This post was originally shared in my DT Email Newsletter here.
This morning, I want to tell you something personal. Here goes.
About two weeks ago, we held our Diligence Wealth Club Summit 2026. It was a blast! I’ve never thought I’d ever host an event myself. Let alone keep doing it year after year.
Every year, our attendance grows a little bigger. And every year I walk away with newfound lessons (new members don’t worry, we run this every year).
There’s so many lessons to learn. But this morning, I want to talk about one that stuck with me most: challenging my fears.
I grew up a shy boy. Unlike my eldest boy, I was never that kid who would go up to anyone and say “HI”.
Most of the time, I rather hide in a corner. I remembered Mom would always egg-ed me on to be “more brave”. I was afraid of embarrassment. And that fear stopped me from doing a lot of things.
So instead of finding my voice, I found a workaround: I took an engineering degree in university, and I enrolled into the CFA Program.
I’d rather face a thousand pages to read than face a room full of eyes. Skill became my substitute for confidence. Looking back, it sounds strange to admit. I think a lot of us do this. We hide behind skills so we don’t have to face our fear.
After I quit my banking job in 2018, I had time to look inward – building the relationship with my parents, working on my temper that can flare up like a blistering eczema and so on.
Nothing happens overnight. It’s the daily compounding of wanting to become better that pulled me forward. It’s always that first step.
This is what my Diligence Wealth Club Annual Summit really is. I wanted to challenge myself, grow and face the fears I carry all the years.
One of them is public speaking and hosting a live event. It took me months to prepare for the summit – making sure members had a great Saturday afternoon.
My favourite segment of the entire summit? The fireside chat with my members!
Btw my panelists walked away with a little “chaos hedge” for their stock portfolio from me as part of a gift – want to guess what it is? 🙂
You see, my best moments during the event are when I learnt from other members their own investing journey. One of our members shared something that stayed with me.
Years ago, he lost a large six-figure sum on a Singapore stock everyone trusted. It didn’t work out. Yet he didn’t quit. He got back up, kept going, and is still investing today, still willing to try again.
That was inspiring.
He faced his own fears, got up and tried again. We often want to get started in our investing journey, but are afraid we might get it wrong, afraid of losing money we worked hard for and afraid of taking that first step.
It’s that same fear of me walking on stage that day.
Sometimes, what we need to do is to face that fear to manifest what we truly want.
For me, that got me to achieve my financial goals, build dividendtitan.com, grow an amazing investing community (having met wonderful people with unique backgrounds) and challenging myself to be a better person, a better investor.
What’s that one fear about investing that’s stopping you from getting what you truly want?
Drop me an email and let me know!
And I’ll see you at next year’s summit.
Sometimes, investing can be simple.
Willie Keng, CFA
Founder, Dividend Titan
