How Dreaming Turned into Planning

Today is day 1 of approximately 210.  

What am I feeling right now? Excited, a bit nervous, and carrying a two-day hangover from ringing in the new year while sitting here three hours into a thirteen-hour flight. 

So let’s talk about the planning.  

How do you physically and mentally prepare to leave home for seven months? Where do you even start when it comes to budgeting, logistics, routes, and the reality of being gone for that long?  

For me, this dream became real through a simple conversation with a friend. One of those moments where someone reminds you that life is short and the only thing standing between dreaming and doing is action.  

Before spreadsheets. Before flight alerts. Before budgets.  I had to answer one thing. 

Why.  

What was I actually passionate about? What did I want to learn, not just see, through this experience? The logistics came later.

First, I let myself build the dream itinerary. Northern lights in Iceland. Hiking Machu Picchu. Scuba diving the Great Barrier Reef. No limits. No practicality. Just curiosity. 

Eventually, a pattern emerged. I wasn’t chasing countries for the sake of it. I was pulled toward history and natural beauty, places that have endured the test of time, places that shaped civilizations and the world as we know it.

Letting that be my guide made decisions easier. It also meant crossing a lot of destinations off my list without regret.  

Naturally, I found myself orbiting the world’s great wonders.  

September 2025 – Building the Macro Itinerary   

Once the why was clear, I zoomed out.  

I started researching the Seven Wonders of the World and the natural wonders of the world, (which frustratingly depends on who you ask), alongside the most historically significant places on Earth. Some articles blurred together. Others stopped me in my tracks and inspired me. Many became reference points.

Long story short, it was hours and hours of reading, watching videos, and talking to Esmerelda, what I call my ChatGPT.  

From there, planning shifted from fantasy to strategy.  

Weather became non-negotiable. I was determined to only pack for one season, so climate dictated everything. Monsoon patterns. Extreme heat. Winter conditions. These details mattered.  

I also had to think seriously about safety, especially as a woman traveling solo. Not in a fearful way, but in a prepared one. Which regions made sense back-to-back? Where would I feel confident navigating alone, and where would I slow down, choose guided experiences, or rely more heavily on structure?  

I started to see a flow, geographically and mentally. I wanted the journey to move with time zones, not against them. Continents unfolding naturally instead of bouncing back and forth. Less exhaustion. More presence and precision.  

And finally, people.

This trip isn’t just about places. It is about crossing paths. Friends and family, I already know scattered across the world. Strangers I haven’t met yet but somehow feel part of the story already. Leaving space in the itinerary for those intersections mattered as much as any landmark.  

That’s when the dream stopped floating and started taking shape. My macro itinerary began to form naturally. I shared it with my closest friends and family to get their input and recommendations, which helped me craft a strategic and beautiful plan at the highest level. 

I had countries. Rough estimates on how long I wanted to stay in each. And the months that made sense to visit.  

October 2025 – Booking My First Leg  

As someone who has never done the hostel thing before, leaving everything up in the air was not in my nature and if you know me well, you know that also goes against every fiber of my being.  

I wanted a clear path, at least at first. Something that felt within my control. Mentally, it felt like a guarantee that things would get off to a good start. It was also a way to test my financial forecast and see how accurate it actually was for the first few destinations. Surprisingly, it was not that far off.  

I started by getting really detailed, probably too detailed, with my first few countries. I created meso level itineraries that included the cities I would visit, must see landmarks and experiences, transportation plans, accommodations, and even the days and weeks I would need to get my roots done.

Completely serious. As a blonde currently living as a brunette, seven months is way too long to go without maintenance.  

I was nervous booking my first hostels. I wasn’t sure I had done enough research. I'm still not sure. But it became easier with every city. I grew more confident in my choices and better at trusting my gut. Once I started booking, it was probably the easiest part of this entire planning process.  

November – December 2025 – Clothes, Logistics, and All Things Prep  

November and December were when things got real. Travel visas. Global eSIM. Canadian consulate locations. Medical requirements. And most importantly, what the hell I was going to wear for seven months and how I was getting everything into a backpack that I could actually carry.  

Luckily, it's easy to find most of that in 5 minutes online with the help of Esmerelda. As I collected information, I stored it in my master excel workbook which made me feel organized. Eventually my list started to get smaller and smaller.

I definitely waited too long to apply for my first travel visa to Kenya – it came at 4:50AM and my flight out of Toronto was at 10:30AM. So yeah, don't fuck around with visas. So much wasted time being stressed about if I would be able to make it onto my first flight.  

Bottom line, anything I wasn't sure about, I researched, from September to December my 9-5 was my actual job and my 5-9 was planning my trip.  

My First Lesson Along the Way

The path and the plan will change. They already have in the days leading up to my departure. I am letting happiness and curiosity take the lead, maybe even some flexibility. Loosening the reins feels really good.