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.
I’m a fan of spring break. I’m a believer in regular vacations. I love it when people I work with get away and disconnect. And, I do it at least four times a year.
Spring break feels like it has gotten out of control. Rethinking it could be interesting. This year, at least 50% of the people I work with regularly are on spring break this week. I think the other 50% go on spring break next week. Easter seems to be the pivot point for this.
Unlike the week before Christmas, which moves around every year, if Easter is the pivot point for spring break, life would be better if everyone in the US decided the week before (or after – I don’t care) Easter was spring break. Then, the rhythm of work in the US would slow (or at least change) for that week, just like it does for the week between Christmas and New Years.
And, everyone who goes on spring break with their family and kids could actually disconnect, rather than what I’m observing, where some people disengage, but others keep one foot in, probably ruining the real value of a week-long disconnect from work for them
I’m not at all cranky about this. I’m at work this week – and next week. Amy, on the other hand, is on spring break with a girlfriend who is five years recovered from a serious illness. While I miss her, I’m using the time as an excuse to stay up late watching silly television shows.
While I know a blog post from me isn’t going to affect anything, imagine a world where we had a real, synchronized, completely off spring break in the US. It would be a better world for everyone.
Amy and I have learned that I need a Q1 vacation earlier in Q1 (vs. waiting until the end of March). We were apart for ten days because of a trip she took to Africa, so we went to San Diego for a week.
I played tennis every day for 90 minutes. I took a nap almost every afternoon. I got a couple of massages. We went and saw Black Panther, which we loved.
I interrupted vacation on Wednesday for some work stuff but stayed off email completely. I played a lot of chess online but realized after losing a bunch of games that I thought I was winning that it was a bad idea to play 10 minutes games while watching the Olympics in the background.
I didn’t read much. I didn’t feel like it for some reason. While unusual for me, I just rolled with it.
We had two friends visit. Ben Casnocha came down for two days of stimulating conversation. David Cohen took a tennis vacation, which he had planned for a more exotic locale that fell apart at the last minute. The friendships were warm, mellow, and enjoyable.
The month of December continues to be a huge struggle for me. I reflected on why and Amy and I came up with a plan for trying something completely different in December 2018 that we are contemplating trying.
I’m back home alone in Boulder for a few days, while Amy spends the weekend with her sisters. I decided to have an isolated, minimal human contact weekend. Yesterday was a digital sabbath that included meditation, running, a float, dinner by myself at Kasa Sushi, Lee McIntyre’s Post-Truth, Radius, and Lo and Behold.
Today is more of the same, except online plus a massage. Maybe I’ll drop the heavy and serious tonight and start working my way through Fast and Furious.
I’ll be back at it for reals on Monday …
Amy and I just spent a week of vacation off the grid in Aspen. I ran, read, and hung out. I had a fantasy about writing, but didn’t get to it. We watched Narcos Season 3, ate at a bunch of Aspen’s restaurants, and had an Amy pre-birthday dinner with our friends Dave and Maureen. And we napped – a lot.
I hadn’t had a vacation since mid-April, which is unusual for me as Amy and I try to take a week off the grid every quarter. On day three, which was a Monday, I settled into a total chill zone which lasted all week. I did my long run on Friday (instead of Saturday) and cruised from Aspen to Basalt. I then slept most of the day on Saturday when I wasn’t reading or eating. Yup – I’m marathon ready.
While I’m not quite finished with Reincarnation Blues, I did knock down six other books this week.
Daring to Drive: A Saudi Woman’s Awakening: Intense, powerful, horrifying, and inspiring all at the same time. Manal Al-Sharif is incredible. I hope I get to meet her someday – I’ll thank her for being brave enough to do what she does and to tell her story while doing it.
The Impossible Fortress: My inner 14-year-old loved this book. Loved, loved, loved it. The Commodore 64 code was a bonus.
Angel: How to Invest in Technology Startups – Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000: I met Jason Calacanis in the mid-1990s when he was peddling his Silicon Alley Reporter magazine. We’ve been friends ever since and I give him a big hug whenever our paths cross. He’s his normal outspoken and bombastic self in this book, which has lots of gems buried in it. I smiled a lot when I read it. And how about that subtitle …
The Rise and Fall of American Growth: The U.S. Standard of Living since the Civil War: This book was a grind, but it had a lot of good stuff in it. It’s only 784 pages so it took more than a day to read it. If you are trying to understand what is going on in the current American economy, and why the future will not look like the past, this is a good place to start.
Teach to Work: How a Mentor, a Mentee, and a Project Can Close the Skills Gap in America: As part of my effort to get rolling again on my #GiveFirst book, I thought reading this might be a useful kick in the pants. It wasn’t.
My next vacation is in mid-November. The tank once again has plenty of fuel to get me to that point.
