artist Damian Osborne beginning an oil painting in the studio
Painting in my studio.


Beginning an Oil Painting

– My 5 Rules

by Damian Osborne


Before even beginning an oil painting, I have 5 rules as an artist for this year. Hopefully I will maintain them strictly for the rest of my life.

Art isn’t easy. While you don’t really have a boss to report to for work, it can definitely be exhausting to keep pushing yourself.

The many voices inside can gang up on you. Sometimes you have to dig really deep to get working on that painting, to find your inspiration, to give your best 100% of the time.

To push your art further than your last piece.

And all the motivation has to comes from within. And it can get pretty lonely being stuck in your studio all day, listening to the internal dialogue.


5 Tips for beginning an oil painting:


  1. Don’t be afraid to start

  2. Paint your best always

  3. Use the best materials you can afford

  4. Paint/draw from life as much as possible

  5. Try to be as original and authentic to your own self and style as possible


1. Don’t be afraid to start

Perhaps you’ve never begun an oil painting before. How exciting! 


“Every artist was first an amateur.” — Ralph Waldo Emerson

I don’t need to reach some point or achievement in my life before I allow myself to feel like I’m worthy. Too often artists put themselves down. I know I do.

Sometimes we are really hard on ourselves and don’t recognise anything special in ourselves. Undercharging just to make a sale? No more.

We are also our worst critics. I shudder when people see some of my older stuff. But I also sometimes swing to the other end of the spectrum and wonder why I feel so deflated when I don’t receive positive feedback.

Either way, it shouldn’t matter if I’m trying my best.

There’ll be days when my painting or drawing is off, and my earlier stuff is always going to be more crap.

But when I believe in myself, and the small, daily incremental steps it takes to achieve mastery, then I start opening the channels to produce my best.

Sometimes the improvement is so gradual that you hardly notice it. And it may even feel like you’re not improving at all!

But the only thing you can do is to believe in yourself and keep on diligently working on your art everyday. Then you notice the huge difference between this year’s work and the year previously.

See also: Where Do Artists Find Inspiration?, where I outlined some of the best sources for your artistic inspiration, to encourage you to get cracking and start painting!


2. Paint your best always

Before beginning an oil painting, I try to visualise it as being better on many levels than the previous one. I don’t think it’s necessary to spend more time on the next painting; in fact, as one improves, time isn’t always the most important factor.

Some of the quickest paintings or drawings show great confidence and mastery, while others that took forever seem laboured and stiff.

Some of my older paintings I kept working on and working on to try and resuscitate some life into them. I did learn a lot, but also at some point, I started wasting my time on them and I should have just thrown them away.

I always do try to finish a painting. And I’ve learnt a lot of interesting things from paintings that I’ve not cared about. But there is also a point where it’s better to just start over.

I write down the things that I’ve learnt from my painting in a notebook, where I went wrong and how I can improve, as well as ideas for future paintings.

But generally, my rule is to put something really special into my art so that I step back from it feeling really proud of myself for producing my best.

I think it’s important to have that intention before even starting a painting. When I believe that I’m good enough and my intention is to produce my best, painting becomes like a prayer and has something like ‘soul’. 


3. Use the best materials you can afford 

Generally, I haven’t had any issues with cracking or discoloration in my paintings because I’m always conscious of using the right techniques and materials. But it goes back to producing your best.

To produce your best paintings that will hopefully last for generations, you need to use the best materials that you can. To skimp on materials means you skimp on investing your artistic soul into the art piece before even beginning an oil painting.


beginning an oil painting with the best quality paints
Beginning an oil painting with the best quality paints.


4. Paint/draw from life as much as possible

Painting from photos is no substitute for painting from life.

It becomes too easy to copy every little detail from a photo, having no focal point or area of interest.

The eyes also see very differently from the camera lens. We have two lenses and see things more spaciously whereas a camera has one lens and flattens the image.

Relying on painting from photos is detrimental to your skill as an artist, especially as a beginner.

And I’ve never been interested in producing hyper-realistic paintings from photos. That is simply being a human photocopier, albeit a skilled copier. See: Why you should draw from real life, not a photograph by Ingrid Christensen.

I don’t think there’s anything wrong with the limited use of photos as tools of reference and inspiration, and sometimes a photo is all you have to work with.

Sometimes birds, animals and people can be really difficult to paint from life as they are always moving. 

But at this point I want to push myself to improve my skills and personal style and expression.


Pen drawing of landscape before beginning an oil painting, Damian Osborne
Drawing from life is really important.


My landscape paintings are pretty much always painted ‘en plein air’ as the French expression goes. Still life is also a wonderful practice for painting from life and for gaining understanding.

Study things visually constantly. I know how birds behave or perch or how their feathers overlap because I was always fascinated with them, and kept species as a kid.

Draw people, landscapes, things, nature from life. Scribble in a sketchbook.

Painting yourself in the mirror is also one of the best practices when you don’t have a willing model. Chloroform is helpful for unwilling models. But in truth, a life drawing class is the best investment for your artistic training.


Plein air painting in the field, easel in landscape, Damian Osborne
Plein air painting in the field.


5. Try to be as original and authentic to your own self and style as possible

Originality is a difficult one. How do you find originally when there are so many amazing artists and influences around one? I have a few folders on my computer and phone where I save photos of artworks by contemporary and old master painters.

If it’s a painting that makes me go ‘wow’, I save it and try to work out what is about the painting that inspires me so. From Google searches, to Pinterest, Instagram, Twitter, Facebook art groups, I’m surrounded by other artists’ works every day.

You could ask yourself, how can one try to be original in the face of so many thousands of original artists? I think that is a true challenge.

Just like copying from photos, there are also a lot of copier artists who hardly come up with anything new under the sun; who are hardly saying anything new or anything in a fresh way.

That is the point of art. To be creative. To be fresh. And share our world and our vision.

It’s good to have a lot of influences, ideas and knowledge. But it’s also important for an artist to produce their own ideas and techniques.  Following too many artists constantly can be distracting and then we end up procrastinating instead of painting.

There are a few billion people on this earth and yet we are all pretty much original specimens. Many of the same universal human experiences we share and connect over, and yet they are unique within us because we are all unique.

Likewise, I think when an artist shares their world authentically, paints from the core of who they are, believe in the space they occupy and paint their best, original art is thus created.

I wrote this rather in-depth blog post Being Authentic as an Artist (and Not Stressing About Selling), where I thought long and hard about how to be more authentic and original as an artist. 


Thanks for reading, and if you have any tips or painting suggestions, please share them below. And please don’t hesitate to contact me if you have any questions. 


Check out my figure paintings here.


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2 thoughts on “Beginning an Oil Painting – My 5 rules”

  1. Thanks Damian. You’re one of the most real artists out there at the moment. I respect that, and that you share your knowledge all the time. A damn fine artist to boot!

    1. Awesome! Thanks very much and thanks for the follow! I still feel like I’m at the beginning stages of this whole art thing even though I’ve been painting since a kid. Have a great day.

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