Inspired by: Harnessing our own powers of creativity with Jenn Overstreet

The first interview for my new series, Inspired by, where I share the stories of inspiring women in my life. 

Jenn Overstreet grew up in rural Pennsylvania (rural as in, Amish country) but spent her favorite, most formative years living in the beach town of Rehoboth, Delaware. Almost six years ago, though, she made the decision to move to Italy—another place that shaped her and gave her the confidence to continue following her dreams and her intuition. Italy is a feast for the senses, and Jenn fell in love with it, never deterred by the chaos of Rome or the Italian bureaucracy, which seems to discourage even the toughest of expats. 

I met Jenn through Instagram, and we quickly and easily connected over our love of Rome and our outlook on life (we’re both Pisces and hugely creative). We officially met in the summer of 2021, when we grabbed a caffè freddo at Bar La Licata and then took a sweaty walk through Monti (Roman summers, eh?), Jenn pointing out her first apartment in Rome and showing me a secret park I had never seen before. 

As we walked and talked during that summer afternoon, Jenn shared so much information with me about how she came to live in Rome and the secrets to staying there. Information that, quite often, is gatekept by other expats for varying reasons. I remember being in awe of how she and her husband James had made their life in Italy, and how peaceful it seemed (despite the aforementioned bureaucracy). 

Jenn and I split ways after a couple of hours, she was headed south to Sicily for the rest of the summer while I remained in Rome, not yet accustomed to the great exodus caused by the unbearable heat in the eternal city during the summer. 

We stayed in touch and met again in Rome several times, whenever we could, and I now consider Jenn one of my closest friends. It only felt right to have her be my first guest for this new series since she’s a woman who inspires me and pushes me every day, to be the best version of myself and not to cut myself short when going after what I want in life. After five years teaching in Rome, she and her husband James moved down to Puglia to focus on their coaching businesses full-time and finally get the Italian citizenship they had been working on (through James’ heritage) since 2015. Now they’re headed north to Milan for an exciting new adventure, discovering another part of Italy and getting back to the teacher life at a new school. 

I’ve seen firsthand the power Jenn’s coaching has, on myself and other women. A yoga teacher by training and at heart, she has helped me work through problems on and off the mat. I’m so excited to share more of her story with you all today, and was so inspired by the conversation we had. 

With each interview, I plan to ask the same series of questions to get to know the interviewee better and share a bit more of their life and perspective and how they make their life art. So without further ado, here’s what Jenn had to say. 

What inspires you?

The first thing that came to mind was being by the water, being by the sea, or then if it’s not by the sea then it’s in the shower or a swimming pool, like near the water element (it’s probably the Pisces vibes). And also in the sun, out for a walk in the sun, in the same way. I think it happens, my moments of inspiration happen in terms of feeling creative, feeling inspired, when I lessen technology, like when I’m actively creating more than I’m consuming, and when I am just living life, not sitting down trying to be like, I have to be inspired right now. Like out for a walk in the streets of Rome…or walking on the beach or in a cafe just experiencing little moments of life. 

Where are you most yourself?

When I’m at home with James, or with James in general.

What’s a ritual you do every day?

You probably know them, I have many rituals. But definitely, I take my greens religiously, every single day, even when I’m traveling I take my greens and I’ve done that for two years. And *knock on wood* the only sickness I’ve had since I’ve done that is Covid. So that’s one of my most important rituals because it keeps me healthy so I can do all the other things, it adds to my health.

I also make sure I go to bed and wake up at almost the same time every single day, even on the weekends…what I have found doing that is that my sleep efficiency has gotten better. I need less sleep because my body isn’t going back and forth between 6 hours, 9.5 hours, 7.5 hours. Now I get a consistent 7 hours and it’s perfect.

I don’t get on my phone in the morning, that’s probably my most important ritual that I’ve been doing for six months now…When you first wake up there’s 3 waves that your brain goes through…until it gets into that active mode and that’s why in meditation you can manifest stuff and you visualize because your brain goes into that same almost hypnotic, very relaxed state that’s the same as when you’re falling asleep and it’s the same as when you’re waking up. So when you get on your phone first thing and start doing stuff on your phone when your brain is still in that hypnotic phase, it needs to transition through all of those stages and if you skip that relaxed state by getting on your phone, it skips over that and it goes right into your active mode which is what triggers the fight or flight, which is what causes stress.

What are you reading?

The A Court of Thorns and Roses series. 

Who is someone who inspires you?

Okay, this is going to sound stupid maybe but myself. I like to think of myself as my own greatest source of inspiration and [I like] when I can pull from other things and other people and the way that they live their life or whatever, but ultimately I have really been working on not outsourcing my power to others and allowing myself to be my own greatest source of inspiration and celebrating and acknowledging that within myself. 

What’s a dream or goal that you’ve recently achieved?

Definitely James getting Italian citizenship, even though I don’t have it yet and I have to apply, but we have been working on it since 2015. So that really shows teamwork, because we both really worked together to find the documents, [also] patience, trust, and not giving up. Constantly finding new or different ways, like if you get told no in one way then that doesn’t mean no for good, you have to find a different way, which is what we did. 

What’s one of your current dreams?

One of my current dreams is one day to have a beautiful Pugliese villa overlooking the sea with an inground pool. It’s almost hard now because of Covid to plan or dream so far into the future, everything feels…where I used to have it all mapped out, now it’s like let’s just see what happens because who knows…It’s almost freeing to be like, I don’t know, let’s see what happens. 

What is one of your favorite places on earth?

I would say Rehoboth, the beach at Rehoboth. Just because it was such a pivotal time in my life, it was like my early 20’s, it’s where I met James, it’s where I met some of my friends who I don’t even consider friends they’re like family…so probably Rehoboth. Also, it was the first place where I did realize that dream of living at the beach that I wanted since I was little. 

If you could be anywhere in the world, where would you be?

Right now, where I’m at. 

What do you do to make every day artful or special?

Definitely catching the sunrise or sunset, for sure, as much as possible. But also just being present, focusing on the little moments. You should see my seashell collection. And I always think too like even if they’re broken I still take them because they’re still beautiful even if they have a crack or there’s a piece missing. 

How to contact or follow you?

Follow Jenn on Instagram and TikTok.

I hope you all enjoyed this first edition of the new series. I’m so grateful to Jenn for the time and the thoughtful interview (and her friendship)! I left feeling inspired and I hope you do too. xx