Great Stories, Great Conversations [TMP #107]
Transforming conversations + Birthday hike! & January book
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Today at a glance:
Great Stories, Great Conversations
The Gallery 🎨
Book Club 📖
Great Stories, Great Conversations
Conversations that trigger something positive in us are great gifts. Whether a chat with a friend, a story on the internet or some long YouTube video, I’m grateful for the recorded accounts, documented stories and transforming conversations I’ve had.
The one story I’m talking about today
On many occasions, I have flirted with destructive humility—the kind of being ‘humble’ that tells you to play small to respect others. This kind of humility is self-sabotage. You subconsciously start limiting yourself so you’re not ‘doing too much’. You try not to have opinionated stances to ‘keep the peace’. And because everything has consequences, you stop being the excellent you and start believing that those who do it well are ‘built different’.
I realized I needed help but calling for help took embarrassingly long—but I’d rather be embarrassed than become a shell of myself. That, ladies and gents, is the story of how I blurted out to someone, “how do you think you can build a business … I keep thinking how dare I?” Thankfully, there was enough context behind the question for it not to come off malicious.
On the surface, it seems like a confidence issue, but because my friend was gracious enough to listen, I got the help I needed. Among many things, she said something I paraphrased as “founders don’t know what they are doing1. It’s a lot of embracing uncertainty, leaning into passion, and taking risks.” I have these things on a daily so having that ‘fear’ is objectively ridiculous. Days later, she shared two sermons (WOFBEC 1 & 2 by Pastor Emmanuel Iren) that my mind is grateful for.
Zooming out
This is just one example. There have been many more that I count as gifts whether I’m the one talking or the one listening like:
Ayomide Oyekanmi’s On Getting into Google - I got to appreciate long-term planning and preparation.
Setemi’s 2023 review - I am putting trustful planning with God into practice.
Gita Wirjawan’s interview with Jessica Tan - I really got to appreciate the role of education in building people and business in elevating lives. (I loved this interview so much that I sent her a message about it on LinkedIn—it has not been read 😭.)
and the many conversations with my best friend that force me to be clear, concrete, and without ideological hubris of my own making.
Heck, even this conversation with my roommate the one time I decided to head out later than usual (because time is a resource I can gift):
The real takeaways here are to have transforming conversations—physical and digital—and to ask for help. We need both. As to destructive humility, here’s a quote worth remembering:
“Humility is not thinking less of yourself, it's thinking of yourself less.”
―C.S. Lewis
Till March!
― Dayo
The Gallery 🎨


Book Club 📖
Still reading Dale Carnegie’s How to Win Friends & Influence People 🙈
Please read this in context. It does not mean founders are clueless.
It's amazing because this was my major takeaway this month. Shrinking yourself in any capacity does disservice to everyone involved. Even the ones whom you think might shine brighter are starved from the light that would have emanated from you. I loved this piece🤍.
Awesome read!