How to build trust through your newsletter

Thinking of writing a newsletter? Your lived experience is your best starting point.

When I wrote my very first newsletter, I had no idea what I was doing. I didn’t have a strategy, a blueprint, or even a proper sense of whether anyone wanted to hear from me. What I had was a story, a messy, unpolished, real story that I’m not even sure I should share, and that story changed everything.

Today, I want to show you how to write leadership stories in a newsletter format, not the kind of stories you would post on LinkedIn for clout. The kind that builds trust, deepens connection, and gives people a reason to invite you into their inbox every week.

Where my story began

The first time I was arrested, I was 15. I had planned a gang fight and was sentenced to a month in Singapore Boys' Home and 18 months of probation. My parents wept outside the courtroom while I kept my head down, ashamed but unwilling to admit how scared I was.

The second arrest came at 16, this time in the Subordinate Court. I remember being thrown into a lockup with grown men, and one of them, in his 60s, screamed into the phone because no one came to bail him out. His family had abandoned him.

That image burned into me because I saw what my future could look like if I did not change. I was angry, alone and forgotten, and that was the moment I learned that reflection, not force, was the real turning point.

I share this not to shock you but to show you the foundation of my leadership story because the truth is, your scars are often more valuable than your successes when it comes to building trust with your audience.

Why stories belong at the heart of your newsletter

When people subscribe to your newsletter, they are not signing up for bullet points and jargon. They want a relationship with you, understanding who you are, what you have lived through, and why your perspective matters.

A leadership story does more than make you “relatable” and makes you memorable. Data fades and opinions blur, but a story, like a real lived moment, sticks, especially when you tell it in a way that helps your reader see themselves in it.

That is why my readers stay, because they can feel that every sentence is rooted in something lived.

The structure that works