Tinkering With Ideas #008: Break the cycle of instant communication

Hi Reader 👋 -

Happy Thursday. Today's issue is brought to you by "typing out ideas on my iPhone last night." I plan topics in advance but somehow this week got away from me and last night I realized "IT'S NEWSLETTER DAY TOMORROW."

Too tired to sit at my computer so I tapped out some notes on my iPhone, hoping they would be coherent the next day. They were, here we are, enjoy.

1) Reflection:

I recorded a podcast episode this week (as a guest) and talked about my different experiences with remote work. Each company came up with its own expectations around response time.

My favorite was a company that had a 24-hour policy. As long as you replied to internal communication within 24 hours, it was all good. (The client response time was different: 4 hours maximum, and 2 hours was the norm). But this policy left a lot of freedom for people to work in a way that they saw fit.

After leaving that company, I found myself with organizations that were working more-or-less synchronously. That was a hard adjustment. I wasn't used to the pressure of instant response. (I like Slack for a lot of things, but wow — it can feel noisy).

While working for these subsequent companies and now as a freelancer, I've had to set my own boundaries around communication and notification in a lot of ways. And try not to let myself feel pressure to reply instantly.

2) Product:

You know how sometimes you send an email and you're waiting for the other person to respond, but you don't want to forget about it?

There's a great app called Boomerang for Gmail. You send an email and then set a "Boomerang" for the sent email to return to your Inbox at a specific day/time if the person doesn't reply (or have it return regardless).

I have my emails return with the Gmail "star" label. Then, I have my Inbox set up so starred emails appear at that top. That way, I never miss a follow-up.

3) Tip:

Speaking of pressure to respond to emails: when is the right time to send an email?

Should it be the best time for me or the best time for the receiver? What if the receiver is in another time zone? WHAT IS THE RIGHT ANSWER?

There is no right answer. In fact, my email signature says "Because I work flexibly, my working hours may not be the same as yours. Please only respond during your working hours and I'll do the same."

But I'm also a big fan of Schedule Send. For two reasons:

1) I wake up very early and I fear that sending emails at 5:00 am will give the impression that I work long days. So I Schedule Send for later.

2) If I need to send a tough email, I use Schedule Send. Why? Hitting that "Send" button can be nerve-wracking, especially if I don't know what the response will be. But I can hit Schedule Send and send it four hours in the future when I've moved on and am no longer thinking about the email.