How One Moment Can Change Your Life with Jenna Kutcher

Jenna Kutcher:

I think we have been stretched as a culture and as a world consistently for the last few years. And in being stretched, I think we've kind of stopped asking ourselves the question, "How am I? Do I love my life? Am I faking that I'm enjoying it? Does my life online look great, but my life offline feels awful? Do I need to change?" And this book is that invitation to come back to your truth.

Marie Forleo:

If you really think about it, our lives are compiled of these tiny little moments, these small decisions that when we look back, add up to huge changes. And my guest today has just written a beautiful book about how asking ourselves the right questions in these key moments can lead to a life of happiness and satisfaction. I think you're going to love it.

Jenna Kutcher is a born and raised Minnesota wife, mother, and entrepreneur, who aims for two things daily, helping others wake up to life, and staying in comfy pants. Creator and host of the top-rated Goal Digger Podcast, she's helped thousands redefine success and chase bold dreams. And today we are talking about her new book, How Are You, Really?: Living Your Truth One Answer at a Time.

Jenna, congratulations. So I still have…

Jenna Kutcher:

Thank you.

Marie Forleo:

...my galley copy here. So I want to say this before we get into the conversation. So I've known how talented you are and, of course, have fallen in love with you. But, girl, I didn't know what a talented, fantastic writer you are, until I dug into this book. You should be so, so... I hope you're proud of yourself, because it's gorgeous.

Jenna Kutcher:

Yeah. Oh, I am. And it's funny, because I've always written in terms of blogs and Instagram captions.

Marie Forleo:

Yeah.

Jenna Kutcher:

But a book is a whole new ballgame, Marie.

Marie Forleo:

Oh, it's a whole new ballgame. I'm curious, did you find yourself... Because again, I love writing. I have a love/hate relationship with it, I should say, because I love it when I have written.

Jenna Kutcher:

Yes.

Marie Forleo:

I love it when it's done. And oftentimes…

Jenna Kutcher:

Yes.

Marie Forleo:

...in the process of it can be a little like, er, er, er. Was it that way for you? For me, specifically, books, for whatever reason, I throw up a lot more obstacles in my own way. I feel like it's different even though I write…

Jenna Kutcher:

It is.

Marie Forleo:

...my emails and my captions and the this and the that and the programs and my web copy, and I've been doing that for over two decades. I don't know what it is, but it's something that I'm working to unwire that a book is different. So I'm curious, did you have that experience too?

Jenna Kutcher:

Yes and no. It's really wild, because I said I would never write a book for years, and with the utmost confidence, like, "I will never do this." And then when I did it, I enjoyed the process a lot. And even the parts that people hated, like the editing, there was something in me, where I'm like, we're in such a digital era that we just have the idea, we create it, we post it, we get feedback, all that. And the sitting with it was very uncomfortable for me at first. But then there was so much beauty in watching it get better and better and better. And I was like, "Oh, this is why we wait on certain things." So I really did like it. There were parts of it that felt really daunting to me. And I think I had to come to terms with the fact that I will contradict myself. And this is a book from a place of, "Here's what I know so far, as a student of life." And that was…

Marie Forleo:

Yeah. That's right.

Jenna Kutcher:

...the biggest thing of like, I don't know if 10 years from now I'll think this, but it doesn't matter, because this is now.

Marie Forleo:

Yeah. You're expressing your highest truth of the moment. I will say this, my favorite part of almost any project is actually editing. I have…

Jenna Kutcher:

Yes.

Marie Forleo:

…friends of mine who are like, "Oh, I can't stand it. Now I would need to go back and edit." And I'm like, "Give me all the edits…

Jenna Kutcher:

Yes.

Marie Forleo:

...I will shape and mold and refine." And, to me, that's where the joy, joy is.

Jenna Kutcher:

Yes.

Marie Forleo:

So I love that. But let's get right into the story. I mean, you told so many beautiful stories in here. And one of the things that I appreciated and our team appreciated about the book is just this lens on how these seemingly small moments in our lives can be these incredible launching off points for profound happiness, satisfaction, or little bit of suffering to teach us a lesson. 

Jenna Kutcher: 

Yeah.

Marie Forleo:

And I want to go back to that moment when you were a kid and your parents gave you and your siblings a choice that you had to either get that bagger for the mower, that would mean you didn't have to rake up the grass clippings anymore, which was a chore that I don't think you were too fond of.

Jenna Kutcher:

No.

