I asked ChatGPT to profile me. It wrote, “once you’ve chosen the uncontrollable thing, you try like hell to control it.”

See, I’ve planned a year in Africa. I booked a 60-day overland drive through Southern Africa. I’m climbing Mt. Kilimanjaro even though I have no hiking experience. I’m traveling through fifteen countries, several non-English speaking ones.

But the irony that Chat is referring to is that I’ve been non-stop messaging it about Mt. Kilimanjaro – how tall is it, what’s the grade, how many miles each day. I’ve booked a driving itinerary that sticks to the main roads. I have an Excel spreadsheet including a dashboard, packing lists, project planner, master planner, budget overview, budget reconciliation, place profiles, among others.

I’ve mapped the route carefully. And I know I’ll change it. Maybe ChatGPT is right…

When I left for DC, I whittled my belongings down to 100 totes. Sell, storage, trash, or take with me. I kept the size 4 pants and my bike, planning for a body comeback with a riding plan.   

When I moved back to Chicago, I narrowed everything down to 31 boxes. I never got to a size 4 so the clothes went to a local shelter. I sold the bike.

Now as I prepare for Africa, everything I own fits in three duffels.  

Last March, I told my boss I was leaving and heading to Africa in 2027.

We planned to tell everyone else later this fall. And while I waited, I started preparations. A move back to Chicago. Flights and lodging booked. Money spent. Every payday, I would look at my spreadsheets. My balances shrinking. Expenses growing.

This fall came sooner than I planned. Now everyone knows. I’m not sure it matters though since my boss already started spending the salary savings. Or maybe it’s because I’ve already spent half of my total budget for the year.

I’d be lying if I said I wasn’t still uncertain if leaving my full-time job for a year of uncertainty was the right path. Ask AI, it can confirm.  

I drove my way around Iceland, camping, hiking, and exploring the famous Ring Road.

I went to Iceland to see if my plan for Africa 2027 was reasonable. I drove my way around Iceland, camping, hiking, and exploring the famous Ring Road. There were successes and there were challenges.

The notes that I share over the next few weeks will share what I learned, what went right, what went wrong, and what’s next.

I rented a storage unit when I left for DC last summer.

In it, I packed the Christmas tree and ornaments. Baby blankets and toddler toys. Pictures that the kids made at daycare. A mop and an empty suitcase. Things I wanted to keep but I didn’t need to take across the country with me.

 But now I’m back in Chicago. The kitchen dishes are in the cupboards, and the bathroom supplies are unpacked. But my clothes, the paintings that I’ve picked up over the last four years, my favorite books, the diploma that the kids had framed for me all need to fit into that same 5x5 unit while I’m gone. These are the things I use to claim a space as my own.

 Now as I’m preparing to leave, I’m wondering does the difference between what I stored then and what I’m storing now even matter?

I’m headed to Iceland at the end of the month.

I rented a car and will camp my way around the outer ring of the country. I’ll sleep in the tent that I paid way too much for. I’ll try to prepare my food rather than paying someone to prepare it for me. Public showers and restrooms. Leaving the comforts of life that I have become so accustomed to behind for a while.

It’s preparation for Africa 2027 and the two-month self-driving trip between Namibia and Botswana I booked. Having too much time between booking and the actual trip means I have too much time for thinking. So I need to make sure I can make it through one week first.

It’s been a while. Three weeks actually. I’ve been gone.

I want to blame it on being busy moving and sure, there is some truth to that. I finally left DC and made it back to Chicago. But I haven’t been moving every day, every night. Maybe I can say work has been busy. It’s the end of the fiscal year and we are trying to get our budget set up. Possibly but work ends at 5 if I’m doing it right. So maybe I’ve just been lost, and I need some time to find myself.

I haven’t found myself but writing this note the other day is one of the first times I have actually felt like writing one of these notes. I’ll hold onto that feeling for a bit as I go look for camping gear for Africa 2027.

The purple tote is filling with things that aren’t clothes.

Towels and washcloths. A blanket and pillow. Binoculars. Plug converters. Notebooks and pens.

I keep wondering whether these are Western conveniences—or staples.

I’m moving back to Chicago in a month.

I’ve been obsessing over the 10 ft moving truck I reserved, calculating every square inch to determine how many of those totes and boxes I could fit. 31.

Fifty-three years can fit into 31 boxes and totes.

I've been listing my belongings on Marketplace.

A bike that was a gift from an ex-boyfriend years ago. Dollars I never spent. An Apple HomePod, bought with gift cards that had no other use.

But yesterday it was a chair and cushion. Brand new. My money.

For the first time, I wondered: Did I give up on DC too quickly?

This isn’t impulsive.

Last week my daughter and I talked about my trip. I tried to explain how I want to keep my itinerary flexible. I’m starting with 90 days. Now I’m planning a year. Maybe I’ll come home in the middle of it. Maybe the whole trip will be a bust. Maybe I’ll stay north of the equator. Maybe I’ll keep the southern region in there.

Planning this trip makes me realize that I’m looking for the sweet spot of spontaneous and impulsive.

I booked the flight.

I told my boss. I sold my car. Today, I’m staring down a closet full of clothes, purses, and shoes.

 Maybe I should have been thinking about leaving my closet.

I open it every few days even if I don’t have any updates. I’ve tried to capture every expense, both at home and in-country while I’m gone. And on paper it works. But I’ve never been good with budgets. Upgraded flights, expensive private tours, and last-minute itinerary changes. The irony that I work as a Director of Finance doesn’t escape me.

I need to leave room for uncertainty. Or is it impulse?

More than thirty countries and I’ve always found English.

Until last winter in West Africa. I took French for many years—grade school, high school, and college. I never became proficient in it. On that West African trip, I was grateful to be part of a tour, so the language barrier stayed in the background. But this place-based inquiry will be different.

 I’ve signed up for French lessons because this trip depends on paying attention.

Last Friday, I told my boss I was leaving. We had discussed it once or twice before. But I don’t think either of us believed I would give up the nice office, the high salary, and the title. Up to now, I’ve been fitting in reading, writing, and thinking wherever I could find time—at night, early in the morning, during work hours.

But that life no longer fits me. So I’m resetting. Some movement, some stillness. My Kindle and iPhone sitting alongside a backpack and notebook.