YAPClassic: Jenna Kutcher on Finding Rest in a Hustle Culture and Building a Business That Actually Fulfills You

YAPClassic: Jenna Kutcher on Finding Rest in a Hustle Culture and Building a Business That Actually Fulfills You

YAPClassic: Jenna Kutcher on Finding Rest in a Hustle Culture and Building a Business That Actually Fulfills You

Jenna Kutcher unexpectedly felt empty after she hit her goal of six figures as a wedding photographer. Burnt out, she cut her workload in half to reclaim her time and happiness. As a result, she reignited her creativity and inadvertently built a million-dollar business. Now, she is the ultimate entrepreneur slash mom, managing several income streams without sacrificing her peace of mind. In today’s episode, Jenna shares some actionable advice and entrepreneurial wisdom that helped her figure out her direction.

Jenna Kutcher is a successful entrepreneur, digital marketing expert, and author of How Are You, Really? She hosts the top-rated Goal Digger podcast, which offers practical business advice.


In this episode, Hala and Jenna will discuss:

– Turning a $300 camera into a million-dollar business

– How she built a hit podcast from her spare closet

– How to keep your team lean and focused

– Authenticity in business and life

– How perfection can turn into procrastination

– When to rest and not quit

– How she balances multiple income streams

– The role of intuition in business success

– Jenna’s journey to work-life harmony

– The impact of personal values on success

– And other topics…


Jenna Kutcher is a successful entrepreneur, digital marketing expert, and social media influencer. She initially gained prominence as a wedding photographer, transforming a $300 Craigslist camera into a successful business. She is best known as the host of The Goal Digger podcast, a top-rated show that offers practical business advice. She is also the author of the bestselling book How Are You, Really?


Connect with Jenna:

Jenna’s Website: https://jennakutcher.com/


Resources Mentioned:

Jenna’s Book, How Are You, Really?: Living Your Truth One Answer at a Time: https://www.amazon.com/gp/product/B09G6SVK5V/


LinkedIn Secrets Masterclass, Have Job Security For Life:

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 [00:00:00] Yeah, bam, welcome to yap classic. And today we are going to be playing my first interview with Jenna Kutcher. Now, Jenna Kutcher came on the show for episode 295 earlier this week, this Monday, where we talked about all the different ways that girl makes money. And damn, she makes a lot of money. 

 But the thing about Jenna. Is that she 

only does what she feels like doing. She tells me no all the time. Like, no, I don't want to do that. That sounds too hard. I'm not into that. For me, I'm like, got to work hard, got to do it, hustle, grind. And I make money that way. And I make a lot of money too, but man, Jenna really like attracts money.

She's so inspiring. She's the ultimate entrepreneur slash mom. She's an expert on online marketing. She's the host of the hugely, [00:01:00] hugely successful podcast, the Goal Digger podcast, which by the way, is exclusively in the Yap Media Podcast Network, my podcast network. And she's also the author of How Are You Really?

Today, I'm replaying my episode 242, where Jenna and I speak about building a business that fulfills you. 

 She shares her best actionable advice, social media strategies, productivity hacks, and entrepreneurial wisdom that helped her figure out her own direction and become a self made millionaire.

Jenna is truly one of the women that I admire the most. And I'm really excited that you guys get to hear her back to back because she is truly somebody that you should be following. Without further ado, here's my conversation with Jenna Kutcher that kicked off our amazing friendship and business relationship You grew up in Minnesota. A pretty small town. Did you have any inkling that you were going to be an entrepreneur when [00:02:00] you were a little girl?

Jenna Kutcher: I would say no. But as I started to unpack different things in my life, I'm like, maybe it was always in me. So I am a first generation entrepreneur. My dad worked at a paper mill. My mom was a teacher. We had no entrepreneurs in our family. But I was this little girl who very early on had to earn money to get the things she wanted.

And so my parents always instilled that value. So we lived on this dirt road and I would host the most epic lemonade stands on a dirt road that was very seldom trafficked. And I'm fairly certain my mom would call our neighbors and beg them to come over to buy lemonade from this little girl who had all these hopes and dreams.

And so when I look back at things like that, there was a piece of me that felt very entrepreneurial, but it was never on my vision board, never something that I envisioned as a possible career choice. 

Hala Taha: Yeah, because when you're younger, When people ask you what you want to be when you grow up, entrepreneur is not really on the table.

It's like firefighter, teacher, [00:03:00] cop. Nobody really talks about entrepreneurship, but it's funny when you look back how you can like think of stories. Even myself, like I used to have slushy stands. I used to sell artwork, put all my cousins to work to make art so I could sell it. I was always a little entrepreneur and then didn't come full circle until like my 20s.

And I know that's same with you. Another thing that I found out about your childhood is that you were a pretty intense gymnast. Now, tell us about that experience. Do you feel like any of that experience has been translated later on in your career as an entrepreneur? 

Jenna Kutcher: Totally. So it's wild because I now have daughters and my daughters are above the age that I was when I started.

So I started when I was three and I got so passionate about it. And there are so many things about it where we had to move to like a club facility that could support my growth and my parents couldn't afford it. It was super expensive. When I look at how expensive it was to do lessons every single day of the week.

And so [00:04:00] my mom, who was a teacher and a nurse. She was smart enough to notice in the gym that there were areas that needed renovation. And so my parents couldn't afford to pay for my tuition, but my mom was like, we're going to figure this out. And so she negotiated with the gym owner and said, Hey, we can put in some sweat equity.

We can paint the locker room. We can fix the kitchen in the gym. If you allow Jenna to go for free. And so every single year, my parents, my grandparents, my siblings, we would all go and work at the gym for a week and update a certain area of the gym to help me afford this passion of mine. And when I look back at that, it like makes me so emotional because I'm like, my parents never said no.

They said, we'll figure it out. And I feel like that's followed me into entrepreneurship, but there's so much about that sport. When I look back, you know, I was. a tween and I was working out eight hours a day in the summer, four days a week. And there was so much work ethic involved in that, but there was also so much joy.