Marie Forleo:

Or y'all could go on a family vacation. And you chose the vacation. And apparently, the pool at the motel, that was a very significant minor, but big moment for you. Do you want to tell us about that?

Jenna Kutcher:

Yeah. So there's this chapter about choosing moments over things, and I feel like in today's culture, where we're getting boxes shipped to us every day, and things are novelty items until they're not two minutes later, this notion of moments and how we can claim them. And I feel like we all have these moments in our life where we can trace back how it was a seemingly small moment, but it literally changed the trajectory of everything. And growing up, my parents didn't have a lot of money. We were never in deep want, but we never had extra.

And so my dad had this immaculate lawn. We lived in the country, nobody ever came to see this lawn, because we lived outside of the town, and we had to rake and I hated raking. And it wasn't raking leaves, it was literally raking grass clippings. So it was like, he would mow, and he mowed way too often, in my opinion, and we would have to rake. And so they gave us this opportunity. They basically had a few hundred dollars, and they said, we can either buy this bagger for the lawnmower or we can take a family road trip to the Wisconsin Dells.

And the Wisconsin Dells are like a whole culture in and of itself. We went there, we stayed at the Shamrock Motel, all five of us in one room. One kid always had to sleep on the floor. I always tried to make that not me. And there was a diving board at this pool, and I had grown up a gymnast. And it was this terrible diving board, but my gymnastic abilities followed me into the water. And so I was cartwheeling and my dad would be like, "Try to do a flip this way. Try to do a twist. Try to do a spin."

And I was just like coming alive on this diving board. And when I look back at my life, after that trip, I became a diver. My diving took me to the college I went to, which led me to Drew, which led me to all of these things. And so it's just crazy, because I'm like, what would my life look like if we had just gotten the lawn mower bagger? Yes, I would not have had the blisters on my knuckles, but I would've never been opened up to this passion that literally followed me into my adult life, and shaped everything about who I am today.

And Drew and I, whenever we drive through the Dells, we stop at the Shamrock Motel, and I take a picture in front of that chain-link fence. Because I'm like, man, I'm so proud of us as kids for choosing that. But I can just see that chasm of the before and after from even when I was an early teen, which is crazy.

Marie Forleo:

And for those who don't know, Drew is your husband.

Jenna Kutcher:

Yes.

Marie Forleo:

So another small moment with a big impact was when you were sitting at your boss's desk being told that you had such potential, and noticing that photo of her smiling with her two little kids. What was that moment about? And, obviously, we're fast-forwarding in time. You're now out of college, you're a professional. What was your job at that point? And then take us into the moment with the photo.

Jenna Kutcher:

Yeah. I worked for Target, inside of the stores. And, basically, I was on this fast track to becoming a store manager, and then, hopefully, moving to headquarters and all of these things. And my boss was a woman, and she's an amazing, amazing leader. But I remember sitting in her office seeing these cute little blonde kids, and I didn't hear a lot about them at work. It was very clear that there was boundaries of work life and home life, which I think a lot of women battle of like, how can I show up as both identities, if that's something I wish?

And I saw her cute little blonde kids and I was like, "Tell me about your children." And she said to me, she said, "If I'm lucky, I get home in time to give them a bath and put them to bed for the night." Which was basically this hour of time where she was still doing, not being.

And I could tell it was like a tough point for her. And so I kind of changed the conversation, and we led into this whole five year plan that she basically presented me with. And I remember thinking, you're presenting me with a plan for my life and there was never any input asked. And basically, she was saying, "You're going to move up. You're going to get more money." But I didn't want more responsibility. I didn't want to work more. And these were never conversations. It was, literally, "Here's your plan."

And I remember I went back to my office, and I still have this picture, I've never gotten rid of it, this picture of Drew and myself at a college party in this red picture frame. And I remember looking at that picture and thinking, do I want to spend the rest of my life looking at what matters to me on a desk, not enjoying it, getting, stealing those hours of time when you get home? Or do I want to try to figure out a way to build a life where we get to look at each other and enjoy it, and it's not a sore spot for us? And so it was this huge wake up call of like, "This just doesn't feel right for me anymore. What do I do next?"

Marie Forleo:

And did you have a lot of entrepreneurs around you? Or was that kind of a new idea for you?

Jenna Kutcher:

None. My parents, my dad worked in a paper mill, my mom was a nurse. A lot of my family were nurses. And that was kind of what I thought I would do for a while. I went to school as pre-med, which is crazy, and totally changed really fast. But no, I was a first-generation entrepreneur through and through. And it was really scary, especially being from the Midwest, where we're grounded in this idea of like, you are so damn lucky to get a really good job and have a 401k and benefits, and you would be crazy to walk away from it. My parents both worked the same job for 30 years. And I think that's remarkable. But that's not for me.

