So This is Goodbye

Jenna Kutcher 

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April 12, 2023


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Taking risks for our dreams is a concept that we talk about on the Goal Digger Podcast all the time, but it is something that can be difficult to put into practice. We often find ourselves held back by fear and doubt, and it can be hard to take those first steps. But as you’ve heard time and time again from the stories shared on this podcast, it is important to remember that taking risks can be essential to achieving our dreams.

Kylie Low has been the producer behind the Goal Digger Podcast for over four years now… But in February 2023, Kylie came to me with an announcement I always expected to hear from her – She was ready to step down from producing this podcast to pursue her dreams and work on her own podcast full time.

In this final installment of the Jenna & Kylie series on the Goal Digger Podcast, Kylie shares the behind the scenes of her decision to leave her full-time job working for me to dive into entrepreneurship and focus on her own projects. We reflect on the almost 5 years working together and what I’ve learned as the boss of someone who I always felt was more entrepreneurial than employee from day one. We get a little teary-eyed, but this conversation is a raw look at what happens when you realize it’s time to say goodbye.

How It Started

Kylie was living in New York City with her now-husband, Chris, and had left a job she loved to support him in pursuit of his career aspirations in the big city. When she moved to NYC, she was unemployed for nine months and faced a lot of self-doubt and identity issues. But then, an opportunity came her way and she took a risk and applied for this very job, managing and producing the Goal Digger Podcast. 

Jenna also took a risk when she decided to hire Kylie for the position. She took a chance on someone she had never met, and it paid off. Kylie not only became an excellent podcast producer, but the two of them also developed a strong bond and friendship.

When it was time for Kylie to move on, it was a difficult decision. She had put a lot of work into the show and it had become a big part of her life. But she knew that it was time to take a step in the direction of her ultimate dream. 

Bet on Yourself

Kylie’s story is a great example of what it looks like to “bet on yourself.” She had been working for me for almost five years and had been prepping for the last four years for the moment when she could leave and pursue her own dreams. She was honest with herself about what she really wanted and was willing to take the risk of leaving her job to pursue her passion. She was willing to give up the security of a steady paycheck to pursue her own dreams. 

As a leader and boss, I had to recognize and not stifle Kylie’s entrepreneurial spirit. I recognize the power of employees who are deeply dedicated and fulfilled in their work, and I didn’t want to prevent Kylie from working on her own projects and side-hustle while also running Goal Digger, even though it meant Kylie eventually leaving the company. 

Kylie finally felt ready to take the leap and bet on herself. She was able to recognize that she would never feel truly fulfilled as a “supporting act” and that her arrival would come when she was working on her own projects. She was able to take the risk of becoming an entrepreneur and taking control of her own destiny. 

Take Risks for Your Dreams

Kylie’s story is a great example of how taking risks can lead to success. Despite the risks, she knew that the only way for her to achieve her goals was to give herself the time and space to make it happen, and leaving her full-time job was an essential part of the process. She knew that if she didn’t take the risk, she would never get to a place where her podcast could be self-sustaining. 

Kylie was also motivated by the memory of her mother, who passed away with unfinished dreams of her own. This was a powerful reminder to Kylie that life is short and that she must take risks and go after her dreams. She knew that if she failed, she could always get another job. But if she didn’t take the risk, she would always regret it.

More from Kylie Low

If you’re going to miss her as much as I am, you can stay up to date on Kylie’s endeavors at darkdowneast.com, @darkdowneast on Instagram and TikTok, and listen to her ethical true crime podcast, Dark Downeast, on Apple Podcasts, Spotify, Stitcher, or wherever you get your podcasts

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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