If You’re Answering Emails On Vacation Then I Have Good News (And Bad News) For You

Gene Marks
3 min readAug 25, 2021


I was on vacation earlier this month and thinking about emails. Actually, I’d been responding to emails. What about you?

Do you leave an “out of office” message when you go on vacation? Do you have a strict “do not disturb” policy while you’re away? Are you the type of person that can go for an entire week without checking emails?

I know plenty of people who are able to go for an entire week — even two, even longer — and never look at their emails. That’s amazing to me. I’m always checking. My friends tell me that adds stress to my time off. I say that I would be even more stressed when I ultimately have to open up my email application on the Monday that I returned and am faced with an avalanche. What catastrophes happened? What fires did I ignore? Is my business still there?

Making sure you’re available to respond to emails, even when on vacation, is a sign that you’re needed. It means that you can’t be away for too long or things will fall apart. Is this a good thing?

That depends.

If you’re an employee at a company, it is a good thing. I realize that it may cause stress or take you away from relaxing, but it’s a sign that people really depend on you. You’re important. You’re essential to the company’s operations. That’s good news, at least for purposes of determining your job security.

Of course, if you’re working for a company and can disappear for two weeks (or more) without anyone even noticing that you’re gone, then that’s bad news. Why? Because it likely means you are dispensable. You’re replaceable. You’re not really as important as you may think you are. It means that if you’re not there the company will be just fine. That’s not a good sign, is it? Take a good look in the mirror if you think this is you. Be concerned about your job security.

What about business owners? If you run a business then I have good news…and bad news…for you too.

The good news is that if you’re able to disappear for weeks without checking your emails, then you’re running your business the right way. It means that when issues come up, as they always do, you have an organizational structure in place that can handle these issues without your involvement. That’s value. That’s something that can be sold to an investor or successor in the future.

Unfortunately, that’s not good news for me.

I run a 10-person company, and I’m checking my email all day even when I’m on vacation. I’m answering questions, responding to problems, dealing with issues. I’m indispensable, which would be great if I was working for a big company, but it’s not great as a business owner.

It means that my business has much less value than the person who can leave their business for weeks at a time, assured it runs itself. It means that if I were to sell my business, I would need to part of the deal, which will reduce the price someone is willing to pay. It means I’m not running an organization; I’m running a business built around me. This is bad news.

If you’re a business owner and you can disappear or go on vacation for a couple of weeks without checking emails, then I’m jealous. You’ve built an organization with value. You’ve been doing something right. This will pay off in the future. You are the person I aspire to be.

Originally published at https://www.entrepreneur.com on August 25, 2021.



Gene Marks

Columnist on smallbiz, economy, public policy, tech for The Guardian, The Hill, Philly Inquirer, Wash Times, Forbes, Entrepreneur. Small Business owner and CPA