And so even just this idea of like, I'm going to walk away from this thing. I knew my parents were going to ask a lot of questions, and while I was an adult, I respect their opinions so deeply. And so I had to make sure that I had answers for every question that they were about to ask. And they asked, they sure did.

Marie Forleo:

And I'm wondering too, I loved this story in the book about you getting a particular, I don't know if you want to call it a vision board please, correct me if I'm wrong.

Jenna Kutcher:

Yes.

Marie Forleo:

But something stuck in the copy machine…

Jenna Kutcher:

Yes.

Marie Forleo:

...at the office. It reminded me, I remember, Jenna, when I discovered the world of coaching, which, again, we're going back to 1999, and I was so enamored and I was working at Condé Nast publications. And I, not only was I in debt after college, but I was like, I couldn't afford the coach training. And this kind of will give you a little bit of an insight to me. I was like, "Oh, but it's continuing education." I made this whole link up in my mind…

Jenna Kutcher:

Yes.

Marie Forleo:

…and I submitted for continuing education through the company, and they approved it. And I went through all the proper channels and put in the application, but they gave me that kick. And so I was thinking, it was like, "Oh, it's like this moment of, you're young. I don't know if you were probably in your early 20s.

Jenna Kutcher:

I was 22, yes.

Marie Forleo:

Yes. And so you're making this board, and you're on the company's copy machine. And so, again, you tell it.

Jenna Kutcher:

I was in this place of like, I don't know exactly what I want, but I know what I don't want. And I think that there's a really interesting differentiation. Because I've been thinking a lot lately about this messaging of like, "Pursue your passions. Go out and do what you love." And I honestly think a lot of adults right now aren't even sure what they're passionate about or don't even feel passion in their lives, right? And so this…

Marie Forleo:

For sure.

Jenna Kutcher:

...messaging is meant to be helpful, but sometimes it can almost be like hurtful in like, I don't even feel passion as a human being right now. How do I pursue something? And I've realized, when I trace things back, a lot of times I don't necessarily know what I want, but I know what I don't want. And I think sometimes that can tell you just as much, if not more.

So when I got that five year plan, I was like, "I don't want this. I don't know how I'm going to get out of this, but I'm going to figure out a way." And so I bought a $300 camera on Craigslist, started becoming really passionate about photography. I bought it as a way to find passion again. It wasn't meant to be the business. It was something that I was curious about. Something I wanted to be creative with. I was in this stage of life where I was like, "I feel like my soul is getting sucked out of me in corporate. How do I remember that childlike wonder or awe?" And photography was something I was curious about. And so I bought the camera, started getting really passionate.

This was pre-Pinterest. And I was planning my wedding to my college sweetheart. And I was going to the few wedding blogs that existed and saving images onto my computer, driving them into a Microsoft Word document, and building my own Pinterest boards. And I brought in, I emailed myself the collage to my work email, and went to print it on the beautiful color printer at the office, and was laminating it, because why would you not laminate your dreams? Right? And the old…

Marie Forleo:

You have to, because there's things like coffee spills…

Jenna Kutcher:

Yes.

Marie Forleo:

…and water, you got to laminate.

Jenna Kutcher:

I need a good layer of protection in my life. And so…

Marie Forleo:

We all do, yes.

Jenna Kutcher:

...I was laminating it, and I heard this crunch noise. And I was like, "Oh my God." And this is after hours, I'm in the office. And I am like prying the jaws of the laminator off of this collage that now says, "Photos by Jenna Lee," in a beautiful script on the top. And I'm like, "How am I going to explain this? What am I going to do?" Because I was so careful to protect my work identity and to really keep my passion separate.

And I think a lot of us have gone through life, almost compartmentalizing ourselves, or shape-shifting based on the settings we find ourself in. And I remember, I'm like looking for the manual. The manual was chucked 20 years ago. There is no manual. Google's not giving me anything. It tells me to find the manual that doesn't exist. And I'm like, "Here I am..." And there's this line in the book that says, like, "I felt like I was riding two Clydesdales going in opposite directions." I knew I had this dream and this vision, but where I was and where I found myself was so in a different place. And I had to figure out what do I do?