And I feel like entrepreneurship [00:05:00] is a lot like that, where they always say like entrepreneurs are the only people that would be willing to leave a nine to five in order to work 24 seven. And I feel like so much of that carried me through. And so when I look back at that, I think a lot about how driven I was, but how I still found the joy in that work.

Hala Taha: I love that. That's such a sweet story. It's so nice to hear that your parents supported you. And I'm actually doing a series with Olympians right now in partnership with the Olympics. And almost all of the people who I interview, actually everyone, had some crazy support system. Because when you're a kid, wanting to do a sport, these things are expensive.

It takes like a whole village to ensure that you could progress in your sports career. It's so interesting to note that you also had that experience. So, your career journey. You ended up going to college, not thinking about being an entrepreneur again, like you were sort of molded into what society wants of you.

And you end up being in corporate. And I know that in your book, you [00:06:00] talk about being in a windowless HR office. So talk to us about that moment. How did you end up getting there? What was the beforehand of that? And what were you doing at the time? What were you feeling at the time? 

Jenna Kutcher: I was so fortunate in college.

I always had an internship going on. So I was a part of this work study thing to earn my way through school. And so before my senior year, I did an internship with Target. And we're from Minnesota. Target is headquartered in Minnesota. It's a big deal, right? Like, we love Target. And so I worked an entire summer in a store.

And was given a job opportunity straight out of college, which felt like a dream come true to be able to graduate college, having a contract, having the security, having benefits and all of those things that have been instilled in me, especially being from the Midwest with that wholesome culture of like, you just work hard.

And so I got in to working for Target and I was in HR and I loved my team. I loved the people I worked for, but [00:07:00] I started to recognize that there was this retail aspect, which meant I was working nights, weekends, holidays, gearing up for Black Friday was like gearing up for the Olympics. And I recognize that in this sort of position, I was never going to have experiences like holidays.

I was never going to experience things through the lens that I had envisioned in my life. My big dream was to end up in the corporate headquarters, in a beautiful office with windows and high heels and all these things. And here I am working the office job plus working on the floor in a store. With this fancy title, that didn't really mean much of anything.

And so I had this really eye opening experience when I sat down with my boss and Target is an incredible culture. They have really great leadership skills. Like I learned so much and she said, here's your five year plan. We have planned out the next five years for you. This is so exciting, isn't it? And never once did they say like, what do you envision for yourself in five years?

Where do you want to go? And as I looked at the map that they laid out in front of me, [00:08:00] all that it meant was more work for more money. It was that trading time for money. And I realized I don't want someone to plan my life out for me. Like I want to be the author of the plan of my life. And that was a huge wake up call.

I remember going back into my office and I had a picture of my then at the time fiance who is now my husband of over a decade. And I saw this picture of him and I was like, do I want to spend my life in this office looking at a picture of the person I love? Or do I want to figure out a way to build something different that allows me to spend time with the person I love?

And that was just a huge wake up call for me. 

Hala Taha: I love that. And so you found yourself 23. Realizing that you want to make a total shift from my understanding. You went on Craigslist, you bought a 300 camera and you started a wedding photography business. Yeah, this is a big thing to do at 23. Talk to us about that.

Jenna Kutcher: Oh my gosh. So I did not buy the camera thinking I'm going to start a business. I have always loved documenting life. I was the annoying kid bringing a [00:09:00] camera to all the college parties in the empty basements. I was the person who like, I just loved images. I would often look through my parents wedding album and have them tell me about their day.

Like, I just loved that. And at the time I was planning my wedding to my husband and we couldn't afford to hire a photographer for all of these big things. And so I was like, Let's get a nice camera and then we'll have nice photos of certain milestones in that wedding process. And I very quickly started to fall in love with the art of it, which is wild because I had never taken a single art class.

So I had no skill in photography. I just had an eye. And I feel like something that in reflecting and looking back, I have always been someone who is so good at reverse engineering results. So when I see that someone gets a result, I'm like, okay, what went into getting that? And that's how it was with photography.

It was pre Pinterest. There were very few wedding blogs at the time, but I would find myself looking at wedding magazines and imagining, okay, where would they be standing in order to get that? And I [00:10:00] started offering to take pictures for friends. I would bring my camera along to weddings, which is a huge annoyance to real photographers.

And yet there I was on the sidelines, so excited about capturing moments and getting home and looking at those moments. And very slowly I started to post these things. I remember my brother and sister in law got married in Jamaica and they had a resort photographer and I was like, no, no, no, that's not going to be good enough.

So I was hanging her dress up from palm trees and putting out her little flip flops with their wedding rings and like styling all this. And I just came alive and I had this Facebook album titled My First Wedding Photography Project. I think it got four likes in total. But that was where it all started for me is I was like, this is a passion.

This is a thing. I wonder if I can actually turn it into a career. And it took me an entire year to do just that. But once I became passionate, it was like, I couldn't turn it off. 

Hala Taha: I love that. I love the fact that you got so passionate about it. That you put yourself in the position to gain experience, even if it meant working for [00:11:00] free.

You were so passionate about it that you probably learned so much about being a photographer, about the equipment itself, about how to capture these images. I always talk about this on my podcast. A lot of people want to be things. But they don't throw themselves into it and like fully absorb themselves into everything that goes along with it.

That's how you become the best and why people want to pay you a lot of money to do the services that you do. You have to be really good at what you do and that takes time and experience and sometimes that means working for free to get that knowledge and experience. So I love that. So you were talking about before how sometimes as entrepreneurs.

We quit at nine to five only to work 24 seven. So you ended up quitting your job your business took off I think you won like many awards of top wedding photographer in your area and everything like this So you were crushing it, but then you started to feel burnt out. Talk to us about that 

Jenna Kutcher: Oh my gosh.

