Welcome to my fifth installment of Faces & Places with Jessica Zweig of SimplyBe Agency! Faces & Places is an interview series that explores the amazing, interesting and inspiring faces of Chicago and the world (finally!), the places that define these makers in their element of creativity and how travel affects their lives. You can check out the rest of the posts here.
You know how they say you feel a spark with some people? People you “click” with, so to speak? Instances where your conversation with them gives you goose bumps and you know it’s going to have some type of profound impact on your life trajectory – even if you aren’t quite sure what direction is yet?
When I had the opportunity to sit down with Jessica Zweig (over a softly candlelit table at Soho House in Chicago, no less), I felt this spark. Jessica gave off this tangible, electric energy and it was impossible not to feel her entrepreneurial spirit and passion for life radiating off her.
Not only is Jessica the founder of personal branding agency SimplyBe and one of Inc. Magazine’s Top Digital Marketers to Watch, she’s got a ton of entrepreneurial experience under her belt as the founder of CheekyChicago.
And as a world traveler who will be taking her business to a global scale with her 3 upcoming retreats in Bali, Costa Rica and Tuscany (beginning in March), I knew Jessica Zweig was someone I needed to talk to. Check out my recent interview for some insight to living your best authentically-you life, and how to balance being a boss lady with being human.
MZ: Tell us a little bit about yourself and SimplyBe.
JZ: Absolutely. I’m Jessica – I’m the founder of a company called SimplyBe Agency. We’re a personal branding agency – I work with human beings to develop their stories and digital platforms. My clients run the gamut on different professional positions, from executives to spiritual directors and anything in between.
I have been and entrepreneur for my whole career. I was an actor before being an entrepreneur – but I’ve run my own businesses for the last 10 years. This last year, specifically, has probably been the best year of my career because I’m finally doing what I want to do, on my terms, full force. I’m building a team and I can’t keep the clients away. And more and more I’m able to incorporate my vision for travel and global scale into the planning.
That’s high level what we do. I always say that I take experts in obscurity and help them to become thought leaders. That’s my mission with my business to do that for my clients. And then as we grow, to not necessarily always do that one-to-one in a consulting capacity, but to do it for more of a larger audience from a digital capacity.
MZ: What is your creative process like? Obviously I know it’s very complicated, but if you could distill it down – for SimplyBe, or acting, or your personal brand for Jessica Zweig, or CheekyChicago, or anything else.
JZ: One of the things I believe more than anything is the power of stories and storytelling. Stories are knowledge, and knowledge is power – and if you are willing to be really vulnerable, honest, genuine and authentic with your story, the more powerful your story will be. I think that’s been a common thread throughout my whole career – whether pursuing the life of an artist, starting CheekyChicago, sitting down to write a blog or coming up with a client strategy – I always ask, “what’s the truth? What’s really going to strike the most important nerve so that it helps someone?”
Storytelling is also of the upmost importance when it comes to personal branding. I recently got asked a question along the lines of if personal branding is self-promotional and egotistical. If you’re doing it wrong, yes. If you’re doing it right, you’re in service of other people. Because no one cares about you, people care themselves and how you make them feel.
So I think from a creative standpoint, I’m always coming from that place. I’m always thinking, I’m not writing this to be indulgent. I’m not sharing this Instagram photo to be indulgent. I’m sharing this with the mission that hopefully someone else can relate to it and hopefully it makes him or her feel better. Or get an idea, or take action, or whatever it might be. But I think being in service to others is really the core of my creative process.
MZ: What’s your favorite part of SimplyBe?
JZ: My team. I love my team so much I could cry. No business succeeds without the right people. It’s all about people. If you can find the right people and create the right culture, a culture that breeds excitement to come to work and passion for the job, it doesn’t feel like just a job and you create great work. And creating great work creates happy clients. And happy clients create revenue and revenue makes the business run, right?
It starts with creating the right team – and I just happen to thoroughly enjoy the company of my team – they’re like my family. And being able to coach them and work with them and be a mentor to them (and often they mentor me – it’s a co-creative process) – that’s my favorite part.
MZ: How long did it take you to find that? Do you have a secret to finding a colleague or partner – whatever it is for anybody in any situation – someone that you’re going to work with?
JZ: Yes. I think you can teach anyone a skill. If you can read or write, I can teach you how to do anything. I cannot teach a person ambition. I can’t teach somebody to want it for themselves – to have that fire in his or her belly and have that hunger to wake up in the morning and do something really big with their lives – I can’t give you that. You’ve got to have that. And so I look for that.
And I also think a willingness to learn and no ego – someone that’s just a good person – those are the qualities that I look for. I want to be able to enjoy spending time with you. It’s always about personality – aptitude, attitude and ability. And attitude is huge.
MZ: Normally my interviews are pretty formulaic. But as I was preparing for this interview I kept thinking, what’s the fun of having someone that has a background like Jessica’s without deviating a little bit and getting a little selfish? So, what’s the most challenging thing about being an entrepreneur?
