Adventures in dictationland


I’m not a dictation-only kind of guy. I enjoy typing and do most of my writing that way. But there’s something liberating about being able to sit down, flap my gums, and have the words appear on the page, and when I dictate, I’m able to crank out a lot of them.

For a long time, I used DragonNaturally Speaking to dictate on my Windows desktop. I recently retired that computer in favor of a new laptop and haven’t installed Dragon. When I want to dictate, I’ve been using Google Voice Typing, which is fast and accurate, at least for me. The only drawback is that you can only use it via the Chrome browser and I use Brave as my default.

A few days ago, I downloaded a free app called LilySpeech (Windows only) and have been trying it out. It uses Google’s servers for transcription and seems to deliver equally impressive results.

The advantage of LilySpeech is that I can use it anywhere on Windows—in any browser or app, including Scrivener, which is something I wasn’t able to do with Dragon. Right now, I’m dictating this into Obsidian, and it works like a charm.

On iOS, Siri dictation works well but times out after 30-40 seconds. I tried Google Docs Voice Typing, both the app and via Safari, and it also times out. But who knows, I may be doing something wrong.

The Drafts app (iOS, Mac, Android) does dictation well. I just tested it on my iPad and it didn’t time out, even after several minutes of continuous speaking. (If you get different results, try launching a new document via the widget instead of the app.)

When I started practicing, I would dictate and record and have a secretary transcribe it. Today, many attorneys record and upload to a transcription service like But unless human transcription is required, I’m a proponent for letting technology do it.

There are many other options for each platform that seem to deliver varying degrees of speed and accuracy. If you’d like something that’s cross-platform and can be used via the web or an app, I recommend giving a try. They have a generous free plan and the paid plan is reasonable.

Otter has a couple of killer features to recommend it. It allows you to transcribe a conversation, identifying each speaker by time stamp. Very handing for interviews and meetings. Otter also adds punctuation (at your option), meaning you don’t have to dictate it.

So, over to you. Do you use dictation? What apps or process do you use on desktop, web, and mobile?

I’m all ears.