Tough stuff first


Dear Artist,

One morning a couple of years ago I got the idea to paint a self-portrait. I wanted one with my dog Emily and me peering around the canvas like that Norman Rockwell cover everyone has seen. Giving the job a bit of forethought, I remembered that if the likeness isn’t there, the whole thing is a loser. A portrait without a likeness is like an Airedale without a wag. I wanted my likeness to be fresh and simply done, with as few strokes as possible. This was going to be the hard part. I also wanted to get that look of stunned smugness that people notice about me. I set up the mirror, squeezed out, and started.


“Triple Self-Portrait” (1961)
by Norman Rockwell

The head was number one, and right off the top I got my face too big. Roughing in the second important thing, my hand, I got it too close to my big head. Taking down a fresh canvas, I started over. This one worked better. In my case I often notice I get a pretty good likeness within a few minutes and then gradually tighten up until it begins to look like another person. My second attempt was also better proportioned, even with its minimal strokes. Applying the enormous self-restraint for which I’m noted, I stopped working on me right there.

The decision to do the tough stuff first makes it easier to complete a work with confidence and élan. The next thing I had to do was Emily. For her, even though she was right there beside the easel resting on a pile of paint rags, I used a photo. Wrangling animals is difficult. Not dependent on actuality, I was able to put her into what I thought was a compositionally sound position. From then on the painting became easier and more fun. The easel, the messy work table and the bookshelves behind it literally fell off the brush. I also wanted to put in some of my other paintings, so I took a not-bad section of a substandard one and glued it on.

This principle works for practically every project. Even with relatively straightforward landscapes, it’s a good idea to cruise around and determine which areas are going to present the most difficulties. While you may be full of confidence and optimism for most parts of the work, you still need to devise ploys for the problematic ones. Tackling the tough stuff first — and even being prepared to abandon — can save a lot of downstream trouble, wasted time and soul-destroying disappointment.


acrylic painting
by Robert Genn

Best regards,


PS: “Why plan to fix it later, when you can get it right at the start?” (Harley Brown)

Esoterica: Tightening up is one of the scourges of the brush-worker’s art. For most of us it’s easier to be loose and fresh at the beginning than in the middle or at the end. If you leave tough stuff till last, which is human nature, you are more likely to tighten up as you move toward it. This is where the old “fear of failure” kicks in. The important thing in life and art is to do your failing early.


Viewing the process
by Janice Vogel, Senden-Bösensell, Germany


“Night Fishing at Antibes” (1939)
oil painting
by Pablo Picasso

I was recently at the Picasso Graphic Museum in Münster, Germany viewing a temporary exhibit on loan from the Picasso Museum in Antibes, France. What was different about the exhibit was that during the brief period (around a year I believe) that Picasso painted in Antibes, his working process was photographed by a friend so one could see the paintings in these photographs in various stages of completion. What I found particularly interesting were 4 photographs showing Picasso working on the same painting. The difference between the starting image of a very full-figured woman (either sitting or standing) and the final image of a very slender woman doing just the opposite, with different coloured hair and other props around her was quite interesting for me as a non-artist. I wish there were more accompanying photos combined with the art hanging in galleries, also giving a feeling of where the paintings were done and in what conditions.


Getting tough stuff builds confidence
by David Jon Kassan, Brooklyn ,NY, USA


oil painting
by David Jon Kassan

This is the exact thoughts that went through my head when I set out to paint a self-portrait 2 months ago. Except to getting everything in as few strokes as possible, I was content with trying to have an energy to the strokes as they described form and an interplay of color in layers. Once you get the tough stuff that challenges you, everything else falls into place by sheer confidence that you can handle any future challenges. It helps to pull one through a work with excitement and energy.




Starting up again
by Angela Sheard, France

As an emigrée in France I enjoy all your letters (learned about your site from an American in Rome) but hadn’t done any artwork myself for years, despite living 9 years in Italy. Yesterday I took the step of phoning a number on a leaflet I picked up in town about classes. Click, an hour’s conversation ensued with an obviously fellow spirit and the class would be the same evening. So I was snatched into the group within hours and found my stiff, way-out-of practice hand trying to capture a very simple still life and creating a too skinny wobbly bottle and a cricket ball where there was an apple. But never mind, it’s a start just walking out the door and going, right?

The stiff hand will loosen up as the leaves outside the window of the third-floor room in the oldest part of town (a good subject in themselves against the old grey stone) will change colour and fall as we plod through the autumn and winter biting our lips and squinching up our eyes to capture our subjects. I know it will be good because the tutor stressed time and again that we were there to discover, to relax and forget the tensions of the rest of our lives, to explore, not in competition, not to be judged or compared with each other as better as worse. Just to do and to be and enjoy.


