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Lift Your Legacy: How successful leaders live wholistic lives of meaning with Diana Stelin and Jacob Rupp

What gives me the most pride is the fact that I do what I love and my kids see that. They have a role model who’s living the life she carved out for herself, and they as a result gain more confidence in their decisions. Diana Stelin is a professional artist, award-winning educator, and mother […]


What gives me the most pride is the fact that I do what I love and my kids see that. They have a role model who’s living the life she carved out for herself, and they as a result gain more confidence in their decisions.


Diana Stelin is a professional artist, award-winning educator, and mother of three kids under ten. Prior to opening Best of Boston’s Plein-Air Art Academy she was a VP of DTR Modern Galleries, a national gallery chain, for over seven years. Ms. Stelin holds a BFA in Painting from Cornell University and an MS from Boston University.


Can you share the funniest or most interesting story that happened to you since you began leading your company?

I’ve seen dozens of people get healed through the power of art, even those dealing with severe trauma. One woman who had a miscarriage would come in completely white in the face, void of emotions, and within a half hour of artmaking I’d see color come back to her cheeks. She was more open and talkative; a lot more relaxed. It was amazing to be privy to that change. It empowers me to keep being there for both kids and adults every single day.

What was your biggest challenge to date either personally or professionally and how did you overcome it?

I’ve left a very lucrative position as a VP of a national art gallery chain because I didn’t see a manageable balance between life/work. I battled depression, had a few miscarriages, and was a complete, stressed out mess. I lost out on my earnings quite a bit, but now lead a more grounded and satisfying life.

What does leadership mean to you and how do you best inspire others to lead?

Leadership means leading by example. In my classes and at home I strive to be very open about my shortcomings and how I overcome them, and do my best to be understanding of everyone’s mistakes.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Yes, my mentor since high school, a great Expressionist artist and educator, Andrey Tamarchenko, saved me on multiple occasions. The most prominent and recent was an opportunity he offered me for an intensive 3-day workshop in Italy. After having a chance to dissolve into my surroundings through painting, (after a 10 year break from the craft), I realized that this is the way I can help other people stay balanced. I quit my job and opened my art school shortly after, which is now enjoying dozens of big and little clients and brings me joy every single day.

Was it difficult to fit your life into your business/career and how did you do that?

It’s still tricky juggling night classes and three kids. Mother’s guilt never leaves me. But I’m extremely organized when it comes to scheduling my projects on a timeline. I make sure I know exactly how each of my days is going to go, so I could be available to my kids when they’re home for dinner and weekends.

Did you find that as your success grew it became more difficult to focus on the other areas of your life?

Yes, being in the moment is a challenge with which I struggle daily. It’s a constant push to force my mind to quiet down, as at any given moment it has a slew of things it tries to solve simultaneously. I have to take official cell phone and computer breaks.

Can you share five pieces of advice to other leaders about how to achieve the best balance between work and personal life?

1. Be vigilant about your project management. Write out each to-do thing, even if it’s grocery shopping or laundry.

2. Make sure this to-do list involves chunks of time each week that are devoted to things that make you happy. For me it’s painting twice a week for 2 hours at a time, and visits to the gym and sauna twice a week.

3. Take cell phone/computer breaks at dinner time and over weekends.

4. Try to set up a time when you can be one on one with each member of your family, be it for a hot chocolate date, or a lunch, or vacation with one child at a time. This creates closeness and understanding and aids in thwarting sibling rivalry.

5. Give yourself more time than you think you need to complete a task, and praise yourself for every little accomplishment.

What gives you the greatest sense of accomplishment and pride.

The fact that I do what I love and my kids see that. They have a role model who’s living the life she carved out for herself, and they as a result gain more confidence in their decisions.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’d love to see people finally realize how potent art actually is. I’d love for schools to integrate more art into their curriculi, instead of cutting arts education. Art heals kids in so many ways: by giving them quiet time to reflect, to concentrate, to create new worlds. They’re growing deprived of their soul without arts education.

What is the best way for people to connect with you on social media?

My school’s FB page is: https://www.facebook.com/ThePleinAirArtAcademy/

My Instagram handle where my art lives is: https://instagram.com/diana_stelin_art/

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