Diana Stelin

Follow your intuition and believe in what you can bring to this world.


Diana Stelin is an award-winning artist, Best of Boston educator, published author and mother of three. She managed DTR Modern Galleries, a gallery chain with locations in New York, Palm Beach, Washington DC and Boston for over seven years and is now also launching a fashion line called Gallerista.

She has received a Bachelor of Fine Art from Cornell University and a Masters in Arts Administration from Boston University.

Where did the idea for The Plein-air Art Academy come from?

My teaching studio name is The Plein-air Art Academy. It derives from a French term, Plein-air painting and means painting outdoors

What does your typical day look like and how do you make it productive?

I have networking days and painting days. They alternate. I would paint or network in the mornings, then handle all my email correspondence or hold a corporate art workshop at lunch time, and teach in late afternoons and evenings.

How do you bring ideas to life?

I visualize them, then test them and do my best to trust my intuition.

What’s one trend that excites you?

Trend for wellness programs in corporate spaces. I think our lives are so crazed and overwhelming that I applaud all companies who choose to focus on their employees mental and physical health.

What is one habit of yours that makes you more productive as an entrepreneur?

I’m excellent at time management. I focus on one task at a time for 2 hours, without letting my mind wander and that gets a lot done.

What advice would you give your younger self?

I would trust what’s in my heart and not go along with societal restrictions and assumptions about how my life should develop.

Tell us something that’s true that almost nobody agrees with you on.

30 min exposure to art a day decreases everyone’s cortisol levels by 50% – a statistical fact. Yet, there’s such a stigma around the art world that no one takes it seriously.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

I spend time on my own mental health by practicing painting 2-3 times a week. I’m not saying everyone should paint ( though they should certainly try it and not through a gimmicky ‘art night’ activity), but spend real time every week on their true hobby be it dancing, hiking or cooking.

What is one strategy that has helped you grow your business?

Being active in Facebook groups and sharing photos of happy kids and adults in action, as well as word of mouth about my giving personality that encourages students of all levels.

With regards to my art sales, which have been a huge part of my growth, actually asking people if they’re interested. If you don’t ask, they won’t act. Furthermore, I’ve switched my model to creating custom pieces in specific palettes and sizes and sales have tripled!

What is one failure you had as an entrepreneur, and how did you overcome it?

I didn’t believe in myself enough. I would apologize for being who I am. I went along with the stigma of a starving artist.
I’ve started to think about my value to the world differently and working on my subconscious beliefs structure and that changed things significantly.

What is one business idea that you’re willing to give away to our readers?

Create an app that predicts trends in any industry based on asking people vis tests on Facebook that everyone loves doing so much.

What is the best $100 you recently spent? What and why?

Hiring help in graphic design and marketing, hiring a VA and an SEO team. I believed I could do it all myself but there’s no real growth if you’re wasting your time on things you’re no expert in.

What is one piece of software or a web service that helps you be productive?

Google sheets, I can access files anytime I want.

What is the one book that you recommend our community should read and why?

“The Fountainhead” by Ayn Rand. It masterfully outlines two parallel lives where one follows his calling and the other follows what’s expected. Perfect for entrepreneurs.

What is your favorite quote?

“No one is perfect”

Key Learnings:

  • Art changes people’s lives.
  • It’s important to incorporate it into your life for decreasing stress levels. Follow your intuition and believe in what you can bring to this world.