Larger than life
by Katherine S. Harris, Rome, Italy


“Barbarano Romano, Courtyard”
oil painting, 45 x 55 cm
by Katherine S. Harris

Your letter today rang a bell! I have often wondered why I so often have to go back and make a head, a hand, a bit of a building, etc., smaller. You are saying it’s because we concentrate on the obvious things first, and they become “larger than life”? My explanation has been that I go first for working on the things I like best, or that seem most important in the painting — i.e. focal points. Maybe we’re saying the same thing. Anyway, today’s article confirmed that I’m not alone in having to deal with over-sizing. I have organized, for years, a group of artists which meets once a week to sketch and/or paint, with the presence of a live model. Nobody else seems to have my problem, but most of the others have studied in art schools or with well-known teachers. I still find I tend to start “too big,” even though others try to coerce me into doing some pre-drawing measurements (perish the thought!). Maybe it’s the “rush” of putting pen, pencil, or brush to your chosen support?


Learn to trust first instincts
by Sally Chupick, Kingston, ON, Canada


“Aemilia the brave”
oil painting
by Sally Chupick

I could completely identify with your comments on working out your self-portrait… In my case, when working on portraits, I also notice that I can get a pretty good likeness within a few minutes and then the longer I work on it, in an effort to give it a more ‘finished’ look, the more it begins to look like another person. We need to learn to trust our first instincts when they’re working and accept them without embellishment… but this is not always satisfying to the artist who is looking for a more in-depth study of the human subject than an initial ‘sketch’ can give us. It is like ‘walking a fence’… when to persevere and when to stop… but it makes finding the balance a sweet victory.

The process of executing a self-portrait can be a conflict of truth versus vanity. If you are painting what you ‘feel’ is yourself, is it truth or vanity? Of course the great thing about painting a self-portrait is that you don’t have to please anyone but yourself, so the enjoyment of the process often takes over. You can do whatever you feel like… even make yourself look younger if you want to!


Precious passage, but wrong
by Helen Zapata, Phoenix, AZ, USA


acrylic painting, 24 x 24 cm
by Helen Zapata

I completely agree that we need to be prepared to abandon a passage that doesn’t work. I keep on the lookout for areas of my paintings that are wrong yet have become “precious” to me. It’s easy to look at your work and know that a particular part is just plain wrong. Yet, it’s become precious to us and so we try our darndest to find a way to hold onto it. We paint around it. We start changing other aspects of the painting in an attempt to hold onto this one thing that we love in spite of the fact that it’s bad! Why do we love it? Perhaps it’s a particular stroke done with panache. Maybe it’s a certain color which charms us. Or that bit of light on the edge. Whatever it is, we’ve fallen in love with our own work and it’s become precious to us. But it’s not working! The rest of the painting is falling flat on its face because of that one precious mistake. We must be prepared to abandon what doesn’t work. If this means getting out a new canvas, then go for it. Or grab some gesso and paint and wipe it out! If you are working in thick oils, take up a painting knife and scrape that baby down! Once you take out a precious, yet very wrong passage in your work and redo it properly, you’ll be so glad you did. You won’t even remember why you thought that keeping that mistake was such a good idea. Oh and by the way, for anybody who doesn’t want to take the time to fix their bad choices: just remember… that bad choice, that precious mistake, is the only thing you are going to see every single time you look at that painting for the rest of your life!


Background first
by Marney Ward, Victoria, BC, Canada


“Northern Lights Azalea”
watercolour painting, 20.5 x 28.5 cm
by Marney Ward

I work exactly opposite to you, almost always painting the background first. I think perhaps because I use watercolour, and my backgrounds are usually dark, I want to get the relative values established right away. With watercolour, it’s essential to save the whites of the paper, so it’s helpful to have the darks in first before you tackle the lights. There is a tendency to make my light subject too dark if I have a white background, instead of the dark background it will eventually become.

I also find that students are often intimidated by the white paper, and starting on the background allows them to work freely and with confidence, until they have broken through their initial fear or inhibition. Once they have played with the background for a while they are “into” the painting and have more confidence. Of course, I make sure the composition has been worked out with an accurate drawing before they start. As you can’t easily correct mistakes in watercolour, you need a good foundation to give you the freedom to play. In that respect I agree with you, do the hard stuff first, get good bones, and then you can soar.


Shadows first
by Susan Jenkins, Cambria, CA, USA


oil painting
by Susan Jenkins

I have always painted the shadows in first. All the darks. Then I continue on to shape up areas with the darker under-color. To me this is the tough stuff. Really looking at the design, shape and color of the shadows. After that I continue on and figure out the middle value by really looking at what I am painting. I teach and many times I notice the student isn’t looking. That’s tough too. Really looking and really seeing. Everything has a color. Looking at the color and the shape as you work. Finishing up is the most fun, all the tough stuff is done really. The finish is the frosting! All the bright finish colors, the highlights.




Archived Comments

Enjoy the past comments below for Tough stuff first



From: Sidney Slivko — Sep 18, 2007

I have this sign hanging behind my desk: Why is there never enough time to do it right, but always enough time to do it over?

