In examining skill development, I decided to go a step beyond the generic ‘slow and steady wins the race’ advice. Instead, I decided to dive into how mindset shifts can lead to massive gains quickly. I didn’t just want to be the tortoise, but the hare as well.

The following are lessons I’ve gained from experimenting with mindset shifts in respect to the skill I’ve been developing in my life, drawing people, but these insights can be applied to any skill you’re developing.

Choose: Make mistakes or Give up

The past seven months, I’ve been rigorously studying how to draw human anatomy: how to capture a person’s personality and expression while they are going about their business in the public. I’ve been attending weekly three-hour nude figure drawing classes, and have been people sketching in public places.

Here’s some recent work:

sketch of people in public

And here’s some from right before I started regular practice:

sketch of people in public

So much of the challenge with skill acquisition is overcoming the fear of failure enough to let yourself make the mistakes required to learn anything.

I’ve noticed this my whole life when people would approach me while I was drawing, explaining how they can’t draw. I’d point to their perfectly functioning hands, and ask, Why not?

It’s not that people can’t draw — that they truly are incapable of making marks on a page — it’s that they won’t. They’re too scared.

Scared of messing up, of making bad art, and of their self-worth being defined by that bad art. This mindset says, “Steve makes worthless art, which means he is a worthless person. He should just give up.

It goes without saying, these fears are not true. Though it isn’t rational, it is the kind of traumatizing event people foresee happening when they consider expressing themselves — so they jump ahead to end result they already predict: they give up.

Unfortunately, in an attempt to avoid pain, they end up causing more of it. The pain of embarrassment is nothing compared to the pain of regret.

Do yourself a favor right now and embarrass yourself.

Do something silly and strange in public. Hug a tree at a park. Walk through the supermarket backwards. Dance in a coffee shop when your favorite song comes on. Have fun!

Come back when you’ve learned that you can embarrass yourself all you want, your world won’t end. To the contrary, you will become stronger.

Done?

Okay, good.

Have it be known that I when I was at the mall with my friends as a preteen, and one of the quarter machines gave us a fake mustache that went perfectly with my red hair, I slapped it on and wore it all throughout the mall. And you know the hilarious thing? Nobody even said anything. People would notice but then would avoid eye contact. I have yet to die of the resulting embarrassment.

Moving on.

You are not defined by your embarrassing moments, and if you embark on an embarrassment-free life, then you are shooting all of your potential in the foot.

Similarly, you are defined by your mistakes, but not in the bad way you would expect: You are the lessons you have learned when your actions didn’t yield the results you wanted.

That’s all a mistake is. See, it not so scary.

You can’t have learning without mistakes.

Developing mastery of a skill demands mistakes as payment.

Mastery has less to do with time invested, like the famous 10,000 hours being proclaimed today, or even daily practice routines.

Mastery is the cumulative result of how many mistakes you have made and resulting lessons that you have internalized. It is about internalizing mistake, after mistake, until you can navigate from beginning to end doing a cleaner run each time.

It’s like flying a plane from point A to B, and making many micro-adjustments along the way. Getting better each time, you learn what to do by proxy of elimination: by learning what not to do.

Soon the ratio of making mistakes to producing results shifts, and people start noticing your work.

mistakes and output over time chart

Never stop making mistakes.

In any field, a master’s work looks like magic to those with less skilled eyes, but a master looks at it always seeing what he needs to improve on.

Leonardo Da Vinci invested so much more time into studying and depicting life than his fellow Renaissance artists. Many of them thought he was a joke because he took so long to finish any single piece, if he finished it at all.

Da Vinci studied plants, dissected human bodies, and learned how life works, from the inside out. In his work he depicted life so well, in such extreme detail, that his work has always induced visceral reactions in people. Owners of his paintings would be caught kissing the women he so vividly depicted on canvas, and museum security guards have often been fired when they would start developing unhealthy relationships with his paintings.

His work remains the most vandalized of any other painter of the time period.

All of that, but he still said this:

I have offended God and mankind because my work didn't reach the quality it should have.
- Leonardo Da Vinci

Oh Leo, don’t be so hard on yourself!

He still saw the mistakes in his paintings, even his masterpieces, even The Last Supper, even the Mona Lisa.

Where we see a masterwork, the master sees what he needs to improve on. Unless you want to stagnate, accept that no matter how good you get, you will always be a little unsatisfied. You will always be noticing new mistakes you have made, even if those mistakes become harder to notice by the untrained eye.

Vision always surpasses execution, and there is always more to learn. This is a good thing, because without learning, there is no happiness. With so much to learn, happiness is in abundant supply.

You learn more when you feel good about making mistakes.

