From "Shadow Artist" to Artist

A conversation with Dipa Halder, software engineer turned full-time artist.

I’ve found that every traditionally “productive” field is full of creatives hiding in plain sight. As Julia Cameron says: “very often audacity, not talent, makes one person an artist and another a shadow artist.” I’ve been following Dipa Halder’s journey for a while now, and she’s one of these people that has embodied the rare courage to take the leap.

Before going full-time as an artist in 2023, Dipa spent years as a software engineer at Figma while nurturing an artistic practice, starting with digital illustration and expanding into painting and murals. From her Brooklyn studio, she now creates ethereal, abstract works in acrylics and large-scale murals for companies like TikTok. Her recent "Traversing" series explores carving your own path through uncertainty and reinvention.

I asked Dipa 30 questions spanning everything from her creative process to theories on life. She reflects on transitioning from tech to art, how immigrant family creativity flows through generations, why she loves the constraint of small canvases, her take on AI and creativity, and her belief that the energy you need only becomes available once you start.

I was struck by many things, including the intention and self-awareness with which Dipa is testing out her relationship to art — whether it’s meant to be a full-time career with financial success, or something else. Here's a deeper look into how she thinks about it all, and what makes her her.

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Behind the scenes: The response to the first issue with Neal Agarwal has been great and still going. I'm now getting pitches to feature specific people, which is making me feel like a journalist or magazine editor. Not what I intended, but fascinating nonetheless.

INNER MONOLOGUE

What’s your current state of mind and body?

I just came out of a big creative push for my spring ‘25 collection, so I'm currently in a state of creative recovery—mentally, physically, spiritually.

After being so focused and deep for months, this is a transition period during which I'm learning to be receptive rather than generative. I'm trying to resist the urge to immediately start the next thing and instead give myself permission to exist in the space between my ideas and refill my creative well.

What head-to-toe outfit feels most you right now?

Black knit vest, white baggy trousers, white leather sneakers, and some gold jewelry. Honestly, it might just be leftover influence from working in tech and being around all the stylish designers at Figma, but this combo is my go-to.

I wear this outfit a lot and I think I feel the most “me” in it because it feels like a blank slate while still being versatile and stylish enough for most occasions. There's something freeing about keeping everything neutral, relatively unstructured, and minimal. When my outfit isn't competing for attention, there's more space for everything else—my thoughts, my creativity, new ideas.

What does it take people a long time to figure out about you?

I like to think I'm not that complicated and I wear my heart on my sleeve, but I’ve been told I can seem really put together on the surface. Underneath, I'm actually quite chaotic and playful, and it takes a while for people to get to that part of me (or for me to feel comfortable enough to share it with them).

What’s something you’re borderline overconfident about?

I have exceptional manifesting abilities, or whatever you want to call it. I have this deep conviction that if I really set my heart on something, I can make it happen—and I have plenty of examples to back that belief up. Oddly specific, statistically improbable things.

The things I want, big or small, have a way of appearing when I put them out there. Some people might call it luck, some might call it magnetism, and others might call it delusion – but I think there's a real power in knowing exactly what you want and letting it be known outside of yourself.

There's that line from Paul Coehelo’s The Alchemist: "When you want something, all the universe conspires in helping you to achieve it." Maybe I'm overconfident in thinking the universe is not only rooting for my dreams to come true, but also conspiring for me, and so far, the track record speaks for itself.

What’s a trait you share (or don’t) with your family?

Two things! Creativity and yearning for a bigger life, though they've taken different forms across generations.

I come from a family of creatives, though my parents would never call themselves that. My dad is a gifted storyteller—it comes through in his poems and short stories, and this man has even mentioned that in another life, he would have been a writer. My mom has impeccable visual taste and transforms everything she touches: gift wrapping becomes an art form, DIY projects around the house emerge as small masterpieces. We're also Bengali, which is a culture with centuries of literary and artistic tradition that has produced some of the greats like Rabindranath Tagore.

