Ask Jenna and Drew Anything 2.0

Jenna Kutcher 

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March 11, 2019


Let me set the scene for you: When we recorded this Ask Jenna and Drew Kutcher Anything episode of The Goal Digger Podcast, I was still very much pregnant, Drew was wearing nothing but his underwear and a pair of socks, and one of our pups was sleeping on the dining room table. Keeping it real with you all.

Our last Ask Us Anything episode was one of your favorites, so here we are again, ready to answer your questions about pretty much anything. When I asked for your questions in the Goal Digger Insiders Facebook Group and the Goal Digger Podcast Instagram account, I have to admit, I was pretty surprised at what you wanted to know and how personal you wanted us to get. If you’re wondering how we balance this crazy entrepreneurial journey, what we say to make each other smile on our toughest days, how we knew each other were the one, or how many kids we want, then this episode is for you.

I should mention, since I was still pregnant with our then-unnamed Baby Kutcher, we make some predictions about parenthood in this episode. Maybe Drew and I should get back in front of the mic now that Conley Kate is here and see just how right (or terribly wrong) we were about our lives after she arrived. Until then, press play on the player above to hear the answers to all of your burning questions about Mr. and Mrs. Kutcher.

Our First Kiss

For the first question, it only seems right to tell you all about our first kiss! Drew and I were best friends before we started dating. We hung out all the time, we knew each other’s families, and we’d always been close. We decided we needed to kiss… Just once. To see what it would be like. Drew says I backed him into a corner and made him face reality. We were watching Home Alone together when I made the first move and kissed Drew. It was like fireworks for me. I was giddy like a little school girl. My friend Bethany said, “Oh my god, you a Drew kissed.” She knew just by looking at me that it finally happened. Fast forward 10 years and here we are, two best friends who got married!

Favorite Part of Marriage

Listener designergrey asked me: “What’s your favorite part of marriage to Drew?” I love waking up next to Drew… I know, eye roll. But it’s true, I just love it. And I love that Drew has a contentedness about him. I am constantly working and building and creating something new. My workaholic tendencies and interfere with our relationship, but Drew holds me very accountable to slowing down and taking time away from my work, too. Drew would never hold me back from my work, but he’s the perfect reminder that there are other (often more important) things to give my time and attention to — like HIM and our family and quality time together.

Parenting Fears

This question comes from kimbakerbeauty: “What are you most scared about parenting?” Drew answered that he’s afraid he will encourage bad behavior because it’s funny — It’s true, he really needs to work on his poker face before Baby Kutcher is old enough to break rules. For me, and this gets deep, I’m afraid of how my identity will change. For so long I’ve been a wife and a CEO, and now I’m becoming a mom. I don’t want to lose myself in any of those identities. I’m afraid of finding balance when I’m juggling all of the things. I don’t have that crazy desire that some women feel that they were put on this earth to be a mother. I am EXCITED to be a mom and I’m interested to see how it feels to be a mom knowing all of these things about myself.

Our First 60 Minutes

Listener Jake Wilkins asked, “What does the first 60 minutes of your day look like?” Let me preface this answer by reminding you that we recorded this episode pre-Conley Kate, so our mornings certainly look a little different now. But in general, our first 60 minutes of the day look like this: I wake up first and Drew shortly after, and we spend some time cuddling our dogs and talking about how cute they are. I read our morning devotional and we eventually get out of bed for the gym by 8:20. Fun fact: We don’t use alarm clocks. We don’t have anything that we HAVE to get up for, but we naturally wake up between 7:30 and 8 a.m. We don’t allow our phones in the bedroom, so we don’t pop open social media the first thing when we wake up but it does sneak into the first 60 minutes of our day before leaving for the gym. We used to hop out of bed a little earlier and ease into the morning by reading a book or something similar, but these days, we love our sleep a little bit more.

More Questions in This Episode

How do you wrestle with being an alpha female/breadwinner in a Christian marriage? How do you tangibly show your husband respect and love? How many kids do you want? How did you knew that Drew was the one? What is the best and WORST date you have been on together? The fight Maui that I thought would be the end of our relationship… And the inappropriate things we say to each other that always turns our frowns upside down. Press play on the player above for the full episode!

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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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