My Favorite Voice Notes App (2 Years Later) | Habit Chess Newsletter


I’ve always been somebody who has been obsessed with taking voice notes. Even before the iPhone existed, I had a handheld recorder that I would record into, and of course, I never did anything with it because it was too tedious to transfer things to a computer and then transcribe them.

It used to be a long process, but now with the Voice Memos app on your iPhone, you can basically see a live transcription once you’re done recording. And not just that—you can copy that transcription, put it into your favorite LLM, or reformat it.

That is the free option, and it’s significantly upgraded compared to the Voice Memos app just a few years ago. If you want to take it a step further, there are other tools like Otter or VoicePal, apps designed to help you talk your thoughts out and turn them into something actionable.

Letterly & Capturing Thoughts

The piece of software I’m gonna share is something you can pay for once and own forever. This is one of the main reasons I love AppSumo—that’s where I’ve gotten tools like BreezeDoc, TidyCal, and Letterly.

I found that with Letterly, if used correctly, it becomes a second Notes app because you want to use it often. It’s kind of addicting.

You want to revisit it so you can take advantage of what you’ve captured, and think of it as a place to talk out things you’ve been procrastinating on. Whether it’s an email or something you need to type out, try talking it out.

Sometimes I use it on a drive. If it’s a 15-minute drive, I’ll turn it on and try to capture my raw thoughts. You’ll be surprised how often maybe 10 minutes is junk, but you find two lines or sentences that are well worth it.

Two ideas that might be pivotal and that you might not have to manufacture.

When I first got Letterly, one limitation—common with Voice Memos and other recording apps—was that if you were using headphones like AirPods or AirPods Max away from your phone, you couldn’t record using the mic on them.

I knew an update would come, and within a few months it did. I could now change the microphone and record while riding my bike, even on an indoor bike.

Even though I mainly use it on my phone, you can also use it on a desktop. The desktop mic is high quality, especially on a MacBook. I have a shortcut set up, though I usually use it to access and pull out text or emails, similar to how I’d use my Notes app.

Of course, you could still do that with Voice Memos, recording raw thoughts and sorting through them later. I was pleasantly surprised when I found out that singers and songwriters record into their voice memos all the time. It’s cool to see how tiny the fragments of that recording can be.

Magic Rewrite & Unlimited Ownership

One of my favorite features is the magic rewrite function. You can use it unlimited times to rewrite slightly, clean up for a casual email, or turn it into an social post. It has all these ways to mold your recording to what you want.

I often use the structured list. I’ll talk through a bunch of unstructured, random, non-linear thoughts, then hit structured rewrite. It gives me an organized list—personal to-dos, groceries, tasks, or random thoughts.

From there, I can copy all the rewritten text and paste it into my Notes app. I do this even though I use Letterly as a second Notes app, because sometimes I check Notes more often. You don’t have to, but I like having both. And this act of migration is what makes me check off the catalog stage in my process.

Before in Letterly, you couldn’t access the original recording—only the transcription. Now you can, which is useful to know even if you don’t use it often.

The biggest reason to own Letterly is the one-time fee for unlimited transcription. Most apps have limits—maybe 15 hours a month—especially with AI features. With Letterly, there’s no limit. I can record, transcribe, and use it forever. That’s a huge advantage, especially if purchased through AppSumo.

If you get in the habit of using it, you feel like you’re taking advantage of AI tools to preserve your voice, not offload or change it. Even if you use Claude, ChatGPT or any LLM for emails, recordings let you preserve your style. Letterly lets you do everything in-app, even if you don’t have a pro version of ChatGPT or Claude—you basically get access to the same AI functionality (with a healthy amount of constraints).

Letterly is a tool that can put your brain in ‘creation’ mode in a very casual way. It’s one of the rare apps I see myself using for the foreseeable future.

In your corner,

Misbah Haque

Founder, Habit Chess, Pod Mahal

Co-Founder, LapList


600 1st Ave, Ste 330 PMB 92768, Seattle, WA 98104-2246
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Misbah Haque

I write about high agency thinking and skill acquisition.

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