There's something beautifully cyclical to me about how this has all unfolded. My parents took an enormous risk by immigrating here, leaving behind everything familiar for a chance at a bigger life. Now my sister and I get to take our own version of that same risk—choosing creative paths over secure ones to cultivate the gifts they never had the space to fully explore.

I think all of us have that instinct to reach toward something larger than what we were given. They just did it for opportunity; we get to do it for artistic expression. But it's the same impulse, which is a refusal to settle for smaller versions of what life could be.

What’s an instinct from childhood that still shows up in your life or work?

I have the classic eldest daughter of immigrant parents upbringing: money was something to save, not spend, because you never knew when it might run out. That kind of conditioning doesn't just go away when your material circumstances change.

I've been thinking a lot lately about how knowledge doesn't equal understanding—there are things you can know to be intellectually true, but that doesn't mean your body or heart has caught up yet. This scarcity mindset around money is one of those things for me.

I'm actually really proud of how I've moved through my life despite it: relocating to Brooklyn for my art career, leaving my stable tech job, choosing long-term abundance over short-term security. But my internal experience of making these choices is still exhausting. Every financially related decision I make requires this internal override and intense background negotiation with the old voice.

You have to prove to your nervous system, choice by choice, that this new way of thinking is actually safe, and that’s been a really important part of my journey these last couple of years.

What would you tell your younger self?

You’ll learn this the hard way, but it’s not worth making yourself smaller to fit into spaces that were never meant for you. Trust that restless feeling when something doesn't align, even if you can't fully articulate why.

Be patient with yourself. Finding the right environment, your people, your work takes time, but I promise it’s out there. The path that scares you but feels true is probably the right one.

THE CRAFT

When did you first start taking yourself seriously as an artist?

I've always known at my core that I'm an artist. The signs have always been there. I don't think there was a specific moment for me, but rather a gradual ownership over that truth—and noticing how much the world seems to open up each time I honor it.

Quitting my stable tech job to do art is obviously a grand declaration of taking myself seriously as an artist, but the buildup to that point has happened over many years. It felt more like finally catching up to something I'd been scared of rather than some grand revelation.

I often joke that my life would have been way easier if I wasn't an artist, but I don't see it as a choice really.

What draws you to the form you work in?

I've moved through a lot of different mediums and styles—classical oil painting, digital art, murals, and now my current fixation: abstract art. I’ve been calling this my "deconditioning" era, and abstract art has been incredibly healing for my perfectionism and control issues. There's no predetermined outcome to achieve.

I work primarily with water-diluted acrylic on raw canvas, which introduces another level of surrender to the medium. The work takes on a life of its own as water evaporates and color soaks into the canvas in unpredictable ways. It has its own agenda, and you have to learn to collaborate with that unpredictability rather than fight it.

I also love how abstract works are suggestive, but never prescriptive. When people look at my art, they bring their own experiences and interpretations to them. It's such a beautiful mirror—what they see often says as much about them as it does about the work itself.

What’s a constraint you secretly love working within?

Small canvas sizes! I keep saying I want to paint bigger, but larger canvases bring me immense anxiety. Smaller works feel so much more comfortable and approachable—they're safer to mess up in. Even if everything goes completely wrong, it's not this massive failure staring me down from across the studio.

If I had to be really honest with myself, I think they're training wheels for practicing letting go. I do plan to slowly work my way up to larger scale works, but there's definitely a part of me that loves creating small ones.

What part of your work feels most unnatural to you — and how do you handle it?

Making the switch from software engineering to fine art painting has demanded a fundamental restructuring of how I approach work. In my tech career, the structure was built around consistent, measurable progress: clear deliverables, logical problem-solving, predictable outcomes.

Art operates on completely different rules. It's wildly nonlinear, and it can't be forced. There are weeks when everything clicks and months of work suddenly makes sense, and months when progress feels invisible or nonexistent.

Some of my most "unproductive" days—when I'm sitting with my coffee or wandering aimlessly through the studio, letting my mind drift—end up being the most generative. Most of the work is happening beneath the surface and is illegible to others, and oftentimes myself.

