First Attempt at Oil Painting

This post is about my very first attempt at oil painting. Well, really first ever attempt at any type of painting, which to my surprise was actually done this past weekend. I feel like I’ve been talking about this for years, but I’ve had “learning to paint” in my back pocket as a long term goal for quite sometime. It’s always been an undefined, vague goal though – I might occasionally say I’d like to learn when I retire, or possibly take a class when the kids graduate, something along those lines. I’ve kept this idea at arm’s length for a couple of reasons. First is that I am a creature of habit, and easily fall into routines. Drawing with colored pencils and then sharing them on this blog, for example, is a pretty well-established routine of mine. Second is that I’ve viewed the barrier of entry, in terms of skills, knowledge, and materials, to be too daunting to take a real step forward.

My painting set up. I used my kids’ easel, a chair no one cares about, the supplies I bought, and lots of paper towels.

That all changed this past weekend. And it happened very suddenly, like so many of my random inspirational moments seem to. Late in the week, I was watching various YouTube videos on painting, which is really not all that unusual. But for some reason, this time I had the thought, “hey…I think I can do that.” I chewed on that notion for a bit, and finally decided that it was true. Not that I could hypothetically do it someday, but that I could do it with my current skillset right now. For some bizarre reason, I decided then that the primary thing I was lacking was materials, but that the other barriers weren’t relevant anymore. This is likely some combination of irrational, foolish, or naive, but I have to admit I’m prone to occasional bouts of foolhardiness.

So, Thursday and Friday, I placed some Amazon orders, and Saturday journeyed to a craft store with the kids to round out my equipment. Normally I would probably go through Blick Art Supply or Cheap Joe’s, but I wanted to strike while the inspirational iron was hot. And then Sunday morning, with my coffee at the ready, I took the plunge! I started with very basic outline on the incredibly thick and textured oil painting paper (or is it more of a board?). And once the paints and workspace were set up, I leaned heavily into lessons gleaned from the many oil painters I’ve watched such as Bob Ross, Alpay Efe, and others to start filling in this painting.

At first, I struggled a bit with mixing paints. Even though ol’ Bob Ross himself has repeatedly warned of how powerful blacks and reds can be, I still underestimated how far a little can go. The entire painting took just under three hours, which is definitely longer than my pencil drawings. But that does make sense. I have to say, the shock of how happy I am with the final result somehow overrides my surprise that I even tried this. I’ll share the portrait first, then talk more about the process:

The final result of my first oil painting. Oil paints without solvent on textured paper.

I opted to go with a solvent-free experience, so no wet-on-wet/alla prima like my Happy Little Tree TV mentor always did in his show. I love the look and concept…but I also have a health history that warrants caution about carcinogens and other such things. In the future though, I may try some non-toxic mediums like linseed oil to thin paints when needed. After my rough outline, I somewhat followed the approach that Alpay Efe uses for his portrait paintings – starting with more difficult details (like eyes, mouth, and parts of the nose) to ride that initial burst of inspiration and excitement.

After getting major facial features, then I just sort of mixed and painted. I know that sounds like oversimplifying, but that’s exactly how it felt. Very natural and normal. I think that the last five and half years I’ve spent regularly drawing actually helped me here more than I expected. My style of colored pencil blending is very heavy, and almost resembles painting at times. When painting with oils, I followed similar patterns and movements, following shadows, musculature, and color variants.

I actually found oil paint to be much more forgiving than colored pencil! That was yet another surprise in this experiment. Although pencil can be erased, it’s much harder to do so (and paper’s tooth is destroyed) when it’s layered as thickly as I prefer. Oil painted areas were relatively easy to fix when I messed something up. I also found the blending, once I got past the initial learning curve, to be easier and more satisfying. Granted, this is only one painting – I hope I always find paint mixing and blending to be so enjoyable.

Usually, I talked about what went right and what went wrong in this section. Well, I keep saying the words “surprised” and “shocked,” but I am both of those things when it comes to how satisfied I am with the final painting. I know it sounds like hyperbole at this point, but I really expected something much more rough looking. Of course, there are always areas for improvement – I need to work on better defined color areas for hair, more precision in the eyes, and some other things. There are also off-the-page areas that I need to research more thoroughly, such as how to clean brushes and palettes. But, in totality, much more went right than I ever could have imagined.

