Founders (and leaders) are addicted to solving problems. It’s their crack cocaine.
That’s what startup scaling coach Rob Bier, author of Smooth Scaling and coach to 40+ startups including six unicorns, told me.
And the more I thought about it, the more it made sense.
Fixing things feels good. It proves we’re still valuable. Still sharp. Still in control.

But the addiction comes at a cost.
It blocks us from building teams that solve problems without us.
And it traps us in an old identity—just when we’re ready to grow into something new.

We explore this and more in this episode of the podcast.

Episode Shownotes
https://howtolive.life/episode/092-let-go-to-grow-with-rob-bier

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Most career transitions are treated like cliff jumps.
You quit the job. Burn the bridges. Bet everything on your dream.

Shiv Choudhury chose a different path.

When he left BCG to build a billion-dollar business, he didn’t go all in.
First, he faked an app. It didn’t even work.
But it taught him one thing: customers wanted what he was offering.
That was enough to move to the next stage.

He calls it “pre-to-typing.”
👉 A way to de-risk big moves by testing the most important assumption before you quit your job or raise capital.

Shiv isn’t just theorizing.
He’s lived it — and thrived.

His career spans P&G, BCG, co-founding a fast-growing startup now valued in the hundreds of millions, and launching a successful private equity firm.
Every move was intentional.
Every leap was tested.

In this episode, he gives a masterclass in how to evolve your career — without blowing it up.

He shares:
✅ The “pre-to-type” method for de-risking ideas
✅ Why staying in your job can be the brave thing
✅ His framework for deciding when to prototype, scale, or kill
✅ How a childhood trauma still shapes his risk-taking
✅ Why humility — not hustle — has been his edge

If you’re in a transition — or quietly planning one — this episode is for you.

Episode Shownotes
https://howtolive.life/episode/091-the-art-of-career-transitions-with-Shiv-Choudhury

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Which of These 6 Success Traps Is Holding You Back?

After my article on The Success Trap in Esquire resonated with so many, I’ve gone deeper in my latest How to Live podcast.

Working with thousands of senior leaders at Google, Unilever, and HSBC, I’ve identified 6 fear-based identities that block evolution:

🧠 The Solver – Fixes everything, but fears being dispensable → micromanagement
🎯 The Perfectionist – Sets high standards, but fears not being good enough → delays
🔥 The Workhorse – Outworks everyone, but fears not belonging → burnout
😎 The Charmer – Inspires others, but fears rejection → avoids tough decisions
📋 The Taskmaster – Executes efficiently, but fears uncertainty → kills innovation
🌟 The Visionary – Sees the future, but fears irrelevance → never follows through

These identities aren’t weaknesses - they’re strengths turned rigid by fear.
🎙️ Episode 90 explores how to evolve beyond them, without losing what made you successful.

Episode Shownotes
https://howtolive.life/episode/090-the-success-trap-when-success-holds-you-back-with-sharad-lal

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You Can Only Make So Many Good Decisions - Are You Using Them Right?

In 1987, we made 100s of decisions daily.
Today, we make 35,000.

Here's the problem: we can only make a finite number of quality decisions each day.

By evening, when we're making important business decisions during work calls or spending time with our children, we've already used up our good decisions quota.

The result? We default to the easiest and safest options - not the best ones.

No amount of coffee, Red Bull, or willpower can fix this. It's not mental exhaustion - it’s decision fatigue.

So how do we ensure our best decisions go to what truly matters?

In the latest episode of How to Live, we speak with Dr. Shawn Watson - a PhD neuroscientist and entrepreneur tackling this issue head-on. His company is one of Singapore’s top 20 hottest startups, and he’s been recognised as a top 10 healthcare professional under 40.

This is a hidden crisis stealing your success. Learn the science behind decision fatigue, how to manage it, and how to preserve your best decisions for what matters most.

Episode Shownotes
https://howtolive.life/episode/089-beating-decision-fatigue-with-dr-shawn-watson

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When scaling a cause, should you pick passionate volunteers or capable ones?

