Episode 32: Real Talk: Body Image, Self Love, Marriage, and Business, With Jenna Kutcher

Melyssa Griffin

33 min



Self Love Quotes, Body Positivity, Time Management Tips, Photography Business, Airbnb Host Tips



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I’m Melyssa Griffin





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I am so unbelievably thrilled to share today’s guest with you. Jenna Kutcher is not only a dear friend of mine, but we’re also in a mastermind together. In discovering Jenna on Instagram awhile ago, I was instantly touched by her authenticity and empowering messages of self-love and body positivity. 

In fact, one of her posts recently went mega-viral, where she talks about the insecurity that she felt as a curvy woman being married to (as she calls him), “Mr. Six-Pack.” 

Jenna began her journey as a wedding photographer and quickly became one of the most sought after in the world. Now she focuses primarily on her online courses and her podcast, which teach women how to do business. 

In this episode of Pursuit With Purpose, Jenna reveals the secrets behind her successful marriage and what it feels like to go through a miscarriage in the public eye. We also discuss how she’s grown her platform, how she manages her time and some of her favorite business strategies.

This interview made me laugh, tear up and ultimately feel empowered to be and do exactly what I want. I have a feeling that it’s going to do the same for you too!

Self Love Quotes, Body Positivity, Time Management Tips, Photography Business, Airbnb Host Tips

Check out the episode below:

In this episode, you’ll hear about things like…

  • How Jenna balances the energy of “wanting to do it all”, with prioritizing her own self-care.
  • Jenna’s deeply personal struggle with self-love and why her body was just waiting for her to love it.
  • Jenna’s #1 piece of advice for couples wanting a stronger relationship.
  • The secret sauce that has set Jenna apart in attracting her devoted audience (and why she feels that not having a filter is a good thing!)
  • The critical role that systems play in Jenna’s business model.

Some Questions I ask Jenna…

  1. You do watercolor art, you have an online shop, you teach courses, you have a top podcast, and you’re a photographer (amond — I’m sure, 900 other things). HOW do you do it all? Do you work 25 hours a day?
  2. Why do you think you’ve been able to grow such a devoted audience? What do you do differently?
  3. In the last year, you purchased a condo in Hawaii and have rented it out as an AirBnB. What made you want to get involved in real estate as an income stream?

Links from the interview:

What do you think?

I’d love to hear your thoughts on this episode. How do you embrace body positivity and self-love in your day-to-day life?

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Thank you for listening!


Read the Interview Transcription Here

Hey, Pursuit with Purpose family, Melyssa Griffin here. Now I am so unbelievably thrilled to share today’s guest and a dear friend of mine with you today. Her name is Jenna Kutcher. I first discovered her on Instagram and was touched by her authenticity from the get go. Now we’re in a mastermind together, so I’ve gotten to know her a lot more. Jenna started out as a wedding photographer and then became one of the most sought after wedding photographers in the world. Now she focuses primarily on her online courses and podcasts which teach women how to do business. Something that I love about Jenna is that she’s a leader in the body positivity and self-love movement. She brings daily empowerment to her half a million Instagram followers. In fact, one of her posts recently went viral on Instagram, where she talks about the insecurity that she felt as a curvy woman being married to, as she calls him, Mr. Six-Pack.

Now this episode was recorded before her post when viral, but trust that we dig in deep to what it means to love yourself and love your body, how she and her husband have built such a successful and happy marriage, and what it feels like to go through a miscarriage in the public eye. Since Jenna is completely business savvy too, we also discussed how she’s grown her platform to hundreds of thousands of people, and how she manages her time, and also some of her favorite business strategies lately. Now this interview made me laugh, tear up, and ultimately feel empowered to be and do exactly what I want. Now I have a feeling it’s going to do the same for you too. Let’s get started.

Melyssa Griffin: Hey, Jenna. Welcome to the show.

Jenna Kutcher: Hey, Melyssa. Thanks for the girl talk.

Melyssa Griffin: So excited to chat with you. I am just really impressed with you over the fact that you have grown this massive audience online. Right now when we’re recording, you have almost 200,000 Instagram followers. You have just this incredible feed and community that you’ve grown. So I’m curious if you have any thing that you feel like has set you apart to create this devoted audience and really grow so big over the last few years.

Jenna Kutcher: Yeah, I mean it’s been crazy, because I genuinely can say the last two years would be where the growth really happened. I don’t believe in overnight success. I think that is such a myth, because I’ve been working at it for many years. I definitely can say that there has just been this change in this organic growth. I think that what happened is, I started to realize that so many of the things I was struggling with, or questioning, or making fun, or like wondering is it only me or are there other humans out there like me, that was when I started to just put that stuff out into the world and it really started resonating. I think that with social media, we joke about standing on chairs at cafes to get the perfect shot of a latte and waiting for the perfect lighting to photograph your French toast that’s cold or whatever that is. And so once I started just being honest about like these are the things we’re doing that we think are normal, but also like these are the things I’m feeling called to talk about or share or things I’m struggling with, I think that people started to see me not as a business, not as a photographer, not as any label, but just as somebody that gave them the opportunity to say me too.

Melyssa Griffin: I love that. I love that so much. You do such a great job with opening up and being vulnerable with your audience. I feel like that’s something that sets you apart from other businesses out there that you’re just 100% real about what it’s like to be a human and an entrepreneur. I love that.

Jenna Kutcher: I’m messy, man.

Melyssa Griffin: We all are. It’s awesome because it’s almost like counterintuitive to the advice that you get online about how to grow an audience or create a cool Instagram feed. You think we have to project this image of perfection in your work, your life. I love Mac and Cheese*, and just like taking naps, wear yoga pants. That’s who I am and that’s awesome, and people freaking love it.

