How a paint 'n sip class expanded my horizons, from a guy who has no idea how to paint

May 19, 2016                 4m read time
Dan Mascola

Fueled by rainy day boredom, ZOZI’s own Dan Mascola decides to try something totally out of his wheelhouse—and discovers how rewarding painting can be (especially when there’s wine involved).

It was one of those rainy San Francisco weekends in early March when all your friends are in Tahoe, but you’re not—because you didn’t want to pony up for a ski lease this year (and are now regretting it). The kind of weekend when Karl the Fog settles in and sets up shop, casting a misty blanket of gloom over the 7x7. A weekend where being a loner and binge watching “House of Cards” is 100 percent justifiable. But after three consecutive months of lazy, rainy weekends, I couldn’t do it again. I needed something fun. Something different.  

Foggy San Francisco over the Painted Ladies Nagel Photography

Foggy San Francisco over the Painted Ladies

Nagel Photography


So… I decided to try something I’ve never done, ever. Painting. With wine. In an actual class.

To preface, the thought of painting anything at all seemed immensely boring. I’m a pretty analytical guy: My world is one of neatly colored, symmetrically formatted excel sheets that calculate patterns to a nerdy degree of accuracy. But then again... I had taken a ceramics class in high school and really enjoyed it. And since I stereotypically categorize all art into the same homogenous bucket, I figured a “Bring Your Own Wine Painting Class” at the Yi Yan Art Academy of San Francisco would be just as fun, no?

Worst case scenario, I’d just get tipsy and let the creative juices flow.

The following afternoon I found myself walking to the Mission District’s east side, bottle of $9.99 red in hand (hey, I’m a classy guy). I arrived 15 minutes early at the studio, where owner/instructor Yi Yan was still prepping materials for the class. After failing to carry on a casual conversation with her, I realized that making small talk about art requires knowing how to make small talk about art. What was I supposed to say? Oh, I really like what you’ve done with this shade of yellow. Or, I think you made her nose too big in this one. So I awkwardly walked outside, then turned right back around since it was raining and pretended to go to the bathroom instead. Sidenote: Art bathrooms are just as cluttered and chaotic as the actual art studios. I guess that comes with the territory?

San Francisco cable car painting from Yi Yan  Yi Yan Art Academy

San Francisco cable car painting from Yi Yan 

Yi Yan Art Academy


I claimed my seat and watched as participants trickled in. There were four groups total: One couple on their first date (come on people, you’re not fooling anyone), one mother/daughter duo, one girl’s night out (where the wine had clearly started long before the art class did), and a pair of friends. Brushes in hand, splotches of colored paint on our individual white paper plates, and a few drinks deep, we were ready to paint. Today’s subject: A San Francisco Cable Car.  

As our instructor guided us through steps and technique, I quickly realized: Calculation and planning isn’t just for Excel sheets—there’s just as much structure and strategy to painting. You need to outline regions, judge distances, and plan for coloring far more often than I thought. Whereas I envisioned an eccentric spectacle of swaying, twirling, erratic brush strokes with classical music blaring in the background (you know, like the movies) making a masterpiece boils down to discipline and method. In this case, it quite literally started with, “Draw a triangle four fingers tall and fill it in.”

Painter in Yi Yan Academy Yi Yan Art Academy

Painter in Yi Yan Academy

Yi Yan Art Academy


My favorite part of the process turned out to be color matching. Contrary to romantic opinion, cable cars aren’t just “fire truck” red. No, no, no. San Francisco’s most iconic fixtures are actually a delicate balance of red, yellow, brown and hints of white. And while it’s fun to add a bit of this and a bit of that to achieve just the right shade, I quickly learned that color mixing can be a fool’s errand when you’re still getting the hang of it.

If you want a darker blue, simply add some black. Easy enough. But sometimes you add too much black, and end up with mostly black paint that has a tint of blue. The next logical step is to add white, because obviously that will ‘undo’ the black, right? Nope. This is a total rookie move. Now you’ve basically got a light gray with some blue in it, which is not the color of “sky” you were going for. Things go downhill from there. You try adding more blue to suppress the grayish mess you’ve made, but now you’re running out of blue—and you haven’t even started on the water part yet. I blame the wine.

Finished painting at Yi Yan Yi Yan Art Academy

Finished painting at Yi Yan

Yi Yan Art Academy


Color mixing fiascos aside, the coolest part of the whole experience is how intimate you get with your work. You start to think about tradeoffs: Should my brush strokes go left, right, or should I randomize? Should I add white streaks here, or is it fine the way it is? I like my pattern over here... I’m going to build off that.

Your whole world becomes the painting—and by the end of it, a sense of accomplishment comes from knowing every detail behind its creation, including the flaws that make it beautiful and unique. And even though we were all painting the same thing, there wasn’t any pressure to compare or compete. We were just stoked to make something we could call ours and bring home.

Dan Mascola and his painting from Yi Yan ZOZI

Dan Mascola and his painting from Yi Yan



After some deliberation, I decided to display my Paint & Sip masterpiece on the wall right across from my desk (you’re welcome, co-workers). Now, whenever I am ripping my hair out because I am three layers deep in a SUMIF function, I find peace by glancing at the cable car painting, admiring the hues and gentle brush strokes of the light blue sky.

Dan Mascola

Dan lives in San Francisco and is constantly looking for new and fun things to do.  He enjoys writing music, doing yoga, and is currently attempting to run every street in SF (90% done!).  

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