Image by Kyle Cottrell

episode 9:


a podcast on creative recovery and transformation

episode 9




Today on The Art of Lost and Found, our guest speaker is Cassey Shapiro. She is an Filipino-Australian living the dream in Amsterdam. We met many years ago when I was working with Impact Hub and came to the city often. Several years later when I moved to Amsterdam, Cassey quickly became one of my besties. 


Her smile, sense of humor and dedication to having a good time endeared me to her forever. 


After having worked in Advertising at Saatchi & Saatchi Australia, she went on to work at several advertising agencies in London, where she gained even more experience working with clients like Emirates, Sky, L'Oreal, and Suzuki before making her way to Amsterdam, where she completed her MBA. Which clearly compliments her Communications, Marketing and Advertising background. 


After spending several years rising up the ranks at WeWork Amsterdam, she got out just before the big epic crash and burn of that company and landed another level up at Reaktor, a European tech consultancy and agency, where she still works today. 


Cass’ creative journey and reinvention was something I witnessed in real time and couldn’t help but be inspired by her journey. 



  • [3:15] Who is Cassandra Shapiro?

  • [5:05] Reinvention & Flow States 
  • [6:07] Reading & Writing & Drawing As Creative Fuel
  • [8:02] Following Instructions > Being Creative

  • [10:11] Strategic Creativity

  • [11:03] Being Ahead of Her Time (hint: it involved Harry Potter Fan Fiction!)

  • [13:40] Recognition & External Validation

  • [17:20] The Tension Between Fitting In & Being Exceptional

  • [20:22] Pressure & The Creative Process

  • [21:45] Creating for Commercial Projects (advertising)

  • [27:15] When Everything Fell Apart (aka "no partner / no job / no home")

  • [30:25] Reinventing Herself Through A Totally New Career Trajectory 

  • [33:20] Self-Reflection and Finding Peace Through Meditation

  • [40:00] Alcohol As A Dangerous Tool to Sublimate Feelings

  • [41:18] Getting Off On The High of Workaholism and "Busyness"

  • [42:00] The Work In Progress Of the Process

  • [43:45] The Value of Failure + Experimentation + the Inner Critic