I’ve been talking to my computer for decades, and it’s finally paying off for everyone.

Yesterday I dictated this entire newsletter into my iPad mini using the Drafts app and WhisperMemos while sitting in my backyard. No special microphone, no training sessions, no leaving awkward pauses between words like I had to do in the old days.

Just hit the red button and start talking. The fact that this works still amazes me.

The Long Road to Here

My dictation journey started with Dragon Dictate, back before it became Dragon NaturallySpeaking. You had to… leave… spaces… between… each… word… or… it… didn’t… work.

Even when I got pretty skilled at it, every document needed serious cleanup afterward. The software had no context, so “their” and “there” were constant battles, and forget about getting proper names right, even with extensive training.

For years, dictation felt like a promising technology that never quite delivered on its promise. You needed professional microphones, quiet rooms, and the patience of a saint. Most people tried it once and gave up.

But something fundamental has changed. The AI models powering today’s dictation tools understand context in ways the old systems never could. They don’t need training on your voice, they handle background noise gracefully, and they make intelligent guesses about what you actually meant to say. It’s the difference between a computer transcribing sounds and an AI re-constructing speech.

There are so many good Whisper-based apps available now. The real breakthrough isn’t any single app, it’s that we’ve crossed a threshold where dictation just works.

The hardware requirements have disappeared, too. I’m dictating this on an iPad mini using its built-in microphone. No headset, no external mic, no special setup. Because I’m outside right now, there birds chirping and a trash truck drove down the street a few minutes ago. It doesn’t matter. The same device that’s perfectly fine for FaceTime calls turns out to be perfectly fine for dictation.

How It Changes Your Writing

Thinking verbally is different from thinking with your fingers or a pencil. When I dictate, I err on the side of abundance in my first draft, then edit ruthlessly. It’s perfect for my natural workflow.

There’s something about speaking your thoughts that makes the writing more personal. When I’m typing or writing by hand, I tend to edit myself before the words hit the page. With dictation, ideas flow more freely. I’m more willing to explore tangents and follow interesting threads. You can always clean it up later.

Part of me still thinks fondly of Captain Picard doing his captain’s log on the Enterprise. That’s basically me every day now, creating content for you.

If dictation makes you nervous because your thoughts come out messy, solve that with preparation. Spend some time making a mind map or outline before you hit record. Then trust that you can fix it in the edit, and let your voice get a little more personal.

Give It Another Shot

Not everyone has delved as deeply into this rabbit hole as I have, but I’m telling you: if you tried dictation in the past and gave up, it’s worth revisiting. We can finally declare dictation a solved problem. I honestly didn’t know that would happen in my lifetime.

The tools are there, they work reliably, and they’re getting better every month. Whether it’s Apple’s built-in dictation (which is acceptable but not best-in-class), or some third-party Whisper-adjacent transcriber, pick one and give it a real try for a week.