SINGAPORE — Playwright Joel Tan’s career has been on the express lane since his debut, Family Outing, at the Singapore Theatre Festival in 2011.

His works have been staged by indie theatre groups, he did one W!ld Rice panto, he recently directed an all-poets performance at the Singapore Writers Festival, and he has two plays coming up. Next week, Checkpoint Theatre — Tan is an associate artist there — will be presenting The Way We Go, a piece about five people whose lives are linked to a convent school, which explores various notions of love. Directed by Claire Wong, it stars Hollywood-based Lydia Look, Neo Swee Lin and Malaysia’s Patrick Teoh.

Then, in January, the M1 Singapore Fringe Festival is restaging Mosaic, a piece about four young people who converge in an ’80s-era mosaic playground slated for demolition. “It concerns my generation’s weird nostalgic relationship with the past and how productive this nostalgia is,” said Tan, 27.

In a sense, these two shows reveal the twin threads of his ongoing journey as a playwright: Working with established theatre groups as well as independent ones.

Next up, Tan is sitting down with mentor and Checkpoint’s co-artistic director Huzir Sulaiman to work on a musical. He’s also slated to write next year’s W!ld Rice pantomime The Emperor’s New Clothes after penning last year’s Jack And The Bean-Sprout!. At the same time, he’s just as comfortable with smaller amateur groups such as Yellow Chair Productions, NUS Stage and Take Off Productions, which had first staged Mosaic at last year’s Lit Up Festival.

“With independent groups, there’s a real kind of ‘running away to the circus’ feel about it. It’s liberating — we’re doing it together, and if we make mistakes, it’s a forgiving environment. But of course, no one’s getting paid,” he joked.

“The professional world is a very different working environment. The stakes feel slightly higher and it comes with a sense of a public that a small show doesn’t have because we play to friends and the occasional curious stranger. Everyone is on the top of their game.”

His works may be shown in different contexts, but what ties them together are his interests in the act of conversation and in human relationships.

“I write a lot of conversation into my plays. I’m fascinated about people speaking and talking to each other and I enjoy writing it. Thematically, human relationships concern me, this painful need for human connection that we all have, despite the fact that people can be hurtful,” he said.

Tan dismissed the idea of being a part of a “new wave” of Singaporean playwrights, but he does see his work — and those of others, such as his fellow Checkpoint associate artist Faith Ng — as an attempt to return to naturalism and more text-centric works.

“I’m wondering if we’ve exhausted the possibilities for naturalism in telling stories for Singapore. Maybe now’s a good time to think about this.”

The Way We Go is from Nov 20 to 29, 8pm, SOTA Studio Theatre. With 3pm weekend matinees. Tickets at S$35 from SISTIC. (Advisory 16: Some homosexual content.)

Mosaic is on Jan 22 to 24, 2015, 8pm, Gallery Theatre, National Museum of Singapore. Tickets at S$22 from SISTIC.