"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.

Shownotes

https://howtolive.life/episode/099-wisdom-from-the-CEO-whisperer-with-jerry-colonna

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"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:

1. Step off the treadmill (take real reflection time)
2. Look at what energizes you (not what looks good on LinkedIn)
3. 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

Shownotes

https://howtolive.life/episode/098-designing-life-in-your-forties-with-robin-speculand

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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.

Shownotes

https://howtolive.life/episode/097-redefining-masculinity-with-andrew-reiner

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