And long story short, the next day, Kathy, our office assistant, was in there, and I had to awkwardly be like, "Hey, Kath, I jammed the laminator last night." And she's prying out these things. And it's these wedding photos of like brides in corn fields. And I'm like, "So I'm really passionate about this thing, and I do it outside of work. And I haven't really told anyone about it. It's really close to my heart, but I really love photography." And something fascinating happened when I shared it with her, because she lit up, and she was like, "Oh Jenna, when I'm at home, I love to scrapbook."

And I should have known, because, literally, her bulletin boards were like the perfect, immaculate borders and everything on it. But it was this first time where I actually expressed my passion to someone outside of the person I shared a home with. 

Marie Forleo:

Yeah.

Jenna Kutcher:

And there is something so freeing about it. And it also reminded me that, when we're passionate, even if somebody has no passion in what we're curious about, they're invited to share their passions with the world. And I think the work that you and I do is a clear example of that. The way you guide people through B-School is like, "Here's what I'm passionate about. Tell me about yours. And even if I have no interest in it, I care about it because you do.” And that's huge.

Marie Forleo:

Yes. Yes. No, I love that story, because it's so indicative of where we all find ourselves at points. It's like, "Hey, we're doing the best we can. We're in a particular job. We're kind of reaching around the dark." And that's how I felt for years. But I loved that, and I loved that you just kind of came clean and you told Kathy what was up. And then Kathy lit up…

Jenna Kutcher:

Yes.

Marie Forleo:

...like a Christmas tree. And she's like, "Oh, this is my thing too."

Jenna Kutcher:

Yes.

Marie Forleo:

I remember the first couple times, like when I had first heard about you, it was in the context of photography. And I remember seeing some of your photos on Instagram, and I was like, "Of course, she's an artist. Of course, she's a photographer." Your photographs are beautiful. And the times that you and I have been together, I'm like, "Girl..." You always capture us in the... I'm like, gosh, it's just, it's part of your artistic nature…

Jenna Kutcher:

It is.

Marie Forleo:

...which I really love. So I'm going to take a little bit of a left turn, but not too much, because I want to talk about the moment, and you can set the context, for when you were in your car, outside of the Irish pub.

Jenna Kutcher:

Yes.

Marie Forleo:

And you decided to post a picture on Instagram of you and Drew, who is a sweetheart, by the way. And I so enjoy him, so adore him. That was a very pivotal moment for you. For those who may not know, this may be their first introduction to the beauty that is you, tell us what was happening at that particular time in your life. And what that picture was? And what occurred after?

Jenna Kutcher:

My husband, bless him, is obsessed with working out. It is his passion. It is his Kathy moment of lighting up. And while I love a good workout, I am not built the same as him. And throughout our relationship, I feel like my body has fluctuated a ton, and there have been seasons of my life where standing next to this man who literally looks like a Greek god, I have felt like people look at us like a mismatched pair. And I feel like we all have these deep insecurities, the thing that we think other people are thinking all the time.

Marie Forleo:

Yes.

Jenna Kutcher:

And a lot of times those are false narratives. But this time for me, it felt way too close to home. So Drew and I spent a lot of time in Hawaii before we had our children. And I was in a season of trying to grow our family after saying I never wanted to be a mom. There's a lot of themes in my life where I'm like, "I never," and then guess what? I change my mind. And when we did try to grow our family, we went through two losses in two years. And my relationship with my body was just so different, because it wasn't just about what it looked like. It was like, what can it do? And why can’t it do this?

Marie Forleo:

Yes.

Jenna Kutcher:

And we were in Hawaii and we were on a beach standing next to one another in this photo. And I remember this girl had sent me a DM and said, "How did you manage to land a guy like him?" And when she said that, it literally just touched my deepest insecurity. It was like, "The world knows. They see it. Every time they see it." Just because this one person said this thing, it was like, "I'm found out. Everyone sees it. It's not just me."

And I am not one to clap back or to respond to criticism. I have just gotten so good at taking feedback, if it's feedback, and releasing criticism. But in this case, she hit me on a nerve where I was like, "Ugh." And so I posted this photo of Drew and myself and just said, "We are so much more than our bodies. This man has loved me through a decade of growth and change and evolution and loss. And he could care less if there is cellulite or pimples or anything. It's not about that. He is more than his body and I'm more than mine."

And this post went viral. And the crazy thing about going viral is like, you cannot plan going viral and you cannot control it. And I can look at it now and say, "Whoa, what a blessing to be able to be in front of an audience of millions, sharing something that I've thought about for a long time, but that a lot of women are thinking and feeling but never expressing." But also, now, there's a lot of debate on the internet happening about my body. I remember, and it's funny how we're wired to remember the worst comments, right? Like…

Marie Forleo:

That negativity bias never goes away.

