I am currently in Vermont on business. This is great on a few different levels. Vermont is a stunningly beautiful state filled with tall mountains, trees and lakes. And because I lived in this area from 1976 to 1991, I know a lot of people here.
I am talking with my friend Jocelyn who shares an interesting theory. She suggests that my love for uncertainty comes from the fact that growing up with alcoholic parents introduced lots of chaos into my life. Even though that experience was negative, uncertainty now feels comfortable and familiar.
I have a lot of time to chew on that idea as I drive the two hours back to the hotel and takeit a bit further. Whether it’s traveling to India, going on long bicycle trips or getting up on stage, I am putting myself in a position that has a little bit of stress because I don’t know what’s going to happen. But each time I face one of those situations and it goes well, there is a sense of accomplishment. It is as if, after dealing with difficulties as a teenager and not being successful, I am repeatedly able to face new things and succeed.
Which brings me to this week’s challenge sent in from a reader:
Hi Todd! I am learning to draw, which is way outside my comfort zone. It turns out I’m into botanical (and other nature) illustration, which I didn’t know before I started. This is a great time of year in New England to find interesting things to draw. Mostly I am taking a lot of reference photos, and getting inspired everywhere way beyond my current ability. But it’s a start. I challenge you to pick up a pencil and sketchbook, and whatever book or video references you may find at your fingertips, and learn how to draw things you see out and about.
My first reaction to this was:

Drawing, for me, has been something I don’t do. If you look at my handwriting you’ll begin to understand why.

At the same time as I was taken to the doctor and diagnosed with “being able to read books in kindergarten”, the doctor said another thing which would change my life. “He’s perfectly fine, ma’am,” he told my mom, “but his coordination is not that good.”
For my parents and eventually me that statement became as true as if the doctor had said “Ma’am, your son has brown hair and needs glasses.” And we acted accordingly. My penmanship seems to prove that. When it comes to moving a pencil on the page, I feel completely without grace – as if I have tied a broomstick to my hand and put a pencil on it and tried to draw. As a kid I would try to draw something and while I knew very well what I saw, what came out on the paper looked nothing like it. Before long I would get a sense of tension in my mind and behind my eyes as if I might cry. And so before I even was in Grade 4 I gave it up. I would grudgingly do the assignments for art classes but set my expectations low. Other children might draw a Christmas tree with their family around it while mine would be a triangle with squares underneath and four stick figures with curved lines for smiles.
Needless to say, I am intimidated by this challenge. But the purpose of the 52 adventures project is not to just do a bunch of things that I know will seem difficult for me for a couple of minutes and then will be ridiculously fun. The purpose is to approach things that are challenging, experience them and share what that was like. In many cases it will be fun, but sometimes it will be hard.
All this week I intended to work with Sage to draw some. Every time I talked to her I would say how I would for sure draw another stick figure Christmas morning until eventually she told me to stop being so hard on myself.
Finally after a drive through northern New Hampshire where the trees were so green and the mountain so blue the world seemed to demand a #nofilter tag, I am back in town. It is time to draw. So I go to the laundromat and do my laundry. And I don’t have any detergent so I go to Target to get some. Then I finish my laundry and go to the store to get some food for dinner. I arrive back at the hotel around six pm and message Sage:
“So, I had lot’s to do and I think probably I won’t have time to draw. I have to eat dinner and then I have Hindi class at eight. Oh, and tomorrow I’m going hiking so maybe we’ll skip a week because I’m on the road anyway.”
Sage is having none of it. She tells me we have two hours which is more than enough to start. She chooses a photo I posted to Instagram that day.
I look at it and think “Look how complicated. there’s no way” but then I just tell that inner voice that we’ll try and see what happens.
Sage tells me to draw a 3 x 3 grid on my sketchbook and I do. I take the side of my ebook and draw some lines and immediately give myself a hard time for the nine squares being more rectangles. In my head I tell myself “It’s OK.” and I continue.
And so Sage tells me to imagine that same grid superimposed over the picture and just take one square at a time and draw what you see. I like this idea because it reminds me of when I’m on a long, difficult bicycle ride and I can’t imagine finishing. But I can imagine going to a tree just ahead and I do that. And then I pick another tree and eventually I’m there. I like it even more when I see how many squares will be filled with sky and require no effort at all.
We start in the upper left hand corner with the leaves. She asks what I see there and I describe the shapes and stems.
“Draw what you see.” she says.
I see several leaves, some superimposed over each other, a handful of stems and a few small leaves. It is really clear what is in the photo. I put my pencil to paper and am dismayed to see how little what I draw looks like leaves to me. I erase and try again and it’s not much better. I feel the same tension in my mind that I felt at 8 drawing that Christmas scene. Except now in my mind there’s another thought “Why in the world am I so emotionally invested in doing this right?” I don’t even have an audience to feel embarrassed in front of. It’s just me and I feel terrible. Out loud now I say to myself “It’s OK.” and it isn’t really feeling OK, but I draw further.
We move down to another set of leaves below and it feels even worse. I laugh wryly at myself as I appear to be drawing a tree whose foliage was giant amoebas. “If only I were doing it fully well,” I think, “It would be a great Dr. Seuss-like illustration.”
Throughout the whole process Sage continues to encourage me arguing directly with my inner voice. “Sure,” she says, “Maybe you are ‘uncoordinated’ – but even so, there are people who draw with their feet. You can do this.”
And so I push on. When I want to quit I am buoyed by Sage and the knowledge that there is a bigger purpose to this and the purpose is not to draw a beautiful image.
Sage tells me to imagine Mozart’s first time at the piano and Daegan’s first time trying to draw a number 2 which resulted in a tantrum when his hands wouldn’t do what his mind wanted him to. Daegan now draws beautifully.

