The Vulnerable Side of Being Successful with The Giving Keys CEO Caitlin Crosby


The Vulnerable Side of Being “Successful”

Jenna Kutcher 

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Tune in as Jenna interviews The Giving Keys founder and CEO Caitlin Crosby all about the vulnerable side of being successful on the Goal Digger Podcast.

Actress, singer, songwriter and entrepreneur Caitlin Crosby from The Giving Keys knows a thing or two about inspiring others. Growing up in Hollywood and in a family that lived and breathed the entertainment industry, Caitlin wanted to rebel, inspiring people to embrace their so-called imperfections, changing our perspective to see flaws as beautiful. While on tour for her first album “Flawz” in 2009, Caitlin started giving and selling keys with inspiring messages like FEARLESS, BELIEVE or INSPIRE. The wearer of the words is encouraged to embrace their word, then Pay It Forward by giving their product to a person who needs the message more.

Seeing the potential of spreading positivity around the world, she started The Giving Keys, a jewelry company that creates jobs for people who have been affected by homelessness, helping many move into permanent housing and achieve advanced education opportunities. Their products have been sold at Nordstrom, Ron Robinson, Starbucks and over 1,400 other retail stores around the world.  

..But what happens when you “make it”? What is the hidden side of success that creates vulnerability?

Have you ever gotten everything you’ve ever wanted… and still felt a little stuck? I am so thankful for the openness of this incredible woman, and I can’t wait for you to hear her real, raw story.


One thing that Caitlin and I talked about a lot was transitioning with your career from the creative artist to the boss CEO. And while this may sound petty or hard to understand, we both deeply resonated with the fact that when we started our businesses, it never occurred to us that one day we would be doing more managing than creating. It is such a blessing our businesses have grown like this, but in the transitioning from creative to CEO, we had to learn how to delegate and let go of things you’ve always done.


Not only is this difficult from a work standpoint, but it can create some inner turmoil in terms of “who you are” when you lose your identity as a creative. In the show, I asked Caitlin to describe herself without using her career, and I strongly recommend you do the same to ground yourself. Seriously, try it! Describe yourself without your job/title, and realize how much weight you put in your work….

One thing we mentioned that as your team grows, personal growth often gets left behind. Goal Diggers, it is so important for us to keep striving and working on ourselves all the while. It is impossible to pour from an empty cup, and I hope you use this episode as a reminder to truly care for yourselves day in and day out…


Caitlin mentioned that she was going through a difficult season. She feels stagnant and like she is failing… But she is pushing forward. When I asked her to describe it she said “Our team recently picked a word we wanted to live by, and I picked the word strong because I actually feel weak right now… I am a girl that is trying the best she can, through the struggle, through the storm, I know that there’s gold in my heart in my uniqueness in my creativity, but there is also a lot of insecurity and negative programming that holds me back from my fullest potential… but I’m fighting through. I’m a girl that’s a fighter to break negative patterns.”

How beautiful is her soul? Her braveness? Her openness? And I hope her story reached you where it needed to… and inspired you to fight– in whatever season of life you are in.



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  1. Adeline says:

    Such an incredible work ! Thank you for sharing those beautiful accounts.
    Have a wonderfull day.

  2. Carley says:

    Wow, this post totally hit home for me. My mantra this year has been, even when I am vulnerable, I am secure. Self care has been instrumental, and reminding myself that taking a few steps back is OKAY and usually a sign of growth. Thanks for being so real, Caitlin and Jenna! xx

  3. Amy Perkins says:

    This company, The Giving Keys LITERALLY changed my life. I received my key a year ago, from an acquaintance. She believed in me and over a chance coffee date gave me a BELIEVE key. My brand Keys to Courage is based on this one experience. I wish I could personally thank the founder of this company. I’ve proabably purchased 30 keys to give to others because of the profound difference my key made in my life.


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