Jenna Kutcher: Yeah. I think that there was definitely a breakthrough that needed to happen. I went to school for PR communication, like Business Administration. There is nothing entrepreneurial about it. And so everything was so formal. You learn how to write formal press releases. You learn how to address people formally. It almost just felt like I was putting this mask on every day when I was doing that. When I used to work in the corporate world, I worked for Target, and I remember my boss telling me that I needed to dress the part that she wanted me to play. I was thinking, lady, I’m wearing red in khaki, there is no dressing the part. This is good as it’s going to get. It was one of those moments where I just felt like so out of alignment with who I really was. I think that it was such a moment where I was like I’m climbing a ladder that I don’t even want to climb. I had to take that same approach with my entrepreneurial journey, because all of a sudden you start climbing a ladder that everyone else is climbing and it might not be leading to anywhere you want it to go. And so I feel like when I flip the script on that and I said, “No, no, no, like the reason you left that office was to be more authentic, to truly be who you are. Why are you not doing that in other facets of your life?” That’s when I started to gain attention in a way that really was able to serve people in a far bigger way than just playing it off like I was just perfect.

Melyssa Griffin: Yeah, I agree. Did you have like a moment where this breakthrough happened? Were you reading a book, or did you do some sort of training, or was it just this like this epiphany where you realized that you don’t want to go on and pretend to be perfect anymore?

Jenna Kutcher: I think that one of my biggest Achilles heels and one of the biggest blessings about who I am is, I don’t have a filter, in a good way. So it’s not like I go off on people or swear at people, but I don’t have a filter when it comes to life because I feel like I don’t want to look back on my life online and say, “That’s not real. That wasn’t what was really happening in my life. I don’t resonate with that girl because that girl is me and that’s my story.” And so I think that one of the biggest aha moments was, we had lost one of our best friends. He was the best man in our wedding. He was in a car accident. I remember when he first passed away, everyone was on his Facebook page typing messages to him, reading his tweets, looking at his Instagram. That was our tie to him. I think that then I realized like our generation, we don’t have diaries anymore. We don’t keep great journals. We don’t have these tangible things that we can pass on. And so our feeds are not just marketing and they’re not just highlight reels. I think they need to be our stories. I recognize the fact that I don’t take pen to paper. And so for me, it just shifted, like this isn’t just about selling things. This isn’t just about pretending to be someone we’re not. This is who I am and someday when I have kids, I want them to look at that and read these posts and say like, “she struggled and she came out” or “she walked this road too and if she can do it so can I.” And so my feed is so much more than just a marketing pitch or anything of this sort, it’s real legacy.

Melyssa Griffin: I got goosebumps. I love that. That’s beautiful. So with your business, what has changed over the last few years? I know you’ve gone through some transitions with what you sell, what you do. What’s been changing for you?

Jenna Kutcher: You know, this will tie into the personal story which we’ll talk about as well, but I think that loss is a way of really putting what you want into the universe in a different way. Sometimes it kind of forces those bigger dreams, those like God dreams on your heart to show up. And for me, I was just in this place of running, running, running. Just like you Melyssa, I was building this business that was so successful, and yet I felt so empty. I wondered like is this really what it’s about. Is it about the six figures or the seven figures? Is it about the followers and the sales? All of those things I love because I’m a strategy person, I’m a nerdy person, but those aren’t the things at the end of the night that are going to be on my gratitude list. Those aren’t the things that I’m going to end my year and say this was the year. And so when I started to realize, one, that I needed help, I couldn’t run this ship alone. If I really wanted to do something big, I had to ask for help and learn how to flex that asking for help muscle, which is so hard to flex when we are entrepreneurs. But also then just looking ahead and saying, “Do I want to be gone on nights and weekends as a wedding photographer? Do I want to constantly be launching things? Do I want to be depleted? Do I want to be on the road all the time?” The last two years, I feel like I’ve gotten to this place where my business can run when I’m resting. I think that that is the most life giving thing, because it means that you can slow down and not worry about anything else slowing down. The world doesn’t know I’m slowing down. No one feels it except for me. And so we’re preparing to be gone for five weeks, unplugged for the most part. I’m so ready. I’m so excited. The world will still be served all of the Jenna Kutcher goodness, and yet I can just be. I think that looking at the last two years, that was not the case if I would have kept going the way I was going.

Melyssa Griffin: Right. Do you feel like getting involved with courses and maybe even your podcast helped you make that transition?

Jenna Kutcher: Yes, I think so. What I think is so interesting is, just like you, I get asked all the time like can you do one on one consulting or one on one coaching, and all this stuff. My heart just breaks because I’m like I want to so bad, I want to help you, I want to be there, but when I write down a goal for the year that says make the most impact, I have to stay aligned with that goal. That goal is only going to happen if I create systems, if I create things that can scale. If I really stay in alignment with that goal, then I’m going to keep putting out resources that can reach the masses, and not just spending my hours every day responding to one off requests. And so it’s so fun now to point people to different episodes or resources that we’ve created without having to take up so much energy.

Melyssa Griffin: Right. You seem like you’ve really mastered that kind of business model, where you are there for your community, but you’re able to take time for yourself. So I’m curious, for kind of my own personal curiosity, I am so with you and so agree with you know about how you want to create a business that feels purposeful and meaningful to you, and gives you time off and that balance to rest, and go to Hawaii, and do things that are rejuvenating to your spirit. Something that I find is that I crave that and need that and want it, but then on the other side, I make my vision for the year and it’s like okay this month we’re doing a huge launch, then we’re going to do an event the next month, then we’re going to do this thing and that thing. I want to do it all, and then I look at my year and I’m like well maybe I can squeeze in a vacation somewhere. How do you balance that energy of wanting to do it all? Because I know you do – with prioritizing your own self-care.

