June 18, 2020
Today’s guest is the incredible Jenna O’Brien, founder and creator of Twenty Seven.
Twenty Seven is a paper goods and lifestyle brand in sunny Lakeland, FL and online that exists to remind you of sunshine! Everything is hand-drawn and reflects retro stylings, bright colors, and messages of hope towards mental health.
Jenna started Twenty Seven out of her struggle with anxiety, depression, and trying to figure out how to pay for groceries in college. She began her freshman year of college with a diagnosis of PMDD (premenstrual dysphoric disorder) and struggled through the years figuring out how to be healthy with a mental disorder. Twenty Seven was born in the midst of trying to feel better, as she took up digital drawing to distract a busy mind. She began selling her work at local markets, and in three short years has opened up a brick & mortar in downtown Lakeland, shipped artwork to customers worldwide, and created a globally recognizable lifestyle brand with over 94,000 following online.On today’s show, Jenna talks to us about mental and emotional health, how she navigated her mental disorder, and through that created a wildly successful business. Her story is inspiring, hopeful, and relatable. Whether you’re a young creator dreaming of starting a business, or you also struggle with mental health, Jenna’s story will inspire the heck out of you and make you feel all sorts of yellow.
Jenna is an illustrator based out of Lakeland, FL. She is the founder of the shop Twenty Seven, a paper goods and lifestyle brand. They have a little brick and mortar in the historic downtown of Lakeland and an online store where they ship all over the country and world.
Jenna makes everything from art prints to nail polish and adult playdough. Everything is incredibly whimsical, colorful, and retro inspired with a message of hope.
Jenna started Twenty Seven three and a half years ago in her dorm room when she was a freshman in college. Jenna was diagnosed with premenstrual dysphoric disorder, also known as PMDD, which is cyclical anxiety and depression with your menstrual cycle. Where a lot of women experience PMS, PMDD is a smaller percentage of women that experience severe anxiety or depressive episodes in sync with their menstrual cycle.
Jenna went to counseling for a while and also saw a psychiatrist. Both narrowed it down that she had PMDD. This was all happening the summer before she went to college. As she moved away from home and into her dorm, she spent the year figuring out what exactly that diagnosis meant for her and how to be healthy. Jenna found herself constantly looking for resources during that time. She quickly learned that while a lot of resources were incredibly honest, they weren’t hopeful. Or, there was the flip side of resources that just said to “keep thinking positively” and didn’t address the severity of the situation.
This was where the idea of Twenty Seven was planted. She wanted to create a resource that was honest, but still hopeful.
Throughout the year, Jenna started to feel better through counseling, medication, and learning to cope with PMDD. She remembers sitting at her dorm room desk buying the domain name for Twenty Seven to start a blog about mental health that was honest and hopeful.
At this same time, Jenna began to make things. She made yarn wall hangings and started to paint, and draw as a way to stop thinking so much about how she was feeling. A lot of people around her enjoyed the things Jenna was creating and she realized she could start to sell her creations.
Jenna went to her first market in Lakeland, FL a small, historic town that is incredibly supportive of small businesses. She made about $80 at her first market and she was so excited. She continued to do markets for years and it was always her desire to have a permanent location that people could come to. In August of 2019, she opened a brick and mortar and her online sales started to take off. Now they have their brick and mortar store and a studio space a block down the street where they make the products and ship everything.
The name “Twenty Seven” is inspired by two things. Jenna has always loved Psalms 27, a psalm about fearlessness. In addition, Jenna and her husband started dating on July 27th. They started dating in high school and celebrated each month on the 27th.
Mental health is so important. The first time Jenna went to the doctor for anxiety was when she was 11. She has dealt with anxiety for over a decade but she experienced depression for the first time with PMDD.
Counseling is huge. For Jenna, her counselor was the first person to help and put a name to what she was dealing with. A diagnosis does not define you, but sometimes putting a name to something makes it easier to conquer. Counseling allows you to process and track symptoms.
In addition, correct medication can be so helpful. When it comes to mental health, people can be freaked out by the concept of taking medication. But, when you can narrow down the medication that your body needs it can be such a huge help.