Jenna Kutcher:

It doesn't.

Marie Forleo:

Ugh, even when we know about it.

Jenna Kutcher:

Isn’t it crazy? Yes.

Marie Forleo:

It's like, I know about it all the time, but...

Jenna Kutcher:

Even when we know about it. And the headlines we're reading, “Curvy Blogger Claps Back With Mr. Six Pack,” whatever, responds to criticism and people were saying like, "Curvy? Call her what she is. She's obese. She's a whale. She's a beached whale in Hawaii," all of these things. And it's crazy, too, because if people haven't known me or don't know me and they go to search me, they're going to say, "What are you talking about? You are a beautiful, average woman." There's really not much to be discussed, yet the internet was talking.

And it was a really tender moment for us, because we were trying to conceive for the third time. So I was like, while all of this criticism is happening, here we are behind closed doors where I'm still battling what I feel and believe about my body to be true. And it was really a moment for me of like, what do I know to be true? And what do I believe is possible? And how do I just stay at home in that while the world is talking?

And so it was a really fascinating experience. It was something that I would absolutely do again, but we were at a point in our life in business, like we don't have a PR team. We don't have someone telling us what to do. We are fielding calls. We are talking to Ellen's producers. And we're like, "What is the story here? That two people love each other and their bodies look different? I'm so confused, but thank you for this opportunity." It was wild.

Marie Forleo:

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For me, having started so early, when it was pre-social media, and it was just about blogs…

Jenna Kutcher:

Yes.

Marie Forleo:

...and emails, and YouTube, wasn't really a thing. And all the things didn't exist. Sometimes it just like hurts my heart, to be honest with you, of how cruel people can be. And simultaneously I just adore you and appreciate you so much for sharing the story, because I don't think there's any one of us who hasn't had really horrible criticisms, words, hurtful things hurtled at us. And it just can make you want to curl up and run away. And the fact that you were like, "There's not really a story here, and we're going to keep going," is just such a beautiful testament to your being and your soul. And the fact that it doesn't have to take you down or take you out.

Jenna Kutcher:

What I think was really interesting to me was I could either have gone into a shell and been like, "I am never poking my head out onto the worldwide web ever again." Or I can just further this narrative that is clearly needed right now, even though it had nothing to do with my business, it had everything to do with just this human experience. And I think a lot of times people, especially when you are chasing a dream or you're pursuing a passion, you forget that there's humans behind it. And I think one of the secret sauces to my brand or the way that I've shown up, or the way I've been able to grow a business that makes an impact in spaces that I've never monetized, are because I'm not afraid to like use the platform for the other things.

It's like my business funds me the opportunity to talk about the things that matter, the things that I will never monetize. And I think that was a really big realization, when I've been able to use my platform to talk about things like fertility and miscarriage and body image and all of those things. A lot of times we think that our passions have to be monetized or our businesses have to be on this platform of the thing. And I'm like, my business affords me the opportunity to talk about these things. And I love that. And that's what I love about entrepreneurship.

Marie Forleo:

Thank you for saying that. Because I've told folks, especially those of us that identify as a multipassionate entrepreneur, right?

Jenna Kutcher:

Yes. Yes.

Marie Forleo:

It's like one of the biggest lessons that I learned and that I love to share is you don't have to monetize all of them.

Jenna Kutcher:

Yes.

Marie Forleo:

You can have a passion you can be absolutely into, desirous of, so obsessed with a particular thing and it can fuel your heart. In your example, it can be something that you talk about publicly or privately. But you don't have to fit everything into a business, and not every aspect of it needs to be monetized. Speaking of just our businesses, one of my favorite parts of the book was talking about your enough point.

Jenna Kutcher:

Yes.

Marie Forleo:

And I loved when you told the story about, I think you were still a full-time wedding photographer at this point, and you were in it. You were in it to win it and you had the dream. And of course, that's a particular type of business, where it's seasonal.

Jenna Kutcher:

Yes.

Marie Forleo:

Weddings often happen on weekends.

Jenna Kutcher:

Yes.

Marie Forleo:

Tell us about how you arrived to what sounds like it was a breaking point, and then discovered this notion of an enough point.

Jenna Kutcher:

Yeah. Oh, it's crazy because I have a visceral reaction to that season. Like even when I think about that moment, my chest gets tight, because we've all been there, right? And I think…

Marie Forleo:

Yes.

