Traveling For Work and Traveling While You Work Are Not the Same

Quote of the week:

"Only the conspiracy theorists know what's going on these days."

- A Friend

Hey there {{contact.first_name}},

Hello from the Caribbean Sea, just off the coast of Costa Rica!

My husband Tim and I are on deck 4 of the Carnival Legend as I write this. We sailed out Galveston, Texas on Monday and will return there late next week. See below for my thoughts about working on vacation. I think you may be surprised.

Nevertheless, I am keeping my newsletter brief this week because it is late, tomorrow I visit Costa Rica for the first time in my life, and Tim is already snoring.

I am responding intermittently to email during my travels and I return to my home office on Monday, March 30th. I do not have access to my phone until I return, so please email if you need anything.

All my best,
-- Kris 🌱🫶

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I receive a myriad of reactions when people discover that I am working over the course of a ten day cruise. None of them have been positive… at least, not at first.

The most common reaction is strongly negative, and an implication that some horrible system or person is forcing me to work when I’m trying to take a vacation. No doubt there are plenty of individuals in this situation, but I smile and let it be known that I am not one of them. This is a choice that I am making. I am self-employed and no one is pressuring me to do this.

The next most frequent reaction or response is sympathy that the poor entrepreneur can’t even take a vacation without having to keep the business afloat. This reaction also seems to occasionally come with a measure of contempt, as if I would be better served to get a “real job” and then I wouldn't have to behave so silly as to work while I am on vacation. My communication is the same as in the first situation: I smile and let it be known that this is a choice I am making, and this isn’t a stress response to trying to “save” my business.

My clients and customers are often apologetic that I “have” to work on their files or businesses while I am away. This does cause me some pain because I don’t ever want them to feel that they are somehow responsible. If I wanted back-up, I have it, or I have the opportunity to arrange for it.

Allow me to state very clearly that I believe strongly in the importance of disconnecting, taking time off, and preserving my capital of self. I have been accused many times of being a workaholic, and I don’t deny it. But I also am very intentional about making time for physical wellness, creativity, and spending time with people who are important to me. I’m sure that I do not execute this balance perfectly. I am also pretty confident that I am not permitting workaholism to have negative impacts on my life or my relationships, which is fairly definitive of most “aholisms.”

That said, I have the privilege of being able to work from just about anywhere that offers reliable internet service. I don’t have to work on a cruise; I get to be on a cruise while I work. I have worked during previous travels, including cruises and camping trips. I recently read:

The Global Entrepreneurship Monitor (GEM) 2024/2025 report indicates that solopreneurship is experiencing a worldwide surge, with 50% of all entrepreneurs operating as solo entities as of 2024. Among these solopreneurs, 76% conduct their work remotely at least part-time.

The privilege of working from almost anywhere is one of the many causing this worldwide surge. It is one of the reasons I chose and delight in the entrepreneur life. I share this with you not to brag that I am on a ten day cruise, but to encourage you to live your life boldly, on your own terms, with intention. Do protect your capital of self. Also, travel while you work, if that’s what you want to do. It’s not the same as travelling for work; it is substantially more satisfying.

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This has been newsletter issue 2611, published on 20260320
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Kristin Fleming, NMLS 804170
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