Painting Steve Jobs

The last words spoken  by Steve Jobs  were “Oh Wow, Oh Wow, Oh Wow”.  That  certainly makes me wonder what he was seeing as he was heading toward eternity – it sounds pretty cool – I like that – it matches my own spiritual view.

Steve Jobs was the most amazing innovator of my lifetime.  If he had only done one of the BIG things he did, he would have been a super-star.  But the fact that he started Apple, did the Mac, then Next, then Pixar, then the iPod, then the iPhone and iPad is nothing short of incredible.

Also, since I spent many years of my life as a software test engineer, Steve Jobs is a kind  of hero to me for another reason – that is that he was such a believer in investing in innate quality.  This was his most revolutionary quality. He simply would not settle for anything being shoddy and it totally differentiated everything that was produced under his tenure.

My favorite quote of his was: “I want to put a dent in the Universe”.  I believe he did.

When I started painting faces a few months ago, Steve Jobs was one of the first ones I did and let me tell you it was challenging!  I had several real failures before I was able to get one that worked to my satisfaction.

In the spirit of “Growth Mindset” where failure is the great teacher (and we should all embrace that) I’ll share a few of my “fails” before I was able to get it right.

This one was way wrong – off to a bad start.


This one was better – almost there, but not quite.

This one was a step back, ugh!  Looks more like Freddy Mercury than Steve Jobs I think



Tried painting on sketch paper – interesting color effect but still not Steve.


This is called “overpainting”.  Watercolor is not oil painting – sometimes the more you try to fix a watercolor, the worse you make it.  Terrible, just terrible.


And then, it came together.

What I learned from all this:

  • You MUST sketch in pencil first
  • If the sketch doesn’t look right, the watercolor won’t be right either
  • You can still ruin it if the sketch is right but I over-paint
  • Knowing when to stop is as important as anything else you do
  • You have to have a feeling of connection to the picture you are painting – if you don’t feel it, it will show in the painting
  • You need to paint in layers – light to dark
  • You  have to believe it will turn out – at first it looks like it won’t – just go with it
  • Painting IS drawing too – allow yourself to use the brush to pull the image out

So, don’t get discouraged if you paint a face and it doesn’t look like the person.  Keep trying!  Sketch the face several times until you get a sense of the key features that convey the key elements of that person.  Then sketch on your watercolor paper until it looks like who you are painting.  Then paint the face and let it emerge from the paper – and then stop.  Knowing when to stop is key.  Again, just like everything else in life.

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