Meet Jessika: Jewish Leadership Coach of the Week

by Rachel Kriegsman / April 13, 2021

Jessika Portney has called the likes of Maryland and Italy home, but lately it’s her neighborhood in Mt Pleasant that she loves the most. On a typical weekend, you might find Jessika venturing into Rock Creek Park for a picnic with friends or exploring the city by bike. When life gave her lemons at the start of the pandemic last year, she put her passion for leadership to work and created her own leadership coaching business, Journey On. Read our 1:1 interview to learn more about Jessika, her favorite coffee spot in DC, and her biggest takeaways from the past year.

Rachel: What brought you to DC and what made you stay?

Jessika: I am a local girl, I grew up in Baltimore – Pikesville, more specifically. I thought Baltimore was a great place to grow up, but I didn’t necessarily want to live there. As an adult, I wanted something a little bit farther away from home. I went to the University of Maryland College Park, and I felt like that’s where I first got to know DC. I’d come in to visit the city and eat at good restaurants and participate in different formals and events with my sorority. After college, I moved to Italy and lived there for a little while and eventually landed back in DC. If there’s anywhere that I would want to be on the East Coast, it’s definitely DC. 

It’s been six years now since my last stint away, and I’ve found a partner and a neighborhood that I love. I live in Mount Pleasant, which is my favorite. It’s actually the only neighborhood that I’ve ever lived in. I’ve moved away and always come back here. And so I felt like I’ve really been able to settle this time around. But for those who have lived abroad, I think they can relate to the idea that the grass is always greener. You know, there’s always something that you miss about your other world.

Rachel: Yes, definitely relatable. So, I hear you have a coaching business, tell me more about that and how you got into it?

Jessika: So, March 15 – in my mind that is the day that DC shut down and for those of us who were in an office all got sent home. I had been working at the Brookings Institution for a couple of years at that point, and was running their leadership programs. I’d spent about the entirety of my career working in some shape or form within the space of leadership development. I had worked in international education and international development in partnership with the State Department and USAID, and then I had the incredible opportunity of getting this role at the Brookings Institution in 2017, which is where I had the opportunity to move from that international lens into more of a domestic lens and support Federal leaders here in the US. 

Oftentimes when folks think of the government, they think of politicians or people who work on Capitol Hill, which is absolutely important work, but there are so many people who work in the Executive branch, that make our government run day-to-day and live through administration changes and so much more during their career-long service. They are very much the backbone of what makes this country run. Getting to step into the role of providing leadership development support for them was awesome. 

It’s also where I got to experience building coaching into the programs that I ran as well as having my own executive coach. So it was my first time not only seeing the impact that coaching had on the participants, but also experiencing that impact firsthand, for myself. 

I had been thinking about going into coaching for probably about a year when the pandemic hit. Unfortunately, there were some layoffs at Brookings, and myself and a few of my colleagues were let go. And I really had to kind of take a step back and think about what my next steps were going to be. I found an intensive summer coaching program that fit well into my philosophy, which is grounded in positive psychology and resilience and courage. As I was reflecting on my values, what was important to me, and what I wanted my life to look like, I realized that I didn’t necessarily need to go back and work for a larger institution, I could go out on my own and start my own company that would allow me to live my values on a daily basis, and get to do meaningful work in the way that I want to do that work every day. 

This decision has been a COVID pivot, as I know, it has been for many. And it’s been a really, really challenging and fun year of figuring out what that looks like, as I created Journey On.

Rachel: That’s amazing. You really made lemonade out of lemons and went for it and now you have your own business.

Jessika: Thanks for saying that because if you had asked me a year ago, if I ever thought I would open my own business, I would have told you that don’t have the guts. I had lots and lots of excuses. But sometimes it really takes those lemons to push you and really think about what’s possible from a point of discomfort.

Rachel: If people are looking to navigate these difficult times we’re living through or just looking for a leadership coach of their own, how can they find you? 

Jessika: First, I just want to say that you don’t have to be a leader of others to be a leader of yourself. And I think figuring out what that means to you has been really challenging for everyone this year, especially women. 

A lot of people are re-examining what they want their work to look like, and the value of their work and how that shows up, and how they find balance with work and their personal lives. Encouraging women at any stage to have the space with someone to intentionally think through that and find support for that, I think is fundamental at any time, but specifically during a global crisis. 

Rachel: Describe your dream day in the DMV from start to finish.

Jessika: My dream day absolutely involves a picnic in Rock Creek Park. I’m lucky enough to live just steps away from the park and try to get out there at least a few times a week for a walk. And there are so many beautiful parts of that park that I feel like are little hidden gems. Some of my favorite memories are just laying out there with a picnic whether it be a Shabbat dinner or a brunch where everybody brings their own snacks and hangs out and talks and everybody is welcome. 

