The Downside of a Dream

After listing their Evansville home and selling most of their possessions in order to begin living abroad in October 2024, Darrell and Penelope Pennington visited 44 cities in 14 countries across Europe before returning home for a visit in December 2025. They embarked on Year Two of their global adventure in January, a trek that started in Mexico and now has taken them into South America. Penelope — who quips she’s “a broad abroad” — shares missives from the road. Read the inaugural column.

People spend a lot of time dreaming — probably not as much as they should, but that is a topic for another column. Daydreaming is the type I’m referring to in this instance: the kind of dreaming that helps you to transcend whatever mundane or maybe even unbearable set of circumstances you’re experiencing and imagine something completely different. Daydreaming can let you develop ideas and plans for the future, or even allow you to eventually right a wrong.

Dreams also can have a downside. I’ve used the phrase “nothing’s 100 percent positive” more times than I can count, so much so that it most likely has lost some of its impact or meaning in my circles of influence. But I believe the sentiment completely. It is an important part of the dream process if the goal ultimately involves moving that dream into some degree of reality.

Darrell and I made the decision to turn our lives upside down in a matter of minutes. We sat at Prime Time Pub & Grill in Newburgh, quickly abandoning our plans for a drink and a movie, and instead hunkered down for a life-altering conversation over enough drinks that we needed to order an Uber home nine hours later. We left the bar as changed people who had come to the conclusion that we were going to travel the world. Now.

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A radically altered version of what we had dreamed about for years as a couple became reality that first Saturday of January 2024. The elation and pure joy of making such a monumental decision soon transformed into “oh, s—” as we set about identifying all the minute details and tasks that would make our dream possible.

Issues that did not have easy answers surfaced quickly. What if one of us died while traveling? A funeral list needed to be made; after some tough calls, only a select few people made that short list. What personal items should we get rid of? When and how to tell the kids, parents, friends, family, and people who depended on us turned into serious analysis of how our actions might negatively impact others. More than a handful of times, we asked ourselves if we were making the right decision. The adventure we had daydreamed about for decades was now a bit of a nightmare from a certain perspective. 

“Nothing’s 100 percent positive,” I reminded myself many times. Dreams are no different. 

This trip has provided so many wonderful upsides, but there is a trade-off. We’ve missed funerals, pet deaths, birthdays, holidays, parties, weddings, and hugs. It’s been difficult at times, of course, but I am still very thankful to have said “Yes!” to this once-in-a-lifetime dream. I’m so glad for that conversation back at Prime Time. Do dreams have downsides? Sure — because nothing’s 100 percent positive. 

Follow the Penningtons on YouTube, TikTok, and Facebook @penelopepennington.

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