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Aspiring Co. is here to remind you to chase your dreams relentlessly and to inspire you when you feel like giving up. We are telling the stories of women who are fighting everyday to pursue a life of meaning.



This interview y’all. So lets back up, I met Jen through a mutual friend, Taryn Jerez, at Fearless (her co-working space!). After chatting with her I knew that she would be perfect for Aspiring Co.. THERE ARE SO MANY THINGS I COULD SAY, but Jen says it better. Just start reading.

Name:  Jen Brown
Age: 36
Job Title/Company: Founder of The Engaging Educator and Fearless Winston Salem
Education Background: Theatre, Dance, Art History, Autism Education, Improv and too much life.

Jen Brown - The Confetti Project

In-depth Questions

1.     Tell us a little about who you are.

Hello! I’m Jen Oleniczak Brown and this is one of the hardest questions for me to answer. I’m a plant mom, dog mom, writer, speaker, teacher, mover, shaker, partner of an awesomely supportive guy, business owner (which isn’t how I love to define myself! That work life balance vibe) introvert that masquerades as an extrovert but is exhausted afterwards…also my strength finder puts me as an activator, which is, the realest test I’ve ever been hit with.

The biggest thing to remember: you have to live with your own choices, so make sure you like you.
— Jen Brown

2.     What sparked your interest in starting your business(es)?
EE started as my side hustle. Every time I think of the story I laugh – I left acting after a decent career, went back to school for Art History. Started working in museums and my supervisors always called me out for being flexible and really great with an audience. One asked me to teach a public speaking course for the other educators, and I was like, hey wow, I think I can do this for more people.

So I rented a studio and posted a class – Improv for Educators – and it sold out in about 24 hours, so I added another one. That one sold out too. I still remember when I told my roommate at the time: I think I have something here.

And he said “Don’t say that. You can never think you have something.” Which is great, and still plays on my imposter syndrome.

Fast forward to me deciding I was going to teach improv to non-actors in general, and I kept adding classes – and answering emails at 1am. I was working almost full-time as an educator in NYC Museums, and I actually made my business, The Engaging Educator – or EE, which is where we are now – my full time gig when I moved to NC almost 4 years ago!

Fearless was a little different – I call it the little sister of EE, because EE went women-centric in 2016. Around the same time, women-only co-working spaces opened up in NYC. I loved the women only vibe. I had a big opportunity last year to be an adult and pay off some loans with a big job – or – open a skill share women only space.

Guess what I did?

Fearless is pretty amazing though, because it pays NO ONE but the women that teach and my bill keepers. I’ve been working really hard to get to self-sustaining with members and memberships, because the whole point of it is to be a community resource. We’re getting there – eventually – but it’s taking some time for people to understand that they are both responsible for the space and empowered by the space!


3.     If applicable, tell us about your full time job and/or any side hustles you might have.

Lord. I write a lot. LMAO!

4.     Who are you most influenced by?

I don’t know if influenced is the best word – I’m definitely inspired by people, but not often influenced. I’ve been really inspired for years by Amy Cuddy. She had research, had a great conclusion – and folks brought her down. Being critical of research is one thing, bullying is another.

She came back with class and is an incredible force and woman I admire greatly!



5.     What was your first job and how long did you hold that position?

OMG I am a workaholic – I worked as a carnival game operator when I was 15! I HATED IT! After that: Subway Sandwich Artist, Taco Bell, Target, Pick n Save (grocery store), waitress, bartender, Starbucks for 5 hours…

6.     Can you share one of your proudest achievements with us?

A current one: my book, Think On Your Feet, has a presale page!

7.     What were your initial goals with your work? How have they evolved?

I don’t know if I ever set goals – and now I do. It’s strange, I just kept working and doing the next thing. I have a weird relationship with “accomplishment” – I don’t feel like I’m ever done and just great, I just think I have to keep working more and more, harder and harder. This is good and bad – I never feel like I can rest, because nothing feels like an accomplishment. It just feels like another thing. I’m sure a lot of this is from my upbringing: super patriarchal! My brother was an underachiever and I was told this was the case because I was an overachiever.

