CNLP 455: Jessica Jackley on the Best Traits of Successful Entrepreneurs and Leaders, How to Separate Your Identity from Success and Failure, and Why Really Honest Feedback Matters

Jessica Jackley is a serial entrepreneur who shares her top lessons acquired as a founder of multiple ventures, including Kiva and Alltruists. She talks about what the most successful entrepreneurs and leaders have in common, what Oprah taught her about preparation, how to ensure that success and failure don’t determine your identity, and why ‘touchy feely’ honest feedback is essential for growth.

Welcome to Episode 455 of the podcast. Listen and access the show notes below or search for the Carey Nieuwhof Leadership Podcast on Apple Podcasts or wherever you get your podcasts and listen for free.

Guest Links

Instagram | Jessica’s Twitter | Alltruist’s Twitter | Website

Episode Links

Pro Media Fire

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Conversation Links

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Jessica’s Website


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Insights From Jessica

1. Effective leaders learn to move on when the situation is no longer working

Jessica talks through how her first entrepreneurial endeavor, Kiva, easily gained traction and grew into a success. Once she began ProFounder, she anticipated the same easy success, but obstacles and new legislature complicated growth.

She recalls that with entrepreneurs, “There’s often a lot of pressure to keep going at all costs and figure it out…We had a great team, but it didn’t feel quite right to do that with so much uncertainty.” Because of this, she ended up shutting the company down. She knows it was the right decision, because stepping back allowed her to focus on other areas of her life and gave her the clarity she needed for her next endeavors.

2. Your identity is not the culmination of your wins and losses

When asked about how she keeps building new things once she had a ‘failure,’ Jessica notes, “I had to sort of step back and redefine myself again. It happens a lot, where you step back and say, ‘I’m bigger than this one venture. I’m bigger than this one event, this failure, this decision. It’s not going to define who I am next.’”

In reality, while some things do succeed because we are a specific ingredient of that success, usually they succeed in spite of us and because of outside forces, the right timing and other trends. Oftentimes, success and failure have nothing at all to do with us, so why should we attach them to our identity? Jessica continues, “[I] remind myself, ‘I’m never just one thing, I’m a child of God. I am a smart person. I don’t know a lot, but I know some things.”

3. If you want to ace leadership, get SUPER comfortable with feedback

When you’re leading a team, producing a product or supplying resources to others, it’s important that you know if your efforts are achieving what you want them to. This is where feedback (positive and negative) shines a light on the reality of a situation.

The formula for an effective feedback conversation is, “When you do X, I feel Y” or, “In order to make me feel X, I suggest you make these changes.” Jessica elaborates, “You understand it’s not good, bad, it’s information about cause and effect…even if it’s hard to hear, I want to know how my teammates are feeling and what they’re thinking and if what I’m doing is working for everybody. And I want to know if my customers like what I’m making or not. I mean, how can you not want to know that?”

Quotes from Episode 455

I feel very completely, utterly convinced that change is possible. @jessicajackley Click To Tweet Success is moving from failure to failure without loss of enthusiasm. - Winston Churchill Click To Tweet It's good to take stock of the finite influence that you have on what's happening to you, and around you, every day, and there's always room to grow. @jessicajackley Click To Tweet My intention is to do work that shows love in the world, and allows other people to show love to each other, by providing community and resources for people to reach their potential. @jessicajackley Click To Tweet The people that deserve opportunity might not be people you know, or they might not be like anybody you've ever met, but they were born with just as much potential as anybody. @jessicajackley Click To Tweet My dream is to make volunteering easier and more interesting, more fun, more rewarding, not just for kids but for families and beyond. @jessicajackley Click To Tweet

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Next Episode: Aj Harbinger and Johnny Dzubak

The path to success is almost never linear. AJ Harbinger and Johnny Dzubak started The Art of Charm over a decade ago and really had no idea of what it would become. 250 million downloads later, they share some of the struggles and high points, talk about how they teach young leaders communication and confidence skills, and give some advice to church leaders about what they wish was different.

Subscribe for free now so you won’t miss Episode 456.

CNLP 455: Jessica Jackley on the Best Traits of Successful Entrepreneurs and Leaders, How to Separate Your Identity from Success and Failure, and Why Really Honest Feedback Matters

1 Comment

  1. Niamul Islam Anan on November 11, 2021 at 8:41 am

    Many thanks for sharing this with us. It looks very informative.

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