As I’m already getting lots of out of office messages for people taking this week off, I thought I’d revisit an approach to how to deal with email after a vacation.
In 2011, Josh Kopelman of First Round Capital came up with what, at the time, was what I thought was the best email vacation auto-responder in the history of email. Now, I have no idea if Josh invented this, but I’m going to give him credit for it.
I evolved this in 2014 when I took a one-month sabbatical. If you ever send me an email when I’m on my quarterly one week off the grid vacation, you now get this.
I’m checking out for a vacation until [date]. I’ll be completely off the grid.
When I return, I’m going to archive my inbox so I’ll never see this email. If you’d like me to read it, please resend it after [date]+1.
If you need something urgently, please email [my_assistants_email_address] and she’ll either help you or get you to the right person at Foundry Group to give you a hand.
On [date]+1, I usually get around 50 emails (in addition to my usual email flow of 500 daily emails) that are resent to me. That’s only 50 to respond to, instead of the roughly 3,000 emails I get each week.
It appears that The Atlantic has caught up with this thinking in The Most Honest Out-of-Office Message. I thought the article was fascinating, both in how the writer addressed the issue, but also in the intellectual and emotional tension around it.
Does it make you nervous to think about “Selecting All” on your existing inbox and archiving (if Gmail) or deleting (if Outlook)? While some of my friends do it periodically – as a result of pain or just to get a fresh start on a new year, I like to do the equivalent every quarter when I get back from a full week of an off the grid reset.
Josh – it was a while ago, but thanks for the inspiration. And, for those of you on vacation this week, I hope you aren’t reading this.
Unlike the person with a similar slogan, this one is highly accurate. Sanebox does indeed make email great again.
I’ve been using email since 1983. I started with MH and Rmail, then cc:Mail, then Microsoft Mail, with Compuserve mixed in. Eventually I ended up using Pine for non-Windows stuff and Outlook for Windows stuff. For a while. About seven years ago I switched to Gmail and never looked back.
Over the last seven years, I’ve tried a bunch of different add-ons and plug-ins and whatever you want to call them to try to clean up my inbox. As investors in Postini, I was able to eliminate my spam problem early on. But I struggled endlessly with bacn. I get 500+ emails a day so the bacn is intolerable in my main email flow and ends up getting ignored, rather than read later.
So I’d go through weeks of unsubscribe fits, where I’d try to mash out my misery by unsubscribing to things I didn’t want. Often, this just resulted in more bacn, sometimes from the same senders but often from others. I once again would go through another cycle where I’d try a different unsubscribe tool, but I’d always end up with better, but not good enough.
Over Memorial Day weekend, I decided to try Sanebox. My partner Seth has used it for a while and several other people I know swear by it. I tried it when it first came out (as one of my endless efforts to tame my inbox) but it didn’t satisfy me then.
This time – about a month later – I can definitively state that Sanebox is awesome. Not sort of awesome. Extremely awesome. It should consider running for president.
Magic trick #1: @SaneBlackHole: If I want to never see a piece of bacn again, I just label it @SaneBlackHole by typing v<downarrow><enter>. Gone, forever. Anything from the sender never ever shows up in my inbox again, kind of like how Ramsay Bolton will never show up in Game of Thrones again.
Magic trick #2: @SaneNotSpam: I trust Gmail’s spam filter so I never, ever look in my spam folder. But Sanebox does look there for me because it knows not to trust it as much as I do. It finds at least one piece of NotSpam every day – sometimes as many as five pieces. Some of the NotSpam is amazing – on Friday a distribution notice from a VC fund I’m an investor in showed up there.
Magic trick #3: @SaneLater and @SaneNews: Sanebox automagically figures out which things I can look at later. It also figures out which email is a newsletter of some sort. It’s easy to adjust these if it gets it wrong, or label an email in my inbox with one of these labels and it then becomes one of these forevermore. At least 20% of my daily email ends up in one of these folders which I can then process once a day.
Within 30 days, with almost no effort, the signal in my inbox has reached about 99%. I read through notifications and news once a day. The crap that I don’t really want shows up once in SaneLater or SaneNews, I relabel it SaneBlackHole, and it’s gone forever.
Suddenly, my inbox is remarkably clean, useful, and free of noise. Thanks Sanebox!
Before you have an allergic reaction to the title of the post and respond with “you are stupid”, bear with me for a second as I set up the problem.
I’ve been a heavy Slack user for at least six months (probably closer to nine). We started using it internally at Foundry Group and then I joined a number of Slack instances of companies that we are investors in. For at least three months, I joined a number of relevant channels for each organization and tried to participate. I use Slack on the Mac primary so I used the left side bar to have multiple teams active, tuned my notifications so they weren’t overwhelming, and engaged as best as I could. I tried to post on Slack when I had an issue with the company – usually around a product – that needed to be communicated to a group instead of one person. And, for a few of the CEOs, we used Slack as our primary DM channel.
