everyone had gone home, Jason Kan found himself alone in the office, staring at a blank wall and asking a simple yet heavy question: What am I doing here? What is my motivation?

He'd climbed the ranks over more than a decade in the international internship space, starting in a junior role and eventually becoming COO of a fast-growing, VC-backed company. He'd built multiple functions from scratch — HR, talent acquisition, partnerships, CRM, IT.

But somewhere along the way, he had lost perspective.

Jason 1.0 to Jason 2.0

Looking back, Jason realized there had really been different versions of himself as a leader.

Jason 1.0 was the hands-on builder. At around 30–40 employees, he was both manager and individual contributor for multiple functions, learning to build processes from scratch.

Jason 2.0 emerged as the company scaled to ~125 people. As the business transitioned from services to a tech platform (2023–2024), complexity and pressure spiked.

Jason turned to the usual leadership advice: be stoic, don't show vulnerability, stay focused on results.

"What I was advising was very tactical… But it wasn't resonating. I didn't acknowledge my team members just wanted to be heard."

His direct reports were under immense pressure. Many of them weren't looking for another checklist from their COO; they wanted to feel understood.

"The real frustration was I thought I wasn't being heard and seen for what I think my skills are as an operator."

That night in the office crystallized the deeper issue.

"For the last five years, I have been obsessed with work… I lost perspective."

The turn: Circle

A few months later, Tara joined as a fractional operator during a critical period — the company was migrating to a new platform and needed alignment across Tech, Operations, and Sales. Watching her work was Jason's first hint that leadership could look and feel different.

"Watching her and observing her… that was my first indication of, right, there is another way to lead here."

By the time Jason came to Circle, he was ready to question the assumptions that had carried him this far.

"Over the course of the three days, it was like peeling an onion… understanding myself."

At the core, he found something simple: what mattered most right now was his family — especially his mum — and how precious time actually is.

"Yes, Circle makes you a better leader, but for me, it made me a better person. It made me a fuller person."

Jason 3.0: A more human leader

The shift since then hasn't been a dramatic external reinvention so much as a steady internal one. Jason is still COO of the same company. But he is moving through it differently.

Weekly standups now open not with status updates, but with check-ins.

"We share roses, thorns, buds… getting a temperature gauge of headspace."

When tension appears between teams, he doesn't just push handoffs. He brings leaders together to explore their "trust languages."

"We identified each other's trust languages… that was a big unlock."

Perhaps the most personal test of his growth came just days after Circle, when he sat down with his CEO and spoke from feeling — fatigue, strain, and the desire to be seen. Their relationship deepened.

Jason calls himself "Version 3.0" — operationally rigorous, but far more anchored in humanity.

"I'm trying my best to not think there are two Jasons — professional Jason and personal Jason."