I’ve embedded a progression video here with some narrated discussion. I’ll admit, this video is not great. I was so hyper-focused on learning and engaging with this new experience, I completely forgot some old lessons about filming (like locking focus on the paper). Also, the camera angle is absolutely terrible, so that’s another aspect I need to work out. But at least I managed to record/capture something, even if it’s perhaps not useful.

So, let me come back down to Earth here for a second. Obviously, this is no masterpiece – it’s a beginner’s portrait from an amateur who’s literally trying to learn from watching videos. But, I like the result a lot, which is very encouraging. I love the unique textures and visible paint flow often found in oil paintings, and this thing that I actually created has that! That’s really so thrilling to me – to see something I’ve admired in other art in my own work. I feel a sense of excitement about the prospect of doing this again, which is quite significant to me. Yet another surprise, that I’d feel this way about painting.

If you’ll pardon some cheesiness, I really get now what Bob Ross meant by “The Joy of Painting.” I mean this very sincerely – it really is a joy to do, and I can’t wait to get back into it. Unfortunately, because setup and cleanup are so much more involved, and life’s schedule always seems to be full, I probably won’t be able to paint again for a few weeks. But I’m definitely looking forward to the next one!


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  • I hope you’re still painting. I love the look and feel of your self portrait. Beautiful!

    • I appreciate that Kelly! I am still painting and still learning as I go – I am a bit behind in terms of actually writing blog posts about everything though. Hopefully I can catch up at some point

      Thanks for checking out the artwork and for the kind comment!

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  • First off – congratulations for getting that monkey off your back. My paints languished unused in the drawer for several months (potentially over a year) before I decided to paint something other than a colour test card.

    Now to this painting, I love how it’s still recognisably one of your works despite the different medium and method.

    And of course, why not start at the hardest subject – oil portrait painting. You removed the armbands and rather than getting in the shallow end you headed for the diving board. Well done.

    Three hours is amazingly quick as well. I often do 1-2 hours slots and there’s no way I’d be looking at something like that within two sessions… King Procrastinator here.

    I am amazed. Impressed. Inspired. Encouraged. Well done Jon 😀

    • Man…I’m really flattered and humbled that you’d say that. Coming from someone like you who is skilled in so many mediums and subject types, that made my day. Really, thanks for that!

      So, would you consider oils harder to work with than watercolors? I had thought about both, but watching videos of watercolor artists, for some reason I couldn’t wrap my head around some aspects of it. Like, how do you control the looseness of the paint? It seems so wild – but maybe that’s the fun of it too, eh? Although oil paints vastly exceeded my prediction for how messy they would be, I still felt some degree of control in terms of how I could apply them

      I’m curious, what was your first painting? Although I’ve been following your art for a long time, I don’t recall ever seeing you as a beginner in any area

      • Well that’s very kind of you to say – made my day that you said that about me as well 😀

        I’ve never done oils so I can’t comment on whether it’s harder than watercolour.

        In fact, for some reason I’d got it in my head early on that watercolours was the easiest medium. After all, that’s what the kids use right?

        Turns out I was wrong about that, or in fact I’m not sure if “harder” should be the right term. It’s different and because there’s no Undo feature you need to maybe have a bit more planning going on before making a mark.

        From my watercolour world I hadn’t looked at acrylics or oils because I considered that was for the serious guys and I’d need to stock up on various bottles of solvents, piles of rags, etc. I’d dismissed it as a possibility. It was only a chance comment that someone mentioned acrylics were water-based and I was like “wait, what did you say?”. I had my order in before the day was out I reckon 😁

        As mentioned, despite getting the paints and doing a colour test card straight away I think I found the prospect a bit scary and so they went in the drawer whilst I made up excuses and got back to my comfort zone. Now I’d say that the acrylics are my main medium, it seems to suit the car art better than watercolour generally though I will still be using watercolour frequently. I do like the permanence of acrylic on canvas – plus there is some potential for that “Undo” feature so it’s ironic that my comfort zone has shifted now.

