Work Like You’re Going On Vacation

How to plan for obsolescence.

Hamza Khan
The Concurrent Project
4 min readNov 1, 2013

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One goal of The Concurrent Project is to get you away from your desk. However, to fully be away from your work, you must have the piece of mind that your projects will advance without you. Chances are, you’ve already achieved this state of concurrence more than once - think about the last time you went on vacation…

“Most people feel best about their work the week before their vacation, but it’s not because of the vacation itself. What do you do the last week before you leave on a big trip? You clean up, close up, clarify, and renegotiate all your agreements with yourself and others. I just suggest that you do this weekly instead of yearly.” David Allen

A key factor in optimizing your work is an unwavering focus on obsolescence.

Plan for obsolescence. Write yourself out of a job from day-one. Counterintuitive? Hardly. I’ve been writing myself out of jobs since 2009, and I’ve been consistently rewarded with more opportunities; perfecting systems increases the bandwidth necessary to take on new challenges.

As David Allen suggested, think of all the things that you do before you’re about to go on vacation — you rush to define the systems, repositories and fail-safes necessary to prepare your team for a period of time in which you’ll be “off the grid.”

I’ve identified five specific components to achieving pre-vacation levels of productivity. Here’s how I’m currently configured:

1) Asset Manager

A cloud-based repository for all your project files.

Google Drive — The idea here is to centralize your team’s knowledge and make their research and expertise easily discoverable. I prefer Google Drive’s simplicity and ability to integrate with Asana. Evernote For Business and Podio are worthy alternatives. Before Google Drive, I used Dropbox to store multimedia and files that were created on Microsoft Office. This quickly became a versioning nightmare. Your chosen solution must allow for seamless cloud-based indexing and collaboration on various assets such contact lists, reports, marketing collateral, etc. Stay organized organized at the office, at home, or on the go.

2) Playbook

A definitive guide to completing your mission.

Your playbook is a document which should be comprised of the following sections: Strategy, Deliverables, Timelines, Tools & Resources and Contacts.

  1. Strategy — What’s the big picture? What are your objectives? Where is your proverbial ship sailing?
  2. Deliverables — What are the specific tasks that you need to accomplish in order to get to your objectives?
  3. Timelines — What are your project’s milestones? When will you complete your deliverables?
  4. Tools & Resources — What specific tools will you use to complete your tasks? How will you use them?
  5. Contacts — Who are the people that you need in order to move your projects forward? What is their role in the process?

3) Workflow

A visualization of how things gets done.

OmniGraffle — I use this bad boy to easily design flow charts and diagrams related to my personal, as well as my teams’ processes. We can always refer back to these sketches and technical figures to get a visual understanding of what steps to follow if we’re stuck at any part of the process.

4) Project Management Tool

A place for your team to get things done.

Asana — Take your OmniGraffle visualization and set it in motion with the help of your project management tool. My weapon of mass production is Asana. Before Asana, I swore by Basecamp and have also tinkered with Podio and Flow as potential alternatives. Through your weapon of choice you will manage tasks, have discussions, share files (ideally stored in Google Drive) and capture ideas.

5) Smart Logs

Records of accomplishments, mistakes and lessons learned.

A more in-depth post on personal analytics and automation will follow in the coming weeks. For now, focus on generating what I call “Daily Recaps.” I use IFTTT to mix my Google Calendar and Evernote accounts into a “recipe” that automatically creates tagged notes triggered by updates to my calendar. As needed, I can generate data on what I’ve done offline to advance my projects. Meeting details, agendas and minutes are automatically paired with project files. Automation alternatives to IFTTT include Zapier and CloudWork. Additionally, I maintain a “Failure Log” — a chronicle of mistakes I’ve made and what I’ve learned from each experience.

Get these five components up-and-running, and you’ll be able to step far away from your projects without worry. Plan for obsolescence by assuming a “plug & play” mentality — ask yourself: “If I were to quit today, could someone — by studying my system — instantly resume work on my projects?”

If the answer is yes, then congratulations — you’ve achieved a degree of concurrence; you’ve created a more open, productive and smarter workplace.

Trust your system. Enjoy your vacation.

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Hamza Khan
The Concurrent Project

Hamza Khan is a best-selling author, award-winning entrepreneur, and globally-renowned keynote speaker based out of New York.