I’ve also been thinking about how art might be one of the only paths that actually rewards you for being in tune with your truest self as opposed to the system. Which means I owe it to myself to really lean into that authenticity, even when it feels uncomfortable or unproductive by traditional standards.

When do you know something you’ve made is done?

Gut instinct, mostly.

There's something almost conversational about it, where the painting stops demanding changes. It settles into itself, becomes self-contained.

Of course there are certain principles I use to double-check my work: Is the composition balanced? Is there depth and movement? Does it have that overall feeling of harmony and resonance?

One area of growth for me: I have a tendency to overwork things, to keep pushing when I should stop. That mindset can suffocate good art and I've lost beautiful pieces because I just couldn't leave them alone.

I'm learning to build the muscle of stepping back, giving things space to breathe. Sometimes I'll walk away from a piece for days before coming back with fresh eyes. The work teaches you when it's done, if you're willing to listen.

What do you want your work to do to someone?

I want my work to disarm people and pull them into a state of pure presence.

There's this great quote by George Saunders from his book A Swim in a Pond in the Rain: “We’re always rationally explaining and articulating things. But we’re at our most intelligent in the moment just before we start to explain or articulate. Great art occurs—or doesn’t—in that instant." That pre-verbal, receptive state is exactly what I'm trying to create through my work.

I want my art to be a portal that allows people to access parts of themselves they’ve lost touch with or maybe haven't even met yet. Abstract art has this beautiful capacity to bypass our analytical mind and intellectual defenses and speak directly to something deeper.

My work often explores themes that challenge where we draw boundaries—thresholds, liminal spaces, dualities. It gently investigates the quality of these separations and asks whether they're as solid as we think they are. My hope is that someone also walks away questioning assumptions they didn't even know they had, or seeing something familiar from a completely new angle.

Is AI a tool, a threat, or something else to art?

I think AI is the great equalizer for skill, but that's never been what real art is about. In my eyes, it actually amplifies what's been true all along: art isn't about what you can make, it's about what you can't help but make. I've always believed that what we seek in art, more than anything, is the unmistakable presence of another human being.

I can see the lines blurring completely in mass media and commercial work, but at the edges—like in the fine art world—I think art that carries the weight and presence of human experience becomes more essential, not less.

AI is giving us a very real test of our ability to distinguish between what is simply impressive and what is alive. It forces us to ask: what is still worth creating when technical execution is no longer a barrier? What still matters when anyone can generate anything?

Mixing business and art is hard. How have you figured out the money part of being an artist?

It is really hard, and I'm still very much figuring it out.

I did have the privilege of building up savings from my tech career, which has allowed me to take this risk so full force. That buffer has been crucial because it’s allowed me to invest in discovering who I want to be as an artist without immediately subjecting my work to market pressures. I'm trying not to "optimize" for money too early on because I think it would stunt me creatively.

I'm also learning how to value my work — this is the first year I'm selling originals to collectors and that's been a really interesting exercise in self-worth. Something that’s surprised me here is that the numbers that felt uncomfortably high for me have consistently sold.

Something important I want to highlight: this leap is as much about figuring out who I am as an artist as it is about making it financially viable. The point of leaving tech wasn't to replace one paycheck with another — it was to see if I could design my life in a way that centers art. It's easy to romanticize the idea of being a full-time artist, and I needed to see what it's really like— how it feels, how sustainable it is— through lived experience.

What advice would you give to someone trying to do both?

My advice to someone trying to do both: only you can decide what kind of relationship with art you're willing to accept. For some people, having financial stability come from elsewhere is what frees them to make honest art. For others, earning money from their art is the only way they can justify the time investment. Both are valid. I'm still learning what that balance looks like for me.

I don't think it has to be so linear either — there can be seasons where you're all-in on art, and seasons where you're not. It’s more about the quality of your relationship to art than it is the outcomes, but the thing you absolutely have to protect is the joy it brings you. To me, losing that is a failure state.

