Daring Creativity – Dare to Embrace the Confidence Rollercoaster w/ Kelly Anna

Host: Radim Malinic
Guest: Kelly Anna (London-based artist & illustrator)
Date: February 16, 2026

Overview

This episode of Daring Creativity explores the winding, often uncertain journey of creative identity and confidence through the candid and insightful lens of London artist and illustrator Kelly Anna. Host Radim Malinic dives deeply into Kelly’s story, discussing her sources of inspiration, the realities of a freelance creative career, the constant evolution of artistic style, and the balancing act between business and personal vision. Kelly’s narrative, rooted in movement, dance, and color, is a vivid testament to embracing the creative rollercoaster, finding validation, and the ongoing quest for authentic expression.

Key Discussion Points & Insights

1. The Emotional Value of Artistic Connection

• Kelly on Validation: As an artist, Kelly describes the feeling when someone connects enough with her work to purchase it as a profound human exchange.
  • Quote: “That feeling… that someone else sees what I see and they connect with it…” (00:08)
  • On art in the home: “When people have artwork in their home, it almost becomes part of their DNA.” (01:00)

2. Defining Your Creative Self

• Uncertain Labels: Kelly struggles with self-definition, using ‘artist’, ‘illustrator’, and ‘designer’, while acknowledging that her work, built on movement, wellness, and female empowerment, is constantly evolving. (03:29–04:10)
• The ongoing process: “It's a constant figuring out because things change and I get really bored … I want it to change.” (04:37)

3. The Confidence Rollercoaster

• Tied to Freelance Life: Kelly unpacks how confidence is cyclical, often “up and down” depending on external factors like commercial success.
  • Quote: “You get more confident with things, and then you lose the confidence, and then you get it back and then you lose it.” (04:37)
• The Commercial Trap: Confidence used to hinge entirely on job flow, but now she finds regeneration through personal projects:
  • “The only way I really get my confidence back is when… I’m going to work on my own stuff.” (06:31)
• The personal nature of art makes separating creative self-worth from commercial success particularly hard. (06:31)

4. Striking a Balance: Art vs. Business

• Freelancer as Business Owner: The conversation dissects how being a creative is inseparable from being a businessperson.
  • “If you see yourself as a business… your worth should be going up as well.” (10:07)
  • On work-life stages: Early in her career, Kelly took more jobs, but with experience, she values alignment with her own values over taking everything.
• Quote (Radim referencing Ozzy Osbourne): “As soon as you start booking your own gigs, you’re a businessman.” (09:33)

5. Beginnings & Influence

• Family Roots: Kelly’s father, an artist who didn’t pursue art professionally, was her toughest critic and foundational teacher.
  • “He’d teach me to sketch, but I wasn’t really allowed to look down at the paper… focus on your subject.” (16:41)
• Movement & Color: Her upbringing in a family of ballroom and Latin dancers profoundly shaped her visual language. Sketching dancers instilled in her an obsession with movement, later synthesized in her vibrant style.
• The role of color: “Color is a language that everyone understands.” (16:41–19:16)

6. Finding Her Style

• A Path of Blending Passions: Kelly blended her dance and sports background with art, eventually developing her expressive, recognizable style by consistently sketching dancers, gym-goers, and athletes. (23:10)
• “Fashion illustration is about exaggerating forms—my style is an amalgamation of all that.” (23:10)
• The struggle to “choose one path” (art or dance) was resolved by merging both into her creative output. (26:27–26:45)

7. Patience & Blind Faith

• Years of Development: Kelly spent years “behind closed doors” developing her work before it clicked.
  • Quote: “There was literally two years where I was just working and trying things, and it just wasn’t clicking at all.” (29:35)
  • The moment of breakthrough: Landing her first Nike commission after years of persistence (29:35–30:23)

8. Validation & Connection

• Why We Create: External validation (a client, collector, or admirer) is pivotal, but the deepest joy is connecting through art.
  • “You can pick yourself up as much as you like … but to have someone outside want your work next to their brand name, that’s another level.” (33:54)
• Art becomes part of people’s lived environment and identity.

