Jason Leow led at Shell and GIC — now he’s teaching C-suites how to slow down

How has the idea of being a multi-hyphenate evolved in your field?

It used to mean ambition. Now it means coherence. When I was younger, I chased what most of us did — senior roles, global exposure, a clear arc of “success”. I’ve worked in newsrooms, run crisis communications during oil refinery shutdowns, led corporate affairs at a sovereign wealth fund, and built a new financial PR business across Asia.

But alongside that, I was always asking: What’s the long game? What happens when these titles fall away?

I started The Doing Well Centre years ago, quietly. It was a bet on a future where people would need support not just to perform, but to stay whole. We now coach C-suites, advise boards, and work with organisations trying to be more human without losing their edge.

Staying ahead, for me, hasn’t meant doing more — it’s about doing what matters, and having the courage to make that call before the system does it for you. 

What do people most misunderstand about balancing multiple roles?

People think it’s about juggling. It’s more like tending to different parts of a garden — some things bloom, some need pruning, and some seasons are just quiet. For me, it’s not about collecting roles. It’s about creating a garden that blooms in spring, summer, autumn, and yes, even winter, maybe just not everywhere all at once.

That desire became really clear during Covid-19, and even more so now, when whole industries are shifting overnight.

The impact comes from coherence. When I coach or advise, I draw on this garden where the plants talk to one another: My experience in media, corporate affairs, boardrooms, and public service comes together to serve others.

They don’t live in separate plots — they all inform each other. The trick is to be intentional about what you tend to every season. And maybe more importantly, what you’re willing to let go of.

How have market shifts and shifting expectations influenced how you define and manage your various hats?

The corporate world is more volatile than people admit. I’ve seen brilliant people cut loose through no fault of their own. That’s why I’ve always built in parallel — even while leading at Shell and GIC, I planted seeds elsewhere. I didn’t want to be left with only one card to play. 

The Doing Well Centre came from that instinct: to create a space for deeper work, more values-driven conversations, and a community that’s not built just around corporate KPIs. I’m still involved in strategy and advising, but I’m also clearer now about what’s worth my time.

If the values don’t line up — if the brief is just spin without substance — I step back. That clarity took years to earn, and a few hard lessons.

What’s the toughest part of being a multi-hyphenate that people rarely see or discuss?

Letting go of the old versions of yourself. I think many of us are quietly grieving identities we’ve outgrown — the high-achieving corporate guy, the crisis fixer, the “go-to” person. There’s a kind of grief in realising that title doesn’t fit anymore, even if it paid well and looked impressive on LinkedIn.

But if you don’t let some things go, you never create space for what could come next. That’s the hard part — the in-between, the not-knowing. That’s where resilience gets built, not in the accolades but in the quiet choices no one sees.

What three things would help you navigate and amplify all the work you’re doing today?

First, the right people. I co-founded The Doing Well Centre with Dr Justin Chin because I didn’t want to do this alone. I wanted to build with someone who gets it — who understands that work can be serious without being purposeless and that leading is about creating meaning and inner drive. 

Second, a culture shift. We still reward people for going fast and looking busy. I’d love to see more organisations reward people for being thoughtful, reflective, and values-aligned — and reward leaders who build trust, purpose and participation.

Third, space to pause. In Singapore, we’re conditioned to fill every minute. But the most important decisions I’ve made came from stillness — taking time to ask, “What am I really building here?” That kind of space is rare, but essential.

Beyond the labels, what does it truly mean to live and work as a multi-hyphenate?

It means designing a life where your different selves can coexist, rather than compete. I’m not just a founder, coach, board member, or someone who runs regional and global teams. I’m all of that — and more — in different seasons. And I think a lot of people are like that.

But we’re very much into singular labels in Singapore, so people get confused and ask: “What exactly do you do?” when you don’t do one professional thing. Organisations need to stop seeing these side identities as distractions or risks to be managed.

When someone teaches on the side, volunteers, or explores other forms of meaning — they don’t become less focused. They become more human and more accountable. They show up better.