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The Unmistakable Creative Podcast

A Journey to the Crossroads of Should and Must with Elle Luna

The crossroads of “should” and “must” is a place we all come to eventually, though many don’t recognize it when it comes OR the importance of the decisions we make once we are there. Elle Luna is the one who coined the phrase, and to her, this crossroads is the place where each of us make one of life’s most important decisions.

Will we do what we “MUST” - what we are called and compelled to do? Or will we bow to the “SHOULDS” of expectation and obligation assigned to us by society, family, and our own beliefs - and play a much smaller game? 

Elle is one of our most requested guests so it’s a pleasure to finally have her on the show. She tells her own story to explain how her own encounter with the crossroads of should and must took place. Her journey includes…

  • A recurring dream
  • A turning-point conversation with a good friend
  • How she took that friend's crazy-sounding advice, and
  • How that bold decision led to her discover the deeper purpose of her life: PAINTING

In her book, “The Crossroads of Should and Must,” Elle writes...

“It’s here, standing at the crossroads of should and must that we feel the enormous reality of our fears and expectations from others, and this is the moment when many of us decide against following our intuition, turning away from that place where nothing is guaranteed, nothing is known, and everything is possible.”  

You’re going to enjoy Elle’s story because though the details are different, it’s the story all of us will one day experience. And you’ll be inspired by how Elle made her way through the twists and turns, cautiously approached her crossroads of should and must, and made the decision that changed everything for her.

Outline of This Episode

  • [2:22] The recurring dream that led Elle to the crossroads of should and must
  • [7:38] Life before the dream: the journey that influenced the way Elle sees the world
  • [12:30] Elle’s perspective about how to tap into wisdom larger than yourself
  • [19:12] Lessons learned working at Ideo
  • [27:56] How to tap into your “musts” and limit the impact of your “shoulds”
  • [35:27] The rock bottom moments Elle experienced along the way (to show you that you’re not alone)
  • [40:20] The moment Srinivas thought about quitting everything - and Elle’s perspective
  • [52:25] What Elle believes makes somebody or something unmistakeable


Rejection can be a gift. It was for Elle

Many of the people in Elle’s family had chosen careers in the legal profession, so both she and the members of her family assumed she would take the same path. But she was rejected from law school. Not once. Not twice. But every time she applied.

Elle says it seemed like an impossible turn of events because her grades and LSAT scores were substantial enough to earn a place in the student body of at least one of the institutions to which she’d applied. Simply put - it didn’t make sense.

It was a hard blow. She cried. A lot. 

But that point of rejection opened her up to other possibilities that she’d not even considered. Listen to hear how she came to see the rejection as a gift, landed enviable positions working on the teams that developed Mailbox and Uber, and took a role as part of the incredible creative community known as Ideo - one of the coolest companies in the world.


On this episode of #UnmistakableCreative, @ElleLuna shares some of the many lessons she learned as part of the team at @Ideo - and how they have served her long-term. #creatives #creativity #calling #purpose

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Lessons learned at Ideo - and how they have served Elle long-term

Elle’s time as part of the Ideo team was...

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Broadcast on:
13 Apr 2015