Working On Vacation

The title of this post sounds like an oxymoron. But it is a fact of life for me and probably many of the people who read this blog.

The idea of a ‘get away from it all’ vacation is a romantic notion that I cannot seem to achieve as much as the Gotham Gal and my kids would like me to.

This week, for example, I am in the middle of assisting two of our portfolio companies close on very senior hires. I am helping with the negotiations and trying to keep the rest of the board in the loop. And we are closing a deal which requires some attention on my part. And we are working with all of our portfolio companies to ensure they have their cash invested wisely. None of these efforts will or should wait for next week

I do have partners and a very capable associate to back me up and I rely on them a lot more when I am on vacation.

But the reality of venture capital is that its a relationship intensive business. You can’t just disengage from a complicated negotiation and say ‘my partner is taking over for me for the next week’. We all wish it was so, but its not.

So what do I do to manage? First, I block out 90 minutes in the morning when my family is asleep for emails and phone calls. Hawaii makes that easy because at 6am in hawaii, its 9am in the bay area and noon in NYC. I schedule all my calls for this time slot.

And I keep my blackberry with me but try to keep it off unless we have some down time like waiting for a tour to begin. I have gotten very good at quickly scanning email to see if there is anything urgent.

I also find time to do stuff, like post on the eliptical trainer, where I am not taking time from the family and the vacation

Most of all, when there’s a question between family and work, family wins. That has to be asbolute

I’ve heard of some amazing tricks. A friend of mine listened in to a board call where he is an observer while skiing with his wife. He had the call on mute and the headphones under his helmet. We’ll have to ask his wife what kind of company he was on the hill that morning but that’s the kind of mutli-tasking we have resorted to at times

My friend Brad Feld does ‘go off the grid’ for one week a quarter every quarter. I’ve asked him how he does it and I honestly can’t see myself pulling it off. I wish I could.

But one things for sure. We all need vacations and we shouldn’t let the need to work ruin them for ourselves and our families.

Posted from the eliptical trainer


Comments (Archived):

  1. Siminoff

    I try to do at least one trip a year where I truly am completely off the grid for 2-3 days. I find that it helps to reset myself a bit and I plan these with my tema members so that nothing gets dropped.For normal trips I find using blackberries, SimulScribe (sorry for the plug) and other tools that allow you to stay connected while away is a great thing and actually allows me to enjoy the trip more as I know what is happening.As well when you love what you do and control what you do work is not really work, is it?

    1. fredwilson

      But it is for those you are with

      1. Siminoff


  2. Tony_Alva

    Great post Fred and I know you make it work as best you can, but I’m a little skeptical re: “I’ve asked him how he does it and I honestly can’t see myself pulling it off. I wish I could.”It’s been awhile since we’ve hung out in person (must rectify that), but I know you struggle with that ADD thing. You seem to have a hard time just sitting down, disengaging, and doing nothing but relaxing. It’s simply how you’re wired. You were like that all the way back in high school. I haven’t done any business deals with you, but I’ll bet you wake up thinking righ away, everyday, no matter where you are in the world. I’ll bet you’d be pain in the ass to vacation with if you forced yourself to go off grid. I know and have known many like you in this sense. It’s served you well and I doubt you feel bad about it either.Those of us who can pull it off (shit, I deploy the same early AM Blackberry tactic as you), are always feeling sorry for your types, but in reality you’re as happy as the rest of us. What ever works for you and your family is always best.Just my thoughts…

    1. fredwilson

      TrueBut what works for me isn’t the pointIts what works for the familyFred

      1. Tony_Alva

        it works for your family sure, but I’m certain, as some of those who have commented below have said, you stay dialed in becuase you want to, not necessarily because the world would end without you. I say that’s okay, especially if you’re family is cool with too. Your work is obviously a tremendously satisfying to you and large component of who you are. People often wonder why corporate leaders who are wealthy beyond comprehension continue to work ungodly hours and I for one have always understood why: It’s not the money, it’s the job that gets them off. it’s the same reason someone might pour they’re life and all their meager treasure into a career in music, it’s what gets them off.Obviously your family comes first, that’s a given with you, but AFTER family I’d bet if you were standing at the gates of the lost city of Atlantis itself you’d be wondering how that board meeting went, or if that deal got inked:-)

