You’re just getting started with the Journey — and that’s exactly the right time to think about this.
The Journey gives you the path. A Working Artist Guide gives you someone to walk it with.
Four sessions with an artist who’s already done this work, who knows what it’s like to get stuck, to doubt yourself, to need a second opinion — someone in your corner as you move through the Flight Paths, not after you’re done with them.
You don’t have to figure this out alone. You never did.
What’s included:
• Four sessions with your chosen Working Artist Guide
• Your investment: $400
Here’s how it works: Claim your Guide Series below and you’ll receive an email where you can choose your guide and book your first session.
Barb Siegel
I help artists find their path, and keep going when obstacles appear. I understand how artists think — I am an artist. I’m particularly good with anyone who has a learning difference, ADHD, or who is smart but stuck.
My background is unusual, and that’s good. As an architect, I designed spaces people felt with their whole body. As a visual artist, I make work that invites people to see beyond the surface. For years I worked as a visual practitioner — drawing live on walls during meetings, capturing not just what was being said, but what was beneath it. I call this “listening under,” and I bring it directly into my work with you.
Deep work with my own family led me to study neurology and cognitive psychology, giving me practical tools for shifting the brain patterns that keep us from our full capacities.
James Drysdale
I’m a Scottish visual artist working mainly in acrylic and oil paint. Before becoming a professional artist, I worked in software development — which taught me that building a creative career isn’t simply about developing artistic skills. It’s about navigating uncertainty, making difficult decisions, and finding a path that genuinely fits who you are.
I enjoy helping artists untangle complex situations by connecting the creative, practical, and personal aspects of their practice. Whether we’re discussing artistic identity, marketing, galleries, pricing, or the next stage of a career, I help artists understand how those pieces fit together.
I particularly enjoy working with artists at points of transition — beginning the journey, returning after another career, or reshaping an established practice. These are often the moments where having space to explore ideas and develop a clear way forward makes all the difference.
Nicola Holgate
I’m a Cape Town-based sculptor and painter who knows this journey from the inside. As a long-standing alumna of the Working Artist Journey, I’ve worked with the course material for over a decade — arriving originally with no exhibition history and no certainty, and building my practice from there. That experience is the foundation of everything I bring to a fellow artist.
My practice centres on figurative and landscape work using handmade paper and paper-clay, materials I came to through experimentation. I bring one core belief to every session: there is no single roadmap. My job is to help you find yours — by listening for what you already know, cutting through the noise, and walking alongside you as you claim your place as a working artist.
I work particularly well with artists in transition: post-education and figuring out what comes next, self-taught and building confidence in how they talk about their work, or re-entering after a break.
Gillian McConnell
I’m an interdisciplinary artist, art educator, and picture framer. I create work that invites the beholder to question the face value of paradigms, beliefs, and narratives — using whatever medium fits the message.
My own journey with The Working Artist gave me a deep understanding of what I create and the bigger why behind it. In the last ten years, that shift has changed how I work with artists — away from teaching skills and theory, toward helping artists create meaningful, engaging work through genuine inner connection.
As an artist whose work is not easily categorised, I understand that one-size solutions don’t fit all. I love helping artists discover their purpose, create from their passion, and build real confidence in themselves as working artists.
Working With Your Guide
Before you purchase, please take a moment to read through how Guide mentoring works.
Your Guide
You’ll work with the same Guide throughout your series, so you can build trust and continuity. If, after your first session, you feel another Guide would be a better fit, simply email [email protected] and we’ll do our best to accommodate your request.
What to expect
Guide sessions are not lessons — they’re conversations about your work. Your Guide is here to encourage you, answer questions, and keep you moving forward.
Scheduling
Your four sessions should be completed within six months of purchase.
Rescheduling
Life happens. If you need to reschedule, please work directly with your Guide.
Between sessions
You’re welcome to email your Guide between sessions. Guides normally respond within 48 business hours.
Cancellations
If you decide not to use your Guide before your first session, we’ll refund your purchase less a $50 administration fee. Once your first session has taken place, Guide mentoring is considered to have begun and is no longer refundable.