Jenna Kutcher: Yeah. I mean, so a year ago, we did our first month off sabbatical. I was terrified. I was working double time. I was frantic. I wasn’t ready to rest. I also believe that we believe this lie that we’re not capable of rest. I think that sometimes our soul yearns for it, but we convince ourselves that our brain just functions at a higher level and it can’t slow down. Those are all lies I told myself, which now I’m like oh my word, so funny. When we mapped out my year this year, we knew, like February off limits. Nothing is happening in February, zero collaborations, zero interviews, nothing. I think what is so cool is to legitimately blackout dates. So our goal this year is to be in Hawaii three months out of the year. We have those months blocked out. For me, I know that I have to get out of my surroundings or else I’m just going to work. I’m the kind of girl that will open my computer at 10 PM to do one thing, and then an hour later I’m like what happened. And so for me, it’s like I need that change of pace, change of scenery. It might not look like that for everyone, but I do want to tell people that when we go for a month, it’s honestly almost the same exact cost as going somewhere for a week and staying at a luxury resort. We did the math and we’re like hey we’re going to live there. We’re not going to do all the excursions and eat every meal out. We’re just going to be. I mean it was really inspiring to me when I wrote down that goal and I actually broke it down and said what would it look like for this to really happen. It suddenly became a real thing that we could approach and we could go after. So I block everything out. It’s like basically once a quarter, we have like a down month. My team is still working. My team is all enrolled in different courses while I’m away. So they’re all going to be learning while I’m gone. They just have time to do some of that stuff that they haven’t been able to because I’m always changing things up and dreaming bigger dreams.

Melyssa Griffin: Right. I like that. I love the idea of just blocking out a month. That I think is something I need to commit to. I’m going to do it after we sign off today. So kind of on a similar topic, I don’t want to beat a dead horse here, but I am just so impressed and inspired by how much you do. You do watercolor art which is gorgeous. You have a shop where you sell templates and a lot of different things. You have online courses that you sell and you launch. You’re a photographer. You have a mastermind. You kind of do every single thing that is possible for you to do. How do you do it all? It seems like it would take 25 hours a day to run all these different facets of your business.

Jenna Kutcher: Yeah. I was telling Melyssa before we jumped on, we’re closing up a course today. It’s our biggest launch ever, and here I am wanting to just hang out with my girlfriend. It’s one of those things where you do the work upfront and then you trust that you did it well. And so we’re not constantly tweaking or changing things. We’re doing it all it upfront. I have found that I am a crazy person. I work like a quarter ahead and it just gives me the space from my work to be non-emotional about it, to be prepared, to trust in the process and not be so close to everything. I also have this incredible team of women. It’s hilarious for me to talk about it because I literally had zero people on my team two years ago. I have this team that has this culture where it’s like each for the other. We are out there creating, and helping, and jumping in, and serving. And so I create a lot of the content, but today I busted out six episodes for my podcast this morning. I have it all blogged and ready to go, and those will go out in a couple of months. So I love to batch work. I’m a huge believer in batch working. I think that we’re looking at doing more with less content. So last year we created over 55 opt-ins which is…

Melyssa Griffin: Wow. Oh my God.

Jenna Kutcher: I don’t recommend that to anybody. We did the math at the end of the year and were like wow, we are creating so much content. Now we’re just looking at why don’t we create one really good piece and then put 90% of promotion behind that, instead of creating 90% new things and 10% promotion. So we’re kind of switching it up a little.

Melyssa Griffin: Yeah. What is that 90% that you’re putting your eggs into right now?

Jenna Kutcher: Yeah. So our 90% is going straight into everything automated. And so we are just so focused on meeting people where they’re at and then guiding them to where we want them to go. So I think that for so often, we miss the opportunity to give people an experience. I think experiences need to be felt. I think people need to feel seen and heard and cared for. I think that a lot of times we were dropping the ball, because somebody would sign up for a tool and a resource, and then they get a generic list, all list email the next week. We wanted to really say you need help with this. We’ve created all of this free stuff for you. Here’s where we can take you and here’s where you want to go. What I think is so incredible is that when you take a step back and you say what is the bigger picture here, is it growing your list, is it growing your profits, or is it truly making an impact. That’s why we want to put out such good free stuff. It’s not this gimmick. It’s like I’ve made these mistakes and I’ve wasted years doing some of this, let me hand this you. It’s up to you to do the work and it’s up to you to make the change. If I know that I gave it to you, I know that I’m doing my part.

Melyssa Griffin: Yeah. It seems like it fuels—it seems so connected to your business because it fuels that balance you have. And then it’s just like you created this community and brand that’s very vulnerable and genuine. To give everybody like a generic welcome to the email list kind of email doesn’t seem like it fits with you. So I think that’s what really cool that you’re focusing on that. It’s definitely something we’re working on this year too, but I know you are just pumping it out.

Jenna Kutcher: I just create content real fast.

Melyssa Griffin: Yeah. Yeah, that is amazing. So I’m also curious about—I think it was last year, you purchased a condo in Hawaii. Is that right?

Jenna Kutcher: Yes.

Melyssa Griffin: Have you started renting it out on Airbnb?

Jenna Kutcher: Yeah. So we’ve had 35 visitors. We’re a super host. It was so fun. I often tell this story because Hawaii was a bucket list item for us. It was one of those far off dreams, maybe on our 10 year anniversary we’ll go there. Finally, I was like why are we waiting for this. And so we went for 10 days. We fell in love. Drew wanted to move there. I said no way. And so then we planned for the month off there last year. Drew had to quit his job in order to make that happen. So it wasn’t just like this whimsical thing. It was like we’re going to likely* stretch, but we’re going to do it. While we were there, we flew my parents out to be with us, because my parents are bucket list people and I’m sick of bucket list people. Go out and do these things. And so he flew my parents out there and we were joking like maybe we should just buy a place here, then we’ll keep coming back. My dad got really excited about that idea. And so we went and looked at a few places. We ended up putting in an offer, buying a condo. And then last year we were there two more times to get ready. It’s so cool because it’s just been such a life changing place for us. And so to be able to create an intentional space and open it up for other people—and we’ve been through a lot a life in Hawaii which we’ll talk about. A lot of big life things have happened while we’ve been there. And so for us, it’s just like this place my soul craves and it’s such a different life there. Yeah, it’s been so fun. We want to get another unit just because we’re so booked that then—we thought we would be able to give free weeks to our friends and family, and like we’re so booked we can’t do that. And so it’s such a beautiful problem, but we love it. We love having the condo there.

