What 100 Days of Making Instagram Reels Taught me

For years, I avoided making videos.

I knew I was bad at them. I’d record something, watch it back, and delete it. Then I’d walk away discouraged, telling myself I’d try again when I was ready. When I felt more confident. When I had something worth saying.

Eventually, I enrolled in a year of Ultraspeaking classes because I wanted to close the gap between where I was and where I knew I needed to be. And the training helped. I got better at thinking on my feet, structuring my thoughts, speaking with clarity.

But here’s what I didn’t expect.

Even after a year of practice, I still hesitated recording videos. I had a sharper sense of what “good” looked like, and that only made the distance between where I stood and where I wanted to be feel more obvious.

I see this same pattern in the founders I work with. They have a vision for what they want to build. They can picture the impact, the product, the company it could become. But they can also see how far away that vision is from where they are today. So they wait. They prepare. They take one more course, run one more analysis, tweak the pitch deck one more time.

What nobody tells you is that the gap never fully closes before you begin.

It closes because you begin.

Last August, I started a 100-day challenge to post a reel on Instagram every single day. No exceptions. No waiting until I felt ready. Just showing up, recording, and posting.

The first hurdle was simply tolerating my own voice on camera. That discomfort didn’t disappear overnight, but it softened with repetition. I stopped flinching every time I hit play.

The second hurdle was content. What would I even talk about for a hundred days? The answer came slowly, then I started to discover where my stories were. Every week I was learning from conversations with founders, insights from books, questions I was sitting with. My videos became a way to process what I was learning, not a performance of made up expertise.

The third hurdle was process. Eventually, I developed a rhythm. I learned how to capture ideas when they arrived, how to shape them into something with a hook and a message, how long it actually took to record something I could post. I went from dreading every take to trusting a system that worked for me.

Then came the fourth hurdle, and it caught me off guard. I started experimenting with multiple angles, drawing on my iPad while I talked. It felt like a step backward. Suddenly there was more to pay attention to, more complexity, more room for things to go wrong. For a while, I felt like a beginner again.

But I kept going.

Now I’ve discovered that the transcripts from those reels can become frameworks for LinkedIn posts and longer blog pieces. One minute of reflection becomes the seed for something bigger. The practice has started to compound.

I’m better than when I started. I can see that clearly. But I’m still not where I’d like to be.

And here’s what’s changed: I’m okay with not being great.

I used to think I needed to arrive somewhere before I could begin. Now I understand that beginning is how you arrive. Not in a single leap, but through the slow accumulation of tries. You fail, you notice what went wrong, you adjust, and you try again. Over and over. Consistently.

This is true for video. It’s true for launching a product. It’s true for building a company that matters.

Your first attempt will probably be rough. That’s frustrating, but it’s also the process working exactly as it should. The roughness isn’t a sign that you’re doing it wrong. It’s a sign that you’re doing it at all.

I think about the founders I’ve worked with over the years, the ones who moved forward and the ones who stayed stuck. The difference was rarely talent or resources. It was willingness. Willingness to begin before the gap closed. Willingness to let the early work be imperfect. Willingness to stay with it long enough for something to shift.

I’m still on that path myself. Still recording, still learning, still getting a little better each week.

But now I’m confident I’ll get there. Not because the gap has closed, but because I finally stopped waiting for it to.