SIGNAL & NOISE

How do you make meaningful things in a world full of “content” and competition for attention?

Part of being a good artist, in my opinion, is learning how to distinguish between what actually matters and what just happens to be loud i.e. separating what's meaningful from what's simply visible.

It's easy to get caught up in what will "perform well" algorithmically, especially when financial pressure enters the picture. You do have to consider commercial viability to some extent, and fine-tuning how your authentic voice can coexist with market demands is a very real and ongoing exercise every artist faces.

There is a real temptation to chase whatever’s working right now. Yet — One of my fundamental operating beliefs is that you can go the furthest when you stay truest to yourself. There's a specific exhaustion that comes from constantly shape-shifting to fit what you think people want. I call it type 2 burnout — you're not overworked, you're just working against your own grain. Many artists burn out not from the creative work itself, but from the performance of being an artist in the industry.

Where do you draw the line — if you even do — between what is art and what isn’t?

As for what separates art from content: content is designed to perform well, while art begins with the artist in conversation with the work itself. The audience discovers that conversation secondhand.

Content optimizes for immediate impact and quick comprehension; art rewards deeper engagement and reveals more of itself over time. I also think art is willing to risk failure or misunderstanding in service of its vision. Content generally tries to minimize that risk.

What’s your relationship to consuming vs. creating?

Consuming and creating feel like part of the same breathing rhythm to me. There's that Ira Glass observation about the taste-skill gap — how your taste largely develops through what you consume, but your skills develop through what you create. Both are essential: you have to fill the well before you can draw from it.

The consuming I do happily comes from wherever my attention naturally wants to rest — sometimes that's external inspiration, sometimes it's internal processing. Most of my art emerges from those unforced moments of attention.

What's interesting is how long the metabolization process takes; things I consume now often don't appear in my work for months, like they need time to transform in my subconscious first.

What do you consume happily vs. begrudgingly?

What I consume begrudgingly is the market research to stay relevant online: scrolling through what's trending to understand the algorithm, keeping tabs on what's performing well in my space. It's necessary but extractive rather than nourishing.

Platforms like Pinterest can also trap you in stylistic echo chambers if you're not careful. The algorithm gets so good at showing you variations of what you already like that you stop encountering the unexpected collisions that actually spark new ideas. The key is staying aware of the cultural conversation without letting it dictate what you make.

What kind of attention do you want — and what kind do you avoid?

Watching someone experience my work (especially in person) and connect with its story is one of the best feelings in the world. This is the kind of attention that feels meaningful.

Attention I don’t optimize for and try to avoid: going viral (500K+ views). When a post blows up at that kind of scale, the worst corners of the internet find you, your message gets distorted beyond your original intentions, and suddenly you're drowning in attention from people who don't actually care about your work. It's the difference between being seen and being consumed.

TASTE, THEORY, & TANGENTS

What’s an underrated sign of intelligence, charisma, or taste?

In general, I think society over-values traditionally masculine traits while undervaluing more canonically feminine, intuitive forms of intelligence. I actually think we might see that shift in our lifetimes because AI can replicate a lot of those logical, systematic processes, and so maybe we'll learn to value the signs that are less legible but equally, if not more, intelligent.

Some examples: somatic intelligence (the wisdom of listening to what your body is telling you), being able to read other people’s energy or auras, holding contradictory ideas without needing immediate resolution. They just operate on frequencies our current (but limited) systems don't necessarily know how to fully measure or value yet.

What’s your version of a perfect normal day?

I start all my mornings at a coffee shop and write for an hour.

It’s sort of a riff on morning pages from Julia Cameron’s The Artist's Way, and my perfect normal day definitely starts this way.

Other things my version of a perfect normal day includes in no particular order: deep work time in the studio, making progress on ideas I’ve been exploring. Something active to get my body moving, whether that's a run, pilates class, or just getting outside. Time connecting with other people. Learning something new.