I would say that that’s definitely a key part of one of my, of my favorite my dream day in the city. I also have been really enjoying the electric Jump bikes – I have had so much fun riding those electric bikes around the city and seeing a lot more of the city. So, I think there definitely would be some kind of fun bike ride around the city on one of those electric bikes as well.

Rachel: What do you do to relax or for fun at the end of a long week? 

Jessika: I’d go to Rock Creek Park, as you know, and get out in nature. One of my favorite things about DC is how green it is. I love to go on walks or have Shabbat dinner at the end of the week with girlfriends. We have been meeting in different parks – Malcolm X Park, Walter Pierce Park, Kalorama Park – during COVID as a way to get outside and enjoy the beautiful greenery that we have here in DC.

Another way that I like to relax is just hanging out with my cat. I think having a pet is just such a wonderful way to kind of decompress and relax. And a lot of some of my favorite moments are just cuddling on the couch with her and my partner.

Rachel: You mentioned Shabbat dinners. If you could invite any three people to your Shabbat dinner? Who would they be? And why?

Jessika: The three people that I would invite to my Shabbat dinner are Stacey Abrams, Margaret Cho, and Ilana Glazer.

Stacey Abrams, I just admire so much. She’s really sparked a revolution and a refocusing on local government. And the idea that engagement doesn’t only start at the top with the federal government, but also starts locally. I think she’s just an incredibly wise, powerful woman, and speaks to the idea that we don’t necessarily have to have held positions of leadership for many, many years to have the wisdom of what it means to be an effective leader. 

Margaret Cho is one of my favorite all time comedians, I think that she has done so much to open the doors for sexual liberation and female empowerment in terms of not only gender identity, but sexual orientation. She’s incredible – she’s a child of immigrants and has had such an incredible success story. And it has been able to do it all with a self deprecating sense of humor, which I so appreciate. Actually, she was the last person that I got to see live at an International Women’s Day event at the Kennedy Center before COVID hit. 

And then Ilana Glazer. I resonate with her a lot – her silliness and spontaneous approach to life, and really bringing the Jewish millennial experience to television. I remember the first time I saw Broad City before it got picked up by Comedy Central. And I was like, “how did they get inside my head?” The script was just so relatable and I love the friendship between her and Abby. And also how the show shines a light on the biases that still exist within the Jewish community and makes fun of them, while bringing them into the spotlight.

Rachel: What are the top one or two things on your life bucket list?

Jessika: Oh, that’s such a good question. So I will say I checked a few of those things off for my 30th birthday – I went skydiving, which was one of the ones that I wanted to check off my list. I really want to be a mom. And so I would say that that’s one of the things on my life bucket list. 

You know, I’ve been lucky enough in the past a little over a year right before this quarantine craziness to have met my life partner, and to have still not murdered each other living in a one bedroom apartment in the past year. And so I’m really excited about what our future will be together, especially in terms of being a mother, that’s something that I’ve wanted for a long time and excited that I’ve met the person that I finally want to do that with. 

I would also like to spend more time working with animals. I had an opportunity to spend some time at an elephant sanctuary in Thailand, which was an incredible experience. I’d like to have the opportunity to do that abroad where I could live and work in a sanctuary space in some way. Pre-COVID, I was doing some volunteer work at the Humane Animal Rescue Alliance, which is where I adopted my cat from and so I’d love to just be more involved with animal rights in terms of volunteering and working with animals.

Rachel: What’s one thing you can’t get through the day without?

Jessika: It’s coffee. I know that that is such a cliche kind of answer. But it’s true. I will wake up when there is coffee available. And I’ll say, we’ve really stepped up our coffee game during the pandemic with a Chemex pour over. I just love everything there is about coffee. I love the smell. I love the taste. I love the ritual. And having lived in Italy, I’d say that I have three high standards around gelato, pizza, and coffee. 

Rachel: Do you have a favorite place in DC for coffee?

Jessika: I love Compass Coffee. I think their beans are absolutely wonderful. There’s also a brand of coffee called Mayorga. They sell it at Costco, so we go to the one in northeast and get a five pound bag from there. I really love their Mocha Java coffee – it’s so good.

Rachel: I’ll have to make a note of that! Last question, “When the Jews of DC gather…”

Jessika: …we are unstoppable. We really live out the ethos of a lot of what it means to be Jewish. DC is such a passionate, mission-driven city full of people who really have causes that they care about. And to me, that’s really the ethos of what it is to be to be Jewish – to be committed to making the world a better place for everyone. And I really see the Jews of DC living that fully.

Editor’s note: If you’re interested in connecting with Jessika, you can schedule a free discovery call on her website and connect with her on LinkedIn.

The views and opinions expressed in this blog and on this website are solely those of the original authors. These views and opinions do not necessarily represent those of the organization GatherDC, the GatherDC staff, the GatherDC board, and/or any/all contributors to this site.