Can I Be Honest With You?

Can I be honest with you? I’ve spent at least two hours everyday for the last two weeks thinking about how I can turn this newsletter into something that will be enjoyable to read regularly as it is to write so that I can — gasp! — make money from it. I’ve now sunken a ridiculous amount of time just ideating and ideating and I’m embarrassed and bothered by it.

I mean, I now have 20+ newsletter theme ideas and I don’t even like ideas because they’re like water that is filling a tiny bucket that is already full. I see no point in it except waste.

I love writing even if it’s for fun but now that I have become a parent, I’ve become wary of how much I’m guilt-tripping myself for writing things just for fun without a strategy.

So I want to keep writing, but going forward I honestly only wish to do it with the end of “potentially making a living from it” in mind. I said I’m being honest with you!

Why a newsletter

I have proven that I can write consistently good pieces on topics ranging from communication, leadership, and tech. Consistency is a promise I can make comfortably.

I have also received many positive feedback from people when I shared blog posts that were honest and fun to read. Honesty is in my character and I have a strong command of language that I can leverage to write posts worth reading.

Before this, I have been blogging for 7 years. Each post went up silently until I remember to share it. I’ve been fighting a never-ending battle of share-or-not. By publishing directly to your email as a newsletter, I can finally put an end to this fight.

So that brings me to the deeper why. Why am I bothering with this? Don’t I have a job?

My main drive is to build something that can allow me to continually create value for people in a way that leverages what I can uniquely offer.

I don’t mean it in a “yeah, I would love to be able to have six packs” way. I mean it more in a “if enough people paid me to do this I’m sure I will do this for the rest of my life” way.

What also drives me to try is a hunch that I may have more impact on people’s lives writing words rather than code (what I do at my current day job). I have a good tech career going, paying the bills a few times over, yet writing (or creating in general) is still closer to what I would like to be doing full-time. This probably needs interrogation because the software I’m developing at work helps millions of entrepreneurs around the world and that’s hard to beat. But a hunch is a hunch.

So to recap, I love writing and believe that I could have more impact on people’s lives (and convince myself that I led a more meaningful life) if I write rather than code as my job. And getting paid to do it will mean that I can justify dedicating more and more time to doing it.

Alright, with that out of the way, let me share the idea for this newsletter…

Consistent honesty & kindness

There’s a video on YouTube where actor Ethan Hawke gave a talk entitled Give yourself permission to be creative, in which he talked about “playing the fool.” It’s one of my favourite videos of all time because it incidentally articulated my worldview perfectly. The pitch is this: someone’s gotta play the fool so that when others feel something that they do not really understand, that honest thing that he wrote becomes their sustenance.

This is a newsletter where I explore the ways in which I am a fool, admit that, and come up with solutions to emerge better from it. In the process it would indeed make me happy if I could provide sustenance to people who are thinking the same thoughts or feeling the same way. In other words, to help us feel less lonely in the bad times and the good.

This newsletter is called “Can I be honest with you?” and so it will require me to push further past the gates of self-consciousness to share even more intimate and honest thoughts than I’ve gotten accustomed to over the last 7 years from blogging. This, I think, is going to be my chief challenge.

For now, my plan is to publish the more sensitive, a-bit-too-honest posts to paid subscribers only. Another perk for subscribers only is closed-door honesty threads. You can already become a paid subscriber now by going here:

It’s hard to articulate ahead of time the ideas that I have, in part because they’re still being formed, but you’ll hopefully see for yourself in the forthcoming posts. It may take a while for a theme to emerge, but I’m looking forward to start being honest with you, for better or for worse, and see where that takes us.

I’ll leave you with the lyrics from a song I’ve fallen in love with since I became a parent:

You put the work in, don't worry about the praise, my love
Don't try to change the world, find something that you love
And do it every day
Do that for the rest of your life
And eventually, the world will change

Growing Up by Macklemore (feat Ed Sheeran)