So I will never forget the day, Hala, when I reached this elusive goal that I had set for myself. And [00:12:00] I think we do this a lot in life, where we set these arbitrary goals of like, once I run a marathon, once I reach 100k, once I do all these things, then my life will be complete. And I had set this goal of earning six figures.

It was a number that felt like 10 million dollars. Like it felt so astronomical. Neither of my parents had ever earned six figures. It felt like impossible. And I remember the day that I hit it. It was three years into my wedding photography career. I had exponentially grown my business. I'd grown the skill.

I'd grown the expertise and the notoriety. And I remember the day I hit six figures. I was standing in the shower, washing my hair with the same herbal essence that I had the day before, thinking I thought this would feel different. And I remember wondering, like, where's the confetti? Where are those gold cellophane balloons?

Where are people on my porch cheering me on? And I had this feeling, not of joy, not of excellence, but this feeling of emptiness, I had created this super successful business [00:13:00] that had robbed me of my number one currency, which was time. And I think for so many entrepreneurs, when we're starting out, we are willing to trade time for money.

That is usually the requirement to get a business off the ground. But at some point we hit this tipping point where suddenly time becomes our currency. We're willing to exchange money to buy back time. And I hadn't recognized that yet. And so I remember the next day. My husband comes home from work. He's slinging wine and selling wine in grocery stores.

And I had this whole spreadsheet and I said, well, you sit down with me. I said, I'm going to say something I never thought I would say. And I said, screw six figures. I was so much happier when I made 50 grand a year. Can we go back to that? And I thought that he would like push back or be like, no, absolutely not.

Like we're doing it. And he looked relieved like he looked like he was about to get his wife back, right? How many of us have lost ourselves in our businesses and we started these businesses to get freedom. And all of a sudden we realized we're shackled to our laptops or we're booked [00:14:00] out every single weekend for months on end.

And so what I did is I cut back to earn 50 K again because that was my currency. Time was my currency. But when I did that, I built a million dollar business. Not through intention, but because I now had time to be creative again, to learn new things, to dive deep into different aspects of entrepreneurship that I hadn't been able to explore because I was too busy.

And so it was kind of crazy because in the year that I wanted to pull back and earn half, I ended up 10Xing my income. 

Hala Taha: Wow. What year was this? 

Jenna Kutcher: So this was probably 2015, I believe was the year. 

Hala Taha: Got it. Okay. So I know that 2016 was a really huge year for you because that's when you launched your first online course, you launched your first email list, you launched.

The gold digger podcast, which guys is like a huge podcast for so many years now, like one of the biggest podcasts in the world. You also have a huge Instagram profile that I think has been around for a [00:15:00] long time. I was curious to understand what happened first. So I'm assuming a lot of this transition happened in 2015 like you're just talking about now.

What did you do first? When did you first started making other revenue streams outside of your wedding business and becoming more of like a digital personality? 

Jenna Kutcher: Yeah. So in 2015, when I finally cut back, I started to take online courses. I didn't even know they were a thing. I didn't know they existed. I didn't know what I would learn in them.

I didn't know. So the first online course I took. I had gotten on the phone with this guy. He was doing like a free coaching call. And I was like, I don't have a business coach. I'll get on this free call. And in that coaching call, he sold me his course. And I said, I will only buy this course if you teach me how you made it.

And I knew that while the content inside of the course would be great. What I really wanted to know and get the steps of is how can I create my own? No one was teaching that at the time. And so he delivered his actual course, but then he also did calls with me where I'm like, what did you use to record [00:16:00] this?

How are you uploading it? How are you delivering it? Because what I had started doing is in the off season, because my wedding season in the Midwest was about six months of the year. In my off season, I had started mentoring other photographers, but I started to recognize there were so many themes In the things they were asking me, they had the same questions.

They wanted the same information. They wanted to understand this one piece of my business. And I was like, okay, I can continue to do these one on one sessions in the kitchen of my condo, or I could create something that could serve many. I could create it once and serve many. And so I needed to figure out how to do that.

And so that's when I started really diving deep into what is this online world? The first time I got on the phone with this business coach, he said, Jenna, how big is your list? And I thought he meant my to do list. And I was like, what did he tell you? My to do list is so long. And he wasn't talking about that.

He was talking about my email list. And I did not even understand why would anyone want an email list? Do people even read emails? What do I have to say? How does [00:17:00] this work? And so that was when I really got turned on to email marketing and understanding that it's an asset that you own. You can't control the experience that your Instagram followers get or followers on other platforms, but an email list is this asset.

It's not shiny, it's not sexy, but it's something that you absolutely have to invest in. And so that was when I started to go deep into this digital space of like email list building, online course creating. What does this all look like? And that was when I really started to see my business start to take off in a different direction.

Hala Taha: Mm. So you built your email list and you launched a course, then you like, tell me the order of everything. Like how did it all blow up? Because your platforms are really impressive. Yeah. 

Jenna Kutcher: The first course that I launched was in 2015 and it was kind of my trial run of like, how do I do this? So I only had 841 people on my email list.

This was not a huge audience, right? I think a lot of people are like, okay, well now I got to get like tons of people, 841 people on my email list. The price of the course was 1, 500. [00:18:00] Get this holla. It was audio only because I didn't know how to do any video. I didn't know how to edit. I literally recorded it into a microphone while sitting into my bed.

And I made 35, 000 on my first course launch with no paid ads back in 2015. This was something that was amazing because I'm like, wait, people need to know what I know. People want the shortcuts. Yes, they could go out and Google it, but they're not going to piece it together in the way that I want. They want the roadmap.

And this is a sustainable way to create something once, serve many and get other people results. And so that was so transformative to me where I was like, I made almost Half of my salary in one launch, if this can work, think about what would happen if I threw gasoline on the fire.

Hala Taha: I love that. That's amazing. I remember having the same experience with my masterclass, no paid ads. And I think we made 60, 000 the first time we did it. But when you have the real experience and the social proof, like you were already an award winning photographer, you had all the [00:19:00] social proof. People want to learn from real experts.



