7 Ways Entrepreneurs Can Avoid FAILING At Vacations


I’m baaaaack!

First, I’d like to thank the folks who participated in this year’s Expert Week. They Knocked. It out. OF THE PARK! I think it was the best Expert Week we’ve had in the history of the blog and I’m so very thankful – both to my colleagues who shared their insight and to the warm welcome they received from the community. It’s hard to go away and leave your baby in someone else’s hands, but these guys made it a lot easier.

If you missed any of the content from last week, forget whatever you’re supposed to do be doing this morning and go read it. From a fiery Point/Counterpoint on why SEOs and Developers just can’t get along (yet) to tackling marketing’s Batman and Robin to phenomenal content-based link building tips to a bittersweet industry goodbye that has me in tears every time I read it– last week had it all.

Now that I’m back, I wanted to share some lessons of my own from last week as I get back up to speed. Because one thing I learned while you were all benefiting from the knowledge of Expert Week is just how hard it is to really go away as an entrepreneur, especially if your vacation doesn’t actually have you going anywhere. And you keep coming into the office. And responding to email.


That’s right. My name is Lisa and I nearly failed at taking a vacation last week. However, I am smarter for my errors!

Below are some tips on how to take a vacation in an Internet-obsessed, just-a-DM-away world.

1. Commit to taking time off

As entrepreneurs and small business owners, this is where many of us fail miserably. We think that to hustle a healthy startup, we need to be constantly working. That we can’t possibly take time off to recharge and heal ourselves.

We are really, really stupid.

A recent post at the Mindful Living Network commented on a Framingham Heart Study which found that women who don’t take vacations are EIGHT TIMES MORE LIKELY to have a heart attack than women who take at least one vacation every 2-5 years. A different study found that men who do not take annual vacations have a 32 percent HIGHER RISK of death from heart attack.

By not taking a vacation, you are literally killing yourself. Feel free to stop any time now. If not for your loved ones, then for all your cats.

2. Plan for your absence

You can relieve much of the stress of going away by taking the time to plan for your absence. What does that mean? It means documenting your process (or sometimes, um, creating processes) for how you do things.

  • What are the steps to publishing something to your Web site?
  • How do you enter in and pay an invoice?
  • What is the process for handling customer returns?
  • How do you answer the phones?

Ideally, this material is already available and you’re using it for training purposes. But if it’s not, consider this a really good time to put some processes in place. Because once established, it’s a lot easier to hand off that documentation to someone and trust that they’ll be able to do the tasks without incident. Know what will need to get done and make sure people understand how to do it.

Planning ahead may also mean bringing in extra manpower or people to cover for you. Like, for example, finding five industry experts to take over a week of blogging for you. It may also mean completing tasks early and scheduling them to go out on the correct date, which I did for the content I published last week on SmallBizTrends. I’d also recommend creating a list of Emergency emails and numbers that people can go to for specific problems so that they’re not coming to you.

3. Notify everyone you’ll be gone

The week before you leave, start letting everyone you know – your clients, your colleagues, your employees, your friends, and everyone and anyone who may have the need to call you/email you/try and track you down – and let them know you’ll be unreachable during this time. Because you don’t want them to track you down. You want to finally be left alone go on a peaceful vacation. Ask if they can wait to send you those 37 emails until you get back into town and explain why you’d prefer not to have that call while you’re sitting on the runway or driving up to your camp spot. Taking a vacation doesn’t just mean not going into the office; it means to stop thinking about work and to let your mind go blank for a while. The more people are aware of your plans to unplug, the more compassionate they’ll (hopefully) be about bombing your inbox while you’re away.

4. Turn off all social media notifications

Go read that again.

Turn. Them. Off.

For those of us who offer social media services for a living, this really is key. Turn off the Facebook notifications. Turn off the Google + flashing buttons. Choose not to get an email every time someone DMs you. Leave it all at home. If you’ve told everyone you’ll be out of town, they shouldn’t be DMing you work-related questions, but they probably will anyway. If you ignore the DM, they’ll probably then go to your email, which will shoot them your carefully crafted auto-responder letting them know who they should talk about this matter. Don’t even check your social media accounts. You don’t need to see what blog posts from which bloggers are getting pushed to hell and you don’t need to read your friends’ passive aggressive status updates. That will all be there brewing for you when you return. You’re on vacation. Probably from these very people who are slowly driving you crazy.