Melyssa Griffin: That is so cool. So your dad was really excited about it. Other than your home where you live now, do you have any other real estate investments or is that your first?

Jenna Kutcher: That was our first and we want to do one more. It’s kind of scary putting a lot of money on an island, I’m not going to lie. I’m like wow, here we go. We want to do one unit that all of the profits get donated. So we want to make like a water condo, and then all of the profits will go to the water projects that we donate to. So that’s kind of our bucket list goal, is to like create this space for people that want to do good and give back, and have that condo available as well. So that’s our big goal.

Melyssa Griffin: That is genius. I love that. I want to talk more about that in a second too. So I want to go back to your Airbnb that you have now. What was it like getting it set up, for anybody who’s like maybe I could do that or maybe I could use Airbnb as another income stream? What was it like to set that up? Do you have any tips?

Jenna Kutcher: Yeah. I mean it was terrifying. Drew and I, we had the worst week of our marriage while we were setting it up, because we flew out to Hawaii and we had 10 days to flip the space. We should have been an HDTV television show because one, Hawaiian contractors do not show up on time or on the day that they say they will. They’re so busy, so they don’t really have like any need to show up on time. The first night we slept on the floor because we didn’t have a bed. There was like lights hanging from the ceiling that weren’t wired. We didn’t have water for a few days. And so getting it all set up was really stressful, but it was so cool when we finished because it’s a very simple, minimalistic place. We don’t want it to be cluttered. We want it to just feel relaxing. We made tons of improvements for like $10,000. Now, I mean it’s profitable, it’s awesome, and all we do is—Drew manages the Airbnb site. So he manages any new bookings. And then we have a manager on the island, who is the person on call, who is ready if they need anything. And then we have cleaners, and that’s pretty much it. So it’s a very self-sustaining process. It gives us a space to say we’re going back to stay at our own place. I can visualize where we’re staying. I’m excited to be back there. We’re flying into Hawaii and our condo is so booked that we can’t stay in it for a couple nights. So if that’s not a good problem, I don’t know what is.

Melyssa Griffin: That sounds like a great problem. What kind of– how are you getting all these people? Is it sort of marketing? Are you marketing it to your audience?

Jenna Kutcher: Yeah. So I think the biggest thing on Airbnb is pictures. I’m so fortunate because I’m a photographer. When we were looking at the Airbnb listings, everything is like these weird sunset photos of like a beach, so it’s not even relevant to get people to click on a link. We’re like what do we care about—we want a comfortable bed and a good kitchen. And so we just were really intentional. I did create a separate website because I’m Jenna Kutcher. I’m a branding freak. So we have our own logo, and we have a surfboard with our logo, and pillows with our logo, and mugs with our logo.

Melyssa Griffin: No way.

Jenna Kutcher: Yeah, I went a little crazy.

Melyssa Griffin: That’s so cool. I feel like creatives make the best entrepreneurs because we just make everything look beautiful.

Jenna Kutcher: We’re just going to slap a logo on it. We have a guest book that is like beautiful. We leave like a bottle of wine and a picture for everyone to take home, that we signed. So I definitely think having an online audience helps, but I mean a lot of people are signing up and we don’t know who they are, they don’t know who we are. And so I think a lot of it is through Airbnb, which is awesome.

Melyssa Griffin: That is really cool. Good to know that you could do that without needing this huge audience.

Jenna Kutcher: Absolutely, good pictures.

Melyssa Griffin: Good pictures. What was your decision behind—and maybe this is because you wanted to stay there, but what was your decision behind not renting it to a tenant versus doing Airbnb?

Jenna Kutcher: Yeah. So the complex that we bought in, we are super lucky because they allow for short term rentals. And so there are properties in every state where they don’t want short term rentals. I know we’ve stated them as Airbnb guests, and you’re like hi, I’m so and so’s cousin, and you’re like I’m not their cousin. Our place is set up almost like a hotel, so our guests can actually check in at the front office and get like a parking pass and everything. They love having short term rentals and so that was awesome. I mean from a business standpoint, it’s a lot more lucrative to have people in and out and charge a nightly rate versus a monthly one. Hawaii is actually really struggling right now with their housing market. And so when we go there, we are a part of the community. So we donate our time at the humane society. We belong to a church. We belong to a gym. I’ve been brought to be like on a bureau for business owners. And so we want to make sure that we’re respecting the culture, we’re giving our guests the information that they need to enjoy their time. We just want to make sure that—Hawaii is so expensive right now. So when we purchased our condo—they’re having just a hard time for locals to live there financially, so we want to make sure we’re giving back while we’re there and not being a part of the problem. And so last time we did a food drive and things like that, where we want to be a part of the solution, not the problem. Our condo is so fun. I think that what was great is just that we found one that allowed for renters to come on in and enjoy their time.

Melyssa Griffin: So cool. You brought this up with the other one that you’re thinking of buying and renting, that you are part of philanthropies and you donate to charity, you give back. You don’t talk about it a lot online. Can you tell us first a little bit about what you, do how you give back?

Jenna Kutcher: Yeah. So I always struggle, because it’s such a big part of what we do and who we are, but it’s also, we don’t do it to share it but it’s always that like delicate, like it inspires other people to do it too. I just can never find the balance in that. Two years ago, I was asked to be a photographer on a project. Basically, it’s with Healing Waters International. They do clean water systems for third world countries. So last year we funded three different projects that are giving clean water to communities, so it’s hundreds of families. I’ve been to the Dominican Republic three times the last two years to see the communities and to talk to them, and to see how we can impact more. And so it’s heartbreaking and it’s inspiring all at the same time. It just reminds me of how lucky we are. Every person can make a difference. So we do a portion of every launch, a portion of every big thing that we’re doing, it all goes out just because people need to know too that when they’re investing in me, it’s not just in me, in my life, it’s in the lives of other people. So I am a little bit more quiet about it, but it’s one of those things too that it just is hard to explain until you’ve been there. You know with Pencils of Promise, you go and see that, like you are changed. Just seeing it online, it’s so hard to get that. It’s just so hard.