From: Chris Everest — Sep 18, 2007

Confessional – I sit down and usually draw (from a photograph usually) the focal point of the drawing – the person, or their face anyway. Then I stop, and I never get started again. I tell myself it wasn’t intended to be a finished work – perhaps more of a detailed sketch – I look at it (them actually) and think that was coming on well, maybe I should…. but I don’t…. How can I…… I get sidetracked. Perhaps I should tidy my millions of art boxes…

From: Darney Willis — Sep 18, 2007

Robert, I agree with you about tackling the difficult areas first, at least far enough until they aren’t a nagging uncertainty any longer. When I am teaching I call these tuff areas “the question marks”. I tell my students to search over the canvas and get rid of the question marks – those areas they don’t know what to do with. I encourage them to bring the whole canvas up together, not just focusing and finishing out the areas they are most confident of first and then trying to retrofit these unaddressed areas later. Painting can be a very intuitive and confident experience and having these uncertainties out there can inhibit the flow of the many choices needed to be made. Finishing out only the area we are most confident first and then trying to bring in the left out areas is sort of like having a committee composed of six or seven people that are supposed to meet many times and all but one of those committee members meet every meeting. The one member comes to the very last meeting and then tries to give input, but is totally uninformed, out of the loop. Hard to integrate much of value to the proceedings unless you are included all along the way. Darney

From: Val Norberry — Sep 18, 2007

I think I’ll go fishin’. You get a line and I’ll get a pole honey, you get a line and I’ll get a pole, babe, (this is a love letter of siloquilous proportions, yes?) you get a line and I’ll get a pole, we’ll all go down to the fishin hole. My friend Hugh showed me all of his best catfish spots on the mighty St. Joe River in St. Joe County, MI, the first 2 weeks I met him. At the time I didn’t appreciate what treasure he was sharing with me. You get a line and I’ll get a pole, we’ll all go down to the fishin’ hole. I got a deadline, it’s called death. I intend, that is I have an intentional life, and I intend to enjoy it. Yes, I work too.

From: Nancy Moskovitz — Sep 18, 2007

When I paint or teach how to paint a watercolor portrait, I insist on starting with the background. That way if the background fails, it’s easy enough to start over. But if you paint the head first, count on a timid approach to the background.

From: Lyn Cherry — Sep 18, 2007

Nancy, I must agree with you about painting the background first; perhaps because I paint in watercolors and frequently have a very nice subject painted and when I try to add a background, I become timid and very frequently mess about too long!! I find that painting the background first works as a way of freeing myself up.

From: Anonymous — Sep 18, 2007

The reason some artists get a good likeness in a portrait in the first few strokes is because they start with the few most prominent features, going into those “marker” details way prematurely. The reason the portrait falls apart with further work is because the anatomy has not been understood and considered from the start. Start with a good anatomy (that is the tough part) and end with the most prominent features (easy).

From: Bob Sheridan — Sep 19, 2007

How about packaging your annual letters like the Raincoast Chronicles? One year at a time in soft cover, then the “First Five” follow in hardcover, and so on. (Like we’re all going to live forever). Regards, Bob

From: Ron Rumak — Sep 19, 2007

I try not to be terrified of mistakes. In the words of Leonard Cohen, “That’s how the light gets in…”.

From: Martha — Sep 26, 2007

I always paint the background first- but not the shadows- as I like to add colors to them later- and so on- as I am never certain which ones I’ll use!! Thanks.






Bunch of hydrangeaa

oil painting on canvas
by Dana Levin, Pawtucket, RI, USA


You may be interested to know that artists from every state in the USA, every province in Canada, and at least 115 countries worldwide have visited these pages since January 1, 2013.

That includes Mary Timme of Aurora, CO, USA who wrote, “Emily looks great in the self-portrait.”

And also Victoria Witte of Bloomington, IN, USA who wrote, “Your letter today reminded me of one of my favorite sayings: ‘If you have to eat three frogs, eat the biggest one first and don’t think about it too much.’ ”

And also Anna Friesen of Huntington Beach, CA, USA who wrote, “This is just the kind of anecdote we artists need to hear — from other artists. It reflects and validates my experience as a Recovering Perfectionist as I advance towards a Practicing Get It Done-er.”

And also Raynald Murphy of Montreal, QC, Canada who wrote, “Portraits are about the most difficult paintings to do, self-portraits probably even more so. I’m reading for a second time around a fascinating, insightful little book called Rembrandt’s Nose by Michael Tayor. The master painted himself some eighty-odd times says Tayor. For anyone who does self-portraits or portraits in general, this is a must read book.

And also Liz Nees of Long Beach, CA, USA who wrote, “You and your dog look a lot alike. That’s nice, seriously.”


by Cooper (age 6)

And also Susan Poole of Mill City, OR, USA who wrote, “I asked my grandson if he used a mirror when he created his self-portrait. ‘Oh, no, grandma, I’ve had that stored in my brain for a long time!'”

And also Ingeborg Raymer who wrote, “I don’t detect the smugness, maybe just a slightly stunned look. And I like the clutter in the studio and the sincerity with which the subject is handled. Thanks so much for sharing your ideas, your work habits and your philosophies with us.”




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