JZ: Honestly, I love my career. As a challenge, though - the overwhelm. The non-stop 24-7 of it – I literally work 7 days a week. I work Saturdays and Sundays. I don’t usually work a full day, sometimes I do, but I touch work every single day. So the overwhelm is one of the most challenging things – the feeling that there’s just never enough time to do all the things I want to do.
MZ: Where is the last or favorite place you’ve traveled? You can answer both!
JZ: I was just in Jamaica for a conference, which was one of the best conference experiences of my life. It wasn’t a typical trip – I didn’t get to see that much of Jamaica because I was in a conference for 4 days; however, it was amazing and I loved it.
My favorite place I’ve ever been is like asking me my favorite child or song – can I give you my top 3? (me: of course) – Bali, Costa Rica and Portugal, (me: you can list 5!) Tel Aviv, Thailand.
MZ: How do you find inspiration from travel?
JZ: Two things, and they’re somewhat counterintuitive. I love being alone. I love traveling by myself. Solitude is really inspiring to me – I’m able to really drop into the energy of a place and notice things that I wouldn’t notice and appreciate things that I wouldn’t appreciate because I’m with myself and not being distracted and talking.
The other side is the people – shop owners and concierge and cab drivers and strangers you meet at a bar – the people I meet when I travel inspire me. And so does food. And music. But I love traveling by myself. It’s my favorite time.
(I shared a quick anecdote with Jessica of a recent experience where I had to dine alone for the first time, that I was nervous and felt weird about it).
MZ: Did you ever feel that way – like, this is weird, being by myself?
JZ: Mm, no. When I was single in my 20s and I had just gone through a breakup, I read a book (it’s one of my favorite books) by Susan Ariel Rainbow Kennedy, (known internationally as SARK) called Succulent Wild Woman. It’s a beautiful book. I can’t even describe this book. She talks about the power of going to dinner by yourself. And that succulent wild women take themselves out to dinner. And I was like I’m going to do that!
I did it once. I took myself to a bar, on a Saturday night – I sat at a bar by myself, as a woman, didn’t want to get hit on – just wanted to drink and eat by myself, absorb it all – and I loved it. And so when I travel I try to do that too – my trips by myself are my favorite trips.
MZ: This is a purely selfish question – how do you balance it all? Being an entrepreneurial woman – though this series will focus on both men and women - I tend to gravitate toward female entrepreneurs; I feel like it would be very relevant to our audience.
JZ: I’ll tell you my easy answer to that. Choose to be with the right person. Marry the right person, date the right person. Who will let you be you, so that you don’t have to feel like you’re choosing all the time. Nothing’s ever perfect, but that’s my answer to that.
MZ: Favorite place in Chicago to find inspiration?
JZ: The Delta – the Delta is this super hip speakeasy, dive bar vibe, southern throwback restaurant/ bar in Wicker Park that feels like my personal Cheers. And I feel like when I go into a place that’s got good vibes, good music, good food, collection, diversity, cool people – I feel inspired.
(Tamara, Jessica’s colleague, jumps in and shares an anecdote).
“The server came over to us and we gave the typical hi, how are you – and he answered the question: ‘I woke up today, I had a great day, I’m alive, I’m healthy, I’m well.’ Talk about inspiration! It was beautiful. And so when we go in there now, we remember that experience.”
JZ: I think going anywhere where the people are really good and positive makes anything inspirational and fun.
MZ: My final and favorite question: anything else you want to share?
JZ: I get at lot of feedback that my life looks so fun and glamorous and exciting and cool (for the record, I was like, the biggest nerd in high school) but my greatest pride is in my battles and in my darker moments that have led me to find the light in my own life, which has nothing to do with what people see on Instagram, or what I look like or the fact that I travel the world.
On that same token, I run a personal branding agency and I talk about the importance of the personal brand as an image – so how do you tell that story and come from that place of battles and darker moments? How do you keep it up and make it relevant? If you’re doing personal branding right, you’re coming from a place of service. Think about things you’ve been through – that’s where you need to come from. That source of gravity and personal power – that makes your flashy career that much more relatable and interesting to people and valuable for people because everyone’s searching for this validation – we all want to be seen – that’s such a human yearning – to be seen.
But as I mentioned, we live in such a noisy space where everyone is putting themselves out there and projecting versions of themselves to others – but if you’re good with the 5-10 people in your life that are closest to you, that’s all that matters. We don’t want to say, “I am insecure” – but we all are. Including me, and I feel really strongly about being open about that. So that’s why I say be good with the closest people to you, because they know the real you and they don’t project on you.
Want to learn more about Jessica and SimplyBe Agency? You can visit these links or head over to Instagram for more! You can also check out the upcoming SimplyBe personal branding workshop at this link.
Calling All Entrepreneurs: the SimplyBe Magic Mastermind Series
Jessica will be hosting a series of 3 fully immersive global retreats (Bali in March, Italy in May and Costa Rica in November) during which participants will mastermind with top-level mindset and business coaches to create and expand their visions with other business and spiritually-minded individuals, develop authentic personal brands and business plans and ultimately become part of a global co-creating tribe of like-minded big thinkers and change-makers.
Want more information on the complete series? Click here!