Melyssa Griffin: Right. For what it’s worth, I think you should talk about it more, because I think it’s—and I get that balance for sure of feeling like you’re just—for me, it feels like I’m talking about it as this privileged white woman who’s like “I’m giving back to this charity”, but then on the flipside I’m like but then maybe other people will find out about this charity or even just giving up* anything… yeah volunteering or any way to give back. So I struggle with that too, but I feel like people would definitely be inspired by that if you share it, but I get that.

Jenna Kutcher: I think the good outweighs the bad for sure.

Melyssa Griffin: Yeah. I bet that the charity, Healing Waters, is very grateful that they hired you as their photographer.

Jenna Kutcher: Right. I’m like I’m still here, still coming back.

Melyssa Griffin: They’re like thank God we hired her. So one of my favorite things that you do is you have this series on Instagram where you post photos of yourself in your underwear. You do it as this ode—kind of sounds creepy that I said that. You do it as this ode to just feeling confident in your skin and I think it’s really beautiful. So when did you first start doing that?

Jenna Kutcher: Yeah. So funny story, but the other day, I was with my dad and he goes, “I saw you on Pinterest in your underpants.” I was like, “First off dad, you have a Pinterest, that’s great. But second off, I’m sorry.” So it all started because I was at a workshop with some beautiful women that I love, women that I am just enamored by and inspired by, and all the sudden, the conversation at the table just got so negative about what we hated about ourselves. And so the next day, I showed up in their hotel room, no makeup, nothing, and I took their pictures because I wanted them to see that they are beautiful from the minute they wake up. And then my friend turned the camera on me and so I was like shoot, this idea was awesome for everyone else, but I don’t want to do this. I posted it and I talked about that struggle of self-love and feeling worth, and hiding behind masks in so many things that we all do. I mean it just resonated. It was not just like the most liked post, but it was so impactful. Over the last two years, we’ve been through a lot of losses that have changed my body and really sent me on this journey of like not feeling at home in my own skin. And so I knew that if like I was struggling with this, there are other women out there, no matter what shape or size or color or sexual preference you have. There are women that just don’t feel womanly or don’t feel comfortable or don’t feel represented. My friend said this one time—I thought it was just so good—she said, “If you’re not seeing yourself represented, you are the representation.” And so it was such a call of like if I’m angry that I’m not seeing plus size women in campaigns, or no retouching done on these beautiful women who are beautiful regardless of any perceived flaws, then I need to stand up and represent that. And so it’s been this crazy thing that has become such a part of my brand that is truly just a passion project that has nothing to do with what I do. It has nothing to do it what I sell, but it has so much to do with who I am. It is one of those things where—I was a really competitive gymnast growing up, and then I went in and dove in college for four years. So I was always in leotards and swimsuits. I was so used to seeing my body in a mirror and not liking it. I felt like that for so long, my body was just waiting for me to love it regardless of those flaws. And so it is such a fun thing. I have gotten so much more confident than I ever was before. I still don’t feel perfect by any means. I still struggle. I think that’s why it’s so cool, is because I’m showing it while it’s still happening.

Melyssa Griffin: I like that; you’re showing it while it’s still happening. I love what you said, “My body was waiting for me to love it.” That’s so beautiful. I love that. What your friend told you too, the advice that they gave, I actually pulled out one of your captions that I wanted to talk to you about, and it’s basically the same sentiment. You said, “I never woke up one day and thought I am suddenly beautiful. I just woke up and said I’m going to show more of what I’m yearning to see in the world, and I did it. See a need, desire a change, be it.” I love that. It’s so true. It’s like if you don’t feel represented or you don’t feel like you’re seeing what you would have needed or what you need in this moment, then you can be that person to give that to your community, your friends, your partner, your family.

Jenna Kutcher: Yeah, it’s crazy. It’s so funny too because people will say like what does your husband think about that or whatever, and it’s my body. Honestly, most of the time, he shoots the photos of me which I think is so cool because he sees me in such a beautiful light, like a light that I would never see myself in. Also, at the end of the day, like my audience, those photos are for women. My audience is women. It’s not a sexual thing. It’s not something that men comment on. I mean there are like zero dudes commenting on those posts. It’s for the women out there, and that’s where my heart lies. And so it’s been really crazy and it’s been awesome.

Melyssa Griffin: How did it feel before you published that first photo? I’d imagine for anyone posting a photo of themselves in underwear to like 100,000 people, it feels scary. How did that feel?

Jenna Kutcher: It was nerve wracking because it was zero retouching, no makeup, underwear. I think too, one of the hardest things about what I feel like my body is, is that I’m in between. So I feel like I’m not a straight size and I’m not a plus size. There’s very little room in the middle. I feel like our culture likes to go to the extremes on one side or the other. And so when I was thinking about it, I think that where I always start is just what do I want to tell myself. A lot of times the people that inspire you the most, are the people that are putting out messages that they need to hear. I think that our encouragers often need encouragement. And so a lot of times I need to read my own captions back and be like sister, listen to yourself, because it’s so easy to tell other people what you think, but it is not—it is what we need. It is what I need. So that’s what I thought. I was terrified, oh my gosh.

Melyssa Griffin: Right. Yeah, oh I bet. I love that you said that too, because I feel like the people who have been through the most pain or who seem to be the most empathetic or knowledgeable, are the people who have struggled a lot. They’re just carrying what they’ve learned through those struggles and they need support too. That’s so important. So you’re this beautiful evangelist for self-love. What has your self-love journey been like?