I hit the Slack wall about a month ago and stopped regularly engaging with the organizations other than Foundry Group. There is a long list of functional issues with how Slack handles things across orgs that makes using it this way a burden that suddenly felt worse to me than email. I could go through them and I expect Slack will eventually address some of them since I can’t imagine that I’m the only person in the world struggling to try to deal with Slack across 15 organizations, but the thing that really perplexed me was a new phenomenon that I noticed a month or so ago.
I’m increasingly being invited to other Slack groups of curated people.
This hit me in the face over the weekend when I was invited to a new Slack group by someone well-known. It’s a fascinating group of randomly connected people who ramped up a handful of channels over the weekend. I stayed on top of it until Monday morning and then was swept away in my normal week.
I just went and checked it again. There are over 60 members, but there were less than 30 new Slack messages since the last time I checked. Most were in one channel. As I skimmed it, I thought to myself that this would have been just as effective, or possibly more effective, as a typical group email list. And, since I do most of my group email lists in Google Groups, they are easily searchable and archivable, so the archive/search argument goes away away immediately.
As the amount of time I have to spend engaging with Slack increases, it suddenly feels more ponderous. And, when I started thinking about it in the context of the very active Foundry Group CEO list, it felt much less effective to switch this to a real time channel, as very few of the interactions necessitate real time.
So – I’m trying to get my mind around the value of Slack instead of an email list for large, cross-organization communication. Other than “it’s a new thing”, what are the foundational benefits of it. If you are someone engaged in a large, cross-organizational Slack group, now is the time to weigh in and give me a clue.
There are two common email conventions in my world that I use many times a day in Gmail. I don’t remember where either of them came from or how much I influenced their use in my little corner of the world, but I see them everywhere now.
The first is +Name. When I add someone to an email thread, I start the email with +Name. For example:
Gang – happy to have a meeting. Mary will take care of scheduling it.
Now, why in the world can’t gmail recognize that and automatically add Mary to my To: line? If I needed to do “+Mary Weingartner”, that would be fine. Gmail is supposed to be super smart – it should know my address book (ahem) or even my most recently added Mary’s and just get it done.
The other is bcc: Whenever I want to drop someone from an email chain, I say “to bcc:” For example:
Joe – thanks for the intro. To bcc:
Pauline – tell me more about what you are thinking.
Then, I have to click and drag on some stuff in the address field to move Joe from the To: line to the bcc: line.
Dear Developers Working On Email Clients Of The World: Would you please put a little effort into having the email client either (a) learn my behavior or (b) Add in lots of little tricks that are common, but not standard, conventions?
Here’s a perplexing thing to ponder.
After trying virtually every email configuration on iPhone and Android devices, the best experience that I have had so far is using Microsoft Outlook on my Apple iPhone to access Google Gmail.
I’ve been using Outlook on my iPhone for the past few months. I’ve tried several times to go back to Apple Mail, but it is impossibly bad when compared to Outlook. I’ve also tried using the Google iOS Gmail client, which – while better than Apple Mail – is still very klutzy at certain things.
I know that Microsoft Outlook is really Acompli rebranded at Outlook, but in the eight months since the acquisition the product has continued to get better and better.
An increasing number of companies that I work with are using PGP to encrypt certain email. While they are comfortable sending a lot of email unencrypted, there are periodic threads that different people want to have encrypted for a variety of reasons, some rational and some not.
Each company is dealing with this a different way. Suddenly I find myself managing a bunch of public keys in different PGP tools on different computers. I started by going with the recommendation of each company and predictably found myself managing multiple solutions that sort of worked some of the time.
Last night I was on a hangout with one of the CEOs trying to troubleshoot the problem we were having with the implementation his company was using. After 15 minutes of fighting with a Chrome plugin, we gave up. Of course, when I went to a different computer, it worked just fine.
This seems like such a simple thing for Google (and Yahoo and Microsoft) to build into their email clients, especially the browser based ones. Keep the keys locally (or even in Dropbox or iCloud). Encrypt and decrypt from within the browser. Only transmit encrypted email. Only display the decrypted email.
Why hasn’t this been done yet? Am I missing something obvious?
Amy and I had a wonderful week off the grid in Paris. No phone, no email from Friday night 5/8 when I boarded the British Airlines flight in DIA until Friday morning 5/15 when we decided to turn stuff on and just lay around the hotel all day getting reading to go home.
