Alena Hennessy is an intuitive painter, teacher, writer, and workshop leader. She’s been doing the art thing for twelve years and making enough money to keep doing art for the last four years. Alena’s learned a lot on this path. She’s learned about what it takes to build a successful art business, how to trust in herself and her creative voice, what to do when the pain is big and where to turn to make it smaller, and how to make art that only you can make.

Some things we talk about;

Mixed media artist, Nikki Cade, left her full-time job as a special education teacher in June of this year to pursue art full-time. Because she’d spent the last several years building an online following and customer base, she could quit her job when her art became more important than the teaching. It’s been six months since then and she loves it. Here Nikki talks about what it took to leave the full-time job, how she prepared herself mentally and financially for the transition, her path to freedom, and how she found her creative voice.

Some things we talk about:

Christa david left a six-figure earning career in public health for a full-time gig as an artist. She makes collages, paintings, and photographs that she sells online, through galleries, and in-person. Here Christa talks about what she learned as a mom at 14-years-old and how that’s informed her art business today, the ups and downs of being your own boss, and what it means to make art as a black woman in America today.

Some things we talk about:

• The three non-negotiables in art and business

Director, photographer and filmmaker, Jethro Waters, is best known for a more avant-garde, magical realist approach to filmmaking. His work has been published in The Guardian, Rolling Stone, Pitchfor, NPR, Spin, and Billboard. Here Jethro shares about the ebbs and flows of creativity, how he got started making films and his launch into the world of documentaries, what it’s like to film your real-life heros and why the work of an artist is never done.

Some things we talk about:

L'Erin is a healer. And by healer I mean warrior. She's been to rock bottom and, like a phoenix, risen from the ashes. Now L'Erin makes her living as a "soul guide, shadow diver, and spiritual teacher."

In this conversation we talk about:

L'Erin is a healer. And by healer I mean warrior. She's been to rock bottom and, like a phoenix, risen from the ashes. Now L'Erin makes her living as a "soul guide, shadow diver, and spiritual teacher."

In this conversation we talk about:

Artist and Illustrator, Lisa Congdon, spends her life making art and teaching others about art. She speaks openly and honestly about things most people never talk about like how to navigate the murky waters of success, social media anxiety, burnout, aging, and money.

Some things we talk about:

We talk about the affect her mom’s cancer diagnosis had on her life, how she made her first film with just a go pro and a mediocre mic, what it’s like to face physical danger in one’s work, and how to go for your dreams no matter how big they are or how little you know.

Ashley and I talk about how Ashley went from "broke as shit" to selling to hedge-fund managers and billionaires, the formula for figuring out who you are and what you want to say, money, and how to never, ever give up.

*warning: the language used in this interview is explicit

It's not an easy leap from employee to entrepreneur. In this conversation with photographer, Olivia Emmer, we talk about taking that leap. We talk about how to make the switch from creativity as a hobby to a full-time gig, charging for your work, the challenges and joys of working on your own, knowing when to leap, and claiming your space as an artist.