Hala Taha: So tell us about when you decided to launch a podcast and how did you launch that? 

Jenna Kutcher: Yeah. So coming from you, this podcasting expert, my story was an experiment.

I look at everything in my business is like an experiment, right? And as a wedding photographer, I was so busy and overwhelmed for six months out of the year. And then the other six months I had time to do other things and projects. And I was lonely. I don't know if you experienced this, Hala. I feel like when I started my business, I was so head down.

I kind of looked at other people as competition. I had a lot of identity crisis and imposter syndrome. And so I didn't really want to be in the mix with other people. Like I was like, I'm just going to keep my head down, stay in my lane and go. And when I finally lifted my eyes, I'm like, there's nobody with me.

Like, I'm really lonely on this journey. I want to talk to other people [00:20:00] who get it. And so when I started my podcast, it was literally this experiment and this opportunity to invite people into conversation. I wanted to talk about How are you handling client rejection or what are you doing for contracts or invoices?

And so at the beginning, my show was interview only, which did not work out well for me. I recorded it from the front seat of my parked car in my garage because I was worried my dogs were going to bark. I didn't even own a microphone. I had iPhone headphones and I was like, all right, let's just do this.

And so I committed to doing it for 90 days. And I was like, let's just see how it feels. I can always quit it if it doesn't work. If I run out of things to say. And here we are years and years and years later, and it's evolved. And I think one lesson from this is that so often when we start a new project, we overthink all the things that don't really matter.

I remember worrying about the cover art, the title, how am I going to sign in and sign off of every episode? How long is it going to be? What is the format? When is it going to be published? All of those things have changed and evolved over the last seven years. And [00:21:00] my show has stayed consistent. One thing that you brought up is so many people don't actually dive in and do the thing.

We think about all the things around the thing, whether you're writing a book or starting a podcast or starting a business, you fixate on all the decisions you have to make instead of doing the actual thing, which in my case was sitting down and hitting record. Once I did that, the rest is history, but it was so easy for us to overthink all those things.

So my podcast started as an experiment, and we're still going strong a hundred million downloads later. 

Hala Taha: And for context, I started my podcast two years later than yours. So 2018, you started in 2016. When I started in 2018, it was a really innovative, unique thing for a young woman to be starting a business podcast.

So I can't even imagine two years before, like what a head start. Did you feel like you were like pioneering this space because there really wasn't much competition right at the time. Like talk to me about that. 

Jenna Kutcher: I remember there were no other women at the [00:22:00] top of the charts. Literally I remember being the only women in the business category, which was wild to me and also super interesting because at the time my experience was in like the creative entrepreneur space, right?

Not a lot of people consider themselves creative entrepreneurs. It's like the photographers, the graphic designers, the digital artists, all those. And so to be able to branch out and speak to a really wide audience was something that was very new, but I didn't see myself as a pioneer. I just saw myself as someone who was.

Imperfectly showing up with a phone voice and trying to get through. And there have been so many like ebbs and flows within that creation process. Times where I have loved my podcast. Times where I'm like just sitting down and showing up to the mic. And I think that the biggest thing is, is that consistency breeds confidence and confidence comes through in everything you do.

And so even on those weeks where I was like, I don't, I have nothing to say. It's like, sit down and start talking. Things are going to come out. And I think that's really powerful. 

Hala Taha: Yeah. [00:23:00] So many great lessons in there. One thing that I want to dig on is that you were saying that. I was really lonely as an entrepreneur and something that I realized we're very similar but very different with one thing.

I was on the phone the other day with the right hand woman, Christy, and she was telling me, she's like, yeah, it's just basically me and Jenna. And I was like, what, how? I had like 10 volunteers since episode two of my podcast and I have 60 people on my team and like 15 people that just work on my podcast.

I was like, how is this possible? Jenna's show is. five to ten times bigger than mine. Like, how is that possible? And what's the logic behind that? And so curious to understand why you've kept your team so small. 

Jenna Kutcher: It's so funny because I like think, Oh, that's just normal. Like we just need one person to help this thing grow.

You know, when I started my podcast, I literally only had one part time VA on my team. So like when I started it, it was still me wearing all the hats, doing all the things with one person who's helping [00:24:00] me respond to emails. I was like, Hey, I got this idea. I'm going to start a podcast and we're going to start it in a few weeks.

And like, we ran with it. I never envisioned myself becoming a boss. I think a lot of entrepreneurs start the thing because they're passionate about the thing. And all of a sudden it grows into a real business. And all of a sudden you feel like you're getting pulled out of those creative endeavors to manage people.

And that was never my vision, especially coming from the corporate world where I had a team of like 150 that I was overseeing. And so we run a very lean team. So even on my team today for a multi multi million dollar business. I have six people on payroll and 10 people like in total with those six as contractors total to run the podcast, the book, the courses, every aspect of it.

And my team, most of my team members have been with me for four plus years. But we just still have that get it done mentality. And one thing that I often ask myself is, what would this look like if it were easy? And I think that a lot of times we [00:25:00] overcomplicate things and make them really big and scary and intimidating so that we don't actually take action.

And so up until this year, I recorded my podcast in a spare closet, not a cute closet, not a decorated closet, a closet with the boxes that say like, Random shit on them. And that was where I recorded my podcast. And I've always just had this mentality of like, I'm going to just show up in the way that I can show up.

And we have created systems that make it totally possible. Now, let me say, Hala, that there is so much opportunity for growth. And Ifeel like I have been.

Intentionally putting my foot on the brake pedal for a while because I want to be so present as a mom in this very like important time in my kids lives. And I've always believed within myself, I can hit the brake pedal and I will not forget where the gas is. I know where the gas is. I know I'm intentionally doing this.

I'm slowing down, but I'm not losing momentum. I believe that. And so now I'm at this place where I'm like, okay, maybe we can expand. Maybe we can grow. Maybe [00:26:00] we can invite more people into the fold. But I have always just approached things of like, what would this look like if it were easy? Because done is better than perfect.

