Little bets


Dear Artist,

In Peter Sims’ book, Little Bets: How Breakthrough Ideas Emerge from Small Discoveries, we see the value of making lots of small failures as a way to get to large successes. While Peter’s book is mainly aimed at entrepreneurs, it’s also of real value to us regular creative types. These days, cutting-edge gurus are passing the word around: “Fail often in order to succeed sooner.”

Nude Series VII (1917), watercolor on paper by Georgia O'Keeffe

Nude Series VII (1917)
watercolor on paper
by Georgia O’Keeffe (1887-1986)

But not everyone is pickin’ up what these experts are puttin’ down. Working from a dated model, many art schools currently expect foundation students to produce two or three major works per semester. The results are often big, poorly-conceived mishmashes of questionable value — either as vehicles for learning or as fine art. On the other hand, when students are encouraged to do volumes of small items they become accepting — even proud — of their failures and are more readily able to move on to ideas that work better for them. Simply put and perhaps surprisingly, less commitment widens opportunity. In a hundred small bets, a dozen or so often ring the bells. With this shotgun effect, even beginners are seen to produce gems. As the lady said, “It’s better to have a small diamond than a large piece of glass.”

Nude Series (Circa 1916-1919) watercolor on paper by Georgia O'Keeffe

Nude Series (Circa 1916-1919)
watercolor on paper
by Georgia O’Keeffe

Here are a few ideas for artists who might wish to quicken their progress:

— Prepare a hundred or more similar-sized small supports.

— Choose a subject, motif or series you feel has legs.

— Start bashing off everything that comes into your head, no matter how glib. Stretch your mind.

— Abandon bad ideas in a timely way. Don’t waste too much time or get hung-up on outright duds.

— Go from one to the other like a bee goes to flowers. Cross pollinate. Ideas breed ideas. Quality breeds quality.

— Keep your strokes fresh, creative and confident — then both you and your work will become fresh, creative and confident.

— Be always in a state of rejection and acceptance. Steadily sort your work like a deck of cards. To win — to get to the stuff that’s really worth enlarging — to evolve — you gotta love the little-bets game.

Nude Series (Circa 1916-1919) watercolor on paper by Georgia O'Keeffe

Nude Series (Circa 1916-1919)
watercolor on paper
by Georgia O’Keeffe

Best regards,


PS: “Life is an experiment where failure teaches as much as success.” (Peter Sims)

Esoterica: Curiously, in a world where imagination rules, roadblocks to the free flow of imagination are commonplace. Andrew Smith, author of The Dragonfly Effect wrote, “Incorporating core tenets of design thinking as practiced at Stanford University’s Design School, Little Bets shows us that many of the things we observe today as great are the result not so much of brilliance but of diligence, humility and empathy. Prior to building something great, it isn’t necessary (or even useful) to have a brilliant, buttoned-down plan, researched to exclude potential errors and risks.”

This letter was originally published as “Little bets” on April 26, 2011.

Georgia O'Keeffe at lake George (1918) by Alfred StieglitzHave you considered joining our Premium Artist Listings? Share your work with thousands of readers. 100% of your listing fee contributes to the production of The Painter’s Keys. Thanks for your friendship. 

“I got half-a-dozen paintings from that shattered plate.” (Georgia O’Keeffe)



  1. Thank you, because I am stuck right now. Can’t decide what to do for an event coming up right away!
    Things I did ten years ago seem better than what I can think of today and they were just little postcards.

  2. I have learned this Little Bets maxim in the last 10 years. When I first started this 2nd career of fine artist (previously ad creative director/graphic designer) I noticed that only about one in ten works were worth framing and showing. At the same time I was researching Picasso and learned that he did over 150 preparatory sketches, goauches, and small studies for Demoiselles D’Avignon. So if Picasso can do many studies so can I. At that point I began to make lots of small color studies, failed often, and began to cull the successes and look at those, analyze why they worked and attempted to reproduce those with a slightly different color, motif or composition. Just change one thing. I would make 3 or 4 a day. This lead to a Lot of smalls, and not all were good so I regessoed the failures and moved on. This is now a daily part of my working method. I am comfortable with it and learn so much….so that now my large work is more confident and more importantly my enjoyment about making art has soared.

    • I used to do a similar sort of thing but instead of small panels I worked in sketchbooks which I filled with ideas and studies. For a long time I seemed to do little ‘finished’ work but eventually I found I was doing less and less of the studies and more and more large scale work.
      Now I do very little in terms of studies but just get stuck in to the painting and deal with the problems as they arise – this, I now realise, is an essential component in the picture-making process for me.
      I suppose my confidence level eventually rose to a tipping point. And not a minute too soon. I’m 75 and tempes fugit!

      • “… and not a minute too soon.” You made me laugh with your “tempes fugit”.

        As I read your comment, I was curious how you progressed from your sketch book . I love that your growth developed from doing the numbers of sketches – “an essential component ” – that eventually morphed into full scale work as you gained confidence.

        I “allowed” myself a tiny flip sketch pad, probably no more than 2″ X 3″. Images would come to me when I momentarily paused at the end of a pier. I had little early training in art. A few of those rudimentary tiny sketches ended up as images on large canvases. Most of the rest changed immediately into something else as soon as I selected a colour or brush. I let the process happen.

        Thanks for sharing. Your experience serves as a support that it’s okay to mess up and learn while you mess up.

        PS A fabulous university level Abstract Painting course later in life recently pushed my thinking and process.
        Semper progrediens

  3. There was that year where I produced 365 paintings of flowers -1997-1998. Today the winners are still being produced and sold as my hand made cards. It surely was one of my best decisions. I just did them and stuck them on the wall, and did some more. Took them all down when I hit kne hundred and started over again. I think its time to do something like that again – after my upcoming exhibit!

  4. Excellent reminers here, and something that when I practice (doing lots of smaller works and ‘what could bes?’ ), generally results in exponential creative growth….and more confidence in brushwork and self esteem. Thank you Sara (and Robert). :)

    • Elizabeth (Betty) Senger on

      Went to your gallery. Love your art, especially the colorful animals. Sorry I can’t make it to your exposition on the 23!

  5. I have a friend who was “stuck” and started doing one small a day following a letter of the alphabet as a jumping off point. Very creative results from her inspirations!

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The use of cold wax merging with collage material reveals a rich surface filled with depth.  Learning when and how to add your personal marks enhances the painting while telling a story.


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