Playing Your Way to the Pivot

Names and identifying details have been changed to protect privacy.

Mei was a UX designer at a large fintech company. She was good at her job. She was also, by her own description, slowly dying inside.

She'd spent two years trying to figure out her next move with the tools she had: spreadsheets comparing roles, informational interviews, a personality assessment she'd taken three times, a career coach she'd seen for four sessions before deciding the sessions themselves were making her more anxious.

When she found me, she'd narrowed it to two options: product management at her current company, or going freelance as a design consultant. She'd been deciding between these two options for eight months. Neither felt right. She was stuck.

I did something a bit unorthodox in our second session. I asked her to stop talking about careers entirely and just tell me about the last time she'd been completely absorbed in something. Not professionally. Just: absorbed.

She talked for twenty minutes about a board game she'd been designing with her partner on weekends. A resource management game with a narrative layer. She lit up describing the playtesting sessions, the mechanic she'd iterated on seventeen times, the moment a rule change made the whole thing click.

I asked her what that experience had in common with her best moments at work.

Long pause. Then: "I was solving a system problem. But the system had people in it. And I cared whether the people were having a good time."

That's product strategy. Not product management in a fintech org — product strategy with a human-systems lens, which looked very different and was more specific, and also happened to map onto several roles she'd completely dismissed because she hadn't thought to look for that framing.

Six months later she was a product strategist at a design-led startup. The board game is still in progress. She tells me the playtesting sessions are where she does her best thinking about her actual job.

Play doesn't just relax you. Sometimes it shows you what you've been trying to figure out the hard way.