The act of creating a portrait is an emotional one.

It goes far beyond capturing a mere likeness; it delves deep, exposing their character and yours.

A finished portrait may exude confidence and calm, but the journey of its creation is often a complex maze of doubts, fears, and self-criticism for the artist.

We can overthink the composition or the medium choice. Then we question, maybe we should have studied drawing a little longer. Maybe we should start when we’ve got more time?

These are often (well-constructed) excuses based on two main insecurities.

1. The fear we won’t do the subject justice
2. The fear of social ridicule

I’ve just started a portrait of my nephew, and before I began the process, those same butterfly feelings bubbled up.

The first fear is dealt with more logically now, compared to when I was first starting out.

I still question, ‘What painting method will I use?” “Will it look like him?” “Will I overwork it?

But it’s the second fear that seems to hit me the most and as hard.

Will someone else judge your portrait attempts and deem you a ‘bad’ artist?

Probably.

But I’ve learnt this can happen if you’re a professional artist with years of painting experience behind you as easily as if you’re an absolute beginner.

On your first driving lesson, if someone judged you as being a ‘bad driver’, you would have laughed at them and said, ‘I know! It’s the first time I’ve ever tried.’

No blame, no shame. That’s the essence of successfully progressing as a portrait painter.

The Challenges

If you’ve overcome the fear of actually starting, painting a portrait comes with different challenges to other subjects.

First, there is the technical challenge of creating a three-dimensional form on a two-dimensional surface.

Then, the colour mixing challenge of expressing realistic skin tones, hair and features.

And finally, the realism challenge of creating a likeness to the sitter.

So, how can I help?

Here are three solutions that I’ve found can really help overcome insecurities when painting portraits:

1. Build Confidence Through Practice:
One of the most effective ways to combat insecurities is through consistent practice.

Many of my paintings are just for personal use and not intended for public viewing. The more I practice, the more my skills will improve, leading to increased confidence in my abilities.

2. Focus on the Process, Not Just the Outcome:
Insecurities often stem from fixating on the end result.

Focus towards enjoying the creative process itself. Self-expression, exploration, and experimentation. When the process becomes the primary goal, you can find fulfilment in your work regardless of external judgments.

3. Seek progress, not perfection:
Imperfections are a natural part of the creative journey, and learning any new skill will be a series of jumps in progress and self-reflection on how much there still is to learn.

When following a course, the aim is just to follow the steps.

“I can’t see a way through,” said the boy.

Can you see your next step?

Yes.

Just take that said the horse.”

The Boy, the Mole, the Fox and the Horse, Charlie Macksey

I have two portrait courses that can help guide you through.

1: Acrylic Portrait Course (suitable for beginners)

Acrylic Portrait Course

The focus of this course is simple, natural colour mixes to help you create realistic skin tones.

The concern for many beginners is that portraiture feels too challenging and would be above their current skill level. So I’ve designed these portrait courses to be as user (and fear) friendly as possible.

We learn about lighting, colour theory and create colour swatches before even starting the portraits. There are line drawings to work from, and we start slow with just a four-colour painting palette.

(You can see some student results here.)

So, will the course be a challenge?

Yes

Will you feel like a ‘portrait imposter’

You will, but only until you start painting.

If you stick to the lessons and follow the steps, you’ll gain huge confidence in what is achievable.

• Creating Realistic Skin Tones, learn the secrets behind mixing and applying skin tones that appear natural and lifelike.
• Gain insights into the nuances of capturing subtle transitions in the skin, from shadows to highlights.
• Material recommendations.
• How to master the Zorn Palette, the amazing power of a limited palette.
• Colour theory, colour strings, and palette choice.
• Lighting theory to create accurate colour mixes for your portraits.
• Paint application & brushwork, from scumbling to palette knife.
• Poster study using a more direct Alla Prima style.
• Includes over 4 1/2 hours of video instruction, three self-study painting assignments, materials guide PDF, and downloadable reference images to paint from.

2. Oil glazing portrait course (suitable for intermediate or have some drawing experience with portraits)

Oil Portrait Glazing Course

This course is a more advanced portrait course teaching a classical painting approach based on multiple layers of painting (called in-direct painting)

It needs patience and more time commitment.

It’s a method that seems counterintuitive. Paint your portrait first in black and white and then apply colour on top.

The art of combining the classical technique of grisaille (black and white) with the mesmerizing effects of colour glazing creates stunningly lifelike and captivating portraits.

• Mastering Grisaille Technique: Learn the foundation of grisaille painting, using monochromatic tones to create a strong value structure and achieve realistic shading.
• Creating your own painting medium (traditional and modern materials)
• Completing a value study painting using the planes of the face.
• Discover the art of colour glazing, layering translucent colours over your grisaille underpainting to achieve luminosity and rich tonal variations.
• Explore the magic of transparent and semi-transparent glazes to enhance the vibrancy & learn about glazing mediums.
• Completing two head portrait paintings.
• Includes over 6 hours of video instruction, two self-study paintings, materials guide PDF, and downloadable reference images to paint from.

P.S. – If you have done either of the portrait courses and have any encouraging words or testimonials for other artists who might be at the point where you were before starting the course, drop me a comment below!