Jenna Kutcher:

...nowadays, if you poll entrepreneurs, burnout is one of the number one things that people are struggling with. I think it's an epidemic in its own way. And for me, it was that elusive six-figure goal, because I went from this place with titles that sounded so fancy to proving myself as a first-generation entrepreneur, to how do I sound successful, impressive? And that six-figure thing really felt big to me. And also being from the Midwest, six figures is a lot of money.

Marie Forleo:

Enormous.

Jenna Kutcher:

It's huge.

Marie Forleo:

It's for most of us, right?

Jenna Kutcher:

It is.

Marie Forleo:

I felt that way too.

Jenna Kutcher:

Yes. And I remember the day I hit six figures, I was tracking my spreadsheet, and I was in the shower, washing my hair with the same Herbal Essence that I did the day before. And wondering like, when are the angels going to sing? Where are my gold cellophane balloons that all the bloggers have when they hit a 100K? All of these things, and I'm like, nothing about my life has changed. In fact, I don't even feel like I'm enjoying my life. And it was just this wake up call, because I think a lot of times we set these goals and we arrive at them and they don't feel good. And we're like, "Maybe I just need to do more. Maybe I need more." But I was like, "Maybe this is enough. Maybe, in fact, I was happier before all of this, before the more."

And I remember I sat down with Drew the next day, because I just had this moment of like, I'm exhausted. I'm missing out on my life. I'm saying no to the things that I say matter to me, and saying yes to more work, just to hit this number that I can't even enjoy. My bank account looks great, but I haven't enjoyed any of it. And I sat down, I had this color-coded spreadsheet, and I said to him, I said, "I was so much happier when I made 50K. Can we go back to that?" I said, "I know this might feel backwards, but I would way rather get back my time. I want time... I left so that I wasn't looking at this picture view on my desk. And now I'm looking at my laptop. And the person you married is like a shell of that person right now, because she's been working so hard."

And it was crazy, because I thought he would be concerned or worried, and he looked relieved. It was almost like this like breath of like, "Give me back my wife." And I think so many of us leave these 9 to 5s, or we leave these careers to start businesses for freedom. And we build a 24/7 schedule that is not sustainable. And there is this thing, and you and I have talked about this offline, there is a necessary hustle to get things off the ground, right? There is necessary…

Marie Forleo:

Of course.

Jenna Kutcher:

...work. But what's happened is that we have created this culture where it's like, wake up earlier, work more. Don't say no. Keep your laptop open. Never shut down. And that's not sustainable. That's not how we're supposed to be humans in this experience. And so the craziest thing happened and I don't think I've told this to anyone. This isn't even in the book, but I cut back to 50K. I said, "No." I drew a line in the sand and said, "I will only book half of the weddings next year. I can't do another season like this." And when I got back my time, which now is my currency through life, I learned the things that you see me doing today that allowed me to grow a seven-figure company. It wasn't the six figures. It was the work.

And I've never shared that, because I never want to get it twisted that like it was the money that was life changing. It wasn't, it was the time that allowed me to build a business that still affords me time. But when I claimed back my time, I went to seven figures, not intentionally, not as a goal on the paper, but because I was building something that could run while I rested. And that's a big difference.

Marie Forleo:

It's huge. And I want to highlight something that you said when you spoke with Drew. Josh and I often have these conversations, and Josh is like an angel in my life and we've been together, I cannot believe this, it's going to be 20 years next year. And whenever we talk about... Because he's an actor and an entertainer, and so his industry is quite different than what I do and being an entrepreneur. But one of the things I so appreciate about him is whenever I'm telling him about like a new project or something that I want to do, he's always like, "You have to promise me, promise me that if you say yes to this… 

Jenna Kutcher:

Yeah.

Marie Forleo:

…that you're not going back to the old Marie, who would push and push and push herself to reach a particular milestone."

Jenna Kutcher:

Yes.

Marie Forleo:

And it's really great because he's like, "It's not worth it. We don't need it."

Jenna Kutcher:

Yes.

Marie Forleo:

This notion of it's enough.

Jenna Kutcher:

Yes.

Marie Forleo:

And every point in my life and as every year passes by, even now, it's like, this notion, I know you write about this in the book, and I say this often, "Just because you can do something…

Jenna Kutcher:

Yes.

Marie Forleo:

...doesn't mean you should."

Jenna Kutcher:

Yes.

