Andrea Jacobsen’s Wisdom on Art & Business
Every month, I talk on the phone with Andrea Jacobsen, a popular and talented painter who I’m fortunate to call my friend. Similar to me, Andrea quit her job to focus on her art. I’m a writer and she’s a painter, but we both have these lyrically artistic brains and whip-smart business-mindedness. This combo makes us natural confidants for the journey we both have ahead of us. One thing I love about connecting with Andrea is she’s a few steps ahead of me and she has this ability to see me and my journey with such clarity. On our call this month, I took feverish notes. It’s magical when Andrea starts telling me the answers I’ve been seeking. Here are my top takeaways from our recent chat:
Last Man Standing
In 2023, Andrea started a series of paintings of 100 women in dresses. She chronicled the journey on Instagram, primarily through reels, and in the process, connected with 100k+ women in their 20s and 30s who are obsessed with her artwork. She now only opens her shop a few times a year and collectors patiently wait for the minute it opens to scoop up her work.
This success is hugely validating for Andrea—and also—she is working toward making this newfound business venture more sustainable.
On this month’s call, we talked about the concept of Last Man Standing.
According to the U.S. Bureau of Labor Statistics (BLS), approximately 20% of new businesses fail during the first two years of being open.
45% fail during the first five years. That’s nearly half!
If we want enduring careers as business owners and artists, then we need to sustain our efforts over the long haul. When we look at it from this perspective, success isn’t an overnight one-hit wonder. It’s a strategic lifestyle that we can sustain for years.
This concept also reminds me that every year that I’m in the arena, someone else is quitting. There’s magic to having staying power. And most likely, we will only have staying power in the ventures that we are truly passionate about, otherwise, we will quit as soon as it gets tough.
Creative Brain vs. Money Brain
Andrea is a keen observer. She noticed my tendency to want to monetize everything that I do. If I’m starting a project, I need to know the path to revenue streams otherwise I won’t do it. However, revenue is unpredictable before you have product-market fit. There’s an early stage of every business where you’re just trying to prove if there’s demand for what you’re doing. In that phase, it’s important to create, launch, and experiment to see if there’s a path forward. Everything else comes later.
As we’re chatting, Andrea will remind me, “You’re skipping a step. You’re focused on monetization and not the creative process itself.”
I’ll admit: focusing on monetization is my way of seeking control. And while it is creative to think through revenue streams, it’s an avoidance tactic to the other form of work I should be doing: the creative work.
Andrea explained the Creative Brain vs. Money Brain like the left and right sides of our brain. When one side is over-active, the other is dormant. Andrea gave me an “assignment” to pause my thoughts on how to monetize every project. Instead, she asked me to simply write every day.
This was exactly what I needed to hear to get back on track, end my avoidance with the writing itself, and create my best work.
Resistance to Creative Work
All artists have this inner resistance that makes them run away instead of sit down and create.
By acknowledging this on our call, Andrea unlocked a freedom in me. I’m not the only one who has a hard time sitting down to write even though that is literally all I want to do. There’s a fear of choking: what if the words don’t come to me today? What if they’re awful? What if there’s no point and no one ever reads them?
It’s not my job to have answers to those questions. And sometimes the words don’t come! But most of the time, once I start, it flows. Once I overcome the resistance, there is Nirvana. I love that Andrea gave me words for this: Resistance vs. Nirvana.
I have to be in motion to experience the Nirvana. Nirvana is the feeling of flow, absorption in our task, and creative magic. I have to have my hands on the keyboard, thinking and writing, to receive the meditative answers that I’ve been seeking.
Keep Experimenting
Andrea left her job at Linkedin to pursue her art career, but she didn’t know if it would work out. She pursued art galleries then commission-style work for individuals but something always felt “off” about these ventures. She kept trying different ways of being a painter. Then she started creating reels of her artwork. And even then, she had a hard time finding her signature art style and audience. She experimented with different paintings and practiced filming for Instagram and Youtube. Over time, she found her groove. She learned that posting on YouTube attracted other painters who wanted to talk craft, whereas on Instagram, she was connecting with other women who loved her work. She doubled down on her Instagram efforts. Then, she committed to painting 100 women in dresses as a way to practice her craft. She didn’t know when she started filming the series that 100k+ people would follow along to watch the process unfold. She kept trying new things and eventually found her way forward.
Often, when I chat with Andrea, I find myself looking for THE answer to know what is my ONE THING. But similar to Andrea’s journey, there is no way for me to know until I keep trying, failing, and pivoting. Andrea wasn’t failing each time she found an avenue that didn’t work (like painting commissions), she was simply one step closer to finding the answer through a process of elimination.
I admire Andrea’s career as an artist because she created when no one was watching. She posted her reels whether people were watching them or not. She was ready to paint 100 women in dresses whether it was a “success” or not. And in the process, she found her way to an audience who loves her work.
Connect with Andrea
You can follow Andrea here. And if you want to be notified of her upcoming releases, subscribe to her newsletter here.