        As you asked, this was my first from March 2020. I still have that tiny painting on the shelf right next to me, it watches over my art desk constantly.

      • I don’t really have a clue what I’m talking about on this topic, but I have this notion that all types of painting might be more difficult than drawing with pencils. Although I’m surprised so many skills/habits seemed to translation from pencil to paint, it just seems like there’s so many more pieces to account for with painting. I’m only two paintings in at this point (finished another this weekend), but what you said definitely seems right to me about having to plan.

        So, acrylics are water based? Haha I’m learning more every day. You like it because it’s a little more flexible maybe, and that you can more easily fix mistakes? I’m going to spend more time getting used to oils, but I definitely want to keep learning about other types.

        Man, that Notorious BIG is great! What a first painting you had there. How in the world did you get such detail in a small area like that? Now that I’ve tried to paint, I see how hard it is to capture finer details…that perspective makes this tiny art you did that much more impressive.

      • Ahhh, okay interesting. I’ve been trying to study up a bit more (via youtube painters) on mixing different types of paints. So, do you ever combine acrylic with other types? This guy Alpay Efe uses acrylic when he needs a fast drying base layer, then goes over it with oil:

        Interesting strategy!

    • It’s a lovely artwork Jon…. You have put your full heart and soul in it and it comes across beautifully 😍

      • Thanks a lot, Sharmla! I gave it my best shot – I was definitely worried in the early stages, but fortunately the paint was forgiving enough to get by as I learned some basics.

  • Congratulations! You should be proud! That’s a very nice portrait and it captures depth of the features. Great job.☺️

  • This is great!!! it has much feeling, looks terrific — it may be your new medium!

    • Thank you! I don’t want to get ahead of myself here, but I hope that what you say is true. It feels a little strange to say, because I do enjoy drawing…but I just had so much fun painting. It’s like another level of enjoyment or something. Maybe I was just in a good mood that day? I suppose I just need to paint some more to see if that continues

  • Well done and keep going! I’ll try to reply on some specific points later, on the early bus to work just now. If solvent is an issue, have you looked at water-mixable oils? Windsor and Newton make them, likely others in US too? Best wishes.

    • I appreciate that! One of my favorite things about WordPress is the incredibly helpful community of artists that share techniques and advice. I got so many great tips when I was learning to draw, I’m excited to try things from experienced painters!

  • Great first try, Jon. I’d be happy with it – certainly happier than your subject.

    • I appreciate it, Graham! Haha yes as long as the look on my face is more satisfied than this subject’s, then I think it’s a good state to be in!

      • Jon, I just noticed – watch that the tilt of the eyes and mouth match. In yours they’re going in opposite directions. It may be the case, but it’s not normal.

      • You have got a good eye! I didn’t even notice that until now – yes there is definitely some, to use a highly technical term, wonkiness going on. I tried to watch the video I recorded to see where that tilt was introduced, but unfortunately the camera angle and poor focus prevent a good view. I think perhaps the sketch was okay, and then as I painted I gradually moved the position somehow.

        Definitely a good overall balance/composition thing to keep an eye out for it, thanks for the heads-up!

  • Good job! Keep up the good work.

    • Thanks much Jack, I appreciate it!

      Also, I’m unfortunately quite behind on my blog reading. As I caught up on your site, I’m so sorry to read about your brother. My condolences to your family. The tributes you’ve done are wonderful, sharing those moments. Take care – Jon

  • Wonderful first portrait. Keep it up!

    • Thanks Phoebe! I still can’t believe how fun painting is, I’m so glad I finally tried it. I definitely plan to keep at it!

      • Hi Jon, yes painting is great, and it goes so much quicker than colored pencils, which I too used almost exclusively for years. Glad to see you are breaking away from these and out of your comfort zone, and trying new mediums! Take care,

      • That’s really good to hear – I can definitely see how, once you get familiar/comfortable, painting would go more quickly. I feel like a lot of the time with this first painting was consumed just trying to figure out how to mix colors and get used to everything

        Thanks for the comments, hope everything’s good!

  • Looks good. Keep on going

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