As the leaves are frustrating me we move on to the bottom and start drawing the land. Each time Sage asks me what I see. Of the bottom left side I tell her I see a piece of pizza with a weird bite out of the side instead of from the tip. “Draw that” she says. and I try. And somehow that looks a little more like what is in my mind. Or if it isn’t fully that, it’s believable as the shore of a New Hampshire lake.
We move on across the bottom of the page and I do the bottom right. I tell her I see a simple curve and am told to draw it. I draw it and fill it in a little. That also doesn’t look quite right but I’m OK with how it looks. It’s also shore-like. I notice the frustrated feeling in my head has gone. I’m still criticizing every pen stroke, but I’m taking it less seriously. I draw a few lines and instead of saying “It’s OK.” to myself to reassure and calm myself, it has become a statement of fact. “It’s OK.”
I am right about one thing. I don’t have enough time to finish this drawing before Hindi class. But the beauty of drawing something is that I can put it aside and take it up later. And I resolve to do that. This is something I need to work on. Whether I become a great artist or improve absolutely zero, getting to the point where I can draw something without feeling horrible as I do it is something I want to be able to do and I resolve to do it.
As I put away the pencil and sketchbook I think more about the idea that Jocelyn planted in my head. Yes, I do like uncertainty because it’s comfortable and familiar. I like it because I can approach an uncertain situation and be pretty sure I will succeed and feel that happy rush of “I didn’t know what was happening but I figured it out anyway.” But what I realized today is that the uncertain situations I avoid are those where for one reason or another I’m pretty sure I won’t be successful. Those situations were difficult when I was young, and they continue to be.
On the other hand, when I am able to approach one of those situations and feel a little bit successful, the reward is huge. I’ll be doing this again.

Have an idea for an adventure? Let Sage know with the form below and she’ll take me on a surprise adventure to do something I’ve never done.
I sometimes think that trying to copy something exactly as you see it can be very frustrating. One of my favourite activities is to find a thin stick, dip it into ink, hold it further back and just start drawing. You’ll get big blobs and thin lines but there’s something very satisfying about the end product. Let it dry and then decide if you want to add watercolour, more lines or just leave it as is. Have fun!
Sage and I were talking about that – how technically photorealistic drawing is really impressive but in other ways it seems soulless to us. I want to see what the artist thinks and feels.
I like your idea of using a stick to paint with. Really cool. And you bring up an important point. This is meant to be fun, not a test!
Funny that you came out of your childhood comfortable with uncertainty and I came out the opposite, craving certainty. I love that you tried drawing and Sage’s approach broke it down into manageable chunks.
It really made it easier. I still had to keep reminding myself of the low stakes. It really was only putting pencil to paper. Nobody was going to grade me on it!
I am the worst at drawing too & would totally feel as frustrated as you did at first! Have you finished this piece yet? Would love to see the finished work! 🙂