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How to Convince Your Boss to Let You Work at the Beach

written by: •edited by: Carly Stockwell•updated: 3/10/2015

Telecommuting can be the key to living a life in paradise, whether that be Hawaii, or your favorite vacation spot on the coast of Maine. Could you convince your boss to let you telecommute from anywhere? Here are some tips to making your dream come true.

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    This Could be Your! How to Convince Your Boss to Let You Work From the Beach (Or Anywhere) Have you ever fantasized about chucking it all and moving to a tropical paradise? Okay, maybe you wouldn’t get rid of everything. Your significant other can come along, as can the kids or pets, if you have them. And let’s be realistic, paradise isn’t cheap, so you are going to need to keep your job. Working at the beach may seem easy enough to you, particularly if the tools of your trade are a smart phone, a computer, and an Internet connection, but your boss may take a different view. Jealousy is one reason for a boss to turn down a request to work remotely, but a more likely reason is fear. Fear that you won’t get your work done, fear that you will be too far away to manage, or fear that you will make them look bad in their superior’s eyes.

    These fears can all be overcome. I know because I did it. One day I was toiling away on the 11th floor of an anonymous office building in suburban Houston and the next day I was squishing sand between my toes at Kailua Beach trying to get psyched for my first Monday working as a telecommuter from paradise. OK, maybe the actual transition wasn’t quite so poetic, but I did make the transition and I have spent the last six years living in Honolulu and telecommuting back to a law firm in Texas. Based on my experience, you can convince your boss to let you telecommute from the beach.

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    Make Your Dream a Reality: 5 Tips

    Don’t be the First Telecommuter in your Office

    Obviously, there’s not much you can do if nobody telecommutes to your office, but if there is already a telecommuter or two employed by your company then you know there is a path out of the office. In my case, a former patent agent in my firm moved from Texas to Wisconsin to go to law school and become a patent attorney. He decided to stay in Wisconsin after law school and continued to telecommute back to the firm until he decamped to another firm, which is also in Texas. Thanks to his trailblazing, my boss understood that telecommuting is a good way to retain employees and nobody in the firm considered telecommuting unusual by the time I was ready to take the plunge. The other telecommuters in your office are fonts of information and probably very happy to talk about their experiences. Send them an email or get them on the phone to ask them for advice.

    Do your Job Very Well in the Office

    This should be self-evident, but I’m going to say it anyway. Your boss will never let you telecommute to a job that you aren’t doing well in the office. On the other hand, most bosses will do everything they can to retain their stars, the people that make their lives easier. Personally, I had no intention of becoming a telecommuter for the first five years that I worked in my firm. The possibility only arose because of a job offer received by my wife. There would not have been any time to build the necessary trust if it wasn’t already there. The die was cast. Fortunately, my boss and I had developed a solid and respectful working relationship during my five years in the office. Neither of us had any serious doubts that I could continue to work at the same level as a telecommuter.

    Negotiate a Work-at-Home Day to Practice your Telecommuting Skills

    The work that you do may stay the same, but practically everything else changes when you start telecommuting. You will have a new workspace, probably a new computer, and endless new distractions. You will also have to develop a new daily work routine that is not bookended by the commute to and from the office. Dip your toe in the water before you take the plunge just to make sure that you can adapt to the changes. If it turns out that you don’t enjoy telecommuting, and many people don’t, better that you find out now. Plus, if you can’t convince your boss to let you telecommute from home one or two days a week, you’re never going to convince them to let you telecommute from the beach.

    Take a Long Working Vacation

    Now it’s time to take off the training wheels. Rent a house, condo, or apartment in your dream destination and take your show on the road. Choose a place in a neighborhood that you might actually live in if you make the move. Spend a week, two weeks, or even a month if you can swing it working out of your temporary home. Work your regular hours. Shop in the local grocery stores. Do the best you can to imitate normal life. The place that was so seductive during your last vacation is going to look completely different when you’re fielding telephone calls from clients and scrambling to meet deadlines. Make sure that you enjoy the view.

    Pack your Bags

    Congratulations! You made it. Nothing left to do but move to paradise and (sigh) get back to work. You may have noticed that I didn’t specifically mention when to ask your boss if you can telecommute from the beach. That’s because you won’t need to tell them. Even the most obtuse boss will know what you’re planning if you do even a couple of the steps discussed above. But don’t make your boss guess what you’re up to. Remember, open communication is one of the keys to making a telecommuting relationship work. Keep your boss in the loop from the beginning and by the time you are ready to pack your bags, your boss will be ready to see you go. In a good way.

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    About the Author: Mark Sincell is a physicist, science writer, and patent agent who lives and works in Honolulu Hawaii, while telecommuting to most of the rest of the world. He chronicles his experience as a telecommuter in paradise in the aptly titled blog A Telecommuter in Paradise. Visit his blog here: