Workcations Rock: Here are your Do's and Don'ts

My family and I recently wrapped up an eight-week, bicoastal workcation with our families in New York and Los Angeles… and it was seriously awesome. In fact, if I could AirBnB review my summer, it would basically read, “5 stars, will come again.” 

As more companies announce increasingly flexible and hybrid policies, there’s no doubt that workcations are here to stay—and our family is already dreaming up plans for summer 2022.

As you dream up your own workcation — or simply get workcation-curious —  here are few lessons we learned this year (including some things we totally bungled) to make yours a blast:

  1. Communication is essential: Additional or different communication with your stakeholders is sometimes required when you’re not in the regular ole’ (home) office, simply because your environment is different. One of my funniest “communication moments” happened with a brand new client (of course, right?). While on the phone with her I was literally stopped in my tracks by the fact that my in-laws’ aging dog had just had a major accident in the room (yes, I am referring to a #2). Totally thrown off, I told her I was sorry but I needed a minute to deal with this. To be clear: this is something that would literally never happen inside my house because we don’t have a dog. We had a good laugh about this, but since I don’t have a pet, I didn’t have a communication playbook for this kind of disruption. Bottom line: communicate with your clients, colleagues, and stakeholders when necessary because sh*t happens.

  2. Plan your time: My husband and I had grand plans of seeing everybody we know in New York and LA (and to be clear, that is a lot of people). We were going to swing through all the museums, do a ton of hikes, go swimming daily, and hit a bunch of our favorite restaurants… I’d say we did maybe 10% of what was on our list? As we were dreaming up our itinerary, we had forgotten that we had the “work” component and our vacation eyes were bigger than our stomachs. We still had a ton of fun, but we also had a lot of missed activities and connections that we could have made with a bit more planning.

  3. Make enjoying your surroundings a daily event: There were a few busy days in New York and LA when I literally did not leave my makeshift office once...and that is actually the lamest thing ever. The best days were the ones when I jumped in the pool (something I figured out by the time we arrived at our second destination in LA), or took a walk to just soak up my surroundings when I had 25 minutes in between calls. Towards the end, I wised up and started to schedule in that “soak it up time.” For example, when we were at the beach, I’d wake up at 6:00am just to walk along the ocean or sit quietly with my journal in the dunes. It’s easy to get sucked into “another day at work.” But it’s also easy to think about how you want to have fun. Per tip #2: plan your time!  

  4. Carve out actual vacation time: One of the highlights of our trip was carving out so many small vacations inside the bigger workcation: from New York we went to Vermont and the North Fork of Long Island, while in LA we went to the beach for a week in Oxnard. Those trips were a blast… but perhaps my favorite day was just a staycation day I had in LA to enjoy our “base camp.” Once again, per tip #2: get these things on the schedule with advanced notice so you don’t fall victim to to-do-list-drift on your calendar.

  5. Reliable internet is a must: You would think this is so obvious, right? We did too! The prelude to our travels was a quick jaunt to a rental house that had god-awful internet. A workcation day without internet is not a joyous and surprising extra day of vacation: it’s that day you had at the office last year when the helpdesk ignored your ticket for six hours. Workcations quickly become stressful when you’re trading hotspots or taking calls from the car, so take care when determining your technology needs. 

  6. Childcare is vital: Perhaps the thing we put the most effort into building for our workcation was reliable childcare. Much of it worked out, but some did not. The days we had childcare rocked… and the days we didn’t: if Covid has taught us working parents anything it’s that being home with our kids and working is really hard. Being out of our usual surroundings only made it harder.  

Like I said, when it comes to a workcation: “5 stars, will come again” and I can’t wait for our next summer workcation... So where are you heading? Keep me posted and send pics!


Randi Braun is a certified executive coach, consultant, speaker, and the CEO of Something Major. Get in touch with Randi via email or social (below). Copyright 2021. All rights reserved.

Randi Braun