Most instinctively say passion. But Uma Thana Balasingam’s journey scaling Lean In Singapore to 7,000+ members tells a different story.

Here’s the hard truth she discovered: Passionate people don’t always make great leaders. When she and her co-founder started delegating leadership roles to their most committed volunteers, they hit a wall. Leading a movement isn’t just about heart - it’s a skill. Managing complexity, making tough calls, and leading others require more than just good intentions.

The dilemma?

• Capable people execute brilliantly but often vanish when things get tough.
• Passionate people stay committed but can struggle with execution.

Early on, you don't have the luxury of choice - you work with whoever shows up.

But as you scale, the reality sets in:

• Passion without execution creates chaos.
• Execution without passion creates emptiness.

You need both.

In the latest How to Live podcast, Uma and I unpack this challenge. From founding Lean In Singapore to leadership roles at VTech, Dell, and IBM, to now building Elevate to champion women across Asia - she's lived this tension between passion and capability.

If you're wrestling with turning your purpose into impact, this conversation is for you.

Episode Shownotes
https://howtolive.life/episode/088-turning-purpose-into-action-with-Uma-balasingam

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When resources are limited, how do you still access the best?

Afeef Hussain wanted his team - and his country Maldives - to learn from the world’s top minds. But bringing in world-class speakers and trainers isn’t cheap.

So instead of saying, "We can’t afford them," he asked, "How can we make it work?"

His solution? Leverage what he had.

He invited top experts - leaders like Stephen M.R. Covey and other global thought leaders - to experience the Maldives, offering them world-class hospitality at Lux Resorts. In return, they shared their knowledge, mentoring his team and raising the leadership standards of an entire nation.

Resourcefulness beats resources.

Today, the Maldives isn’t just a paradise for tourists - it’s known as a place where top talent comes to learn, grow, and further their careers.

We talked about this mindset - and much more - on the latest episode.

Episode Shownotes
https://howtolive.life/episode/087-wisdom-from-the-maldives-with-Afeef-Hussain

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Forget six-packs - in your 40s, fitness is about feeling good, not looking good.

Let’s face it - most of us in our 40s aren’t hitting the gym for six-packs or beach bodies anymore. The idea of chasing aesthetics just doesn’t feel exciting or meaningful. But here’s the twist: strength training and fitness aren’t about looking good- they’re about feeling good.

When you feel strong and healthy, everything changes. You’re more productive at work, more present with your family, energised for your friends, and - most importantly - happier within yourself.

In the latest episode of How to Live, I speak with Alex Mearns, founder of Levitise, who works with C-suite leaders to transform their fitness and health holistically. His clients include leaders from BCG, UBS, Morgan Stanley, and Goldman Sachs.

We dive into:
✨ Why cholesterol isn’t the real health villain
✨ How to master the "upward spiral" approach to sustainable fitness
✨ Breakthrough strategies that actually work
✨ Designing a health plan that fits your busy life

This episode is a reminder that fitness isn’t about vanity - it’s the foundation for thriving in all areas of life.

Episode Shownotes
https://howtolive.life/episode/086-forties-fitness-guide-with- alex-mearns

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Feeling stuck? You might be looking in the wrong place.

When we hit a crossroads, our instinct is to look outward - more advice, more inspiration, more answers. But here's the plot twist: the most powerful guidance system isn't out there. It's your own story.

Our lives leave breadcrumbs - moments that light us up, decisions that felt right in our bones, and work that made time disappear. These aren't random. They're clues to what's next.

In the latest episode of How to Live, I sit down with Fabrice Desmarescaux, who walked away from his McKinsey partnership to pursue something that called him deeper. Through reflection and mindful exploration, he discovered that purpose isn't a destination - it's a trail of discoveries.

We dive into:

✨ How to read the breadcrumbs of your past to shape your future

✨ Why most big decisions are rarely permanent (and why that's liberating)

✨ The sweet spot between ambition and self-awareness that creates lasting fulfillment

The path forward isn't about perfect clarity - it's about curiosity and courage.

Episode Shownotes
https://howtolive.life/episode/083-life-lessons-2024

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