How To Deal With Email After A Long Vacation

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 ( 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 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.

  • Dave

    Interesting and good guidance. But I think this is an area where a professional investor has it a little easier than those of us with a regular job, even an executive level job. While you have a ton of demands on your time, at the end of the day people will make the world revolve around you. They will follow up, your portfolio companies cannot fire you, Board meetings and other meetings get scheduled around you, you have partners to deal with your investors. Not saying at all that the life of an investor is easy, but in this area your control over your life is much higher than that of others. For those of us who are execs in companies, I don’t see our investors, management peers, bosses, customers, etc. being so understanding to allow being off teh grid for a week.

    • Rick

      You’ve raised some good points. VC has to be difficult. I saw a post on where someone said something like “VC – good work if you can get it.” I agree.
      Brad handed a ticket to the VC world to David Cohen years ago. But most of us don’t stand a chance of getting in. Especially not getting a full-blown first class ticket.

      • I didn’t hand a ticket to Cohen. He earned it.

        • mark gelband

          one way to deal with copious amounts of emails (or personal interaction) is distinguishing what merits a response. Rick, like my ex-wife, rarely does because it is clear that the only intent is to get a response – positive or negative.

          • Rick

            I don’t use email mark.

        • Rick

          You still handed him a ticket. I might not know a lot about VC but I know that being the outside investor at $100K is giving someone a ticket to ride the VC train. He had other connections I’m sure but other people don’t get what you gave him and it made all the different.
          With you and his other contacts that he has mentioned he could have just slept at work. Don’t get me wrong. He had gumption and has done some great stuff. But you can take almost anyone with what experience he had at the time and give them a list of the right connections and a $100K ticket and they’ll be on their way.
          When I asked you if you use interns just so I could get some inside experience in VC you didn’t even respond.
          I respect your knowledge Brad. But don’t try to blow smoke with me. I’m not a teenager. I know what the real world is all about and you gave him a ticket my friend! A first class ticket to VC land!!!

    • Totally agree, but it’s a philosophical approach. For example, when the CEOs of companies I’m an investor in go of the grid for a week, I completely respect (and actually encourage) that.

      I think you can institutionalize this in the culture of a company, especially a startup / fast growing one. But you have to articulate what you are doing, and then allow / enable everyone in the organization to do it.

      • mark gelband

        Brad – as mentioned the other day in your Q&A, it’s the heartfelt subtext of even a post about the mundane that makes your writing jump off the page, feel “authentic.” what shines through is the respect you have for your personal growth, emotional evolution, and how much you care about the value of personal work/life “harmony,” as you’ve called it.

        whatever one’s practice for dealing with the mundane – sorting emails after escaping in this instance, the larger issue of caring enough to take – and give – sabbatical with your biz partners, to focus on your wife and relationship for a week offline shows an immense amount of concern for the important things.

        your second paragraph gets exactly at what i was trying to ask on Friday. Dave, by feeling he cannot go off grid, sends a horrible message to the people he loves, and, as importantly, the culture he is creating at his company. too often in my experience – nightclubs, small business and large corporations, alike – what leaders say is not often reflected in their actions and/or policies they implement in dealing with others.

        when it comes to work/life harmony, the message gets heard loudly and clearly by the workforce and causes disruptions that can only swirl negativity. how can anyone in Dave’s company feel as though he/she can honestly check out if Dave cannot.

        hope you’re having a wonderful weekend.

        • Rick

          Brad is a disciplined venture capitalist mark.

  • yesimahuman

    Very timely post for me, as I just did this while on my honeymoon (also I’m CEO of a 15 person startup).

    Instead of archiving all at the end, though, I set up a gmail filter to archive *everything* (basically search for “*” and auto archive). My vacation reminder just stated I was redirecting all email to /dev/null for the week with a list of other people and places to get help.

    The nice thing is I could still check my All Mail folder to see it if necessary, but otherwise I was at inbox zero for a week.

    And the world didn’t end!

    • Rick

      “email to /dev/nul”
      Another super geek. Welcome to

      • Super geeks are my favorites!

  • Moe

    Deciding on an email response policy usually begins with what assumed state of leverage the responder takes w.r.t. to all conversations arriving at his inbox

    • Yup. I operate under a deeply held belief that I try to respond to anything that is personalized and aimed at me. But that’s hard to maintain when the daily number of emails gets bigger than 100.

      • Moe

        With 100+ people fighting to get your time everyday, something’s clearly not efficient here. Not talking about you – just the pipe. Generally the high number of people trying to get a piece of someone might work for hollywood, but hey, we’re in tech and supposed to be much smarter and efficient right? 🙂

        • I think it’s local efficiency at work, not an effort to coordinated global efficiency. I don’t think we’ll get to global efficiency, so I’m focused on my own local optimization.

  • I received that response in November and immediately decided I would use that myself. 🙂

  • Rick

    I already said to use an autoresponder saying “Don’t pester me”. But I can see you want more. So…
    Use this autoresponder: “I only take into consideration business proposals that are almost guarenteed to provide me with 10x+ returns within 3 years. So if your email is not about that I won’t be responding.”
    That doesn’t mean you are commited to not responding. People will want to just say Hi and you can respond to them as well as the good proposals.
    This is REALLY a great approach. Because it takes into consideration the context of the email. If the email is about business then it lets people know what you are looking for and whether or not they sould expect a response.
    I’m glad you posted something today. I was over at Fred’s blog and he keeps trying to get me to sign up. He’s like a girl at a bar trying to get me to take her home because it’s 2am and she’s too drunk to drive. lol If Fred wants to do business I don’t know why he doesn’t just say so. There’s no need to beat around the bush.

    • I like getting all kinds of emails and feel no need to limit myself. This was more about how to deal with the feeling over being overwhelmed when you return home after a disconnect.

  • Great hack.

    It’s amazing how longstanding problems can simply evaporate with a simple shift in mindset followed by communication when someone is being authentic.

    • Well said. The mindset shift for me was a hard one to get to since I’ve got such a deep seated need to be identified as “the response guy.”

  • I think you described the key. You have the choice to take control of it or allow it to control you. You took control of it and reaped the reward without damaging your image or your business.

  • What amazes me here is (1) this presents the psychological effects of email in a different way (of accumulated stress that is hard to escape) and (2) um, you get 3.2k emails per week???

  • Rob Ryan

    So Brad, what’s your preference on people replying after you’ve replied to their email with “Have a great day!” or “Thanks so much!” I know it’s polite and nice, but man, it is just another email to go through when you want it to stop. I’ll accept a simple “None” or “You’re being a curmudgeon, Rob” as your answer, lol. Side note…Using Otherinbox as of yesterday…thanks for the tip man!

    • I’m mellow – either way works. I’m very good at archiving messages

  • The real lesson here is not about handling vacation email. Yes, it’s a terrific technique, but the fact that you and your wife go completely off the grid for vacation and have so for 15 years to remember why you love each other… that’s the value here. My hat’s off to you Brad.

    • Thanks John and I agree. That’s the big magic!

  • alex

    Nice one and very much recommended! Have you ever thought about taking it even a step further and take an email sabbatical as danah boyd ( is propagating it?

  • worker

    That’s nice if you have partners that agree to that. For all us “working stiffs” who are dictated otherwise by our bosses – no-so-helpful advice…