And that's how I've run my entire life and my career. 

Hala Taha: Yeah. And it just goes to show that you can do things in so many different ways. And I do know that the more smaller the team, the more aligned everybody is, the more that the company culture is super strong. As you get really big, it gets really hard to control everything.

And that's when little mistakes happen. So I'm always trying to like, okay, how can I make my team smaller and more compact and have the best talent ever? Right? So let's talk about the business behind your brand. You just said your multi million dollar business. You're absolutely crushing it in so many different areas.

What are the different revenue streams that Jenna Kutcher has today? 

Jenna Kutcher: Yeah. Okay. Let's see if I can do this. Okay. So online courses, we do really well as an affiliate for different products. So products that I love are courses that I've taken that have changed my life. I will sing those praises and share about them until my face is blue.

[00:27:00] So we do great with affiliates. The podcast is his own entity that does incredibly well. We also have rental properties, so we have a few different rental properties and we run Airbnb is as a side gig. I also do different Instagram partnerships and sponsorships. We have a digital product shop where we sell different templates and presets.

I have a journal and a book that I sell. So there are many different revenue streams. I remember hearing years ago that. The average millionaire has seven revenue streams. And I was like, okay, let me make eight. Let me make nine. What does this look like? And one thing I love about that is as someone who is creative and I also have ADHD.

I never want to feel like I have to keep doing something or the business will crumble because as a wedding photographer, that's where I found myself. I only got paid if I showed up and we were in a really hard season in a personal season trying to grow our family. And I remember having to show up to a [00:28:00] wedding when I would rather have been in the fetal position.

and promising myself, I'm going to figure out a different way to do this so that if I need a human moment, if I need to rest, I have a business that can run while I rest. And so if you notice, Most of our revenue streams are all kind of self sustaining. They're, they're not totally like passive. We definitely work on them, but they also don't require me to be showing up every single day in order to earn income.

Hala Taha: You are such a great example of an influencer that has taken her brand and has monetized her expertise. And to your point, now you're able to sort of take breaks when you want to take breaks, hold off on things when you feel like holding off. So I absolutely love what you've built. So let's talk about a new revenue stream that you have, which is your latest book.

It's called, How Are You Really? Living Your Truth One Answer at a Time. And I'd love to understand the genesis of this book. Why did you write it? [00:29:00] 

Jenna Kutcher: Yeah. So I don't know if you've ever done this, but I have said multiple times, I will never write a book. I will never do something right. And I'm like, never say never.

So for a very long time in my business, I was like, I don't get why anyone would write a book. It takes so much time. You don't make a lot of money. What is the point of this? And the point of that statement was I didn't have a message that I cared about enough to do all the work that is required to not just write a book, but to get it out into reader's hands.

And it's so interesting because I'm sitting in this space right now. We're on the shore of Lake Superior. We bought this lake house. And the second I walked into this space, I said, if I ever write a book, it's going to be in this space. It's just this beautiful, inspiring space. Well, guess what happens. The world shuts down, there is a pandemic, and suddenly we're living up at our cabin in the woods and I'm sitting in this leather chair.

And I had this very interesting experience, which I tell the story in the book, but I'll give the short [00:30:00] version. I had booked us massages. The world was creeping back open. It was our anniversary. And I was like, I'm going to do something nice for us as a couple. So I booked us these massages. And the woman who did our massages in this tiny town of 1, 200 people was this very intuitive woman.

And she introduces herself and says, Hi, I'm Thea. I'm an intuitive healer. I'm doing your massage today. I lay down on the table. I get my rub down. At the end, she says, Can I tell you what came up for you today? And I was like, Sure, whatever. And she goes, there is something that you need to do and you're avoiding it.

And I need you to go out and do that thing. And the second she said that to me, I knew right away. And she goes, do you know what I'm talking about? And I said, dang it. It's write a book. And it was so weird because she never said to me like, Jenna, you need to go write a book or, you know, why haven't you written a book?

She just said, there's something you need to do. And you already know what it is. And I think that this is so powerful for you as a listener. Is when you hear that line, what is the first thing that pops into your head? [00:31:00] Because there are things on our hearts that we have either said, I'm never going to do this, or I don't have time to do this, or why would I do this?

And the minute that I got that clarity, it became so crystal clear that night. I went home, I opened up a Google doc, titled it. I'm writing a book. And I sat down and started writing. And what was really interesting about my process is that so many people, if they have a platform, they go out and get an agent and then they write the book proposal and then they do the pitch and then they get the book deal.

I did everything backwards because I said for so long, I said, I'm never going to do this. I want to do this and I want it to matter even if nobody ever reads it. I don't want to write words that sell. I want to write words that tell. And even if they tell my story to my daughters someday, it's worth it.

And so I went into this writing process with no book deal, with no deadline. Because for me, as someone who's creative, the two things that kill my creativity fastest are money and deadlines. And I said, if I want to do this in a way that feels authentic, where I can present and say, [00:32:00] this is the story I want to tell.

I don't want to tell the story that you want me to tell. I want to tell this story. And so I wrote in silence. I didn't announce it to my audience. I didn't announce it to my family, just my husband and I knew that I was working on writing. We didn't know what it would become. We didn't know if it would become anything.

And it was such a beautiful process because I felt like when I finally made that decision, like I'm going to do this. The words just poured out of me and it was such a like sacred creative experience for someone who had been in that business space of like just more, more, more. It was like, let's do this because we enjoy it.

And it brought back the joy into my work in so many different ways. 

Hala Taha: What you're saying is so unique because I talk to authors all the time. I'm in the process of writing a book and what you're saying is correct. Like you get an agent, then you got to pay for somebody to help you write your proposal and you got to, and I'm like you where I want to write my own book.

I want to care about my own book. But what you did was obviously so magnetic because I went and when I study for my interviews, I read all the book reviews that people are obsessed [00:33:00] with this book and really transform their lives. And it's because you poured your heart into it. You didn't do it so you could get more speaking events or make money like you just wanted to give back.

