--- title: How To Make a Working Vacation Work For You – Pressboard description: by One of the perks of working for a start-up is that I can literally work from anywhere. And after my boss wrote about the ultimate flexibility of working image: https://www.pressboardmedia.com/hubfs/Imported_Blog_Media/FullSizeRender-2-1440x925.jpg --- ![](https://www.pressboardmedia.com/hubfs/Imported_Blog_Media/FullSizeRender-2-1440x925.jpg) ![Pressboard](https://www.pressboardmedia.com/hubfs/pb-icon.svg) by [Pressboard](https://www.pressboardmedia.com/magazine/author/pressboard) [January 31, 2017](https://www.pressboardmedia.com/magazine/author/pressboard) # How To Make a Working Vacation Work For You ![](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/66d096a0d382ce19c55c12d4dc1f0ec3-Jul-23-2020-03-54-11-73-PM.jpeg?width=68&height=68&name=66d096a0d382ce19c55c12d4dc1f0ec3-Jul-23-2020-03-54-11-73-PM.jpeg) by One of the perks of working for a start-up is that I can literally work from anywhere. And after my boss wrote about the [ultimate flexibility](http://www.marketingmag.ca/sponsored/7-reasons-you-should-work-for-a-startup-174153) of working at a startup, I decided that it was going to be my mission to prove him right: I was going to work from the beach. In December, the perfect opportunity was presented to me: a week in the Dominican Republic coupled with reliable Internet access. This was my chance. ![giphy-13](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/giphy-13-2.gif?width=450&height=368&name=giphy-13-2.gif) Was it as magical as I thought it was going to be? No. But was it worth it? Yes. Here’s my breakdown on the good, the bad, and well, there wasn’t really any ugly. **The Good** Waking up early to work seemed inconsequential when you were woken by the sun streaming into your master suite with nothing but the ocean in full view. That, coupled with the fact that “working” meant making my way downstairs, setting up shop poolside and sipping on piping hot fresh coffee. ![giphy-8](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/giphy-8-2.gif?width=320&height=160&name=giphy-8-2.gif) The hours I spent working in the mornings were some of the most productive. Knowing that I only had a few hours to work really motivated me to buckle down and get my sh*t done. There was no frivolous internet surfing happening here. Coming back from a pseudo-vacation without having email-anxiety and sky-high piles of work to catch up on was a breath of fresh air. **The Bad** My paranoia about cell phone service (or lack thereof) when we were away from the house during working hours was at an all-time high. *What if there was an advertising emergency?* This also meant that I missed out on experiencing some excursions fully because I was glued to my phone. ![giphy-9](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/giphy-9-2.gif?width=480&height=264&name=giphy-9-2.gif) I couldn’t “work in advance”. With my line of work, if I knew I wasn’t going to be online for too long in the morning, there wasn’t really anything I could do about it the night before. This probably made my vacation mindset suffer a bit. **The Not-So-Ugly** [![picture1](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/Picture1-3.png?width=975&height=975&name=Picture1-3.png)](https://www.pressboardmedia.com/hubfs/Imported_Blog_Media/Picture1-3.png) *Not the worst office views, eh? * Honestly, the first day of my pseudo-vacation (Monday) was the hardest, but as the week rolled on, I really found my groove. For me, the pros of the experience outweighed the cons. And to clarify bit further, I was lucky enough to be travelling with a few entrepreneurs – so the fact that I wasn’t the only one waking up early and clocking some hours on the computer was reassuring, and even a little motivating. That doesn’t mean this work set-up is for everyone. You should only give it a try if you feel you can stay motivated to work with a beach always in sight. If not, maybe try a location that’s less likely to lure you away from what you need to get done. Here are **four tactics** I used to ensure that I had a successful working vacation: ![giphy-11](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/giphy-11-2.gif?width=432&height=250&name=giphy-11-2.gif) Tell your coworkers what your working hours will be while you’re going to be gone. Trust me, they’ll hold you accountable. Wake up around the same time (the consistently clear, blue-sky sunrises help with this!) ![giphy-10](https://www.pressboardmedia.com/hs-fs/hubfs/Imported_Blog_Media/giphy-10-2.gif?width=450&height=255&name=giphy-10-2.gif) Set a “delayed response” out of office. Setting expectations with your clients is key. Treat it like a vacation before you leave. This means, ensure that someone else in your company knows what’s going on with your work and how to help if you’re not able to step in when needed. While it might be a while before I try working from the beach again, I feel very lucky to work for a company like [Pressboard](https://www.pressboardmedia.com/). Working for a start-up can be [hard work](https://www.linkedin.com/pulse/young-urban-professional-seeks-strong-wifi-anita-kapadia?trk=prof-post), but the opportunity to mix work and play is just one of the amazing perks that keeps me going. 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Those cool, young professionals working from coffee shops – probably over caffeinated. *What on earth do they do..* [Load More](https://www.pressboardmedia.com/magazine) ### Get your Content Marketing Fix Sign up to receive tips on storytelling and much more. We promise to respect your inbox.