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Lisa Dailey

Square Up

April 7, 2022
4 PM PDT | 5 PM MDT | 6 PM CDT | 7 PM EDT

Square Up is the story of my family’s journey around the world as well as my own personal journey through grief.

Though I don’t mention it in the book, the idea for a trip around the world came about when my husband and I took our 8- and 10-year-old children to New Zealand for a two-week vacation. The trip proved to be educational, adventurous, exciting, and best of all, our young boys turned out to be amazing travelers. We set our sights on a year-long world trip in 2015. But the intervening years would prove to be some of the hardest of my life. In quick succession, I lost my father, my maternal grandfather, and great grandmother. Most devastating, my twenty-three-year-old brother died of a drug overdose just as he was gaining a foothold in sobriety. Within months my mother was diagnosed with aggressive melanoma. We then said goodbye to my father-in-law, my sixteen-year-old cousin who committed suicide, and finally my mother, who finally succumbed to the cancer. The final tally: 7 deaths in 5 years.

My life was turned upside down as I struggled just to function from day to day. It’s safe to say that I longed to escape my life and seek the hidden corners of the world where grief couldn’t find me. I was going through the motions of life, but only half present. And then, at the lowest point in my life, when I was begging for the universe to give me a break, it did just that. the pieces began to fall into place for our dream of a trip around the world. But embracing the unknown, even as I longed for this escape, was easier said than done.

On Writing

I’ve had the dream of writing a book since I was very young. And I’ve had an idea about the story I wanted to write for at least 25 years that has nothing to do with travel. But, during the trip, I blogged about each location we visited and when we returned home, I considered taking all of those posts and putting them into a book, an idea supported by friends and family. So I put them all together and it was the most boring … and then we did this, and then we went here, and then we saw this … story ever! The epitome of telling.

About the same time, I found Cami Ostman and The Narrative Project, a nine-month program designed to help writers get their books done. I learned about storytelling and dialogue and scene and openings and closings and, most importantly, that my book was missing the human element, the story behind the story … the so what part of the story. So, I wove my personal story in, reflected on what the trip meant in my personal journey, the grief I was feeling, and how I processed that along the way. I got a great first draft after those first nine months, then took a follow-up six-month class through TNP to refine the story even more and came away with a second draft. I had been involved in critique groups all along the way and thought once I was through with the final critique of my book I was done. But something was nagging at me that it needed another look. So I sent it to a developmental editor who returned it with a 50 page memo on things I should look at. While I wasn’t completely shocked, I didn’t want to go through it again, so I put it away for another nine months. Only then was I ready to go through and tackle the notes from the editor—review all the dialogue, openings and closings, cut the last two chapters, and rework the ending. And even after that, I sent it through my critique group one final time.


I am not even sure I realized what I was learning as we traveled, but through the process of coming home and digesting it, one chapter at a time, I was able to see that I was, in fact, able to link our adventures to healing. I got to see how other cultures healed from traumas and in some cases how death is looked at from another culture’s perspective. I started the trip filled with anxiety and fear and reeling from grief but ended knowing I was going to be alright. I also learned the power of giving yourself time to grieve.


  • Giving yourself time to grieve
  • Stepping out of your comfort zone
  • Square up and the multiple meanings
  • Long-term travel with only a backpack
  • Traveling with kids

Lisa Dailey is an avid traveler and writer. In her adventures abroad, she’s unearthed new ways of looking at her life through her discoveries in remote corners of the world. She is currently working on a recipe anthology all about soup as well as her first work of fiction—a family saga set in present-day Montana with an underlying theme about the alarming rate of disappearance of Native Americans. Lisa now makes her home by the ocean in Bellingham, Washington, but returns to hometown in Montana every summer for a healthy dose of mountains and Big Sky. Lisa is the owner of Wayfaring Writers, Silent Sidekick, and Sidekick Press where she helps guide authors through their writing, technology, and publishing journeys.

Social Media links:

Author website: https://lisa-dailey.com
Travel blog: https://northwestrambles.com
Sidekick Press: https://sidekickpress.com
Silent Sidekick: https://silentsidekick.com
Wayfaring Writers: https://wayfaringwriters.com

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