I’m always fascinated by the email patterns I have when I’m off the grid for a week. I almost always go off the grid late Friday or Saturday morning so there’s the weekend lull followed by an intense flurry on Monday. By Tuesday my regular emailers have seen that I’m off the grid and their pattern of copying me slows down, but doesn’t stop completely. The emails then become more random.
By Wednesday, I’m getting three kinds of email.
- #Important: Important stuff from people I know that I’m being copied on.
- #New-Known: Stuff from people I know who didn’t email me earlier in the week.
- #Random: Stuff from people I don’t know.
#Important and #New-Known tend to have similar tones. They are things for me to respond to, send to someone, make a decision around, or acknowledge receipt of information. Occasionally they require me to do something, but the action requested rarely takes more than five minutes.
#Random is completely different. Almost 100% of the #Random email has a specific request for me. These requests are often for meetings, phone calls, interviews, or speaking engagements. Some of them are specific sets of questions about a topic while others are long essays that never really get to the punch line, but clearly are begging to get to a question of some sort. Some are requests for introductions. And others are direct asks for financing.
This trip, when I went through my email upon my return, I left all the #Random ones for last to process. I had over 200 of these. This time I responded to all of them, but it wasn’t very satisfying. It took about four hours on Sunday and when I was done, I felt relief to be done, but when I reflected on it, I didn’t feel like I ended up with any new knowledge. That was disappointing as processing four hours of email to result in zero learning mostly just sucks, at least for me.
In this case, I packetized appropriately. Rather than getting bogged down in the stuff I needed to do while getting worn out by stuff that wasn’t that important to do, I only responded to stuff in #Important and #New-Known, ignoring the rest until I was completely finished with these categories. I think took a break and dealt with the rest later when my headspace was clearer.
As I sit here, I wonder why I responded to the other 200 #Random emails. I have a long-standing self-identity of responding to all emails that I get. For some reason, that’s important to me, but I’m no longer really sure why. It’s not satisfying in any way and the signal to noise ratio, or at least the value to non-value ratio, is way out of control at this point.
I guess I have something new to ponder in therapy. At least something good came out of responding to the 200 emails.
A few days ago, David Brown at Techstars wrote a great post titled “Staying Organized with Workflow” about how he stays organized. Brown and I work across the hall from each other and interact regularly. Often he’ll send me a note about something and I’ll just wander over and talk to him. He’s always available, super responsive on email, and very good at having a three minute meeting that results in a decision.
There was one thing in his approach that was something I used to do a long time ago, but stopped doing when I started using Gmail.
“Email Order. I process my email from oldest to newest. Yes, I cheat sometimes and answer a new one, but I try not to. It’s harder in Gmail because you can’t sort chronologically, but I just start at the bottom.”
A long, long time ago, in a galaxy far far away when I used Outlook, I processed my email in chronological order – oldest at the top. Gmail doesn’t let you reverse the sort order from newest at the top, so I just got out of the habit of this. But when I get behind on email by a few days and end up with 100 or more to grind through, I always go to the bottom and work backwards.
When I saw Brown’s note, I thought “duh.” Often, I have an almost empty inbox (as I do now – there is literally one message in it – read, but not responded to – right now.) So, even when there are 17 brand new emails, just clicking on the bottom one and reading backwards works just fine. In fact, it’s even better in the current world than my previous Outlook galaxy because of conversation mode.
Unlike Brown, I don’t use tasks or filters. I find that when I move things to a task list, I’m literally exiling them to the land of never-get-done. The only exception is longer form writing that is not urgent, which I just star in Gmail, archive, and periodically grind through my starred folder.
Regardless of the process you use, contemplate reverse the order of response from oldest to newest. If you aren’t going to do something with an email, just archive or delete it – don’t let it sit there. And, if you want some additional good tips, go read Brown’s post Staying Organized with Workflow.
Since I’ve had dealing with email on my mind recently, I thought I’d write about how to deal with email after a long vacation. Over the years, I’ve heard over and over again from people who never going on vacation or getting off the grid explaining that they can’t imagine doing this because they would be more stressed out when they return to all the email they have to respond to. I don’t think it has to be that way.
For context, I’m a huge believer on completely going off the grid for vacation. Amy and I have been taking a weekly vacation off the grid for 15 years. No phone, no email. Just the two of us. Given the pace of our lives and the amount of time we spend apart, it’s an awesome way to reconnect. There’s nothing quite like spending a week with your beloved on a periodic basis to remember why you love each other.
Whenever I’m off the grid for a week, I always come back to loads of email. I used to organize my trips from Saturday to Saturday so I’d have Sunday to go through all my email and catch up. That works, but ruins the last Sunday of the vacation. Then I shifted to Monday, so I basically scheduled nothing on Monday and just went through all my email during the day while getting back in the flow of things. That made for a shitty Monday and usually damaged my calm that had resulted from my week off the grid.
