How to Live

05/08/2025

28/07/2025

"How have I been complicit in creating the conditions I say I don't want?"
Many of us find ourselves trapped in patterns we claim to hate - overworking while craving balance, tolerating bad bosses, accepting toxic work cultures.
This question cuts right to the heart of it. It's not about blame. It's about awareness. The word complicit cuts deeper than responsible, because it asks us to look inward, without self-attack.
This question comes from Jerry Colonna - former JP Morgan partner, co-founder of a top-tier VC firm with Fred Wilson, now known as the CEO Whisperer. He coaches Founders and CEOs at Etsy, SoundCloud, and Fortune 500 companies.
I've wanted this conversation for years, ever since hearing him on the Tim Ferriss podcast. When he agreed to come on How to Live, I honestly couldn’t believe it.
In our conversation, Jerry opens up about his journey from massive Wall Street success to a near-suicidal moment on a subway platform, and how radical self-inquiry saved his life.
We dive deep into self-growth, leadership, practical journaling techniques, managing the voices in your head, and why the most successful people often create their own suffering without realizing it.
If you're exploring the next frontier of growth, it might not be outside.
It might be within.
This conversation will help you start the work.

15/07/2025

"Chase passion, not pension" - but how do you actually figure out what you love?
Robin Speculand nailed this. At 34, he was making VP money at Citibank — but still didn't know what his "passion" was.
So he did something most of us never do: He stepped off the treadmill and took time to reflect.
On a beach, he asked himself: – What have I truly enjoyed? – What gave me energy? – What problems do I see that others miss?
That's when it clicked. Every company had a strategy. But 9 out of 10 failed at implementation. Nobody was solving this. It was a blue ocean.
His passion wasn't "helping people" or "being a founder." It was this specific, unsexy problem everyone ignored.
📌 If you're in your 40s and feeling stuck, maybe passion isn't something you find. Maybe it's something you recognize:
Step off the treadmill (take real reflection time)
Look at what energizes you (not what looks good on LinkedIn)
Spot the blue ocean problem only you can see
Your passion might not be trending. It might be the overlooked thing that quietly lights you up.
And that's exactly why it could change your life.
🎧 Full episode with Robin — How to Live, Episode 98

01/07/2025

𝐌𝐞𝐧 𝐡𝐚𝐯𝐞 𝐚 𝐩𝐫𝐨𝐛𝐥𝐞𝐦.
We're taught to "man up" and handle everything alone.
When we struggle, we don't reach out. When friends share problems, we jump straight to solutions.
We think asking for help is weakness. We think giving advice is helping.
But here's what we miss: We never build emotional safety nets.
Women often do this instinctively. They listen first. They create space. They support before they solve.
The result? Deeper friendships. Stronger teams. And, as research shows, better leadership outcomes.
The best male leaders I know have learned this. They know that sometimes, people don't need your solution. They just need to feel understood.
Men: Try this. Next time someone shares a challenge, don't jump to advice. Ask: "How did that feel?" or "Tell me more."
It's time to redefine masculinity.
🎙️ I explore this with Andrew Reiner in the latest How to Live episode. Andrew wrote the bestselling Better Boys, Better Men and writes on masculinity for The New York Times. We discuss male friendships, emotional support, and why redefining strength might unlock better leadership and deeper relationships.
Listen wherever you get your podcasts.

17/06/2025

Be interested, not interesting.
𝐈𝐧 𝐧𝐞𝐭𝐰𝐨𝐫𝐤𝐢𝐧𝐠, 𝐛𝐞𝐢𝐧𝐠 𝐢𝐧𝐭𝐞𝐫𝐞𝐬𝐭𝐢𝐧𝐠 𝐢𝐬 𝐞𝐱𝐡𝐚𝐮𝐬𝐭𝐢𝐧𝐠. 𝐁𝐞𝐢𝐧𝐠 𝐢𝐧𝐭𝐞𝐫𝐞𝐬𝐭𝐞𝐝 𝐢𝐬 𝐜𝐨𝐧𝐧𝐞𝐜𝐭𝐢𝐧𝐠.
Most high performers approach networking like a performance.
Say something clever. Be impressive. Stand out.
But being interesting takes energy. It puts pressure on you.
And it often keeps things at the surface.
There's a better way: Be interested instead.
Ask thoughtful questions. Listen deeply.
Let others do what they love most - talk about themselves.
It's lighter. It's more human.
And it builds real trust. The kind that leads to long-term relationships, not short-term transactions.
🎙️ This shift from performing to connecting is exactly what Ryan Lim and I dive into in the latest How to Live episode. Ryan wrote the #1 Straits Times bestseller The Business of Networking, and he shares why introverts often make the best networkers, and why curiosity is your greatest tool.
Listen wherever you get your podcasts.

03/06/2025

Most people stay stuck because they’re waiting for clarity.
Big mistake.
When you’re 15–20 years into your career, the destination will never be what you imagined anyway.
What’s really keeping you stuck isn’t a lack of direction. It’s fear.
Fear disguised as “being strategic.”
Fear disguised as “waiting for the right moment.”
Fear disguised as “needing more information.”
But here’s the thing:
You don’t overcome fear by thinking your way through it.
You overcome it by moving through it.
The path doesn’t appear before you move.
It reveals itself because you moved.
Start small: One conversation. One experiment. One step forward.
Your next chapter is waiting on the other side of action, not analysis.

🎙️ In the latest How to Live podcast, I’m sharing part of my conversation with the amazing on her .podcast
We talk about practical ways to find purpose, how to move when stuck, and why your 40s might be the best time to reinvent yourself.

20/05/2025

You’re running faster.
You’re winning.
But are you running in the right direction?
The success script teaches us to outrun others.
Outrun, Outwit, Outlast.
But it rarely asks:
Is this the race you want to win?
Bhavna Toor followed that script.
She rose fast in New York finance.
But eventually, she realised she was running the wrong race — without ever choosing it.
Mindfulness helped her pause.
Reflect.
And choose her own path.
Mindfulness did not stall her ambition.
It pointed it in the right direction.
Today, her ambition burns stronger than ever.
Because it’s aligned. Conscious. Sustainable.
Mindful ambition isn’t about slowing down.
It’s about choosing your direction — with clarity.
If you’re questioning your own race, this conversation on How to Live might resonate.
Are you running your own race — or just running faster?