Making A Plan

If you know anything about me, you probably know that I am and have always been an avid planner. I’ve never been one to go with the flow, and have always been partial to having details at least mapped out mentally, if not on paper. 

By the time I was in 6th grade, I knew I wanted music to be a part of my career path (check). At the end of high school, I submitted applications to only colleges in state and kept a seasonal job at Whole Foods Market in my hometown because I thought I was going to marry my high school boyfriend and wanted to stay close (check for planning; I did not marry that boy lol). In college, I dedicated every hour in my planner towards getting something done, whether that was working out in our haunted condo at 5am, going to class, attending ASI board meetings, doing community service with Mu Phi Epsilon, practicing, talking friends down from existential crisis ledges, working for my ABA therapy job, nannying, planning wine & cheese nights (callback to my Whole Foods days), and the list goes on. You name it, and it was probably already in my calendar (check). Since that time, I’ve made moves in my career and still have big ideas and big goals for what the future has in store. I even started a business (y’all, I can’t believe it’s like a legit LLC, what the heck) to plan other people’s plans (double-check).

From August through May, I am a public school teacher for elementary and middle school general music and choir. I’ll be starting my 7th year of teaching this August and truly can’t believe it (the students don’t fail to remind me that I’m old every day). While I love my job and almost my entire personality revolves around being a teacher, there is a big part of me that is envious of those who can travel the world and work remotely. Yes, I have the summers off, but even then we all know that a teacher salary is not really conducive to travel the way I dream of doing it. 

At the start of the COVID lockdown, I found some comfort in drawing outlines of places I’ve always wanted to go: Italy, Greece, Canada, etc. I would make lists of historical landmarks, hotels, activities, workshops or retreats, FOOD. I would never call myself an artist in the fine art realm (that title goes to my brother and my mom), but something about simple lines, highlighters, and washi tape in a notebook or planner really gets me going. These types of plans were merely hopeful manifestations of trips that I would someday get to take. Hence the genesis of this passion project and business! 

Having a plan, to me, is a way in which I have always felt that I can maintain being the main character in my own story, and a way in which I can feel confident about my options, even if the plan takes a different path than expected. Plans give us a glimmer into how our expectations might play out (whoa). While we can’t possibly know or control all of the consequences or outcomes of our life experiences (and shouldn’t try to), it still feels nice to have a foundational idea of what the next step could be. “What if ____, then what?” Part of the reason why I’ve wanted to turn this passion project of planning travel itineraries into a real business is because I want others to be able to dive deep into this main character energy, especially on their vacations and especially if they don’t have a deep-seated need (or let’s be real, desire) to be a planning over-achiever like me. 

You know when you tag your best friends in vacation giveaway posts, or send them incredible photos of dream places you want to travel just hoping that someday it’ll happen? Or maybe you’re the only friend in your lil clique who ever sends out ideas and the plans never come to fruition because everyone (including you) dreads the actual prep-work? Hi, hello! 🙋‍♀️ Let that be my job. I’ll take it from here. Over-achiever, Aries, ENFJ, Enneagram 3 lady, comin atcha. I know not everyone is like me in that planning takes up so much brain capacity. Think having-53-tabs-open-in-your-Chrome-browser kind of brain capacity. It’s just how my brain works best; busy, multi-tasking, and problem-solving. Just fill out the quiz, won’t you? And hey, stay a while! I’m coming up with some more freebie blog posts, digital tools and PDFs, and low cost itineraries that might be of interest to you until you’re ready for a curated trip just for you. And if you’ve made it to the end of this little post here, you’ll be the first to see this attached freebie packing list. You’re welcome. Tell your friends. What kind of posts or tools are you interested in seeing more of??

Thanks for being on this journey with me, y’all. I’m living vicariously through these trips and these projects already. 

Jess

Packing List
$0.00

This is a basic (but ultimate) packing guide if you need help getting everything into your suitcase, whether it’s 3 days before or 3 hours before your flight!

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What I Look For In A Vacation

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Weekend Getaway - Charleston