Choosing Courage

Today, we are sharing a motivational message from Milan Art's Chief Product Officer, Alannah Anderson. I first knew Alannah as a Mastery Program student. She messaged me about getting a motionless selfie stick so my videos wouldn't shake so much! Then we hit it off when she came to an in-person workshop. She became a finalist on The Outstanding Artist Season 2 and came on multiple art retreats to Greece.

On one retreat, she told me that she felt super connected to our vision and wanted to help us. She brought her brand expertise and big heart to the team, and now we are life-long friends. Alannah is a sublime force, and I adore her! I think you'll be inspired by what she has to share.

-Elli

I’ll never forget being invited on my first business trip with my new boss. We were heading to the headquarters of a major global luxury fashion brand for a high-stakes client meeting.

I was relatively new to my role as a creative director, developing concepts for brands where perfection was expected. But this felt different. My boss, who held unwavering standards, looked to me to uphold those values in front of the client. I admired him, and I didn’t want to let him down.

The pressure was intense.

My heart pounded, my palms were sweaty, and familiar doubts crept in: What if you fail? What if you’re not good enough?

These thoughts weren’t new. Growing up, I learned that worth had to be earned. My father worked tirelessly to support my family, and he expected the best; anything less wasn’t enough. I began to tie my value to my achievements, always striving to exceed expectations. The fear of not measuring up became a constant shadow, challenging me at every new step and opportunity.

That meeting was just one of countless moments where those doubts resurfaced. Yet, each time, I was faced with the same choice: to let fear hold me back or to act with courage. In that moment, something shifted. I realized the fear wasn’t only about that meeting or my boss’s expectations—it was about whether I would let fear control me or choose courage instead.

That insight grew even stronger when I joined The Outstanding Artist show, where being openly judged on my art and abilities with cameras rolling felt like a high-stakes test every day. Old fears resurfaced, and the stakes felt high.

But by that point, I’d come to understand that my strength didn’t lie in defeating fear but in choosing courage, moment by moment. This shift allowed me to keep moving forward, even when doubt lingered.

Fear often traps us in worst-case scenarios, while courage brings us back to reality.

I took a deep breath, began the presentation, and chose to act despite the fear. The meeting was a success, but the real victory was in realizing that courage could push me through fear and back into clarity.

Every opportunity I’ve had has come from pushing through those moments of fear. Each time I leaned into courage, I grew—not just as an artist but as a person. Courage opened doors that fear would have kept closed. Now, when familiar doubts resurface, I ask myself: What if this moment is an opportunity to choose courage? 

Fear isn’t a roadblock—it’s a challenge.

The real choice is whether we’ll act with courage when it matters most. Each time we do, fear loses its grip, and we move forward with strength and clarity.