How I Email: Saya Hillman of Mac & Cheese Productions

Email is a non-negotiable part of everyday life. For some, it’s an unruly time suck, but enlightened email users have systems to ensure they’re not a slave to the inbox. We’re asking smart thinkers to give us a peek inside their inboxes, share tips, ideas, gripes, and everything in between.

Saya Hillman, founder of Mac & Cheese Productions, which curates lifestyle experiences like adult sleepaway camps, minglers, and idea potlucks, shares the strategies and tools she uses to ensure email conforms to her “Life of Yes” philosophy.

Interview by Jaclyn Schiff. This interview has been edited for length and clarity.

What’s your email strategy?

People seem to be over hearing about Inbox Zero, but I’m a huge proponent. On average, I’ll have zero to 10 emails in the inbox. I delete or archive. I used to go label-crazy but now I think we spend too much time labeling and foldering. I just have “Personal” and “Work,” as opposed to tons of sub-labels nested within those two categories. I don’t use my inbox as a calendar, task reminder, or to do list, which helps keep the number down.

Like more and more folks these days, I rarely post my email address anywhere. You won’t find it (or my phone number) on my website or business cards. This stems from people adding me to their e-lists without permission, which is one of my biggest pet peeves. I’ve unsubscribed from friends and family mailing before, which can lead to awkward scenarios. A friend even emailed the next morning and (very nicely) asked why, which led to a great conversation about email etiquette.

I’m making a cognizant effort to stop apologizing for getting back to someone “late” or “delayed” when it has been a day or three. When you do that, you’re ok’ing the expectation that we’re always available and that you’re doing something wrong if you’re not tethered to email. I don’t want to feed into that mentality. Plus I think we (especially women!) should just stop apologizing in general! This article on removing the word “just” from your vocabulary stuck with me and I’ve gotten good at sending out emails without those types of permission or apologetic terms. Model the behavior you wish to see, right?!

You host a variety of programs to help people lead better, more fulfilled lives. How does email management fit into that? What kind of advice do you give people about email?

I help people live a Life of Yes℠ and a huge component of that is “make life easy.” For example, your service providers — mechanic, dentist, gym, salon, etc. — should be within a 12 minute walk from home. If you have to get a root canal, you don’t want to spend 45 minutes driving in traffic there and back to get it. Going to the gym is difficult enough, do you really think you’ll go if it’s a train and bus ride away? You want your time and brain space to be used for fun things not for the mundane.

As “make life easy” pertains to email management, I suggest to others that they figure out their pain points and then work to lessen or eradicate that pain.

One pain point for me was inbox overwhelm, where I was just getting too much and it seemed like all I did was be annoyed and delete, or avoid the inbox altogether. Once I spent some time thinking about the problem and looking at various solutions though, I came up with a system that works really well for me. I have two accounts, my “Conversations” account and my “Everything Else” account. “Conversations” is any personal and work email that is me actually talking to people, as opposed to “Everything Else” which are travel confirmations, shopping receipts, newsletters, financial accounts, you name it. Any time I have to sign up for something, I use that email account.

Additionally, I use Feedly as my RSS feed to keep the number of website posts I get in the inbox minimal and just head to Feedly when I want to read them. helped me mass unsubscribe initially so that I could start over and be more thoughtful with what I let into the inbox.

Another tip I give is to stop believing in the Perfect Time Unicorn and his siblings Better Time and More Time. “I’ll deal with my email at a better time, when I have more time, I’m waiting for the perfect time.” Not coming, ever! Your future self will have the same time as your current self. It’s about prioritizing and what you deem important enough to actually do.

Also, sometimes you just need to go nuclear. If you’re one of those folks with 20,000 unread (or read) emails in the inbox, it might be time to open a new account and start with a blank slate, of course, incorporating best practices from the start so that you don’t wind up in the same situation again.

Any specific Gmail tools you love?

  • Boomerang:

Couldn’t live without Boomerang’s “Send Later” function or the “Boomerang back at (specific date)” function! I love answering emails as they come in but don’t want people to know I’m doing so at 10pm or on vacation, so I’ll respond and choose to send it the next morning or when I return to town. The boomerang back function allows me to bypass adding a reminder to myself on my To Do list to follow up on email if a response wasn’t received, as it’ll come back to my inbox on the specified date and remind me to follow up.

  • Canned Responses:

If you have emails you send repeatedly — directions, requests, event descriptions, asks, etc. — you must use Canned Responses (CR). Sure, you could write out the same email over and over. Or you could keep the text in Word or Evernote, and every time you need it, go to that application, copy, go back to Gmail, and paste. OR you could write the text once, save it in Canned Responses, and then when needed, without leaving Gmail, select the applicable response and insert into the email body.

My two frustrations with the GoogleLab are that you can’t alphabetize your list of Canned Responses so it takes awhile to scroll through and that the Create, Save, and Delete options are very similar so it’s easy to accidentally choose the wrong one. A safety tip is to keep a backup document of all your CR’s so on the chance that you delete one, you’ll be ok.

Even though it’s pretty basic and not sexy, I love the “Add to Calendar” function, where you can click on a date, e.g. “Let’s meet on Saturday at 4pm,” within the body of an email and without leaving Gmail, add it to Google Calendar.

  • Filters:

Automation rules. I use filters to do automated tasks like add a label or archive an email.

HelloSign makes e-signing of documents so easy and doable without ever having to leave Gmail.

Any email faux pas that really get on your nerves?

I mentioned the adding me to your e-list without my permission.

Grrr. Another grating situation are e-intros. I get ‘set up’ by email all the time, usually in the “You two should know each other!” vein. While I appreciate that someone deems me worthy of being added to someone else’s radar, such intros usually lead to a gaggle of folks asking me to “get coffee” or “hop on the phone for a quick phone chat.” Multiply that times 5, 10, 15 times a week, when most of them don’t lead to anything but me rehashing my story and what I do and 30 minutes to an hour of time I’d rather have been doing many other things, it quickly became a sore spot.

What I wish would happen — and some folks are doing this now — is that if you have someone you think I should “meet,” to ask me first instead of putting me in the awkward position of telling someone “No, I’m sorry I can’t grab coffee or hop on the phone.” Sometimes I’ll say yes, sometimes I’ll say no. Also, less wasting of people’s time.