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How to Take Vacation as the Lone IT Pro


As the lone do-IT-all person in the office, you’ll eventually want to take vacation. But it’s not a matter of when. The question is how?!

Your job is to lord over everything from the workstations to the light bulbs. If it blinks bright red, makes strange beeping sounds, or needs a screwdriver to open, you are first on the scene.

You’re irreplaceable. And for that same reason, unvacationable.

More than 50% of U.S. employees did not use all their vacation time in 2015, and IT pros are among the worst offenders when it comes to skipping out on vacation.

A common reason for not taking vacation is fear. Perhaps you badly want that promotion so you keep working harder than normal, or maybe you don’t want to come back from vacation and find you’ve been replaced by the new IT knight in shining armor.

Here’s how to leave your kingdom behind for a while, and still retain control.

Don’t Mess with Infrastructure, Use Cloud Services

Livestock farming is hard. Even taking care of a pet is hard. When you have upwards of 10 hungry farm animals (servers and PCs) and dozens of roaming pets (smartphones, tablets, and pagers) on your digital ranch, do you have systems in place to manage them while you’re not physically there?

If not, look up. See that silver lining? That’s the Cloud, and it’s your ticket to a stress-free vacation.

Key benefits of Cloud-based IT:


  • Automation: Complex provisioning, deployments, upgrading, and backups can be done in a few short commands, and even clicks.
  • Self-service: You don’t need to be bothered about every new app or service someone needs. Teach your users how to spin it up themselves.
  • High Availability: Designed for redundancy and high availability, the Cloud is extremely resilient to failure.
  • Remote Monitoring: Performance and health monitoring are easy.
  • No Managing Hardware: This is done by well-trained elves.


Put all those benefits together, and you end up with more time for yourself and less worry, whether on vacation or not!

It might seem like a bold move, but you don’t have to move everything to the Cloud at once. Take stock of your most essential computing resources and start by switching over the smaller stuff in stages. If you plan to do the migration yourself, you should check out Ben Finkel’s awesome course on AWS: Technical Essentials and learn how to leverage the world’s most popular public Cloud provider.

Before you know it, everything your organization needs will be within reach at all times, even when you’re not. The real challenge is that there’s a single point of failure for public and hybrid cloud operations: ensuring the internet is available to users all day, every day.

If the Cloud is simply not an option for you, then consider these options.

Hire Contractors (if you can)

When relaxing on vacation, there are hundreds of blinking LEDs back at the office that threaten to go dark at a moment’s notice. No one knows when or which one will bring business to a standstill, but someone  needs to physically be on site to handle the odd emergency lest your non-vacationing coworkers turn their office block into a riot zone over a downed internet line — leaving  you to get  blamed.

Thankfully, you don’t need someone with a Master’s degree to take care of that in your absence. What you need is an IT mercenary who learns quickly and who you can train rapidly for part-time contracting work.

If you feel you need to work on your managerial confidence before training others, push to get that certification you’ve been considering to boost your real and perceived expertise.

Train Your Users (if you have the patience)

You don’t have to go as far as individualized Post-It notes stuck to each workstation’s monitor, but end-user training should be high priority.

Whatever your training style, make sure it is tailored to the users who will benefit the most in your absence. You know who they are.

In preparation for your vacation, you can offer seminars and informal training sessions, disseminate flowcharts for common issues, or even go big and set up a company-wide training campaign with the support of the higher-ups.

Document Everything

Make sure that all common problems have some documentation or notes that someone can consult while you’re away. You don’t have to go all ITIL® or PMP in the process, but the last thing you want is to be riffling through paperwork or emails for some forgotten document instead of spending that perfect day at the beach.

If your temporary IT support personnel need to know what IP address workstation X uses, draw out a network map and make it easy to find that information. Also, check that there are no software licenses expiring soon, or any other documentation that needs attention in the near future.

Fall Off the Face of the Earth

At work, you’re constantly on call, and you’re OK with that. You enjoy being the first port of assistance, even when you’ve finished up for the day. But when planning for vacation, this mindset needs to change.

Don’t get sucked back in just because someone in Accounting declared a fax machine failure to be an emergency. This is doubly important if you have paid time off; you have a right not to be guilt-tripped.

Once everything has been fail-safed to the best of your ability and you’re a day away on vacation, activate your email auto-responder, turn off your work phone, and be free!


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