Jenna Kutcher: Yeah, it's so interesting to all because being in the experience yourself, it is a long tail thing. And I think in a digital world where we're so used to like ideating and creating and publishing and getting feedback, writing a book is a really personal experience, right? Because you don't know if people are going to love it, if they're going to get anything out of it.

You have to love it enough to want to talk about it, to wanting to land into people's hands. And it's so funny because so many of my friends are authors and amazing authors and so many of them hated the experience. And I feel like I'm one of the few that have come out of the experience of writing and marketing and selling and enjoying the book process.

I loved every bit of it, but I did every bit of it in a way that protected my creativity and my passion. And [00:34:00] so I am still on fire for my book and I love that about it because I just feel like so many authors after a while, they're like, I'm done talking about it. I don't want to talk about it anymore.

And I'm like, let's go. 

Hala Taha: I love it. I can feel the energy and how much you just really enjoyed this. I got to take a page from your book. Maybe I should write my book first and then go through the process. To your point, it's like a lot less pressure. Okay, so one of the things that you talk about in your book is creating a life inventory because you need to know where you want to go and where you are in order to make a change.

So how do we go about creating a life inventory? 

Jenna Kutcher: Yeah, I love this. So the premise of my book is not to hear my voice as you read it, but to like come back home to yourself. I think that so many of us have gone through life and we've kind of numbed out like that inner intuition, that knowing that whisper that we often don't hear because the world is so noisy.

And so one of the things that I love about the life [00:35:00] inventory is it beckons you to really think about when is the last time I felt joy? When is the last time I felt alive? When is the last time I felt frustrated? And it's funny because as I was writing the book, I was dealing with a toddler who had a lot of feelings.

And so I'm like working with her through her feelings. And I'm like, you know, as adults, we just try to rush through feelings. If we're sad, we try to get to happy. And I think that there is so much shame around the different feelings that we have of like, surely I must be broken, that I'm not satisfied or something is wrong with me.

Maybe it hasn't been enough. Maybe I just need to go after more. And so I love this idea of like this forensic style inventory of your life, because I think what has happened for so many of us is that we think success looks a certain way, but we never ask ourselves, what do we want success to feel like?

There's a chapter called feelings are meant to be felt because We have rushed through or numbed out our feelings. We don't even know how we feel anymore. And then we wonder like, why am I waking up at three in [00:36:00] the morning with my brain racing and this feeling of like, is this all there is to life? Like, is this what I've worked so hard to get?

And so I love just really taking an inventory and saying, you know, when was the last time I was happy? When was the last time I was satisfied? When was the last time I felt successful? And really trying to see if there are trends in there or signals that maybe you need to pivot or change or move away from something and move towards something else.

Hala Taha: And I know that when we are on autopilot in our life, we might not realize that we've golden handcuffs on. There's something that we think is good that actually is preventing us from going out and accomplishing our true dreams that we have for ourselves. Can you talk to us about that? 

Jenna Kutcher: Yeah, so when I think of the golden handcuffs, it's all of these promises that people make to us that keep us stuck.

And so for me, it was that five year plan that they thought was pretty, but really made me want to shift. You know, the benefits, the 401k, all those things, they're all amazing, right? But those are the things where we find ourselves saying, I [00:37:00] should feel really grateful for this. I should feel fulfilled with this.

And yet there's something missing. And I remember having this conversation with one of my best friends, and she has been so deeply unsatisfied with her job for so long. And I felt like it was groundhog's day. Every time I talked to her, she would tell me all the things she hated about her job. And then she would try to wrap up those statements with a pretty bow, but.

You know, we have unlimited vacation time and there's a ping pong table in the break room. And I said, one, do you take vacation? The answer was no. Two, do you like ping pong? No. And I said, all of these things that are painted as benefits are actually just keeping you stuck. I think that it's so powerful for us to really understand what is holding us back and what are these things that people are painting as shiny, but they really show up as dull in our lives.

And how do we actually pursue the things that really give us this full, vibrant life that we want? And what does that look like? And I think it could look different for all of us, even as entrepreneurs, there are different things in our aspect where we're like, this just doesn't resonate or this doesn't feel [00:38:00] in alignment anymore, but I should keep going with this because it's like that sunk cost fallacy of like, well, I've already invested so much time into this.

I might as well finish it out. Wait, you're missing out on the time to pivot, to change, to evolve. And I think that we need to celebrate those choices just as much as we celebrate those shiny successes that we see all over the internet.

Hala Taha: Totally. And one of the things is that some people sometimes don't understand. their own intuition or how to follow their own intuition, trust their own gut. So something that I thought that you did really, really good in your book is you struck a balance between spiritual alignment with what you want to do, as well as practical goal setting, practical goal getting.

You actually need to visualize, you know, manifest, but then do the thing, right? Like we were talking about in the beginning of the podcast. 



Hala Taha: So I want to read an excerpt from your book that really touched [00:39:00] me. And it's because I think a lot of people in my life, I know, are just like sort of on autopilot.

They have bigger dreams for themselves and a lot of listeners, I feel like, that reach out to me, they also feel stuck. They don't know what to do. They're doing okay in their job, but they just don't know how to change. So, You say beyond getting really honest about the things that might not be okay. We stifle the things that make us come alive It's like we all end up chattering about on this banged up planet Carrying these big dreams and audacious goals and boundary breaking ideas and we keep them quiet All throughout the week in the checkout line on the conference call around the dinner table We are walking around with wild parts of ourselves unspoken So let's spend some time here.

What do you think of when you hear this quote? 

Jenna Kutcher: I think about how often we belittle our life's work. I don't know about you all, but like when you're starting your show and stuff, if somebody asks you like, what do you do? It's like, Oh, I have a little podcast or I do this little side thing, or I'm trying to start this [00:40:00] thing.