Jenna Kutcher: It’s been rough. This year, I hired a life coach. Her name is Erin. She’s through Raw Beauty Talks. She’s incredible. After our second loss, she approached me and she said, “I want to help you.” I think that a lot of times we tend to bury that hard stuff. We don’t want to bring it to light. We want to turn to other things, whether it’s work or relationships or achievements, in order to kind of bury the real work that needs to be done. And so I have been like digging into a lot of the hard stuff lately. It’s one of those things where I want to dodge her call every single week because I’m like I’m not ready, I’m not ready, but we’re never ready to deal with some of that crap. And so I think that being an athlete my whole life and looking at successes, I was often the girl that would do things because I was good at them, not because I was passionate about them. I’m a risk taker, but a calculated risk taker. And so when I was in athletics, I was just really good at the things I chose. Even if I wasn’t super fired up by them, I did it because I knew I’d be good. And so once I was done with athletics, I was like who am I. I’ve always been this athlete. I gained weight. My body finally caught up to me. I started to develop female body parts that I didn’t have before. And so it just kind of hit me like a ton of bricks. I think that our bodies are just so capable and so strong and so beautiful. I never understood things like yoga and meditation and intuition, and all these things that you do such a good job about talking about and that you’re passionate about. I think I just blocked them out because I believed that hustle and grit and tenacity could overcome all of that stuff. It wasn’t until I started digging in and saying like what are my biggest fears and what am I worried about. Even yesterday on a call, I was saying I’m worried that if I get pregnant, I’m not going to love my body and I’m not going to be able to talk about loving yourself because I might not be there. That was a fear that I had, but it was legitimate. It was one of those things that was maybe holding me back from something that I wanted even more. And so when I started to dig into that, was because I want to be this example. Sometimes the people that are examples, are struggling and flailing. I know that when it comes to loving yourself, it’s retraining those conversations in your mind. I think that that is the hardest work you will ever do in your life.

Melyssa Griffin: I agree. I feel like that’s—and thank you for sharing that by the way. I feel like that’s where all of the hard work of our life stems from. It’s like anything that you want to achieve needs to start from that place of working through those things that have been blocking you, maybe even subconsciously for your entire life.

Jenna Kutcher: Yeah. That’s the hard work, like that’s the hardest work I’ve ever done over anything business related. I think too, there’s just so many things that we’ve hidden, and when they’re unearthed, it’s uncomfortable, but it gives you so much room to grow.

Melyssa Griffin: Yeah, exactly. Now it’s like—and I’m sure you have this experience too. It’s like when something’s not working in my business or we’re running up against a block, I never think anymore, like what’s a strategy that I could use or like what book can I read or what can I implement? It’s like where am I blocking this inside of myself, what story am I telling myself that’s keeping me back from success in this realm, and how can I change that, and then there by change the outcome in this business or relationship or anything. It always goes back to me.

Jenna Kutcher: Yep. Amen.

Melyssa Griffin: So you talked a little bit in this conversation about loss. I know that over the past year, you’ve experienced miscarriage with you and Drew. I just appreciate you so much for being vulnerable in that way. I know you opened up to your audience, to our mastermind about it. That takes a lot of courage. I know that that was not and probably still isn’t an easy experience for you. What was it like to go through that?

Jenna Kutcher: Yeah, it was crazy. So we’ve been through two miscarriages in almost two years, and so it’s been a process. I feel like a woman’s biggest fear is that she’ll want children but it won’t happen for her. I think that deep down we all feel innately broken or that something might be wrong with us. Regardless of where we’re at in that journey, I think that that’s a fear, that we put womanhood on this pedestal. And so, like I said, Hawaii has been such a pivotal point for us because we found out we were pregnant both times in Hawaii. And so it’s kind of been this place of healing, but also a really hard place; a place that we buried a lot of things in the sand. And so the first time we went through the miscarriage, I had had this intuition—now I can call it that because I know—where like I called to tell my sister the news. I said, “If we lose this baby, I’m going to share it.” She was like, “Why are you telling me that? You just found out you’re pregnant.” I feel like it had been on my radar, it had been on my heart. I had asked my grandma if she had had any miscarriages. I think it was just something that I was really sensitive to because I knew so many people had been through it but didn’t talk about it. And so our first loss—both of our pregnancies were up to ten weeks, and that’s two and a half months of your life where you’re like exhausted, and tired, and excited, and hopeful. The first loss really hurt, but I felt like okay, God has a purpose in this. I’m meant to share it. I meant to give it a voice. I meant to honor this baby. It still was really hard, but the second one, man, that ripped me off my feet. I think that I was waiting for that redemption song. I think I was waiting to be like, “Look at my God, is so good. He gave us this baby that we prayed for.” I had believed that. I so believed that and I still believe that even though it didn’t happen the way I thought it would. At the time, we saw the heartbeat, we were getting past these milestones that we hadn’t the first time. It felt different. I was sick in the mornings and I was so excited about being sick because it meant something was happening.

That second time we found out, oh my gosh, I was angry. I was so mad because that wasn’t supposed to be our story. I felt like I had done the hard work of sharing our first. It just wasn’t what I pictured for my life. And so when we went through the second one, I definitely think it just wreaked havoc in my life in different ways. I buried myself into work. I didn’t want to process it. I didn’t want to honor the baby in a way because I was angry that it didn’t stay, but it led to so much bigger work like we’ve been talking about. There was so much I needed to do and to prepare and to change. To be entirely candid, we’re thinking about trying again soon. Just that thought is exciting and terrifying all at the same time. For me, I just needed a long grieving period. I know some women can get pregnant right away after, but it just—it felt like gosh, I can’t move on. I just can’t let go of this idea and this child that I had dreamt about. And so putting it out there has been such an incredible thing and it’s also been a really hard thing, not in the way you would expect, because we get messages every day of people going through it. When you’re trying to get in the headspace of like this can be it, like it’s going to be good, it can be really hard where you want to like put the blinders up and say this is our time. And so we’re giving women a stage and a voice to share and a place to share, but it’s also just one of those things where it’s a hard calling to answer. We’re doing our best to step up to that, but it’s just crazy to me that there’s still a stigma around something that so many people go through. One in four pregnancies ends in miscarriage, so chances are someone you love dearly or yourself, has been through one. Just like with body image, it’s like we have to start having those conversations and we have to stop being silent. There is so much power in saying me too. And so it’s definitely been a challenge. It’s challenged me in my business. It’s challenged our marriage. It’s challenged my dreams that I have for my life. It’s also made me ask myself like what kind of mom do I want to be and do I want to be working all the time, or do I want to be present, and things like that. So it still leaves me hopeful.

