Hustle Profile - Jaye Whitehead


Hustle & Flo focuses on young entrepreneurial people, women specifically as well as fun and interesting lifestyle bits I'm very happy to introduce the Hustle Profile of the month - Jaye Whitehead! Jaye is an amazing artist whom I had the privilege of working with when she designed the images for my very first hustling side project, my blog and I was very happy to find out that a few years later she had also moved to New York and was living with a friend of mine! So as a fellow young woman who is trying to strike a happy balance between working on side projects, paying bills and living a great life I thought I would feature Jaye as my first Hustle profile of the month! 

Have you always wanted to be an artist? 

No, it just happened. When I was a kid I really wanted to be a vet. I used to sneak into the garage and play with the spiders behind my dad’s old wood piles. I was such a creepy child.

When was the first time you considered yourself an ‘artist’?

If I’m being honest, I don’t think I ever have. I started painting when I was  4 or 5, like everyone else; but I never stopped. What’s interesting is you start creating things, or showing interest in a medium...drawing/painting whatever,  and people say “You are an artist” but you don’t feel like an  “artist” just feel like you.

I remember being placed in my graduating thesis class feeling completely fraudulent. All of the students were so eccentric, smart, mature, well read, insightful and I kept wondering when they were going to realize I wasn’t supposed to be there.

The Purity in Overexposure Show

The Purity in Overexposure Show

For me personally, there must be some sort of pressure associated with the word artist. I feel as though I am not qualified to use it yet. I always say “I want to be a painter”, and friends correct me “You are a painter”. Yea, no, not yet.

When did you decide to seriously pursue art as a career?

The first time I saw strangers’ reactions (positive and negative) to my work was incredibly moving. The first time I saw my work in a gallery…truthfully; there were a lot of small moments. I cannot image pursuing anything else.

How do you balance your art with supporting yourself, paying bills etc?

I plan and structure my time as if I have two jobs. I decided a while ago the only objective aspect of my success that I could control was my ability to work hard. You have to accept there will always be someone in the world who is doing your craft better, and more effortlessly than you are doing your craft. You do not have to accept that they are a harder worker than you are.

The Purity in Overexposure

The Purity in Overexposure

Tell me about how your style evolved.

My grandmother is a painter and taught me the basics of watercolor when I was very young. I wanted, and still, want, to be exactly like her, so I tried to imitate a lot of things she did.When I got into college I started painting in oil, mostly traditional portraits. I thought oil painting was the great love of my life. Until I picked up a watercolor brush again. Something clicked.There is a level of honesty in watercolor that cannot be duplicated in any other medium. You have one shot to get it right and zero room for error. I learned the technical rules and then began to break them. No more clean transitions… I began breaking space into planes and then further into geometric shapes. Looking back through my work over the years this has always been my aesthetic, watercolor just lent itself best. 

A lot of your art focuses on these kinds of whimsical views of people, tell me about that. How did you land on that?

I have always painted people- girls, mostly. The presence of the human face is powerful to me. The androgynous woman. Forcing eye contact between your viewers and your work is disturbing and direct and I love it.

Do you have a favorite/special piece that you’ve created?

A series I recently started about our seemingly disparate interests and my personal subconscious ties to my femininity. The first painting is about my grandmother who is a brilliant and completely nonsensical woman, and everything I want to be in life. Her life has gifted me with a lot of really fascinating imagery about femininity, dead birds, and rocking chairs etc.



What would you consider that your best piece?

I am learning to be more vulnerable in my work. I think this piece (above) is the closest to transparency I have come so far.

How long do you typically spend on a piece?

Usually, the large portraits take 8-10 hours. I try to finish them in one sitting. I think that detail is important to the nature of the pieces. They are large paintings but they are meant to be snapshots/ quick glimpses of a person.

What do you find most difficult about balancing work and art?

My roommate can testify to this- I get very little sleep. At work, my art director tells me very frequently how tired I look. Worth it though, so worth it.

Luke Austin Show

Luke Austin Show

Do you sense any competition between artists, especially in NYC where there are so many artists trying to make a living from their art?

Personally, I have felt only the opposite. The artists I have met thus far have been incredibly generous and kind. I am learning confident professionals champion each other’s success…there is room for everyone who is willing to work for it.

So right now you’re working full time and creating and selling your work as a passion project. What’s next (a year from now, 5 years from now, etc)?

Everything is wide open! No plans or self-judgment. I will keep painting and following where the path leads. (This is the yogi in me talking) *Namaste*

Where can people reach you if they have questions or would like to buy your art?

On my website, my Society6 shop or email me at

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