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Heading on vacay!

Taking a little time off– back in a few weeks!

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Hi friend, 

I’m going on vacation next week!

I’ve done an absolute shit-ton of traveling since leaving NYC a decade ago, most of it by myself, but I never took an actual “vacation” until my 33rd birthday, when I spent a magical week in Hawaii with my mom. 

I say that was my first vacation because it was the first time I actually took the entire week off work! I had always brought my laptop and maintained a more or less regular work schedule for all my trips and travel before then, so while I still got to see and experience cool stuff, that stuff was always scheduled around my full time work. 

In Hawaii, I didn’t even bring my laptop—lest I be tempted to work lol—and I actually planned a whole itinerary (even booking things in advance, which I never do!) to make the most of our time there. 

I’m not gonna lie, that trip was awesome. (Here’s a few highlights!)

Highlights from Jessi's trip to Hawaii

Because I wasn’t working, we got to see and do so many cool things there, and the natural topography of Hawaii is truly unparalleled in its beauty; I’ve never seen anything like it. 

But the real treasure of the trip for me was the fact that I got to have a special one-on-one adventure with my mom. She had just found out she has the gene for FTD (a genetic type of early onset dementia), and we were making memories, goddamn it.

That trip helped me finally embrace the idea that vacations are good, and working all time is bad… even when you can work from anywhere. 

Anyway, my mom is thankfully still not showing symptoms (thank you everyone for your support every time I talk about this in my writing!), so a few years ago the two of us and my younger brother Jason went to Greece to have another adventure!

It was, again, an incredible trip, and I’m very grateful to be able to cherish those memories we made forever. 

Photos from Jessi's trip to Greece

But I actually have two brothers, and we’ve been trying to figure out a way for all three of us to do a trip together with my mom for years! (My older brother Ben has kids and works as a personal trainer, so… ya know, he’s busy.)

Anyway, it’s finally happening next week— the four of us finally got our shit together (and our passports lol) and we’re heading to Tulum, Mexico!!

Fun fact: when I was researching ideas for this trip months ago, I was browsing travel blogs with the TV on in the background, and getting excited reading about how Tulum is both affordable and beautiful, when I looked up and realized the episode of The Bachelor that was on was actually set in Tulum! 

The couple was in a sunlit partial cave about to jump into a cenote, which are these naturally occurring pools of underground water that Tulum is known for, and it was stunning. Now, I’m not usually a “signs” person, but I’m not about to argue with the universe when it goes out of its way like that. So that was it, I decided: we’re going to Tulum!

I’m so excited to finally get to have an adventure with the four of us, and I’ll be taking next week completely off of work so I can focus on making those damn memories. 

Then I’m actually flying straight from Tulum with my family to Portland for a friend’s wedding— eek! 

Admittedly, the scheduling isn’t ideal. I definitely prefer to have lots of down time and alone time after a big social trip like this, but it couldn’t be helped… soo I’ll just have to mask up, take my vitamins, and try to sleep on the plane!

The logistically tricky part of this story is going to be packing– how the hell  pack one suitcase for both a week in Tulum and a week in Portland, especially when the Portland trip needs wedding attire?! The differences in weather alone will require some creativity, but how do I pack for beach days, cave-diving, mountain hiking, and fancy-but-chilly dinners? 

All I can say is that it’s a good thing I like a challenge! I’ll just have to pack some all purpose adventure clothes, like my Adidas shorts and backpack, and of course, my trusty walking sandals.

Anywayyyy next week there won’t be a Tuesday email for the next two weeks, but I’ll be back June 25th!

Hope you make some memories of your own this week!


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