Melyssa Griffin: Yeah. Thank you for sharing that. I appreciate you so much. I feel like there’s this misunderstanding about it, where it’s like you didn’t lose a baby that was born so why are you so sad. I love that you are changing the conversation about that, that just because you didn’t get to hold it in your arms doesn’t mean that it was any less of your child or that it felt any different when you lost it.

Jenna Kutcher: I totally thought that. When people used to tell me about it, I was like okay well, at least it happened early, and it was just your body’s way of doing things. I totally said all the things that people probably shouldn’t say because I didn’t understand it. When I looked at like I’ve been pregnant 20 weeks out of the last two years and I have no baby to show for it. When you go through labor pains because you’re far along and your body is expelling what you thought was your child, like that is the hardest, messiest thing you can ever go through, and nobody talks about it. I think too, it’s just—you have this idea, it’s like—especially creatives, you’re like I’m going to plan on our announcement, and I’m going to plan the nursery, and I’m going to have a baby and this is—all these things. Our brains are just so powerful. And so it’s hard to not be guarded going into it a third time, but I also just want to like release and surrender and be expectant and allow myself to go there too. So it’s definitely another delicate balance we’re walking, but I’m excited. I’ve done a lot of work this last year to prepare my body and my mind for it.

Melyssa Griffin: Yeah. You talked a little bit about God and God’s plan for you and your life. Please let me know if this is insensitive in any way. What I love about you is I almost feel like you were chosen for this experience, because you said that in your first miscarriage, you used it as an opportunity to share with your audience, to educate them, and to really create this movement and paradigm change of what it means to have a miscarriage and how we talk about that in our culture and society. And then in your second miscarriage, you used it as an opportunity to work on yourself and to love yourself more and to heal those things inside of yourself that needed healing. It’s almost like maybe this process that we go through sometimes where maybe it’s from a miscarriage or maybe it’s from like a divorce or something that happens, we lose a business or something that just alters our world and then brings these beautiful blessings to our life.

Jenna Kutcher: Yeah. Oh, I see God’s hand in all of this. I think that—I was talking to my doctor about trying again and I was like honestly, there’s a piece of me that has gratitude because I have had to dig into the hard work and I’ve had to ask myself what am I afraid of. I’ve had to eliminate things from my world in order to prepare. I’ve had to make lifestyle changes and all of these things. There is so much beauty that has happened in the last two years that I don’t think would have happened. And so there is still so much beauty in our story, and though it’s not written the way I would have wrote it, I have to trust that somebody that has this bird’s eye view of where I’m going can see so much more than just me with a little flashlight trying to figure out where I’m headed next.

Melyssa Griffin: Yeah. Yeah, I like that. Thank you for talking about that. So you also, another thing that I want to talk to you about is your relationship with your husband, Drew. So he’s somebody who you talk about a lot on your Instagram. He talks about you on his Instagram. You guys are just so cute. I’ve met both of you in person. I know you guys. You just have this really beautiful relationship together. You’ve been married for like five/six…

Jenna Kutcher: Six years.

Melyssa Griffin: Yeah, you’ve been together for a long time. It seems like you have still found things to be passionate about together. You both work from home too. So you’re like with each other all the time. I’m curious, what are some of the things that have helped you maintain and create this really beautiful marriage?

Jenna Kutcher: Yeah, so we’ve been together going on 10 years, which is crazy. We were babies. So when we got married we were 23. What’s been so cool about our relationship is that we have grown into ourselves while still growing together. I think that we are very different people than we were when we first met, when we first got married. Have you taken the Enneagram test?

Melyssa Griffin: Yeah, I have.

Jenna Kutcher: What number are you?

Melyssa Griffin: I’m between a two and I three.

Jenna Kutcher: Okay, I’m a three and Drew is a one. We just found out about this. A one is like a very introspective, very thoughtful, has like an inner dialogue. And then I am like let me shine, here I am, I walk into the room. And so what is so funny about our story is that we were best friends for three years before we ever dated. I had this mad crush on him but he thought of me as like too good of a friend to date. I told him, I was like if you date me, you know we’ll get married, and look who was right. Our relationship is just hinged on this fact that we genuinely enjoy each other’s presence. I think that what is so fun about it is we like still hold hands when we go to bed at night, and we say three things are thankful for every single night, and we read devotionals together. Don’t get me wrong, we were totally fighting today about buying a new vehicle. I don’t think we need a new vehicle. It’s not all perfect, but it’s just funny because I feel like I’m waiting for the honeymoon phase to end and I think that I don’t want it to. I don’t think it will. I think we’re still pursuing each other. We definitely have had to figure out a balance, working both from home is hard work because you’re in each other’s space. It’s like what do you talk about at dinner, because you’ve literally had breakfast and lunch together, nothing has happened without the other person being there. We’ve pursued things in parallel lines but not together. I think we have ownership over what we’re doing. And so I just really love hanging out with him. His love language, he loves quality time. I am like the person that’s go, go, go. And so now taking this time off in Hawaii together is just like this life giving experience for him and it’s so hard for me to rest. It takes just as much effort to rest as it does to work really hard, but he’s totally worth it. It’s fun. We’re together all the time.

Melyssa Griffin: Yeah. That’s awesome. I think if you can be with someone all the time and still love them, that’s a good sign. What is your love language? You mention his is quality time.