When Amy and I took a one month sabbatical in November, I tried something different. Here is my vacation reminder from that trip.
I’m on sabbatical and completely off the grid until 12/8/14.
I will not be reading this email. When I return, I’m archiving everything and starting with an empty inbox.
If this is urgent and needs to be dealt with by someone before 12/8, please send it to my assistant Mary (firstname.lastname@example.org). She’ll make sure it gets to the right person.
If you want me to see it, please send it again after 12/8.
My partners covered for me when I was gone and dealt with anything that was important. The three of them had each taken a month off before my sabbatical so we had a nice rhythm around this.
At the last minute I chickened out on archiving everything without looking at it. Instead, I just scanned through my inbox, archiving messages without responding to them. I didn’t save anything, even if it asked me to do something. I archived it just like I said I was going to. But I had some context around what was going on. It took me about three hours to get through the 3,200 emails I had waiting for me. Not surprisingly, when you don’t send any emails, you get a lot less.
On Monday morning (12/8) when I came back to the office, I had an empty inbox except for the emails that had come in since I did the scan (which I did on 12/6 – we traveled home on 12/7). It was unbelievably liberating. I sat down with each of my partners and went through things that had happened when I was away in companies I was on the board of. That took less than 15 minutes per partner. At lunch, I got caught up on the overall portfolio.
By Tuesday I was back in the flow of things and felt very calm and relaxed. My vacation mellow wasn’t harshed at all.
This approach works for any length of time. Amy and I took a five day off-the-grid vacation for Valentines Day week. Same drill, although this time I responded to a few emails that came in when I reappeared and did my scan. But I set the expectation that I wasn’t going to look at anything, so plenty of “resends” happened on Monday and Tuesday, which meant that folks who really wanted to interact with me took responsibility for it.
There’s something about taking control of how email interacts with you that is very satisfying. I’ve heard the complaint, over and over again, that email allows other people to interrupt your world. That’s part of the beauty of a low barrier to communication (e.g. just send something to email@example.com and it gets to me.) But it’s also a huge burden, especially if you want to engage back.
I’m always looking for other approaches to try on this, so totally game to hear if you have special magic ones.
I get 300+ non-spam emails a day. No matter how diligent I am at unsubscribing from stuff, I still get an endless stream of valid, opt-in email that I want to unsubscribe to. Google takes good care of my spam and they even jumped all over my complaints about their spam filtering, figured out the problem, and fixed it (thanks friends at Google). So, I’m not talking about spam, but all the rest of the stuff that I don’t need to see right away.
I’ve tried to use Google’s categories, but it doesn’t really work well for me. Others are emails I never want to see and want to unsubscribe from, but (a) it takes longer to do that, (b) trying to unsubscribe from a mobile client is painful, (c) many of my unsubscribes don’t seem to work (I just end up seeing the email again in a few weeks), and (d) the whole experience / UI is sucky.
Now, before you jump to “use a different channel than email”, recognize that I have also Slack, Kato, iMessage, Twitter, Facebook, Skype, and Google Hangouts open on my desktop with stuff hitting them all day long. Voxer lights up regularly on my iPhone, along with notifications from each of these apps. Channel proliferation has become a mess for me and one of the companies we are investors in is working on that problem earnestly.
Ultimately though I spend most of my time in Gmail especially given the amount of email I get from all different senders. It is unyielding – here’s an example from last week.
About 25% are emails that I do not need to see right away. Probably 10% are ones that I want to unsubscribe to.
OtherInbox’s Unsubscriber and Organizer solves both of these for me. Josh Baer, a long time friend and leader in the Austin Startup Community, was the co-founder. OtherInbox was acquired a few years ago by Return Path, which I’m on the board of. I used OtherInbox for a little while before and after the acquisition, but in one of my mad Gmail / Chrome plugin-performance-misery-slowdown-cleanup-fits I stopped using it.
Last fall, after playing the endless unsubscribe-to-clean-things-up-each-morning I decided to try OtherInbox again. I went all in this time. Within one week I was in email heaven.
Here’s how it works. If I want to unsubscribe to something, I simply label it “Unsubscribe” using Gmail labels and I never ever see it again. Then, OtherInbox constantly moves new emails that match certain criteria to folders. This happens automatically and in the background it figures out the organization of the emails.
I can adjust it if I want, but I’ve found that I spend almost no time adjusting it anymore. Typically, I have some unreads in there and they show up as unreads normally do in Gmail, so at the end of the day I just go to label:oib is:unread and take a quick look.