I think my best days have included a small dose of each, and I also just realized that this describes most of my days now, which feels pretty incredible.

What’s a piece of media (a film, song, book, etc.) that changed how you think?

Big Magic by Elizabeth Gilbert is a book I keep coming back to, and one I get more from each time I read it. She offers a very whimsical lens on the creative process that has played an important role in shaping my worldview, though I'll caveat that you have to be at least mildly spiritual for it to fully land.

The core premise is that ideas are their own entities that choose humans to collaborate with. When you have an idea that won't leave you alone, it's because that idea chose you specifically to bring it into the world. If you're too busy or scared to answer, it will simply go find someone else, or in some cases, come back to you later in your life.

It's given me a deeper sense of reverence for the creative process and taken a lot of the pressure off because the responsibility as an artist then becomes showing up consistently and being brave enough to collaborate with whatever wants to emerge. I'm just trying to be the kind of person good ideas want to work with!

What’s something you’re a little jealous you didn’t come up with?

To the whole team behind Severance, thank you for your service. I think both the show, and the timing of it, are brilliant. I'm not even jealous I didn't come up with it myself, just grateful it exists.

What’s the last thing you recommended to a friend?

A red light mask! Specifically the Omnilux. One of my friends recently commented on how long my lashes look, and it's because I started using one about three months ago. It took a couple of months to see the benefits, but using one has noticeably helped my skin texture and tone. The longer lashes are just a very nice bonus. She went home and ordered one immediately.

How did your most recent real friendship come about?

I moved to NYC less than a year ago, and the vulnerability of starting over in a new city has created space for many new friendships to form in my life recently.

The first person that came to mind when I read this question was my friend Mari. We met at an event back in September of last year when I was just visiting to test the waters. A lot of our initial chemistry came from being at similar points in our lives—recently quit jobs in tech, slightly burned out, not fully sure where life was headed. But what really allowed this to bloom into real friendship was working on creative projects together and becoming trusted sounding boards for each other.

I know "collab" is such an overused word, but I genuinely think it's one of the most meaningful ways to form adult friendships. When you're both invested in bringing something into the world together, it creates a different kind of bond than just maintaining the friendship for its own sake.¹

A favorite memory that really deepened my friendship with Mari was when she flew out to Seattle with me in January to help with a mural I painted for TikTok. My other recent friendships have formed in similar ways—hosting floral workshops, throwing dessert pop-ups, creating experiences and art together.

What’s the best compliment you’ve ever received?

A friend and I had just finished a beautiful hike in Marin and were sitting at the top, catching our breath and taking in the view, when suddenly she turned to me and said, “Being around you makes my life feel so much more alive with possibility and beauty.” I still hold this one very close to my heart.

What’s one ‘working theory’ you have about life, work, or the world?

The strength and energy you need for something only becomes available once you actually do it. I think people index way too much on needing to feel “ready” before they start.

What’s your “endgame”?

At the risk of this answer sounding like a cop out, I want to push back on the premise of an “endgame” a little bit. I've just experienced, several times in my life, the way the goalpost moves almost immediately after I achieve something I’ve been working towards. When I was in tech, becoming a "full-time artist" felt like the endgame. Now that I'm here, that just feels like the beginning and now there's this whole landscape I couldn't even perceive from where I was before.

This isn’t to say I don’t have certain aspirations or hopes but I want to be ambitious in a way where I'm still open and curious about where my life takes me because I think the human imagination can be kind of limited sometimes.

I try not to attach too much to specific outcomes but rather focus on how I want to orient toward my life, which is to live bravely, to love deeply, to take the risks that really matter, and to work on the things I’m meant to be working on.

I loved exploring Dipa's story and craft through this profile and am excited for her next phase. You can find Dipa on X, Instagram, Substack, her website, or join her mailing list. Also check out her Spring 2025 collection "Traversing," and consider supporting her work.

If you enjoyed this conversation, share it with a friend or community that might enjoy it too.

1. I’ve always agreed with this — let’s all work on more projects together.