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Get Jene' to Italy: Plane, Train, BOOTS

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The title "The Boot by Boot" arrived in my mind & heart almost two decades ago. I finally want to write this book! I am going to hike the entire length of Italy, from as far north in the Dolomites of the Italian Alps to the very bottom of Sicily. I’ll record the whole thing in video and writing, share daily videos, and interview women along the way. When I get back home, with all of that, I’ll write the memoir and tell the story in film. Could you please contribute to the very first, most essential step? The plane tickets to get there.

The plan is to get there in late September, take public transport as close to the northernmost point of Italy as I can get, then start walking south. Hopefully, I can do it in under three months, and I'm learning Italian and a bunch of other stuff to be prepared. But the point is not to plan every second, to step off the edge of my world and see what happens. But I will finish this even if it takes into January! Walking the whole way is going to be a fascinating way to see one of the oldest cultures in the world, and I can't wait to share it with you.

The plan & its rules. You will be sending me to walk between 800 miles to 1000 miles.
  • Fly into a major city, then use public transportation to get as far north as possible
  • Start walking south, aiming for an overall average of 10 miles per day, with some 5-mile days and other 15-mile days.
  • A few times, I will stay in one place for a few days to go see classic Italy things and visit nearby cities. To get to these sites, I may use transportation other than my feet. :)
  • This is a truly "off the edge of the world" kind of project, and though I'm resisting overplanning in order to see what happens, walking the whole way is going to be a fascinating way to see one of the oldest cultures in the world, and I can't wait to share it with you.“

The general breakdown of costs (for 90-100 days...I'll be running a separate fundraiser for the rest soon! I've been told that it's WAY too low for three months of living and exerting over there, but I'm frugal!):
  • $3000 includes all airfare and public transportation
  • $3000 for food, including groceries and meals
  • $6000-7000 for lodging, an average of camping, supercheap monasteries/hostels, and midrange hotels (I'll be carrying a bare-bones bivy sleep system just in case)
  • $1000-2000 for "the sights". I want to bring Italy to you. Not just the inside of the grocery stores or my feet on a trail. Getting access to and knowledge of special explorations like volcanoes, art, history, and interviews often costs the price of a tour or guide or boat.
  • Costs for gear: Boots, backpacking & documentation gear (trying to figure out how to film it all, for example). I'll be uploading regularly for you to my YouTube channel and Facebook/Instagram/TikTok. I'm also working to get some official gear sponsors.
  • $1000? I will be making a movie/show about the trip and sharing large prints at an in-person/online exhibition
***I am researching online and with people who know, but a big part of this is to go even if I don't know. So this breakdown may change, but I'm doing my best....phew!

Follow your heart.” “What would you do if money were no object?” “Don’t give up on your dreams.” What comes to your mind? What is your dream? Since childhood, the dream that has come to my mind is of wearing sturdy boots, a backpack that holds pen and paper, a laptop, versatile clothes, my passport, an unlimited plane ticket, enough money to eat and live…and a camera around my neck.

I have always poured over maps, have wanted to GO, then meet, see, experience, connect, and tell the stories, for travel to be the frame on which my life is built. But for reasons we’ll be talking about in the months before I leave, it has always seemed impossible. Every choice that led me away from my dream seemed absolutely necessary and good. One after the other, they led me to a life full of children, friends, work, and a community, a life for which I’m full of gratitude and love.

But now is the time to choose the dream of my heart. Like older contestants on American Idol who finally go for it, this is me taking my shot. And you all are like the relatives who send in videos of the ones they love singing the songs.

So why Italy? So, one of my quirks as a writer and creator is that if I fall in love with a title that pops up out of my consciousness, it never leaves me. And "The Boot by Boot" arrived almost ten years ago. I thought Italy was bigger than it is, and I was raising my three children, so it stayed inside my mind.

But several things have changed in the last few months (besides the obvious, COVID):
I learned that Italy fits inside California and that planning to walk it in three-ish months isn't crazy. I have accepted that how I am, with this dream, is fine and good and valid, that we need every sort, and thus my sort is worthy, too. People who remind others to look up. People who catalyze action and connection. And finally, I discovered the courage inside myself to do something this big.

During the trip and in these months before it, I want to shine a light on a few things:
  • How there is no lost time in our lives, even when it feels like it. It's just as crucial as how air between layers of clothing keeps us warm.
  • How we have to keep taking back our humanity from the daily expectations from industrialization. And what's more rebellious than to go slow and focus on connection instead of performance? And what's the slowest? Walking.
  • Being a midlife, menopausal woman and seeing the world through that lens. How many more travel medias do we need hosted by older men? I'm here for the rest of us.
  • POTS. Since childhood, I've had this thing where my brain doesn't tell my arteries to pump blood back up from my feet. I get dizzy, and just standing in one place takes way more energy for my body's setup. I want to walk for those who can't, whether it's Postural Orthostatic Tachychardia Syndrome or MS or other debilitating conditions.

I'm ready to go on a pilgrimage to a place where people have been walking to find something inside and outside themselves for thousands of years. Rome just celebrated its 2776th birthday this year! Holy crap! What would it be like to go SLOW, in order to not just “do” Italy, but to get to know Italy?

I hope you'll help me get to this EPIC adventure and join me here and online to share the trail!

Jené is an entrepreneur, author, and speaker. Her memoir, The Oat Project: How I Faced My Fear and Came of Age in One Wild Summer, about how she finally sowed her wild oats, has been called “raw,” “courageous,” and “fearless.” She is working on her first novel, and this second big project, The Boot by Boot, will also become a memoir to inspire.

Though known for her writing, speaking, and idea generation, Jené is an accomplished photographer and founded two just-getting-going online stores, YoniFlower Collections and LowKeyMad, for which she designs all products.

By authentically and joyfully connecting with friends, strangers, and audiences, Jené is challenging the status quo, shifting how we judge “lost” time and life’s worth, and leaping off metaphorical cliffs to learn from risk, inspiring people to say, “I never thought about it that way.”

Jené was raised all over the U.S. as a preacher’s daughter before finally rebelling. She is a single mom of three, a GenXer in midlife, in menopause, has POTS, and is finally becoming who she is.

She lives in Colorado Springs and you can connect with her on Facebook, Instagram, her website, on her blog This Little Light of Mine, and can see her designs in her just-getting-going online stores, YoniFlower Collections and LowKeyMad.


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Jene' Jackson
Colorado Springs, CO

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