And I think that we've gotten so good as a society at compartmentalizing our lives into these tiny little containers saying, okay, this is the mother's side of me. This is the wife's side of me. This is the business side of me. And we don't really show up as our whole selves. And I think that in order to live a whole life, we have to figure out ways to integrate each aspect of ourselves into the work that we do.

Me being a mother doesn't take away from me being a CEO. In fact, it can add to that if I bring some of those feminine vibes into my work. And so what I've tried to kind of break down is that there are so many of us who are moving through life and we're belittling our dreams or we're just kind of shrinking down to fit into society's standards or what people expect from us instead of bringing our whole self to the conversation and saying, Yes, I am this, but I am also this.

It's like the both and conversations instead of either or. And I think for so many of us, especially in such a polarizing world, we feel like we have to choose, right? You either [00:41:00] have to be the girl boss, or you need to stay at home and homestead. You are either the hustler or you are the present one. And I think there's room at the table for everyone.

And that's why I think what I love about my book is it's kind of what you were suggesting. It's where the woo meets the work, where yes, you can manifest, but you also have to take action. What does that action look like? I love showing up as my chaotic whole self, because I feel like if I'm only giving people this one piece of me, they're not knowing the full picture.

And I think it's so powerful when we kind of pull back the curtain and say, here's who I am. Here's how I show up. Here's what I'm dreaming of. It also invites other people to dream a little bit bigger. 

Hala Taha: I love that. Everything you're saying is so beautiful. In terms of actually following your intuition, you always say pursue what feels good.

How can we tell what feels good? 

Jenna Kutcher: One thing that I often think about is I have ADHD and for years and years and years I told myself I can never be a person who meditates. All the successful people in the world be [00:42:00] like, I meditate for 10 minutes a day. And I'm like, I can't even imagine sitting alone with my thoughts, like what that would look like.

And what I've learned over the years is that what we need to bring into our lives is more awareness. When we start to notice things, we are able to change, we're able to evolve, we're able to dive deeper. And I feel like so many of us don't even notice our lives. We don't pay attention to the things that feel good.

We are so consumed by what looks good. When I was a wedding photographer, I would always say, I want to shoot weddings where the marriages are more beautiful than the wedding day. As an online influencer, I want to live a life that is even more full and beautiful offline than the one that you see online.

And I think that a lot of people get it flipped and twisted where they're like, here's my highlight reel. But behind the scenes, I'm falling apart. And I think that when we can bring a level of awareness to the work that we do, to the way that we show up to the relationships we're in, it allows us to grow and stretch as a human being.

But it also allows us to [00:43:00] pay attention and notice the things that feel good, that feel right. Because I am not someone who is going to tell you, follow your dreams and you'll never work a day in your life because most of us don't even know how to dream anymore. And so for me, if I am paying attention and aware, I might be noticing the things that no longer resonate, that are no longer in alignment, and that might guide my path just as much as knowing where I want to go does.

Hala Taha: And so, curious to understand, do you feel anybody can turn What they're passionate about, what they're interested in learning about, into a career. Like how do we know if we should actually pursue and turn our passion into a career? 

Jenna Kutcher: I love this question. So for a very long time, I was someone who preached entrepreneurship is the way.

Until I realized that the world cannot be filled with entrepreneurs, right? Some people are meant to be employees and joyful employees at that. What I think is so important is if you can [00:44:00] protect your passion and monetize it with joy, go for it. But not every passion needs to become a business. And I've had to learn that throughout my entire career.

There are certain passions and hobbies where I could find myself thinking of a million ways that I could monetize it. And I'm like, No, keep this sacred. Keep this just as a piece of your passion. And so the big thing is, is that Is it something that you will still find joy in when you start to bring in those parameters like we were talking about like with the book deadlines and invoices and money?

Are you still going to be passionate about that thing? If the answer is no, keep it and preserve that passion for yourself. But if you would feel like a million dollars if somebody paid you 10 to do the thing you love, then maybe that's a sign that it is something that you should pursue as a potential business.

Hala Taha: So something else that you speak about a lot is this small steps approach. You've got to take the small, consistent action. You even talk about taking unbelievably small action to get started. Talk to us about why [00:45:00] you think that's really important and how it builds confidence. 

Jenna Kutcher: How many people listening are using perfection as a means to procrastinate?

I think that everyone, right, you want to be able to show the after without ever showing the messy middle, right? We want to see that transformation, whatever that looks like in your life. And so, so many of us are moving through life, waiting for the after to happen so that we can finally reveal it to the world and share all the secrets behind it.

And what I think is so powerful is showing up and taking those teeny tiny steps that no one's going to clap for, that no one's even going to notice if they were following you. Because what happens is, is as you start to take action, your confidence grows. And when your confidence grows, you become consistent.

And when you're consistent at something, you're putting in the reps that allow you to get the results. And so I am so sick of people that are holding back and they're saying, someday I will launch a podcast or write a book or start the business someday. I'm working on it. I just, I got to figure out this and [00:46:00] this and this and this.

And they're procrastinating and using perfection as a means to do that. And so if you look at my career in any step of the way, I feel like I could scroll through the hundreds and thousands of posts that I post on Instagram and say, that wasn't fake. That was exactly where I was in that moment. I was learning something new and I was showing people.

And let me tell you that it is so much more inspiring for people to see someone that is just one step ahead of them than a million. And so if you're waiting to unveil this idea or business or project until you're a million steps ahead, you're going to miss the most beautiful opportunity to actually transform people's lives, including your own.

Hala Taha: I'm like vigorously shaking my head because I'm like, preach, Jenna, preach, because it's so true. Businesses don't happen overnight and also they don't need some big master plan. Every single business stream that I've started was some idea I had at midnight and like started creating a PowerPoint and then I started selling, like it just, it evolves, right?

So I feel like a lot of people think that they need to get from zero to 100 [00:47:00] and it's like, no, there's one, two, three, four, five, six, seven, like there's so many different steps. Along the way, and that's how you learn and build confidence and become an expert and all those things that we were talking about.