  3. Alex Stevens

    “But the reality of venture capital is that its a relationship intensive business. You can’t just disengage from a complicated negotiation and say ‘my partner is taking over for me for the next week’. We all wish it was so, but its not.”Here’s my wife’s take on that: “If you were in an accident and in the hospital unconscious for a week, what would happen?”Sounds extreme, but its a good point – all those relationships and partners and associates and businesses would deal with it and not fail, generally speaking. Just as Brad has made the decision to go off the grid, you’ve made the decision not to. He pulls it off because he’s committed to that decision, and you could too.In my days as a cable network executive, I was managing hundreds of projects with continuous deadlines simultaneously and also felt like I couldn’t do it – until I just did it. I was amazed, given the right team and the right notice, how well it all went. There were a few frantic calls, but having the right gatekeeper knowing how to filter the genuinely urgent needs kept that to a minimum. After a few times doing this, they dwindled to zero.Pick a future vacation, tell everyone you’re doing it, and try it. Good luck!

  4. bijan

    boy this post cuts awfully close to home. too close.I’m getting better but I have a long way to go.

  5. andyswan

    LOL halfway through that I thought I might have written it. The great thing is, my wife knew she was marrying an entrepreneur. She doesn’t just accept it, she embraces it and helps me turn my…um….”characteristics”….into positives for us and our family. She sees the blackberry as a TOOL that enables me to spend 20-30 “slightly distracted” hours per week at home that would otherwise be spent in an office or something stupid like that.It would definitely have to be an open-bar vacation for me to go off the grid and not go nuts 🙂

  6. daryn

    my wife actually encouraged bringing the laptop on the last couple vacations, because she knew i’d go nuts without it. And it served us nicely for non-work purposes too!In return, I’ve learned (am learning) to not pull out my phone and check email when we’re out at restaurants.

  7. kenberger

    I have a very different framing of this that begs the title of this post.I too am deeply empowered and motivated by travel, and have integrated lots of it (both biz and pleasure) into my life. But it’s super rare that I say I’m doing a “vacation”.Times are different/better, in part due to the technologies that our industry helps create (yes Simulscribe). “Don’t mix biz w/ pleasure” is defunct. Innovating a lifestyle where you can work while on the go and integrate it with the rest of your life, rather than having to put that life on hold to do it, is a hard task to pull off. And that’s what you’re working hard at, Fred.”It’s all about what works for the family”– exactly. So shouldn’t it be acknowledged that you guys are able to take way more great trips than most people can, specifically because you’ve innovated this great work/play mix lifestyle?Here has been my ‘sell’ to family/gfriends, and it’s an honest choice: “ok fine, we’ll go back to the workworld-standard 2-4 weeks of vacation per year where I’m 100% unplugged… or would you rather be able to sneak in more frequent trips if you’ll work w/ me through these adjustments. Which do you guys prefer?”This blog shows you do a ton of cool travel. If they really were standard-def “vacations”, it couldn’t work vis-a-vis your job, right?It’s an art that takes a ton of work, but I hope it’s the way of the future. Some of that work includes being able to spend some traveling days truly unplugged and really “on vacation”, btw.

  8. DonRyan

    I feel your pain. I work in a small partnership and am the only person who provides some of our services. What makes it worse (on some level) is that I love what I do and am passionate about my work. I don’t think I could go completely off the grid (nor would I want to) but I have, on vacations, implemented similar limits to what you have (limit call times, use the blackberry, etc.). I sometimes wonder if I’ll ever find balance.

  9. Karen E.

    “But the reality of venture capital is that its a relationship intensive business.” Bingo, you’ve hit the nail on the head – twice. Any business at the high levels is a relationship intensive business. And it’s exactly the reason that women drop out of the workforce – from any field – when they have kids. They eventually find that high levels of career performance and satisfaction are totally incompatible with raising kids. Most reliable route to poverty for a woman? Have a child.