9. Navigating Style & Commissions

• Niche vs. Ubiquity: Her unique style makes her easy for the right brands to find, but can limit broader applicability.
  • “You can’t be everywhere at once, I wouldn’t want to be … It’s important to know what interests you and connect your style to that.” (39:16–41:09)
• Building Community & Reaching Brands: Her Rapha collaboration (cycling apparel) was a “full circle” moment, tying back to a community project she’d started years earlier. (41:53)

10. Staying Inspired & Evolving

• Personal Practice: To stay creatively alive, Kelly experiments with new media, makes time for spontaneous sketching, and seeks out fresh influences.
  • “Trying different mediums… experimenting with mediums is the most exciting thing.” (43:49)
  • Example: Charcoal birds that began as a personal obsession ended up in her commercial work. (45:12)

11. On AI and the Future

• Kelly approaches AI with curiosity but emphasizes irreplaceable human connection and valuing the “mistakes” of real collaboration.
  • “I love the fuck ups … how we mess things up and go, ‘actually, I really like that.’” (47:12)
  • She uses AI for mockups but chooses human partnership for meaningful projects.
  • “People are yearning for human connection. I don’t think that will ever go.” (47:12–50:20)

Notable Quotes & Moments

• Kelly Anna:
  • “I think it’s a human connection thing for me as well. It’s like someone else feels what I feel, and they felt what I’m trying to get across. That’s what I find really beautiful.” (00:28)
  • “I’ve been freelance now for coming up to 10 years. I haven’t figured it out, and I don’t think I ever will completely.” (04:37)
  • “For me, I have to say 50% of what I do is business and the rest is, yeah, creating.” (10:07)
  • “I always say, like, when someone buys a piece of your work and puts it in their home… it becomes part of their DNA.” (01:00)
  • “I love seeing artists and creatives pivot… even though you will not get the validation you want online, I just know that I am there fangirling you on because I love it.” (38:03)
  • “Color is a language that everyone understands. Wherever you are in the world, everyone understands color.” (16:41)
  • “You just became your person who wanted to be your own artist … The secret breakdancer is a great story.” (28:09)
  • “I don’t know how I’ll use [AI] moving forward… but something is missing in that for me right now… I love the fuck ups.” (47:12)
• Radim Malinic:
  • “As soon as you start booking your own gigs, you’re a businessman. And I feel we are in the business of creativity.” (09:33)
  • “I have known about you and your work for as long as you’ve been out there doing your stuff… your corner of the internet, your corner of the world is colorful and it’s so joyful.” (53:11)

Timestamps for Important Topics

• Art as Human Connection & Validation (00:08–01:09)
• Defining Artistic Identity & Its Evolution (03:29–04:37)
• The Confidence Rollercoaster & Freelance Life (05:08–06:31)
• Business Versus Creative Practice (09:33–11:10)
• Family Influence, Dance & Color (16:41–19:16)
• Journey to Finding Her Style (23:10–26:27)
• Breakthrough After Years of Blind Faith (29:35–30:23)
• Navigating Commissions & Managing Personal vs. Commercial Alignment (39:16–41:09)
• Personal Practice & Influence (43:49–46:05)
• Approach to AI & Meaningful Collaboration (47:12–50:20)
• Closing Reflections on Creative Evolution (53:11–end)

Memorable Moments

• Kelly’s story of being a “secret breakdancer” in the indie-dominated art school scene (26:27)
• Describing how her “obsession” with birds and charcoal sketching made its way into a Paris shopfront mural (45:12)
• Her refreshing take on AI and the irreplaceability of human creativity and error (47:12)

Tone & Style

The conversation is candid, warm, and full of mutual respect. Kelly’s openness about her struggles, family history, and continuous process of self-discovery are met with Radim’s deep curiosity and appreciation for the messiness and magic of a real creative life.

For Listeners

This episode is ideal for anyone who finds themselves on their own creative journey—especially freelancers, artists, or anyone wrestling with confidence, commercial pressures, or how to evolve while staying true to their vision. Kelly Anna’s story reminds us that fulfillment often comes not from perfection but from embracing uncertainty, evolving continuously, and daring to connect through creativity.