5. Plan for OMG, I HAVE AN AWESOME IDEA syndrome

Even if you’re taking a vacation because you’re burnt out/have nothing left/ can’t think of a single worthwhile idea to save your life – as soon as you go on vacation your brain will be flooded with genius thinkings. This is not a reason to conclude your vacation WORKED and to immediately break out your laptop and start working on things. This, instead, is when you should pull out a tiny orange notepad (well, mine’s orange), write that idea down, and then go back to drinking your frozen strawberry margarita with the tiny purple umbrella. Keep track of the ideas and blog posts that will be smacking you in the face the moment you “turn off”, but do not let them intrude on your You Time.

Simply write them down and go back to your vacation. It will be nice to have a million things to get to when you return back to the office. Or… your basement. Wherever you happen to work from. I’m not judging.

6. Make “off” your phone’s new default

Let’s face it – many of us suck at unplugging. We live our lives on the Internet where ridiculous things like checking in, twitpicing, and keeping up with industry gossip is our idea of fun and normal. But it’s not normal and it’s exactly why you need to take time off. Otherwise, you may be attempting to twitpic your own funeral.

As a Web-obsessed person, your phone, your iPad, your whatever-shiny-gadget is your enabler for these tasks and they need to be turned off. Better if you can just NOT take them with you, but that’s not always realistic. Instead, force yourself to detach from the Internet by leaving all of your electronics in the off position, as if there’s a flight attendant standing over you and giving you the stink eye.

7. Come back a day earlier than everyone thinks

This probably sounds counter-intuitive. Why would you want to come back from your vacation a day EARLY? Easy. Because no one else will know you’re back and they’ll leave you alone to dig out at your own pace. Muahaha! Even better if during your Planning To Be Away stage you’re able to complete a couple of tasks for the day you return – like having that client document already started, having a blog post written, scheduling some tweets, etc. All this will allow you to slowly get back into the swing of things without having to deal with the mad rush of that first Monday (or whatever day) back. Let’s not undo the good effects of your vacation by throwing yourself into a bender your first day back.

You need to take time off. You need it for the health of your mind, your body, your soul and your business. So make sure you’re taking it. There’s a difference between taking a vacation and just not showing up at the office.

Also, it’s good to be back. :)

Your Comments

  • Dana DiTomaso

    Welcome back! Thanks for the tips. I’m getting married next summer and am already planning how I’m going to completely unplug while I’m gone.

    • Lisa Barone

      Congrats! And make sure you do. Because it’s important. And, well, because your new spouse may not appreciate it if you don’t. ;) Luckily impending nuptials typically give us lots of time to prepare.

  • Josh

    While I’m not an entrepreneur my wife tells me from time to time I am a workaholic and these tips would work for any workaholics out there. One more thing I’d add is if you can’t turn your phone off remove the email from your phone and have your better half control your phone. After all when you go on vacation there are usually other people with you :)

    Glad to have you back Lisa!

    • Lisa Barone

      Valid. Entrepreneurs and SMBs aren’t the only workaholics on the planet. I have to admit, I didn’t do a very good job disconnecting during my week off, but I started to get the hang out of it toward the end. Clearly, I just need more vacation time to practice. ;)

      I forget people actually use their phones for phone calls. I only use mine for email and Twitter. ;)

  • M_Roberts82

    I’m not an entrepreneur or SMB but I understand how hard it can be to back away from work in order to take a vacation. Four years working in a Legal Office taught me that vacationing will kill a man (completely counter intuitive and a bad habit). I took 2 short vacations during that time… one was a four day weekend to upstate NY and the other was… oh wait, I guess I only took one…. because the other was two weeks off due to surgery. What I found there was that when you’re gone, no one covers your work for you at all and Attorneys magically have more work that only YOU can get done than they do when you’re not on vacation. This pretty much lead to nervous breakdowns upon coming back to work because those few precious days off amounted to twice as much work as usual due in half the amount of time.
    Mainly this leads to my being happy I am no longer in that field and have joined the ranks of the SEO. :) But I understand and wholeheartedly agree that in order to keep yourself from actually going insane you need to truly step away from the work now and then to allow your brain and body the chance to recover from all the stress you put it through (whether it seems stressful or not at the time).

