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Working For Yourself Means Working on Vacation

Updated: Oct 3, 2022


How to Work while on Vacation

If you’re a small business owner like I am, you no longer work a “9 to 5” job, instead you work 24/7. This means taking work with you everywhere you go, yes even on vacation. In fact, this sentence was written just outside of Omaha, Nebraska. I’m a virtual assistant and that means being there for my clients when they need it and making sure that I am meeting those monthly deliverables even when I am "out of office". So, when we were planning our trip to Northern Michigan, a two day drive from Northern Colorado, it was no question that work was coming with me.

I wanted to document my experience and share it with other business owners in hopes of making your lives easier. This is how I turned productivity up to the max when it was needed but still allowed time for down time and much needed relaxation with my family.

I knew I wanted to keep my routine as close to normal as one can while driving cross country. This meant setting aside time to be productive. We discussed how we wanted to tackle the two 9 hour days we had in front of us. I drove in the morning shift, a straight 4 and a half hour drive to Kearney, NE, and saved time after lunch (and a midday nap) to get some work done. My husband was fed and rested and jamming out to our road trip playlist while I shifted to business mode and started working off my phone. I also took this time to take the essential road trip montage videos because obviously.


We really can do almost everything from our phones these days, I still brought my laptop but it was riding safely in the back while I had my feet on the dash and water bottle in hand. I don’t know about y’all but I’ve got the iPhone 10 and I’ve got apps for Honeybook, Loomly, Canva, FB Ads, and Lightroom. Just to name a few of my faves. I was able to work on new content for a client, edit some photos and send an invoice to a newly onboarded client. Cut to the intermission where my husband shouts “There are so many Runzas!” and we digressed somehow the conversation ended on us talking about a friends 2018 wedding and the song “get low” by the Ying Yang twins. I told you that I left room for fun.


By the time we hit Iowa, I was exhausted and ready to get to the hotel and enjoy my evening with my husband. If there is one place to splurge, let it be your accommodations. Be sure to pick a hotel that suits ALL your needs. We needed something that fit our budget but that also had a list of other amenities. On our way to Michigan we stayed overnight in Des Moines at the the Hyatt Place Altoona. The pictures online really didn’t do it justice, the hotel was beautiful, affordable and had everything we needed. There was workspace in our king room so I could log into my laptop comfortably to make some quick website updates, a 24 hour fitness facility so I could go on a quick run before we hit the road at 7am and it was close to an area of town we wanted to explore while we were there! We ended up going to Bass Pro Shops to get a gift for my dads 50th birthday and I gambled for the first time ever at the casino across the street!


When we arrived in Michigan, we opted to stay with family. This was a big money saver but was also super cathartic because it had been over a year since I got some quality time with them. It worked out perfectly because I could enjoy all the comforts of home, keep my schedule and get work done while hanging out on the couch or at the dining room table. I set goals and time limits on my work schedule to ensure I didn't go down some crazy rabbit hole because as we all know, one task always leads to another.


I still woke up, showered and got ready for the day. That was really motivating because I felt prepared to take on the day, not just work, but all the fun things we had planned. I also set aside entire days where I refused to look at anything work related and I had a "no phone at the dinner table" and "no working during family time" policy. I was not about to sacrifice these precious moments just to get another word written or another image edited. There is a lesson in there somewhere, work will always be there in the morning but memories are made in the moment.


It was pretty easy to stay on track while on vacation, easier than you might think. I managed my expectations and set myself up for success by thinking about the accommodations and schedule ahead of time. By setting realistic goals and allotting very specific work hours for myself I avoided that overwhelming feeling and was able to let my worries go and actually enjoy myself.

We saw a lot of amazing things on our cross country journey. And despite the differences in terrain, weather and license plates I noticed one constant on this trip. I not only saw what my family has accomplished, I also saw a lot of cars, trucks and trailers belonging to small, local companies doing the same thing I was doing. Just trying to make it happen. It made me think about all the people out there who don’t think owning a business is possible, or that they could never do it. And that’s just not true. Let me leave you with this, just get started, if you are passionate about something, go out there and do it. There are resources available to you and a community waiting to support you. If you need support or just want a sounding board to talk through your ideas, call me and let's get coffee. You've got this.


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