What Painting Can Teach You About Pivoting

Startup Lessons from an Artist

(1) Just Start.

It can be paralyzing standing in front of a blank canvas, especially if it’s big. It’s thrilling to have a big idea or a big canvas in front of you, but the bigger the canvas the harder it is to make that first brush stroke. Painting teaches you that no matter how big your canvas (or idea) you have to start somewhere. Make that big bold gesture across the canvas, or start with a corner. It doesn’t matter; it will likely get covered up at some point. Some painters start by painting their canvases brown or gray. It’s just a foundation that’s going to get covered up but it makes the next layer and the next, easier to paint.

(2) Discipline.

Painting like any other creative endeavor such as building a company is about harnessing creativity and turning into a discipline. Some days painting is effortless, and other days, you lack inspiration and motivation, and picking up a paintbrush is difficult. Building a company is much like this. Some days are euphoric and other days everything goes wrong. It’s important to stay focused and disciplined and work through these days. Good painters paint every day whether they feel inspired or not.

(3) Facing fear and failure.

Every artist from Monet to Michelangelo has discussed the struggle they experienced through the creative process. Every painter comes face to face with paintings they don’t like, and creates work that no one will see or paintings that are never finished. Every painter fights the fear that his or her work will not be liked, and that they will fail. Painting requires working through these fears and continuing to create. Failure results when you quit, and learning to keep going in the face of fear and doubt is perhaps the most important lesson a painter learns.

(4) Risk-Taking.

Many artists paint in series and paint multiple canvases at one time. Painting in series has a lot of benefits, but one of them is the ability to take risks, step outside your comfort zone and try new things. Risk-taking is often rewarded in painting, and it is the canvas that you throw paint at that might result in a one-man show at an art gallery. While you want to focus on your core mission at a startup, don’t let it keep you from taking risks and experimenting.

(5) Perspective.

Step back. It’s easy to get stuck in the details of a painting, but it’s always important to step back to see the big picture (pun intended). Look at it from different angles and turn it upside down. Another great thing to do is to cover up a piece of it that wasn’t working to be able to see the rest of it. Holding up a book to cover up the left side of your painting might reveal that you’re onto something brilliant on the right. Stepping back lets you see things more clearly. It lets you see what’s working and what’s not, when to charge forward, when to make changes, and yes, when to pivot.

I learned these lessons from Glenn Hirsch, a painter who teaches an advanced painting class at the San Francisco Art Institute (SFAI) through its adult continuing education program. I credit painting with giving me the courage to pursue a more creative career.