Marie Forleo:

Taking on more responsibility. I remember this point, Jenna, you've probably experienced this too, I remember this kind of period when I would hang out with like fellow entrepreneurs, and I would get pelted with like, "So how big is your team now?" As if how big my team is any kind of indication of success, and the context was, well, if you have more people, if that number is higher, you must be a bigger baller.

And there were only like a handful of friends, you being one of them, who 's like, "How can we do this in a really lean way…

Jenna Kutcher:

Yes.

Marie Forleo:

...where we are really effective…

Jenna Kutcher:

Yes.

Marie Forleo:

...and impactful, and for my particular unique style, taste, flavor of dream, it feels just right?"

Jenna Kutcher:

Yes.

Marie Forleo:

But it's like, there's so many notions. Anyway, I just wanted to unpack that a little bit, because it's really important, because not a lot of people in this space talk about it and there's so much messaging that bigger is better and more is better. And I've always pushed against that. And I love that we're having this conversation, because we need more of us, I think, to do it.

Jenna Kutcher:

We always laugh, because whenever I come back from Masterminds, there are certain entrepreneurs who come back from like a gathering or an event or being with peers in your industry, and they come back with eight million ideas. And I remember one time I came back and like I was at some fancy place with fancy people and amazing human beings, and we were like sitting on our living room floor, eating takeout sushi from Duluth, Minnesota watching Top Chef. And I was like, "They might have way bigger businesses, but I have a way higher level of happiness." And I mean that in a place of like, I'm just like in a peaceful pursuit.

I think you and I recognize that when you put that dot on the map of the goal, if you're not enjoying the 98, 99% of the journey that leads to the dot, you're missing it. And I think…

Marie Forleo:

Totally.

Jenna Kutcher:

...a lot of people miss that pursuit. And I'm like, "I want a peaceful pursuit in everything I'm doing." Even with getting this book out into the world, I was like calling you, because I was like, "I'm getting advice from people who work in a different way than I do. And I'm just not willing to do that or to go there." And I think that's beautiful.

Marie Forleo:

That's why I think you and I are friends, because it is, it's like, "Hey, what's this 80/20 rule?” Jenna, here's what I did. Here were like the handful of things that really moved the needle in the biggest way. And that I was super passionate about, and had like fun doing.

Jenna Kutcher:

Yes.

Marie Forleo:

Rather than the gajillion different strategies that are potentially possible, that we've witnessed other people kind of drive themselves into the ground over. I want to talk about this, another small moment that you had that I think was really important. You sent a three-word email that really changed your business and your life forever. Can you tell us what that email was? And what were those magic three words?

Jenna Kutcher:

Yes. Okay. So many people right now find themselves wearing all the hats, doing all the things. Entrepreneur or not, we are all wearing a lot of hats, and playing a lot of roles these days. And I think for a lot of us, it became so obvious during the pandemic, when you are 18 different identities under one roof. You could be mother, wife, partner, I mean, caretaker, there's so many different ways that we found ourselves.

Marie Forleo:

School teacher.

Jenna Kutcher:

Yes. And I white knuckled my way through a lot of things. I think there's a lot of pride in doing everything on your own. And I feel like I did that for many years, when it came to my business. And thankfully, to someone's persistence, I finally was able to say the words, "I need help." And I feel like a lot of times in life we often say, “I'm good. I'm good. I got this. I got this." Until, life literally sweeps your feet out from under you, and there's no other option. And I feel like when I hit the point that I was able to utter those words, it was when we were experiencing our second loss. And I recognized in that moment, I had built something that required me to keep going. If I don't show up, I don't get paid.

And I had to go to a doctor's appointment, discover that we had lost the baby, but my body was still pregnant, and go shoot a wedding the next day. And I remember just feeling so trapped in what I had created. It was almost like that identical moment with my boss where she said, "Here is what is your next five years? Do you like what you see?" And I realized in that moment, "I don't like this and I will do anything in my power to get away from this."

And there was a woman in my area named Caitlin who had reached out two different times before. And she said, "I'm a virtual assistant. I support people like you, who do what you do. I know how to do all of these things." And I said, "Thanks, but no thanks." And unknowingly, she sent a third follow-up email, which again, bless her persistence. And all I responded with was, "I need help." And those words were so freaking hard. It's like those moments in life where you're like email is the last thing I can think about, social media, screw it. I mean, we've all had those life moments where you are just rocked, and you are like, "None of this matters." And it did matter, because I had clients to serve.

