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  • Kelly Gilfillan

Journey of a Lifetime


My name is Kelly Gilfillan. I am writing to you from a recreational sailing vessel in Mexico waters on November 1. I’m on a journey that actually began in 2009 that led to my retirement on October 8, 2022. My heart needed to travel which led to early retirement and this sailing journey with friends is part of the plan to see more of the world.


I’ll share with you a bit about our business, Home Page Media Group. My business partner, Susan Leathers, and I started an online news publishing business serving the community of Brentwood, TN over 13 years ago. We expanded to three sites before Susan

exited the business in 2014. From that point, we expanded to a total of eight sites.


In 2017, a big change happened in my life and my marriage of 30 years was ending. Of course, this one change would affect many aspects of my life. The constants were there, deep friendships, the love of my children, the support of my family, but I was shaken to the core about what was next for me. Because of this life shift, I decided to hike the Camino de Santiago in Spain, a 500-mile pilgrimage. I had a friend who had hiked the Camino and I knew how it had affected his life. It was with fervent hope for my new yet-unimagined future that I began to train.


That Camino journey began with the decision, grew with the training and became a reality on April 29, 2018 when I left Nashville. My three daughters spent the weekend with me leading up to my departure, helped me pack and repack and saw me off at the airport with sweet gifts to encourage me along the way. I was not afraid. I somehow knew that I was where I was supposed to be and that the path ahead had been prepared for me.


The Camino was a very personal journey filling 7 weeks with challenges, joys, tears, laughter and rebirth. What I learned on this journey was how simple life can be and you have a choice in how you want to live. Each day, you rise with the sun, eat a simple breakfast, walk for a few hours, eat again, walk, eat, walk, eat and then you sleep. The next day you do it all again.

(Check out the organization Kelly and friends started to give back to the people along the way who made the 7 weeks possible at the end of her post.)


Decisions for great change are not quick and easy to enact - it’s been 3.5 years that my life has been unfurling. When I sold the company, I committed to stay for three years and continue to take the Home Pages forward. This was a gift because it showed me the runway and gave me a timeline with which to plan.


So what’s happened since then?


One idea that might be controversial among you Type A planners like myself is that my plans were made to get me started but not necessarily to follow. Having that checklist provided me courage somehow to take steps forward, but it was what happened along the way that actually guided me to the next plan. What I hope to impart is don’t feel like just because you have Plan A that it is your only option. Plan A is only there to lead to Plan B - and this is so because you just can’t see yet what is out there for you.


The pandemic opened my heart to think about how my life might be full of travel and adventure. I started dreaming of what that would look like. I was blessed to have my supportive family to talk through the options and see what it would take to make it happen. A good financial planner makes all the difference and I think many women don’t take advantage of this resource. If you don’t know someone, ask a friend for a recommendation.


I might actually be on Plan X by now with all the changes in my life. But this journey of late has been completely about following my heart and soul. Yes, I have retired but it is hard to imagine not working again. We will see where this plan of traveling for 15 months leads to me.


This is my time and I very intentionally walked toward this moment. The kids are grown, healthy, happy, employed and off mom’s payroll. My obligations in the business world are completed. My grandchildren have not arrived yet (looking forward to that). So here I sit in Mexico, looking at the ocean, drinking a Cerveza.


What is next for you?

  • What would you do if you had no obligations?

  • Is work something you love to do or need to do?

  • What, if anything, could bring more joy to your life?

Think deeply about where you want to be next year, in three years and in five.


I encourage you to think about your path and where you might go next. Live in the moment but dream for the future.


Kelly Gilfillan along with her Camino friends created Camino for Good. Initially, the good that they could do through their For Good Mission was obvious to them. "Facing a halt in travel amidst the pandemic, the selfless albergue owners who provide homes to pilgrims asking for little in return, suddenly found themselves in dire situations. For the first year of our business operations, we committed to giving 75% of our net income to albergue owners to help cover basic expenses, like rent and electricity, just long enough to stay afloat until the Camino reopened. We are proud and so thankful to say that we were able to give away a total of over $74,000 USD to 24 albergues to achieve just that. " Check out Camino for Good

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