As a sometime entrepreneur, contractor, founder, and freelancer, I know how difficult it can feel to take a vacation.

When I was a salaried employee at a newspaper company, it was hard enough, making sure that important stories would be covered while I was away. Now, when it’s just me and time away from work can mean things don’t get done or the money doesn’t flow – that makes things even tougher.

I was reminded of that when I took a few days off recently to celebrate my son’s birthday, so I turned to some friends to ask their advice on how to turn on the email auto-responder and be present in the moment when you’re not in the office. (Some answers edited lightly for length and clarity.)

For those who work with others, one theme came through loud and clear: Make sure people can handle the job without you there:

Gary J. Nix, Chief Strategy Officer bdot. An Integrated Branding Agency:

My biggest vacation secret, should not be a secret. I make sure that business is handled by making sure those that need to know realize I will be gone for a specific period of time and ensuring that someone who knows the work and is able to handle it is there in my absence. My contingency plan is to provide that person covering for me with a way to reach me in case of an emergency.

Stacy Sailer, COO, Paired Media

I plan everything ahead that needs to get done, and delegate the checklist items to my team. They execute on it seamlessly, which puts my mind at ease.

Truthfully though, you don’t get to unplug completely as a founder the same way that a parent can’t disconnect from her newborn. Thankfully, we have a solid team, and my partner and I have complete trust in each other in the same way that a newborn has 2 parents to take care of her. That helps.

But how about if you don’t have a whole team to rely on? Hire someone — think that’s too expensive? What’s the cost of not having a backup?

Hessie Jones, Founder and CEO, ARCOMPANY

Virtual Assistants are amazing. A friend introduced me to Zirtual. Whether you’re on vacation or you just want to concentrate on the “stuff” that makes you money, Zirtual is great for getting rid of the tasks that are time sucks. Everything from scheduling meetings, moderating all emails, social presence, list building, research. It all can be done at a cost that’s affordable. This is where I’ve learned to ask myself, “How much is my time worth and what would I rather put my time towards?”

Julie Pippert, Founder and Director, Artful Media Group

You know what I did when I went away for a month? I hired someone. She started back in March. We did real-time training. In May before I left she took over so I could be there if needed. In June she did the job well under challenging circumstances. When I returned, I realized it was such a relief to have a backup and someone reliable and professional so I could let go that I put her on retainer to just remain apprised of my work — in case of emergency, busy schedule or vacation. I can’t even tell you how amazing it is to know I have backup.

Isn’t there always someone who goes on and on and on longer than everyone else, but has such great advice that you find yourself having to share all of it anyway? In this case, that would be from:

Dino Dogan, CEO, Triberr

Here’s my biggest vacation secret. When you own your own company, every day feels like a vacation. And if you also happen to speak at conferences within the context of your expertise, not only do you get paid to travel, but you also get to advance your company’s goals in the process of — essentially — being on a paid vacation on another person’s dime.

I don’t put too much stock in getting yourself 100% unplugged since it’s so easy to stay connected and answer a sporadic email here and there.

But if you insist on being 100% off the grid, there are a few of staple techniques for handling issues which come up while on vacation.

1. OOO – Set up an Out Of Office message that lets people know when you’re coming back and who to contact in case something needs to be addressed right away.

2. Hire smart. I have full confidence in my team that they can handle whatever emergency comes up without me. This has in fact happened several times, most notably when I forgot to renew the Triberr.com domain.

3. MVP your vacation – Entrepreneurs are skilled at building a Minimum Viable Product, so why not MVP your vacation as well? You don’t have to take a month off to go to Italy and Spain. Start by taking a few days off and see how your team does without you. You might be surprised when productivity increases without your presence. Then graduate to taking a full week of or longer.

Finally, another friend had a cautionary tale of how the stress can affect you if you don’t let yourself take that vacation and set up a plan to take care of things while you’re off the grid.

Liva Judic, Founder, Merrybubbles

Once I went to unplug in an ashram in the south of India. The first couple of days, I was really stressed not to be able to check my emails and not to have a phone to check them on. I had to line up to use the “Internet room” and use old computers with a dialup connection. I gave up.

The switch happened on Day 3. I just needed to unplug, it was December during holiday season, nothing would happen. Instead, for the remaining week, I focused on meditating and getting better at yoga.

Then the real challenge occurred. It was not the unplugging that was the most painful, it was the re-plugging — the insane amount of anxiety before I landed in New York City and was finally able to check my emails.

So unplugging is doable. The pain point is getting back and plunging yourself into your daily amount of emails, tweets, posts, etc. It took me 2 months to readjust.

It wasn’t all bad, though — that experience led me to launch a new service, helping others through that pain point. #LivaLive is my way of helping others achieve mindfulness in their daily work and life.

Published on: Jul 31, 2015