I like Memorial Day weekend and Labor Day weekend a lot. They are my bookends for summer and kick off the official “back to school” fall cycle. I realize that kids are back at school already, but even when I was in school I viewed Labor Day weekend as the official market.
I’m noticing an enormous amount of anxiety in the air. When I reflect on what’s causing it, I suspect some of it is the public market gyrations along with the endless discussion around it. Some of it is the Republican Primary circus and the crazy and apparently unwanted popularity (at least by the Republican establishment) of Donald Trump. Some of it might be that it’s just been really hot outside for a while and it’s time for the cooler, softer tones of fall. And some of it might be all of the construction everywhere, which is at a fevered pitch right now.
I’m in a consistent conversation with a lot of entrepreneurs. “Is my burn rate too high?” “Will I be able to raise the next round?” “Are valuations going to go down?” “What should I do about the coming _fill_in_the_blank?”
Fall is coming. I don’t know what the public markets will do, nor do I know what the private markets will do. But the weather, at least in much of the United States, will cool off and the leaves will turn different colors. And, if 49 years of life on this planet is any guide, there will be an emotional shift from summer to fall.
Let your body, soul, and mind reset this weekend. Turn off the electronics. Don’t try to “catch up” before things get crazy. Watch a movie with your sweetie. Eat some ice cream. Sleep late. Go for a long walk in the mountains somewhere. Read a book. Take another nap. Have a long, slow dinner. Play with your dogs. Or do whatever you like to do to relax.
The fall is always intensely busy. Charge up your batteries and get ready for it.
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.
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 (email@example.com). 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 firstname.lastname@example.org 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.
Amy and I take a week off the grid every quarter. It is one of the things that has kept me sane and us together over the past 14 years.
This morning I saw a great short clip from the Today Show that got forwarded around on the US becoming a no vacation nation. They include an interview with Bart Lorang discussing FullContact’s Paid PAID vacation policy. It also shows an iconic picture of what stimulated this, which was Bart checking his email on his iPhone while riding on a camel with his then girlfriend / now wife in front of some pyramids.
Everyone in my universe works incredibly hard. But the really great ones know the value of disconnecting for periods of time to recharge their batteries and refresh their brains. If you want more on this, grab a copy of the book Amy and wrote called Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur.
Wow. I needed a vacation. Amy reminds me that I say that on day three of each of our quarterly weeks off the grid. It doesn’t seem to matter how I try to pace myself or how recent my previous week off the grid was. On day three, when I’m not looking at email, anything on the web, or checking my phone, I just breathe deeply and say “wow I needed this vacation.”
Oh – and I decided to get over my fear of horses. I’ve been afraid of horses since I was a teenager. As a kid growing up in Dallas I rode a lot, but my brother had a nasty fall when we were riding together and that was that for me. Amy loves horses and has started riding regularly now that we live in horse country outside of Boulder so I decided it was silly for me to continue to be afraid of horses. So we spent a week at Miraval where I could ride every other day and do a few of their horse specific activities.
For example, here’s me painting a horse. Bonus points if you figure out what I painted on him (his name is HeartWind). Hint – count the vertical lines carefully.
As with most of my vacations, I read about a book a day. Here’s the list, in order, with short commentary.
Red Bang: I wanted to love this book. From the review it felt like a current day version of Microserfs: A Novel or JPod, two tech culture masterpieces by Douglas Coupland. While some of that came through, “The Company” (a thinly designed version of Microsoft) was too over the top ridiculous and many of the satirical moments fell flat for me. It was ok, but not great.
Sting of the Drone: I’ve devoured all of Richard Clarke’s fiction and they are all well written, incredibly relevant, and better than what a modern day Clancy treatment of the topic would be. The only issue I had with this one was the ending – it was too contrived, too many good guys died while the bad guys got shut down, and the neat tidy bow that wrapped everything up consisted of almost all of the protagonists dying in a fireball ending. Boo – more reflection after the climax needed, but otherwise outstanding.
The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph: I don’t know Ryan Holiday, but I heard of this book from Tim Ferriss and was intrigued by the description so I decided to dose myself in some stoicism. Dynamite book – I’m glad I put the time in. Holiday covers the topic well in a very accessible way.
Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising (APenguin Special from Portfolio): I figured I’d read the cannon on Holiday so this was next. If you don’t know what “growth hacking” means, this is a good intro. But if you do, this is a waste of time.
Stress Test: Reflections on Financial Crises: This was the heavy one of the trip – it took three days. Geithner has always been a cipher to me so I figured his autobiography and memoir on the financial crisis would help me understand him better. He did an amazing job with this book, both explaining what happened while explaining himself. The depth of his own introspection and understanding of his own being came through in the midst of incredible pressure and crisis. Once you realize he’s a deep introvert in a context that begs for extrovert energy, a lot of the puzzle pieces about him slide into place. After reading this book, I’m glad he was at the head of the NY Fed and the Treasury for the past decade. Regardless of your position on what went down during this time, this is a book worth reading for a clear perspective from Geithner’s point of view.
