The Anxiety of Entrepreneurship

My story of anxiety, pain, and regaining hope while working on my dreams.

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The Anxiety of Entrepreneurship

By: Jenna O’Brien

Dealing with anxiety as a young entrepreneur has been one of the most challenging experiences in my life. Starting a business when I was 18 years old in my college dorm room came with many uncertainties - opening a retail store at 20 came with even more. But anxiety has been present in my life since I can remember… My business was born out of my coping process with existing anxiety and depression.

It was the stretch of 2020-2021 that was the absolute worst two years I’ve ever lived. My small business (and lifelong dream) were demolished by COVID, I lost someone I was incredibly close to tragically & suddenly, I battled with my identity and worth, and had horribly prickly experiences with work that left me shattered. Many of my circumstances absolutely flipped my perception of self and even of hope.

I became very familiar with grief, sadness, loss, and shame. The rollercoaster of the entrepreneurial journey was all the sudden a free fall.

I had to learn how to capture my thoughts and hold on to hope. I met with individuals and loved ones for guidance. I sought therapy and doctor’s advice. I shared my pain, even when I could barely get the words out. It is still incredibly hard to share. I made these two illustrations as I was learning how to go through the free fall. 

These images were shared on my social media platform with over 50,000 people and have since been used at conferences and it seems as though they have resonated with many. It appears that I’m truly not alone. 

During the deepest anxiety I still had employees to take care of, products to sell and a brand to keep strong - I made illustrations like these during the darkest of times. 

But there were a lot of illustrations (if you want to call them that) that I didn’t share. They weren’t meant for instagram. They were for me. But I’ll share them with you now, these vague, dark and raw images. 

For me, the journey of healing from trauma and anxiety has been a long and difficult one. And it’s a journey I am still on. I have had to confront my own fears and insecurities, and learn how to work through them in a way that allows me to continue to create and grow as a designer. Is it the hardest thing I’ve ever done? Oh yeah. Is it worth it? Yes. Some days are more convincing than others. But I’m convinced that it is. 

Making art has always been how I process through my circumstances and my feelings. It always will be. It is such a privilege to share my journey with so many people and I’m so glad you’re here. We are all learning together. Thank you for your support and for reading this. 

Everything is going to be okay. 

Hello all, I hope you are so well! Here is a calendar download for your phone screen – I hope it brightens your day every time you look at it!

This is a fun teaser of our wallpaper access that will soon only be available to our supporting subscribers. Monthly, our supporters will receive new desktop and photo wallpapers I design, as well as access to exclusive stories, and a free downloadable print for your wall!

If you’d like to support us in our magazine endeavor, or even just want some colorful art for your walls every month - consider becoming a supporter!

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Here’s the wallpaper freebie: