As A CEO, I Tried The "Work From Anywhere" Model — Here's What I Learned

While I enjoyed my work-from-anywhere experience, we made several mistakes in planning and execution. But along the way, we discovered how to improve this model for our next attempt. Here are the lessons I learned.


For many, remote and hybrid work have been an overwhelming success. Since COVID-19, the shift to these work models, along with employee expectations, has continued largely unchanged. As increased access to high-speed broadband continues to expand this option for more people in more places, the studies show that we can now work from anywhere.

As a CEO, I had my doubts. Many of my friends had been spending their winters in warm weather, doing "work from anywhere" successfully for years before the pandemic, but I found it hard to imagine being away from the office for so long. My concern wasn't productivity, but losing access to people. But after diving into the experience for myself, I had a change of heart.

The Trip That Changed My Mind

Once everyone started embracing "work from anywhere," my husband and I decided we no longer had to wait for retirement to travel. We planned to go away for a month and found a nice cottage on the water in Pensacola, Florida. Warm but not hot, the weather was like a typical Minnesota spring day—but in winter.

While we were there, my father-in-law and my kids, along with my new grandbaby, came to spend a few days with us. I learned that an extended period of time together at a vacation spot with adult children, grandchildren and/or parents is so much more fulfilling than spending a few hours with them for an afternoon visit or even a day-long holiday gathering. Vacation time gives you an opportunity to be around each other long enough to get closer and talk about more than superficial things. Watching the baby explore while sitting with my laptop at the water's edge in 60-degree weather in February, I thought, "Working from anywhere couldn't get any better."

Actually, It Could Have Been Better

While I enjoyed my work-from-anywhere experience, we made several mistakes in planning and execution. But along the way, we discovered how to improve this model for our next attempt. Here are the lessons I learned:

1. High-speed broadband is a must. When you're searching for a place to stay, whether a hotel or private residence, look into their internet connection before you book and make sure they have the speeds you need to do your job. Not only did the internet at the cottage work as expected, but to our delight, it was fiber, which made doing our work a seamless experience. Without high-quality internet, however, you won't be able to do much work at all.

2. Consider the space you need to be productive and healthy, including the workspace you need to work well. Our cottage had a kitchen table, a picnic table and an Adirondack chair, but it lacked what I needed to spend extended time sitting in front of a computer. At the end of the trip, I went home sore. It took time, physical therapy, a massage and a really nice hot tub to feel fully recovered. With my history of back issues, I realized that an appropriate office or workspace must be a top priority for working from anywhere.

3. Avoid overpacking, but bring everything you need to be productive. We brought so many clothes, but not all the tools we needed to make working from anywhere efficient. My husband's setup was quite comical: a semi-circle of storage tubs with a half dozen different computers balanced on top while he sat in the center. Instead of packing what you need to play, remember to pack what you need to work.

4. Start small. Don't make your first excursion traveling across the ocean for three months. Even one month was too much time away for our comfort this first time. Start with a shorter trip close enough to the office to return if you need to but far enough away that you can enjoy the distance.

5. Give yourself flexibility by making sure you can return to work if the situation demands it. Both my husband and I had to fly back to Minnesota in the middle of our work-from-anywhere experiment. My husband's visit was planned, but mine was not. Make sure you are able to change your plans if necessary.

6. Carve out enough vacation time for yourself. Even with a month, we didn't have enough time off. We were so committed to working from anywhere that we ended up mostly working on our vacation. Don't forget to schedule time to enjoy it.

Experience Is The Best Teacher

Before my trip, I wanted my company to prioritize working from the office and offer the opportunity to work from anywhere where appropriate, and I struggled with the idea that my workforce wanted the opposite. Now, I've started accepting the work-from-anywhere model, and I'm glad for the opportunities it gives people to rekindle relationships and explore. Even when far away from the office, I discovered I could still reach my people and get the speed I needed in most cases. Give the work-from-anywhere model a chance and you'll likely find that it can work for your company in one form or another.

Of course, the office still has an important role to play, and not all positions can realistically work from anywhere. I'm committed to the concept and see the benefits, but remote and hybrid options should always have management approval. For many positions, however, offering some form of work-from-anywhere flexibility can be a nice perk to draw talent to your team.

While working from anywhere is not for everyone or every job, with the widespread adoption of hybrid work models and continuing improvements in broadband, we have more opportunities than ever to do it well. If you're struggling with the idea of accepting this for your workforce, try out a work-from-anywhere experience for yourself and see what happens. You may be surprised. Mistakes are bound to happen the first time, but each time you try, the more prepared you'll be to do it better the next time.

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