Sleep Your Way to the TOP: *and other myths about business success: I finished my trip by reading the final version of the second book from FG Press, our new publishing company. I’ve probably read the book a half dozen times during the edit cycle, but I hadn’t yet read the final version on a Kindle. More soon, but I love this book and Jane Miller is an absolutely star.
I’m going to start doing something new on my posts. Rather than having separate posts promoting stuff I’m up to, I’m going to begin including a short header in each post with either a thing I’m involved in or something I read recently that I think is particularly germane. For now, I’ll style these in italics – at some point I’ll come up with some new CSS to set it apart more clearly. Feel free to offer any/all feedback on this. Today’s tip is from Alex Iskold, the Techstars NY Managing Director and is 7 Calendar Tips for Startups. If you struggle with your calendar, it’s highly recommended.
Last week Amy and I went to our favorite place in Cabo San Lucas for our Qx vacation. We went off the grid (no phone, no email). I ran a lot, slept a lot, and ate a lot. I watched all of Orange is the New Black and almost all of Caprica thanks to hotel WiFi and Neflix on my iPad. But most enjoyably, I read a lot. Following is a summary with links.
Is Amazon Bad For Books?: What a yummy article that gives a lot of history about what has been going on between Amazon and the traditional publishing industry. Highly relevant for a lot of our thinking around FG Press.
The Science of Battlestar Galactica: I listened to this on Audible while running. If you are a BSG fanboy like me, this is a must read.
How To Defend Against Patent Trolls Without Breaking The Bank: Ken Bressler has been super helpful in one of the more vexing and annoying patent troll cases I’ve been involved in. As the Supreme Court once again has a chance to do something about software patents and patent trolls, I remain cynical and pessimistic that this gigantic tax on innovation will get resolved anytime soon.
The Underwriting: More Startup Fiction – this time in a weekly serialized format. I paid for it before I left but for some reason I only had two episodes. I just paid for it a second time so hopefully they’ll start coming in a steady stream. It’s pretty fun – a little too much sex and investment banking for my tastes, but we’ll see where it goes.
Battlestar Galactica Series Bible: The original series bible written by Ronald D. Moore. Another BSG fanboy must read.
The Secret of Raising Money: Seth Goldstein and Michael Simpson have written a really strong book on how to raise money from angels and VCs at the early stage. I’ve known Seth since the mid-1990’s and think he and Michael did a great job of capturing the essence of this very hard and often complex process.
Who Says Elephants Can’t Dance?: I hadn’t read this since it first came out a year or so after Lou Gerstner retired as IBM’s CEO. This is his memoir of his experience at IBM and was a fantastic history lesson. While some of the strategic advice felt a little dated and “big corporate”, there were endless gems throughout the book, including a clear view on key decisions that Gerstner made relatively early which dramatically changed IBM’s downward spiral into the depths of mainframe doom. I’ve felt for a while that Microsoft is having its “IBM moment” that occurred for IBM in the early 1990s and to date have been uninspired with how they have approached it. I don’t know Satya Nadella but I hope he’s read this book.
Giving 2.0: Transform Your Giving and Our World: Amy and I plan to give away all of our money while we are alive. We’ve been active philanthropists since the late 1990s and are always trying to learn more. Laura Arrillaga-Andreessen’s book is a wonderful combination of personal history, advice, and storytelling about what other people are doing. I was especially pleased to see a long chapter on our friends Linda Shoemaker and Steve Brett’s efforts in Boulder around their philanthropy.
The Trial: I’ve been describing our annual fund audit process as “Kafkaesque” to whomever I talk to about it. I realized I had never read The Trial so I grinded through it. I thought I knew what I was in for, but the copy I read fortunately had a Kafka history as well as a history of The Trial with a short summary at the beginning, so it made a lot more sense as I read it. And yes, the audit experience is still something I believe is Kafkaesque. Hopefully they won’t kill me like a dog at the end.
Orange Is the New Black: My Year in a Women’s Prison: I randomly watched Season 1. I figured I’d bounce after a few episodes but found myself deeply engaged in it. So I grabbed the book and read it. The book was even better than the show. Piper Kerman blew my mind – both with her experience and her writing about it. So powerful, depressing, upsetting, and enlightening, all at the same time.
Neuromancer: I read Neuromancer my in college shortly after it came it. I loved it then. I haven’t read it since so I decided to listen to it my iPhone while running, just like I did earlier this year with Snow Crash. Like Snow Crash, it somehow felt richer when I listened to it during my long runs. Case, Molly, Wintermute, and the Dixie Flatline still delight, as does Gibson.