How to Send Voice Messages Hands-Free with Siri

In a recent edition of my weekly 2×2 newsletter, I shared a link to a cheeky article on the Guardian about 100 Ways to Improve Your Life Without Trying.

In my link to the article, I noted that that tip #8 is totally my jam:

“8. Send a voice note instead of a text; they sound like personal mini podcasts.”

Long-time readers may recall my affinity for recording mini, personal podcasts (a.k.a. “Shawn Today”).

Well, sending voice messages is something I began doing consistently back in 2019.

(And, to be clear, by voice messages, I mean the audio recordings that you can send folks in iMessage. Not a siri-transcribed text message.)

And — for whatever reason — I often think of sending voice messages when I am in the car. You cannot safely do them without being able to be hands-free. Thus, in my newsletter link, I was quipping about how I wished there was a way to do this completely hands-free with Siri.

Welp…

Turns out, dear reader, that you can send voice messages to your iMessage contacts via Siri. (Huge thanks to reader Aidan for pointing this out to me.)

I could have sworn I’d tried this dozens of times over the years, and it didn’t work, but who knows.

All you do is tell Siri:

“Hey Siri, send a voice message to So-And-So.”

Give it a beat for Siri to start recording.

Then you speak your message.

When you are done, stop talking for about 3 seconds and the silence will trigger Siri that you are done. Whatever you do, don’t press any buttons or tap the screen. If you do, it will cancel out the whole recording.

Like most things related to Siri, sending voice messages seems to work about 75% percent of the time for me. It can be maddening when you record something for 90 seconds and then Siri tells you something went wrong. But, other than that, it’s great.

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An aside about engaging in non-disembodied communication

On an episode of Jocelyn K. Glei’s podcast, Cal Newport shared about how he views all communication and interaction as either “real” or “not real.”

• Communication done in person or over the phone is real. Meaning we can see people’s expressions and we can hear their voice (and the tone of their voice).
• Communication done via texting, DMing, etc. is not real because it is disembodied.

When I heard this, something I began is to send my friends voice messages to tell them how awesome they are. Or if I have something important to share but there isn’t time to arrange a phone call, then I send a voice message.

Asynchronous voice messaging isn’t quite as deep as a phone call, but it can be better than a disembodied text message. And now you know that you can even send them hands free.