So let's talk about some of the common mistakes entrepreneurs make. This one ties in really well with what we're talking about. What's wrong with wanting all this success to happen so fast? A lot of people just want things to happen too fast. 

Jenna Kutcher: I will say that the common mistakes are that you want to have it all figured out before you start showing up.

And I think you have to start showing up while you figure it out. Because a lot of times we'll finally have something that we want to launch and we'd have no one to launch it to. They didn't know we were passionate about this thing. They didn't know we were working on that project. And so all of a sudden we do this grand reveal and there's no one there.

It's not if you build it, they will come. They will come as you build it. And so I think that's the number one mistake people are making is they're just waiting and saying, okay, when it's finally ready, people are going to be there. But it's like if you let them in on the process and the production of it, then they will be [00:48:00] bought in before you ever have something to sell.

Hala Taha: Yeah. Document your life. So I know that something else that you talk about in terms of being an entrepreneur, you is the need to take breaks. And you were alluding to this earlier in the conversation where you were talking about, As an entrepreneur with many different revenue streams, you've got all these revenue streams because sometimes you might want to turn things off and take a break and focus on your family, focus on your personal life.

So a couple of questions around this, first of all, talk to us about the importance of breaks and resting as an entrepreneur, and then also what about the entrepreneur who's like, I suck. I just want to quit. 

Jenna Kutcher: I often say, rest, don't quit. I believe it's a quote from Banksy. And I love that because I think so many of us are ready to quit when really we just need a nap or a break or time away from the project.

And so I think we're too quick to quit. And for me, I feel like rest has become [00:49:00] something that I've had to learn. Like my autopilot is to go hard and go after it. And rest felt hard. It is harder for me to be intentional with rest than it is to go full steam ahead. And I think for a lot of achievers, that's the thing.

And I recognize that just like you would do a couch to 5k program where you're training each day to take a few more steps. We need to go. We're running the 5k every single day, and we need to learn how to sit on the couch. And so I have to have so much intention behind resting that it now has become natural.

But at the beginning, it was so uncomfortable. I didn't want to be alone with my thoughts. I didn't want to slow down. I had this belief that like if the momentum slowed down, Everyone would realize this was all a fluke and it would all fall apart and no one would want or need me anymore. And now I recognize I create the momentum.

I put my foot on the gas pedal, but I can also know where the brake is and vice versa. And so I think that for a lot of times, We get so caught up in the hustle, and I think the hustle is required to get the business off the ground. But if hustle is [00:50:00] the only way the business will succeed, it is not sustainable.

And so how do we kind of draw lines in the sand where we say, and now I can rest. Well done. Now it's time to take a break. Now it's time to step away because I've actually found that in those seasons of rest and slow down where I really do treat time as my currency, those are when the next best ideas happen or the next creative endeavor comes to me or the next passion reveals itself.

And so I think rest is just as important as hard work and I think that it's up to us to discern when is that needed and how am I going to learn how to do it. 

Hala Taha: Mm. My last question to you as we wind down this interview, I know that you're a big proponent of self love and body acceptance, and you have a big theme in your book about the way that we feel in our own skin.

Can you elaborate on why it's important to actually have self love, the accepting of our bodies, because you say there's so many times where we've missed out on opportunities and disqualifying ourselves because of how we feel about our bodies. [00:51:00] 

Jenna Kutcher: Yeah, it's crazy to me that more people don't talk about body love and acceptance when I think about how many thoughts a day we have that involve our bodies.

And I have recognized over the last decade, I have been in many different shapes and forms and weights and sizes. And every step of the way, the way that I feel about my body impacts how I show up, how I put myself out there, what I believe I'm worthy of. And what is so interesting to me, there's a line in the book that says the way we show up for battle is directly linked to the type of warrior that we believe we are.

And I think for so many of us, women especially, but men too, so many of our thoughts are occupied with what do I look like right now, not how do I feel. And so I think it's a really powerful thing to talk about because as we talk about chasing dreams and starting businesses and growing your audience and showing yourself and, and Letting people into the messy middle, the way that we feel about ourselves impacts the way that we do that.

And so when we can start to really bring a level of awareness of [00:52:00] what stories am I telling myself? What am I believing about myself? How is that impacting the way that I'm showing up? It can change absolutely everything. And so I definitely think it needs to be a part of the conversation because it impacts our confidence.

And as we've said, confidence impacts everything. And so I love talking about how we feel in our own skin and how we talk to ourselves about ourselves and how that changes things for us in terms of how we show up successfully in life. 

Hala Taha: Well, Jenna, thank you so much for helping us get back in touch with who we really are.

Yeah, fam, I definitely want to say go cop Jenna's book, How Are You Really? It's a path to coming home to yourself. She gave so many tips today, but it's just a sliver of what is covered in her book. We really didn't get through it all. So Jenna, the last two things I asked all my guests is, what is one actionable thing you think our young and profiters should do today to become more profitable tomorrow?

Jenna Kutcher: I would say do an inventory, whether it's of your life or your business, and see what is actually moving the needle for you the [00:53:00] most, whether it's through profits or joy. And I think both of those can tie together beautifully. 

Hala Taha: And what is your secret to profiting in life? And this goes beyond just finances.

Jenna Kutcher: Building different avenues of revenue that can run while I rest. 

Hala Taha: And where can our listeners learn more about you and follow you? 

Jenna Kutcher: I would love to invite you to the party. I am on all the platforms at Jenna Kutcher, just like Ashton. And I would absolutely love for you to come on over to my podcast, The Gold Digger Podcast.

Tune in. We drop two episodes a week. It is the number one marketing podcast for a reason. And I love sharing tips, tricks, and strategies, both for business and for life. 

Hala Taha: Amazing. Jenna, I'm going to stick all that in the show notes. Thank you so much for coming on Young and Profiting Podcast. 

Jenna Kutcher: Thanks for having me.


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