When Every Fear Comes True

We tried everything. Prepared. Inspired by our own pep talk. All that work to push our fears to the side. The time comes. We fail spectacularly. Every fear comes true.

Last Saturday I attended a drawing event on the East side of Manhattan, in a highschool cafeteria with a few hundred strangers. The sixth annual Portrait Party.

What’s a portrait party?

  • Artists assigned to separate groups
  • There are twelve, ten minute rounds
  • Each team member sits once for their portrait
  • The group finishes when everyone has sat for their portrait
  • Set drawings from each team into a grid
  • All attendees walk around viewing portraits and socializing

I had prepared. I gave myself a pep talk. I warmed up at home. I warmed up on the train. I arrived early and warmed up sketching attendees as they walked into the caffeteria.

Two things about warming up

  1. I warm up every day for ten to twenty minutes
  2. As I warm up I notice any tendencies that need correcting

I ignored what I was seeing. Everything was a little off. Gestures, straight line and ellipse drills. But I pushed through without adjustment. Convinced I would do well and those kinks would magically melt away.

Don’t confuse arrogance for confidence

  • Confidence draws on attention to planning, preperation and familiarity.
  • Arrogance is misguided and blind to gathered information

I decide maybe an extra cup of coffee that I didn’t need would help give me more energy and focus. That extra cup had my hands go from slightly unsteady to nervous breakdown. The organizers called on everyone to get to their groups. The event was starting in the minutes.

We sat down and prepared to begin. With one of the “rules” being to use big, bold lines and colors, I decided on using markers. While I keep markers for quick sketches, they’re always thumbnails, not full drawings. But I had a plan. Create a background of fun shapes with limited bright colors. A bold, black line drawing would take up the rest of the ten minutes.

For this to work the lines, contours, proportions had to be perfect. The first try was the only try. Anything after that would just show the mistake as the lines were equal in weight. At best the drawing would look like a ball of yarn among creative kittens.

Most of the attendees painted their portraits. Forms and layered shapes allowed for softer, elegant mistakes. It was a smarter approach allowing a forgiving process during ten unforgiving minutes. In contrast, I compounded an unforgiving bold, black line with an unnegotiable, ten-minute time limit. My arrogance to set me up to fail.


Yes, I was unhappy with the drawings I made. Embarrassed, I set them down in our group’s grid. I walked away, taking the sour ball of self-consciousness with me. I made this day solely about every portrait turning out terrific, patting myself on the shoulder before the day even started. Was it all about the end product? Is it ever?

Our group’s final grid. I was amazed at what attendees accomplished in short time

I’ve always held the idea that growth, self-discovery, needs uncomfortable moments along the way. Something alien, new. Something known. A deep fear.

Planned or unplanned, we need these moments. Not to make us better. To reach an understanding. Yes, it can lead to improvement. Sometimes dramatic. Improvements are great. Understanding is why we want to improve.

While we’re deeply embedded. Our moment of crisis, unsettling confusion exposes the worst. Every fear, humiliation and mistake we’ve ever made swell from this one moment. Our thoughts overwhelmed. We go from what was a bad afternoon to a full blown crisis.

It isn’t. The waters will recede in the following days. Revealed will be the lessons we weren’t seeking. Answers from our undiscovered selves.

I unpack and make a full inventory. What went wrong that will end up being right?

I know that afternoon had roughly half a dozen variables of fear and discomfort. Collected, what do they tell me? I went when I wasn’t up for it. I stayed when I wanted to tear up everything and walk away.

I finished. Gathered everything. Said my goodbyes and thanked the organizers.

Sometimes experiences don’t mean anything. There are no deep answers. Accepting that the time spent had it’s own unique value that lived and died that afternoon. Accepting that sometimes understanding what failure is and isn’t has value. Once in a while we need a bad afternoon to remind us of that.