Community is huge. You can’t walk through a mental illness in a healthy way by yourself. You need to tell someone, even if it is just one person. It can relieve so much if you can tell someone. If you wake up and know it’s going to be a hard day, don’t be afraid to text someone to let them know what is happening. It can feel so freeing. Then, you can have people that will keep you accountable and watch over you.
For Jenna, making things with her hands was so helpful. It has helped her feel better on off days to continue to make art.
Distraction can often get a bad rap. If you are in the middle of a time where you are chemically anxious or depressed, it’s okay to put that down and not think it to death. It’s okay to put down your depression and pick something else up.
Colors are incredibly important to Jenna, and you can definitely tell this if you see her art!
When getting diagnosed and going through her first year of college, it was really hard to talk to people about it all. Jenna needed community but didn’t know how to explain what was happening.
Jenna began using colors to explain where she was on the spectrum of her emotions. The color yellow represented inhibited Jenna. She felt her feelings but was still in control of them. It would go to blue on the spectrum when the depression was really severe.
Jenna also did this with the weather. She would be able to tell if there was a day of sunshine, or a day where there were a few clouds but the sunshine was still there. Or, some days there was a complete rainstorm. It was how Jenna was able to explain how she was feeling.
Jenna began to draw and paint with yellow as well as wear the color to turn her day around. If she woke up blue, she would put on a yellow sweater.
As she has shared this and made a ton of yellow products she has learned just how much this color means to other people.
It’s an ongoing battle, but the beautiful thing she’s lived through is that her days did eventually become more yellow than any other color. It doesn’t mean it’s a perfect day, but it meant she felt like herself.
Through Instagram stories, Jenna will ask how people are feeling today on a scale of 1-10 or have you been sleeping lately, etc. Jenna started doing this from the very beginning when she had very few followers and kept with it. The responses are incredible. It always blows Jenna away just how vulnerable people are and that they would be willing to share their feelings. It has been such a humanizing thing for Jenna to know that other people out there feel the same way she does. She is able to share these responses and show that other people feel the way we do. It makes everything seem less huge and scary. We are all just people with feelings.
Over the course of a year and a half, every now and then Jenna will post a guide to a specific mental illness. The last one she did was schizophrenia.
Now during quarantine she has focused on keeping things super positive.
It’s been so interesting to learn about different diagnoses and try to understand them more. Jenna has become extremely empathetic and tried to highlight them in a way that is not belittling the severity but talks about something that people normally don’t talk about.
Often it is all about Jenna’s feelings since she is the one making the content. The words she is drawing are often the words that she needs to hear that day.
Every week and every day brings something new. Every month there is something that they haven’t figured out yet.
Growth is very intimidating and it’s good to talk about how much you really want to grow. There is a huge difference in Jenna’s life now as she operates Twenty Seven than there was when she did a few markets. Jenna continues to love it and thinks that is why she is able to keep up the growth. It’s her favorite thing that she gets to do.
Jenna has learned to hire people that like things that she doesn’t. Find people who are great at executing the things you may not be the best at. As the business grew Jenna has learned to hire out the tasks to people that could do it better than she could.
Jenna draws out everything and produces all the products, and that is where she comes to life. She loves thinking of new ideas, connecting with people, and making beautiful things.
Jenna was so nervous to be a boss of any sort. She knew she could not do it all by herself. The more Twenty Seven has grown, the more she has been able to hire, and even started loving that aspect of life as well. She gets to build a team that gets to do this mission together.
Every day Jenna is doing something she hasn’t done before and is just figuring it out.
Every day is Jenna learning something she hasn’t done before. It has molded her into a more flexible human. She is constantly realizing she doesn’t know what she is doing.
Jenna has learned to be a human. It can be really intimidating to enter into a world where everyone seems like they know what they are doing. Jenna has been adamant about letting people know that she doesn’t know what she is doing. She strives to bring a human element into the workplace. Her employees can know when she has had a bad day.
As long as you keep being a human, it can bring something different to both small and big businesses and we need more of it.
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WASSUP FRIENDS. We’re Evie + Lindsey, co-founders of this wild partayyy called The Heart University. Our goal is to empower entrepreneurs to kick freaking BUTT in their businesses, dive down into the heart of their why and how, and serve you with all possible tools you’ll need to up-level your business game and CRUSH those goals of yours.
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