LIFESTYLE

A peek into the life of Maheesha Ratnayake

UNPLUGGED

IN CONVERSATION WITH NATALIE SENEVIRATNE

What do you do at the beginning of your day that sets the tone before work begins?

I call my kids no matter where I am in the world. It’s a small ritual but it grounds me and reminds me why I do all of this. Success means nothing if you lose sight of the people it’s for.

Which personal habit or routine has had the greatest impact on your professional life?

Training and time spent with my family – that balance isn’t a luxury, it’s the foundation. Everything I bring to the table professionally comes from being whole outside of it first.

How do you maintain a healthy balance between your personal life and a demanding work schedule?

I’ve made peace with the fact that weekdays belong to work, travel etc. But weekends are sacred; they belong entirely to my family. Boundaries like that aren’t restrictions; they’re what make the rest sustainable.

If you had a month to unplug anywhere in the world, where would you choose to go and what would you do there?

I’m not made for switching off completely; but if I had to, Montenegro or Azerbaijan. Somewhere untouched enough to remind you how small your worries really are.

On challenging days, what helps you reset your mind and regain clarity?

I snap out of it – a hard workout clears everything; it’s where I remember that discomfort is temporary but momentum is everything.

What’s been the defining moment in your leadership journey so far?

Realising that babysitting trust fund egos was never my calling and learning that gratitude isn’t always a two-way street. That lesson freed me. It taught me to lead from purpose, not from the need to be thanked.

Where do you draw inspiration from beyond the world of business?

Mostly from within; but nature and travel do the rest – they strip away the noise, and open pathways in the mind that keep me centred, focussed and honest with myself.

One facet of leadership you’re consciously trying to improve…

Learning to stop helping people who never asked for it. Real leadership sometimes means stepping back and trusting others to find their own way.

If you could capture the essence of your leadership style in a short phrase, what would it be?

I’ve been told I inspire others; and if that’s the mark I’m leaving, it’s the only one that truly matters. Titles fade and numbers are forgotten but the people you’ve pushed to believe in themselves carry that forward long after you’re gone.

What legacy do you hope to leave behind as a leader?

One that teaches people to treat each other with kindness because in the end, that outlasts every title, deal or achievement.

What book, podcast or piece of content has influenced you recently – and why did it resonate with you?

Titles fade and numbers are forgotten but the people you’ve pushed to believe in themselves carry that forward long after you’re gone 

The Mamba Mentality – Kobe Bryant’s philosophy of relentless self-improvement. It’s about constant growth no matter how far you’ve come, obsessive attention to detail, turning failure into fuel instead of fear and loving the process itself, not just the outcome. 

If you could give your younger self one meaningful piece of advice, what would it be?

Be careful who you give your energy to – not everyone deserves it – and protecting it isn’t selfish; it’s strategic.

An unconventional leadership insight you’ve learnt that others may find surprising…

A sense of humour is non-negotiable in any situation – it disarms tension and reminds everyone including yourself not to take yourself too seriously.

What personal value or principle do you refuse to compromise?

Respect – for everyone, regardless of who they are or what they can do for you – it’s the truest test of character.

How do you spend your ideal weekend when you’re not working?

On the beach with my family. No agenda, no meetings – just presence.

What’s the most memorable travel or life experience that has shaped the way you see the world?

A visit to Japan. I learned that attention to detail and respect aren’t just cultural values; they’re a way of life and a lesson I’ve tried to carry into everything I build.

If someone shadowed you for a day, which one of your routines would surprise him or her?

That I eat with my team – every one of them, regardless of their title. Hierarchy has its place but not at the table.

What’s a simple everyday pleasure that brings you unexpected joy?

An activated charcoal, coconut banana smoothie with peanut butter – small rituals like this keep me happy amid the chaos.

Respect – for everyone, regardless of who they are or what they can do for you – it’s the truest test of character

And what is the most underrated skill that today’s leaders should cultivate?

Humility – it is quiet but it’s what separates leaders who last from those who simply climb.

Looking ahead, what excites you the most about the next phase of your life and career?

Everything: the opportunities ahead and watching my children grow up – and that more than any achievement, is what I’m building towards.

Maheesha Ratnayake is the Managing Director of Winfinity Holdings.