For me now, I set goals – and log my accomplishments! It’s helpful for me to see what I’ve done and where I’ve been, as well as where I’m going next. I’m still working on feeling “accomplished”.

8.     What do you think is the most important life skill you learned through your work?

People will always dislike you – you’re damned if you do and damned if you don’t. The biggest thing to remember: you have to live with your own choices, so make sure you like you.


9.     Where do you hope to be in five years?

Still in business? HA! Seriously though, I hope EE is still thriving and growing, and I hope Fearless has moved to a bigger location and expanded the services it offers.

10. What is a typical day like for you?

I get up pretty early: doggo is a morning pup. When it’s my turn to walk him we have a nice conversation about the weird shit he does, then breakfast. Always breakfast. In NYC I never ate breakfast and here I make my own granola. Then I usually get to Fearless around 815 and rock out to musical theatre while I do my opening checklist. Emails come next: I only take one pass through each box (I have 3) a day – otherwise the hydra that is email destroys my day.

If I have meetings or calls, I usually try to get them done in the morning – same with writing projects. When I was writing my book I did 1500 words a day, and couldn’t answer emails until that was done, so now, the articles I write are SO MUCH EASIER. By the afternoon, I’m catching up on projects (today, this interview!) and doing everything from social media updates to contracts or calendar updates. When I get home, my computer is usually closed for the night, unless I have something big I’m working on, because I need the balance. It’s really easy for me to creep back into working too much or working all the time, so I have to be careful. My husband calls me out when I’m too absorbed in work or online or on my phone too much and I actually really need and appreciate it.

11. What was the biggest obstacle you’ve faced so far in the process of pursuing your goals?

My depression. I was diagnosed with PMDD two years ago and first, it was the actual disorder, then the drug they gave me to fix it. PMDD hits about a week before your period and for me, gets better when it starts, and then is tough again right before I start my birth control pill. PMDD looks different for a lot of people: for me, serious depression, suicidal ideation (and eventually, attempts), rage, hopelessness, apathy – not great for a business owner! I got on Zoloft, and while it saved my life, it dampened everything and gave me aphasia. It all broke when I couldn’t remember the word for spinach or my husband’s name. I worked myself off of Zoloft (with the help of my therapist!) and that was a month full of dizziness, brain zaps and weird mood shifts. Now, I manage it fine but still have moments of struggle. A big part of it for me is the apathy, which makes it very, very hard to get things done. And when you work for yourself? WOOF.

I learned to trust my gut, listen to my intuition and not be scared that something is “too big” for me.
— Jen Brown

12. What is the best piece of advice you have received?

It’s not advice someone gave me, but advice from my favorite artist: learn to rest, not to quit.

13.  When do you get your best ideas?

If I’m being honest, it’s when I feel helpless. When things are the hardest, or something failed, or if I’m in a tough moment, I find my ideas are on point.

14.  Can you share with us one time that you failed and what you learned from that failure?

I had two other partners when I started Fearless. Not financial partners  - more collaborators. WHOOOO that was a mistake – I knew what I wanted from Fearless and what I wanted it to be: the idea that there is no right way to be a woman. And my collaborators wanted two different things – and I thought it might work, but boy, when you are on different pages for mission, and if you’re a person that rolls up their sleeves and does everything? Maybe don’t collaborate. I learned to trust my gut, listen to my intuition and not be scared that something is “too big” for me.

15.  How do you unwind?

My plants! I spend so much time with plants and buying new plants and growing them and caring for them…it’s so wonderful! I also cook a lot with my husband – we try to master really hard kitchen skills and that’s actually one of the most relaxing things to me – even if a recipe is awful!

16.  What would you tell someone else who is interested in entering your field?

What I tell everyone: keep doing good work. Even when it’s hard, and it seems like nothing is working. You have to ALWAYS do good work. Even when it looks like people are doing “better” with less work – you should still always do good work!

17.  What do you hope people take away from your story?

The above. =)

Follow Jen and her work:

Engaging Educator:

Youtube | LinkedIn | Twitter | Facebook

Instagram | Facebook

Jen Brown