About 100 Days In

I’m just over 120 days into posting written content five times a week on Facebook, Instagram, and LinkedIn.

I’ve also been sharing short videos five days a week on YouTube, Instagram, LinkedIn, and Facebook.

I made a promise to the most important person in my world that I’d do this.

That person, by the way, is me.

Now I know that might not be the most socially acceptable thing to say. I love my wife and my son more than anything. But if you’ve ever flown on a plane, you already know what I’m getting at. When the oxygen masks drop, you’re told to put yours on first. Not because you’re selfish… but because you’re useless to everyone else if you’re unconscious.

This habit is my oxygen mask.

Not because I’m trying to go viral. I have missed a few days (less than 5%) along the way, but have not used it as an excuse to stop.  Not because I’m building a content empire. And not because I think the world is desperately waiting to hear my thoughts about entrepreneurship, education, and the occasional bad parenting metaphor involving Mario Kart.

I do it because it forces me to manage my time very well and most importantly… it  makes me think.

This is my version of what Keith Cunningham calls Thinking Time, which is one of the most valuable concepts I’ve ever pulled from a business book. If you haven’t read The Road Less Stupid, it’s in my personal top 5.

Here’s the idea in a nutshell: Cunningham argues that most business problems are really thinking problems. Not execution. Not funding. Not marketing. It’s that we’re too busy reacting to the urgent and not carving out enough space to think about the important.

And I agree. But I also know myself.

If you sit me in a quiet room with a leather-bound notebook and a fancy pen and tell me to “think deeply,” I’ll be scrolling my phone before the coffee even cools.

But if I commit to publishing… daily… I’m forced to wrestle thoughts into words. I have to clarify half-baked opinions, challenge my assumptions, and ask myself whether what I’m saying is actually true or just convenient.

Sometimes I write something and realize I’ve been lying to myself.

Other times I write something that makes me pause and sit back and say, “huh… that’s actually good.” It’s like finding a part of myself I didn’t even know was hiding in there until I tried to put it into words.

It’s not always profound. Some days, it’s just a weird metaphor that links curriculum design to being stuck in a level of an old-school video game. Other days, it’s a reflection on how trying to get my five-year-old to brush his teeth has made me a better coach.

But every time, it’s a mirror. I see a little more of myself. Who I am. What I value. Where I’m still bullshitting myself. And what kind of man, entrepreneur, husband, and father I’m trying to become.

The truth is, creating every day is hard. And it’s only going to get harder from here.

Some days the ideas don’t come. Some days the words fight back. Some days I want to toss my phone out the window and move to a place with no internet and no expectations.

But I made a promise.

Not to an algorithm. Not to a personal brand. Not even to my future customers.

To myself.

And keeping that promise has became a cornerstone of my personal integrity.

That’s something most entrepreneurs underestimate when building their business: the weight of the promises you make to yourself. Because if you break those, eventually you’ll stop believing yourself at all.

And if you can’t trust your own word, well… good luck getting anyone else to.

Which brings me back to the real lesson here. This habit I’ve built (of writing daily, even when it’s not good) isn’t just sharpening my thinking. It’s helping me grow into the kind of person I want to be.

That matters. Especially for me, since I build online schools and help others do it too.

I’m 120 days in. 240+ to go.

And even if nobody else ever reads a word of what I write, I’ll still be doing it.

Because the real work of becoming who you want to be starts with the promises you keep when no one else is watching.

That’s not just business. That’s life.

And I ain’t planning to break that promise anytime soon.

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