  • K Tanksley

    Lisa, I want to thank you for the great tips. I am an SEO that works with my husband (software development) in a small firm. I have sent your tips to eveyone in this office, and several times to the boss (hoping she will read). I am actually taking my software addicted husband camping, with no signal, so he can just get out of his head. I’m thinking that might take the whole week.

    I also wanted to thank you for the guest speakers you had this week. It gave my husband and I a chance to figure out the developer/seo headbutting that does occur. Now for us to check out/shut down for a week. Thanks again.

  • Jill Whalen

    For those of us who really do enjoy our email, forums, blogs, twitter, etc., as an alternative, when I’m on vacation I’ve found that I can just spend an hour or two in the morning catching up with the online world. That leaves me feeling refreshed to know what’s going on, and I can enjoy the rest of the day living in the real world!

  • Kae Kohl

    Very timely, Lisa. We are headed to SES SF next month and I truly want a few days to visit my old stomping grounds without being plugged in the whole time. The process tips and not getting sucked in by brainstorms were particularly helpful. Glad you’re back!

  • Chris Miller

    You went on vacation, and somebody important in the SEO industry left entirely to go write a novel. Don’t worry, I’m sure it’s just coincidence. Just sayin’

  • Jerry McCarthy

    Lisa, wow! I was just talking about this. I’m on vacation right now. Between the kids and my wife, its all work and no play. No more “‘me time” :-).wouldn have it any oter way but the anxiety has already kicked in about business. I’ve been going to Starbucks every morning but still feel like I’m not worthy of a vacation. This is right on as everyone keeps telling me I deserve it, and you’ve reaffirmed it. The beach is a great place to ponder future business plans. Thanks Lisa!!!

  • TrafficColeman

    I just came back from vacation and the only thing I did was to longing some accounts and check a email or two..I left it as that.

    “Black Seo Guy “Signing Off”

  • Ryan Popovic

    This is a great article Lisa. More entrepreneurs need to take the time to truly unplug not only while they are on vacation, but for a few hours daily. Take the time to exercise, read (non work related stuff), take a walk, play with their kids/dog, meditate, spend time with his/her spouse, whatever; with the phone (or at least social media notifications) OFF.

  • Elisabeth Osmeloski

    er.. welcome back? Doesn’t quite sound the same does it.. well, hope you did enjoy some quiet time at least, Lisa.

    The “Plan For Your Absence” part is good in case of disaster / accidental death – hit by a bus scenario / unexpected illness too… of course, we hope that never happens to anyone – but it’s especially important for small or lean running businesses.

    we do a pretty good job for covering each other at SEL whenever necessary, but sending / keeping central process notes is always a good idea.

    Lastly, for people who REALLY have trouble unplugging, the best advice I can give – go somewhere REMOTE, where you literally have ZERO access to the interwebz or digital stuff (like no tvs either.) And there are a ton of amazing exotic, upscale resorts that still offer this – so remote doesn’t always have to equal rustic camping:) I promise, the Internet will survive if you don’t check in daily…

    worst case scenario, some of their offices will have a shared computer that charge you by the minute, and at those rates, you may not stay on that long anyway:)

    Of course, I’ve already committed vacation fail too before heading out on my vacation.. I know we’ll have Internet access.. and worse, I know it’s likely I’ll need to use it, at least a little, because I’m behind in my pre-planning. oh well.

  • Gabriele Maidecchi

    This is all very common sense, but realistically no one will follow all of them. Especially the phone and/or emails, SM notifications etc. We’re just already too far in our addiction to simply turn things off.

  • Farnoosh

    “We are really, really stupid.” < Too funny and sadly true.
    Ok, on my next vacation, I commit to trying this for all of 48 hours. Is that a good start, Lisa? :) And I promise to delve into a Tolstoy just to prove that I have really taken leave of the real world. Seriously, thanks for the wake-up call tips!
    PS: LOVE your writing voice, Lisa!