Ask Jenna Anything Birthday Edition: I Never Expected This Surprise!

Jenna Kutcher 

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April 8, 2020


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Pssst… We planned a surprise for Jenna and you get to hear it play out on this episode of the Goal Digger Podcast!

Hey friends, it’s Kylie, the manager and producer of the show. When Jenna told me she wanted to do a new Ask Jenna Anything episode this month and we realized it would land on her birthday, I couldn’t waste the opportunity to surprise her.

You’ll hear from some familiar names and voices of Team JK in this episode… But you’ll also hear a few surprises, too. Jenna had no idea what she was sitting down to record. I’ve gave her strict instructions — No listening to the questions before hitting record (so no preparation!), she must listen and answer in order, and she must keep the track rolling the whole time so we could hear her reactions.

I am so excited for you to hear this candid, off-the-cuff version of Jenna as she answers questions about her personal life, business, what makes her laugh and more.

Okay, here’s Jenna.

What day would I relive?

So Kylie asked me this question with one caveat — major milestones are excluded! My first reaction was definitely the day Coco was born. It was just such a special day as our family grew by one precious little girl. Actually, I definitely tear up about this day later on in the episode… Press play to hear who made me all emotional.

If I could relive any day of my life, it would be the day that I saw my work published for the first time. As a photographer it literally made me cry.

We were living in a tiny apartment in this little village in Wisconsin and every day I would run to the mailbox to see if the magazine had arrived. On the day it finally arrived, I was standing outside in my pajamas, flipping through every page until I found my photos.

I felt so validated in my choice to become an entrepreneur. I remember feeling joy and pride. I remember feeling overwhelmed. I felt like I had made it, even though it was such a tiny moment in my career.

Do I ever feel jealous?

I won’t tell you who asked me this question (it’s part of my surprise) but the answer is yes. I find myself jealous a lot, actually.

What I’ve trained my brain to do when I feel jealousy is think of all the steps and work it required for that person to reach that end result. And then I ask myself if I’m willing to do that work to get the same result? Most of the time the answer is no.

A jealousy pang to me feels like a deeper desire to achieve more, or get the result that person earned without full knowledge of what they put in to get there. When I actually think through that work and those steps, I realize that it’s not in alignment with my version of success.

Jealousy might spur your creativity… But it shouldn’t be the single driving force behind what you do or create.

What do I see in the future for my business and brand?

I’m not sure I’ve ever answered this particular question in great detail on the podcast before: What does the future hold for Jenna Kutcher, the brand?

I see this business evolving as a media company that’s less about me and even more focused on the education and resources for our students.

I want to be a reliable source of high-end information with people who are using “Google University” to piecemeal things together. I wasted so much time doing that myself. When I talk about time being our currency, I sincerely believe that. I don’t want you to waste time when you’re getting started, or ever.

This brand will continue to create content that’s super thoughtful and delivers systems and steps to help you do what you love.

More Questions from this Episode

Woo, lots of big deep questions in this episode… But also some light, fun, and silly questions to break it up, don’t worry.

Who do I wish I’d met sooner in life? When will Coco get a sibling? What job would I have if I wasn’t an entrepreneur? What are my favorite childhood memories? This episode manages to cover the full spectrum of topics. I even give my stance on tooting in front of your loved ones. I hope the internet critics don’t mind!

Press play on the episode above or tune in on your favorite podcast app.



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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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