Jenna Kutcher: So I’m physical touch and words of affirmation. And so it’s funny too because looking at the Enneagram, like I need to be told that I’m great and that I’m killing it and that I’m doing all these things. I need to help train that inner dialogue in Drew. The more that we’re digging into those personality types, it’s making so much more sense and it’s giving us such empathy for each other. On the Enneagram, you can do compatibility. It’ll show you your relationships based on what number you and your partner are. We are super compatible when it comes to that. It’s helping me to really make sure that I’m reinforcing the things that mean a lot to him and that I’m paying attention to those things and vice versa, because I think that a lot of times the way we give love is not the way we will receive it. It’s so important to nurture your relationship and to really just root for each other and to be on each other’s team and to respect one another. And so it’s a learning process. We definitely have our moments, but we’ve never slept in separate beds. I’ve definitely tried it a few times when I’m really mad and it doesn’t work. So we still like each other.

Melyssa Griffin: That’s awesome. I like that you bring in these personality tests, love languages, Enneagram?

Jenna Kutcher: I don’t know how to say it.

Melyssa Griffin: They made up this cool word and decided to make up an entire word. Would you have any advice for people who are in relationships or marriages and they want a connection that’s strong like yours or they just want to improve it in some way?

Jenna Kutcher: Put your phone down. That’s my recommendation. I think we are just so connected to what other people think of us and what other people want from us, and to feel needed by their people. I am speaking from experience. There are so many times where Drew just wants to be seen and heard and I’m sitting there on my phone not paying attention. There are so many opportunities to build that relationship and that connection, and yet we’re so distracted by external factors that literally have zero influence on our lives. And so creating that space where you truly are unplugged so that you can be with the people you’re in the presence of. I have definitely challenged myself lately. I am the worst texter on planet earth because I hate text messaging, either call me or it’s not worth it. I will not have a phone in the bedroom because I know I’ll go on it. I will not have a phone when we eat meals together because it’s not—he’s just so much more important than that. It’s so easy to see it other people and it’s so hard to see it reflected in yourself. And so put your phone down. That’s my best advice.

Melyssa Griffin: I love that you brought that up. That’s something that me and my boyfriend try to do too. It makes such a difference to like put it in another room, put it out airplane mode. It’s like what you said, the person you’re with is probably someone who’s way more important to you than what’s happening on Instagram right now.

Jenna Kutcher: We put our phones in the glove box when we go on dates. And then we’ll like be eating and we’re like, “Look, everyone’s on their phone. How dare they!” Even know it’s like totally us normally. We’re so proud of it, but it’s like man, you do look around and it’s like people are so disconnected these days. It breaks my heart.

Melyssa Griffin: Yeah, me too. It is scary. It is really scary. One thing I just want to acknowledge you on, throughout this conversation and just knowing you, you are so good at taking ownership over things that maybe you’re struggling with, or anything that you did, or like you were talking about being on your phone. You just are so good at being responsible for how you feel and what you do. It’s something that I love about you.

Jenna Kutcher: I am highly self-aware to a fault sometimes, but I’m also highly coachable. So that comes with it.

Melyssa Griffin: Yeah. I feel like taking ownership, you need to be self-aware, but you also need to be honest like willing to go there with people too. So I think that’s a beautiful quality.

Jenna Kutcher: Thank you, Mel.

Melyssa Griffin: So I have one last question I want to ask you. I love asking this to all of my guests. It is: what is one thing that you feel like people can do to live a more meaningful and fulfilled life?

Jenna Kutcher: I think that the biggest thing—and I knew this question was coming because I tune into the show. I think that one thing that people can do is to write down your story, whether it is in a note on your phone, or a pen to a paper, or an Instagram post. I think that it’s time that we start documenting our stories now and not waiting to document them until we get clear or we get through to the place we think we’re going, because there are so many beautiful things happening now. And so often we’re just so busy wishing for what’s next. It’s easy in hindsight to look back and say like those are beautiful times or those were times of growth or those were times where I wish that I could remember. And so I would absolutely just say start writing your life. Let there be traces of who you are when you’re gone for the people that love you and the people that need to know you and your soul and your story. Write it down. Share it with the world if you feel comfortable, but leave that bit behind because there are going to be people that are going to be so thankful that you did that. If anything, you can look back and see how far you’ve come.

Melyssa Griffin: Such beautiful advice. I love that. What I love so much is your advice is not like wait until you’ve accomplished the thing, wait until you get to the goal, share the story that’s happening right now and the messy parts. That’s what people want to hear and what’s going to help you grow the most.

Jenna Kutcher: Yes. Let your mess be your message guys. We are all messy. I don’t know if I made that up or if I heard it.

Melyssa Griffin: I like that. I like that a lot. So I’m sure everybody’s going to want to know everything about you, if they don’t already know you. Where can people go to find more about Jenna Kutcher?

Jenna Kutcher: Yeah. So the mothership is the main website, just jennakutcher.com. I am not married to Ashton. He is not my cousin, unfortunately. Instagram is @jennakutcher. And then the podcast is the Goal Digger podcast, G-O-A-L. We’re not digging gold, though Kanye West does. That’s where you can pretty much find everything that you need, and that’s about it.

Melyssa Griffin: Perfect. Thank you, Jenna.

Jenna Kutcher: Thanks, Mel.

Hey, don’t go yet! Listen up. Did you get something meaningful out of this episode? Well the most meaningful thing you can do right now is go and leave a review on iTunes, because those reviews are what keep us here. Make sure to subscribe and share this episode. Finally, are you pursuing your purpose? Show us on Instagram with the #pursuitwithpurpose. I’ll see you over there, and thanks so much for listening to the Pursuit with Purpose podcast at pursuitwithpurpose.com. Bye.

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Melyssa Griffin

I believe that an unstoppable mindset can be your #1 business tactic. So, my job is to lead you back to yourself and to help you reprogram the limiting beliefs and patterns that are keeping you small. 

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