But at the same point, I was like, "I cannot show up right now. And I built something that requires me to show up and I will never build something like this again, that doesn't allow for a human moment." And that was the first time that I started to get help. And what's crazy is, is her and I met in a really tiny coffee shop in a small town in Wisconsin. And I said, "I'll give you my email password, and if you can just make sure that people are responded to, that would be great." And I remember like two days in, I go to my like sent inbox just to check, like, "How are we doing? Is everything going good?" And she had sent the most beautiful responses to my clients. My clients felt loved. I felt this like just weight come off of me. And I wanted to be like, "Here's my social security number. Here's my PayPal account. Take it all. Do it all."

It was this moment of like, "Oh." And I realize, even as a mom, asking for help is not weak, it is the strongest thing you can do. And the other side of that is a lot of times we don't want to ask for help because we don't want to inconvenience someone. But I have learned, and I am surrounded by humans in my life who their joy comes from helping others. When I give them a humble opportunity of like, "Would you be willing? Or could you offer this?" They come alive. And me being so prideful, me having that white knuckle grip is not allowing some people to live into their greatest gifts.

And now I'm like, "Give me all the help. I will take all the help.” I remember going to my first follow-up appointment after having Quinn. And the nurse was like, "Can I carry your car seat for you?" And I was like, "Please." And she goes, "So many moms will say, no, when all they need is just an extra hand." And I said, "This is my second rodeo. I will take all the help I can get. Will you walk that out to my car with me?" And it's just funny, because once we get used to asking for help, it becomes second nature. But it also becomes such a blessing, not just to yourself, but to others.

Marie Forleo:

It's such a connection point too.

Jenna Kutcher:

It is.

Marie Forleo:

And I've found that. Much of the time I'm here in New York City and I get such joy…

Jenna Kutcher:

Yes.

Marie Forleo:

...when people ask whether it's for directions or someone needs help crossing the street, for whatever reason, or, you know what I mean?

Jenna Kutcher:

Yeah.

Marie Forleo:

There's something happening and I get to connect from my heart to another human and love them into whatever that little next moment is.

Jenna Kutcher:

Yes.

Marie Forleo:

It's awesome. And also, too, traveling where sometimes need a little help here, a little there. It's such a beautiful moment.

Jenna Kutcher:

Yes.

Marie Forleo:

Jenna, I think this book is just fantastic. I am so happy for you. And I'm so happy for everyone that's going to get their hands on, How Are You, Really? And I think it's filled with so many beautiful questions that we can pause and ask ourselves, and then have really the honesty to answer, right?

Jenna Kutcher:

Yeah.

Marie Forleo:

And that space to say, "It's okay if the answer's like, 'I'm not okay right now.'" Or that something needs to change. Is there anything that you want to leave us with today? Anyone watching MarieTV or listening to The Marie Forleo Podcast, anything you want to let them know?

Jenna Kutcher:

It's funny, because there's a lot of themes in my life where I've said, "I will never do something." And I think that we are at a beautiful place in the world, and for a lot of us in our lives, where we have this opportunity to say, "I've changed my mind," whether it's a relationship, a career, a business, motherhood, whatever that is. A changed mind is a beautiful thing in our lives, because it shows growth and it shows that we're being stretched. And I think we have been stretched as a culture and as a world consistently for the last few years. And in being stretched, I think we've kind of stopped asking ourselves the question, "How am I? Do I love my life? Am I faking that I'm enjoying it? Does my life online look great, but my life offline feels awful? Do I need to change?"

And this book is that invitation to come back to your truth. Yes, my stories are sprinkled in there, but it's not a how to be like Jenna. It's a how to come home to yourself moment. And I hope that with those questions and with this invitation to lean in, not just in conversation with people you love, but in conversation with yourself to get past the good and the busy and the fine, but to really say, "How am I really? And how are you, really, in your life?" I think it will absolutely transform the days to come. And I'm really excited to watch that unfold for other people, because I know it's happened for you and I in our own ways and in our own lives.

Marie Forleo:

I love that. Jenna, you're fantastic. Thank you so much for making the time today. And I can't wait to see you again very soon.

Jenna Kutcher:

I know. Thank you for having me. This is literally a dream come true. I remember when somebody shared your Facebook page with me, I mean, over a decade ago and said, "This woman is a really big deal." And so to be here with you, feels like a really big deal. So thank you.

Marie Forleo:

If you loved this conversation, you have to watch this next episode about the mental exercise that will help you turn dreams into reality. It’s amazing. I still use it all the time. Click here and watch it now.

There is real genius behind this simple phrase. You know, so many of us get stuck in our own small thinking, and this is how to get out of your own box.