    1. fredwilson

      KarenThe point you are making is that raising kids is a relationship intensive business. The most important relationships, other than your spouse.That’s a great thing for all of us to keep in mindFred

      1. Karen E.

        The other point I’m making is that it is very scary scenario to contemplate having children when you are used to the payoff that relationships in business provide. Having children means – eventually, ultimately – you simply cannot truly, deeply “be there” for your clients because their needs are (as a category) at odds with kids’ needs. Which might not be a problem, but if you need to pay bills, kids don’t give you a paycheck after you’ve nurtured them by text message from the elliptical trainer. Can you please fix that, Fred? Isn’t there a startup working to change that? Oy.

        1. fredwilson

          I think that’s not fixable, and maybe it shouldn’t be

  10. LGBlueSky

    checking emails while the kids are sleeping is my trick right now from turks and caicos. i went off the grid for the afternoon today and missed an important conf. call . the time with the family was simply more important to me. thanks for the tips re: time management. my tip to you: maybe you need to work a little harder on that eliptical !

  11. Bill Davenport

    Impressive typing skills on the bb while hitting the elliptical! Your portfolio companies are fortunate to have an investor as dedicated as you, but that said maybe you could get a few straight days of total disengagement, if not the whole week. I actually hope you don’t read this comment while you are on holiday! Better things to do.

  12. jackson

    You can rationalize all you like, but face it, even if you were unemployed you’d fill every moment of your day. You simply can’t sit still. I don’t see that as a flaw, obviously you’ve channeled your energies well.At any rate, one must make hay while the sun shines.

  13. hmmm

    You spelled absolute incorrectly. Use spell check maybe?

  14. Offbeatmammal

    Totally randomly… you’ve been pinged by 8 Random Things!What doesn’t the world know about you…http://blog.offbeatmammal.c

  15. Guest

    Can definitely relate… Going through a little burnout and was planning on taking next week off because kids are on Spring Break. I have meetings on Thursday and Friday now and conference calls on Monday. A bit of a bummer but it’s what I do…I might peel off a day or two the next week to spend some time alone, been thinking about going to Joshua Tree to get some photos

  16. Giordano

    I’m on a long week-end in Penang, Malaysia (absolutely recommend it, it’s fab and the Shangri-La resort is heavenly), and I spent last night getting up every 2 hours to check on some urgent stuff in the US, and providing feedback. My girlfriend slept through it, fortunatelyPlease spare a thought for all of us working for US companies in different time zones, and with different holidays. We need to adapt, naturally, not viceversa… and the fun never stops :)Cheers, Giordano

  17. johndodds

    I’m just in awe of your ability to type on an eliptical trainer (whatever that might be).

    1. fredwilson

      A self torture device 🙂

  18. joe bruzzese

    Kudos to you for finding a set of tricks that can keep your career on track while maintaining a balance with your family. Not many folks can find the balance. Most folks fool themselves into believing that the “headphones under the hat, listening to the board room conversation, while your wife is unaware” is actually being present and spending quality time.Imagine it can be real and it will be. Isn’t that the spirit you would hope your budding entrepreneurs would bring to any venture with you?

  19. Jessica

    i hope you find time to sleep! waking up at 6am on vacation would make me sad.

    1. fredwilson

      That’s noon nyc time!

  20. Steven Kane


    1. andyswan

      Comment of the week!

    2. fredwilson

      nice one citizen kane

  21. Jesse Chenard

    Interesting part is that we entrepreneurs have the same dilemma. It is hard to just abandon your baby for a week or longer (even though we usually have partners as well). My last trip to Hawaii I was spec’ing and developing a new product line. This involved coordinating with a guy in Vancouver, 2 in Boston and 8 in the Ukraine via email, IM and telephone. Since we were there for 3 weeks I managed to limit the intensive project work to the first week and then it was more maintenance mode for the remaining 2.It is hard to find a balance but I think you have it bang on, when on vacation family always comes first.

  22. charlie crystle

    Family is a relationship-intensive business, too.I have ruined enough vacations that at this point my planning for vacation has little to do with where I’m going and much to do with how I hand things off and complete things before I go. There is no such thing as a working vacation. You’re either shortchanging the vacation or shortchanging work, and feeling crappy about both. Or at least I do ;)So what I do now is work on the travel days, plus the first day there, then put everything away. And it works so much better, and my work is better when I return.

