How To Vacation Like a Startup CEO

by / ⠀Entrepreneurship / October 29, 2013


Any small business or startup CEO will attest that it is nearly impossible to take a vacation.
The combination of endless work to be done, constant race against the clock in managing cash flows, push to acquire customers and downright passion for your business makes the thought of stepping away almost laughable. Nevertheless, stepping away can be important and a vacation is sometimes vital either for your own personal well being or for your family’s.

As the co-founder and CEO of Travefy, an online tool that solves the coordination headaches of group travel, I understand these struggles first-hand. Oh the irony – I’m in the vacation business, but I can’t take a vacation!

With my wedding and honeymoon coming up this fall, however, I will be taking time off and have recently been reflecting on the best way to vacation like a startup CEO. If you, as a CEO, are lucky enough or compelled to take a vacation, here are some tips that have worked for me in the past to ensure you maximize your time away while realistically staying plugged in at work.

Right-size your vacation.

All businesses are different and there is no set best length for a vacation. The best length depends on your particular business and staff, as well as your own state of mind. Be honest and ask yourself how long can the company function with a roadmap but without you. Additionally, and perhaps more importantly, how long can you realistically walk away before all of your thoughts are consumed with fear about being gone. This information will help determine how long your ideal vacation should be .

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For me, I’m a big fan of long weekends. Taking off a Friday or a Monday is the perfect amount of time that I can honestly unplug mentally.

Compartmentalize your trip.

It’s a given that you’ll likely have to do work on your vacation – from emails to regular deliverables. This is the way of the world. Go to Disney World, sit at the beach, etc, but don’t divide your time haphazardly. You owe work 100% when doing it and your friends and family your true attention as well.

The best fix for this is to honestly assess how much you need to do daily and compartmentalize. If you have 3 hours of work daily, that’s fine, plan accordingly to work in the morning and join vacation activities (with undivided attention mid-morning) for example.

Keep everything at your fingertips.

Be kind to yourself and have comfort that if something big does come up you can access everything you need whether you’re vacationing in Chicago or Bangkok. Technology today has truly broken down the barriers of geography. Personally, I can access every file we have at Travefy on any device via Dropbox, video chat with teammates using Sqwiggle, and/or collaborate on code using Github.

Communicate & manage expectations.

Clear communication with your team is critical. The best way to ensure you enjoy your vacation as well as support your team is to clearly articulate your plan in advance and manage expectations. For instance, a compartmentalized work schedule is fantastic but can only work if your team understands exactly when you will be working and how best to reach you.

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Make sure to tee-up your vacation plans as far in advance as possible and to document your out of office work plan in a group email or file.

Create opportunities.

Remember that every situation can always lead to new opportunities. In this case, taking a vacation is also the perfect environment to create development opportunities for your team that empowers them to grow as employees (but also saves you valuable time).

As a part of your communications and work plan, look to see if there are responsibilities that can come off your plate while you’re away. This gives you less to worry about while also giving you the chance to empower, challenge and test your employees, which is important for any healthy work environment.


Lastly, and most importantly, relax. There’s no right or wrong way to take a vacation, but know yourself, plan ahead, and make sure you enjoy your well earned vacation!

David D. Chait is the Co-founder and CEO of group travel tool, Travefy. He previously served as Senior Policy Advisor at the U.S. Small Business Administration and worked as a consultant at McKinsey & Company.

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About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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