If you can release your fear of failure and let yourself learn from mistake after mistake, then you can hit the turbo-speed on your learning. You could even travel at warp-speed, leaping ahead and accomplishing years of lessons in the fraction of the time.

I’ve been drawing consistently, though rarely daily, for as long as I can remember. Still, I would often fall into emotional traps that stifle growth: comparing myself to others with more experience, feeling inadequate, feeling pressured to make a living with drawing, etc.

You learn best in a flow state, or when you are so totally immersed in the task at hand that hours pass by unnoticed. This state is delicate and requires peace of mind.

Negative thoughts easily override flow, and if you ignore any of these feelings, and try to learn in spite of them, you will only bring frustration.

Doing creative work in the company of negative emotions is like putting a dark blanket on a beautiful stained glass window. Some colored light might get through, but it’s only when you take the blanket off that the light can flow through unhindered and you can admire its beauty.

For the sake of saving time and preventing unnecessary suffering, deal with any unresolved negative emotions before diving into work. Make this is a daily practice of mindfulness.

Drawing is a mental game.

One of the reasons I love drawing is that it concretely shows me my state-of-mind in the given moment; it’s an instant feedback loop on my mood.

When I feel good, confident, and am interested in what I am drawing, I can easily fall into a flow where making good drawings is effortless.

However, the second a negative thought slips in, a fear, my hand will slip. What used to be a woman’s gorgeous face now has a Hitler-stache. Whoops, how did that get there?

Usually I can redirect my thoughts and get back into the flow. If not, the act of creating feels less like fun, and more like a sacrifice, and the entire thing derails.

Here’s a list of mindset shifts I’ve applied that have virtually eliminated that kind of negative emotion downward spiral and have kept me in consistent and longer flow states:

  • Seeing mistakes as learning instead of something to feel embarrassed or ashamed about.
  • Developing a strong sense of self-worth that isn’t dependent on the quality of my work that day.
  • Emphasizing quantity over quality so I can output more mistakes and learn from them faster.
  • Having an intention, a specific thing to learn, for each piece. Focusing less on how it looks and more on what I learned while making it.

Drawing only with permanent pen.

…or as I call it, diving in ink-first!

I quickly internalized the above shifts when I put my pencils away to collect dust, and started only drawing in pen.

Drawing in pen gives permanence to the mistakes I make, meaning that they will always be there for me to learn from.

Rather than erasing, drawing over, erasing and drawing over, which can eliminate the mistake from memory, a mistake in pen is here to stay. I even make notes next to it, and try again. I can refer back to it. I can build on top of it.

It’s not always pretty, but that’s not the point; learning is.

sketch of people in public

Making a successful drawing in pen requires trust. A good output only happens when I trust myself to be okay with any mistakes that come up.

Interestingly enough, the more I am okay with making mistakes, the less I actually make.

How can you give permanence to the mistakes you make in your work?

How can you give yourself no other alternative than to let go and trust?

Art as Athletic Performance

Lately when I sit to sketch, I’ve been seeing myself less as an emotional artist, and more as a dedicated athlete.

Athletes visualize the end result. They see themselves crossing the finish line and imagine what it feels like to win. They have a clear goal in mind, yet make mistakes all the time. When they fall, they get back up. They learn how to adjust their muscles, diet, and sleep in order to do amazing things.

I’ve started viewing my art less like a physical embodiment of my self-worth, and more like how an athlete views his most recent performance: It’s a score to be improved upon next time.

The score is the summation of how he has challenged himself in training, incrementally, slowly building difficulty, endurance, patience, flexibility…

In this performance that is making art, I get to appreciate all the work I’ve invested to reach this point, all the micro-adjustments I’ve learned to make from countless mistakes. I give myself the opportunity to practice appreciation.

In this mindset, I don’t worry about whether or not people will like the end product. Making my art is a performance, the needed release of accumulated study, trial, and effort. From it I learn where to go next. It is a journey that is an entirely internal process with internal gratification.

Don’t let impatience kill your growth.

Along the way to mastery, it can be easy to become impatient, to desire an output that we aren’t capable of producing yet.

Impatient, we become frustrated with our mistakes, and so stop experimenting. We unconsciously do what feels safe, which is repeating what we know. We make the same kind of work, saying the same thing, the same way, over and over again.

Unchecked, this can lead to stagnation, unhappiness, and a lot of wasted potential. The creative process that fuels our learning and happiness requires continual risk-taking.

Leonardo Da Vinci understood the dangers of impatience. He even had a motto to combat it: ostinato rigore, which translates to stubborn rigor or tenacious application.

His motto means to cultivate pleasure in pain, like an athlete: To learn to enjoy the rigorous practice where you push past your limits and go further than you ever have before…

Go forth, tenanciously apply yourself, and don’t hold back.