  23. Rick Sparks

    Step one – tell them to shut the f*** up and let you work so you can keep making money.

    1. fredwilson

      This comment thread is getting interesting. Thanks for joining the discussion craigFred

  24. LoungeALittle

    I think this is really sad. The only thing that you have no more of is time. Why dont you spend it doing things that really matter? … like family or saving the planet? Seriously … if you dont do that deal will you lose your house, family or not be able to put dinner on the table? I doubt it.I used to get caught up in the rush of work until i realised that is not what life is about. Life is not a competition. Relax a bit.Just before you take your last breath you will wonder why you didnt pay less attention to work. Thats not cool.-Lounge.

  25. peterarmstrong

    Heh, I used to have a Precor elliptical trainer and I built a laptop stand for it out of MDF and a couple C clamps — worked great for reading emails / writing them / debugging code…

    1. fredwilson

      Brad feld has something like that on his treadmill

  26. notreallysure

    Story is Nepoleon would not read correspondence until it was 3 months old. He assumed most anything would have taken care of itself by then and anything real important he would have heard about directly. I like that theory a lot.

    1. fredwilson

      I am not sure that would work in this day and ageMaybe a 24 hold period might work!

  27. racy_rick

    Vacations are needed to combat stress. I believe a work-home relationship is needed, but barriers must be setup. I think your own self-importance is probably stressing you out all of the time.Take a vacation from your vacation sometime. Clear some time from your work so that you aren’t needed.

  28. Antman

    How do ya type on an eliptical trainer?

    1. fredwilson


  29. gregory

    having been doing nothing for fifteen years in south india, except for a bit of art and a lot of meditation, i got what i wanted from down time, and am ready to enter the stream again, for, let’s say, fifteen years of flat out…. should be easy, just let it flow

  30. Matt Douglas

    Fred,I just posted a response to this post on my blog. Consider it a gift from me to you.

    1. fredwilson

      Thanks mattTried leaving a comment. Not sure it took itFred

  31. bfeld

    Fred – I finally got around to posting a response to this post – it’s titled What’s A Vacation

  32. greenskeptic

    Last week, I took a vacation in Florida with my family. It was my first real time “off” since starting a new role six months ago and my wife and kids really needed me to focus on family for the week. My boss, however, had asked that I participate in an executive team conference call on Monday. “If you have one hour to spend on work next week, that would be it,” she said. Frankly, it felt a bit like a command rather than a request.So, I participated. It went for an hour and a half and, based upon the results of that meeting, I had to spend another half hour crafting an email to do “damage control” in response to some comments made in the meeting. My wife, kids, and mother had gone to the beach and I was to follow. However, I missed the opportunity to join them.I resented it and was grumpy for the rest of the day. So, I decided to fulfill my pledge to my family, turned off the email and phone and stayed away from it until after we had returned (although I did continue to twitter and blog during the week).Folks at work were probably pissed at me for tuning out, based upon a few emails that I received after my return, and there were a couple of things that would have benefitted from my response. But my family felt better about my presence (I’ve been traveling a lot in the last six months, including commuting from Philadelphia to DC almost weekly) and I actually started to relax by the middle of the week. Tuning out was definitely worth it.The bottom line: my family is the most important thing in my life. And if I haven’t been paying enough attention to them during my working days (of necessity), then I need to recharge with them and reconnect with them and be reminded about the true purpose of the work I do.Thanks for sharing your thoughts, Fred. Always stimulating.

  33. Vacation

    A vacation is a way to pull our family closer by spending some quality time together. We basically don’t extract time to spend with the family. Children are busy in schooling and we are busy in our work. So heading for a vacation is a wonderful idea to minimize the stuff.

    1. JohnClifford

      You post makes sense and if youre spouse has a blackberry and work to follow up on , it makes sense to schedule working time slots and non working time slots. Since paragliding is my passion while on vacation it makes it easier to put the blackberry away for most of each day on vacation.

  34. dickspotter

    you’re a dick