What No One Tells You About “Success”

Jenna Kutcher 

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February 20, 2019


I want to preface this whole thing by saying that I am so, so grateful for every ounce of success that has come my way. I’m showing up super honest about how my life has changed since I left the corporate world and started my own business back in 2012. I think it’s worth devoting an episode that’s honest and true about my personal experience of growing a large brand, building a multimillion dollar company, and how it’s changed things for me, specifically how it’s changed my relationships. Get ready to sprinkle some grace over everything I’m about to say, and know that I’m showing up to tackle something that I’ve been personally struggling with in hopes that it will help you to understand what success can sometimes look like behind the scenes.

Before Success

Growing up I was a social butterfly. I was the kid that smiled at everyone, talked to anyone, and made friends with any human who would give me the time of day. I remember being a kindergartner and getting invited to sit with some 3rd graders because I was so outgoing and talkative. I loved people and that followed me into my high school and college life. I always had many different groups of friends: work friends, sports friends, school friends, and church friends. One year I went to 3 different schools proms because I was in different friend groups and didn’t just have one little social circle. I was BUSY.

Looking back now, I think that some of the way I was stemmed from insecurity. I loved being known, I loved being affirmed, and I needed to know I was wanted. While I had a TON of friends, I didn’t have a lot of depth within friendships and all the social floating was kind of exhausting. I’ve always had confidence, sure, but I also had this desire to be affirmed and I know looking back now that I was kind of searching and trying to find my identity, though I was also just simply more social and loved being out and about and with people.

In being outgoing, I’ve never dreaded public speaking, I’ve loved working in groups, and was always a team player. There are so many aspects to me that scream extrovert but within the last few years they have definitely shifted in big ways and I don’t think that success is solely to blame. Awhile back I interviewed my mom on the podcast in episode 186 and one of the sad things that came out during that interview happened when I asked my mom how all of this had changed me: she basically called me a hermit and expressed concern over the fact that I really don’t get out of the house much and love being and working alone. I think it’s easy, if you’ve known me really intimately to see the changes the most but for the majority of people, they probably have no clue.

I honestly feel like a lot of things changed for me back in Corporate America and not just in my entrepreneurship journey. We moved to a tiny village of 1,200 people, were newlyweds and living together for the first time and I was suddenly working between 50-60 hours a week. We had no roots to where we lived, we didn’t know a soul, and we were in a season of just being so excited to be together we didn’t really pursue friendships. Unlike high school or college, we didn’t have built in networks by means of major, the dorms, or sports. Making friends kind of felt like online dating: awkward, a lot of effort and you’re never really sure if it’s worth it.

I worked every other weekend alternating days and nights and so I didn’t really get out too much and at the end of a long day, all I wanted to do was NOT be around people since I had spent an entire day leading a team. I loved my co-workers, my team members, and loved being with them daily but that filled my quota of people for the day. We struggled to find new community where we lived and it wasn’t until I joined a CrossFit gym that we made any friends at all.

I remember the first time my new Crossfit friends invited us to the local pub to play poker and I remember telling Drew, “Put some pants on, someone invited us to do something, we’re going to do it.” Turned out those friends became our closest friends over the years and they made moving home to Minnesota hard because they had become our little family. They were with me when my business was still a small-town wedding photography business, before all the growth happened, and they were with me through it all.

The Cost of Success

Now, a lot of times people ask me: what has becoming successful cost you? Honestly, I love this question because it tells me that people realize that even good things do come at a cost and it’s easy to see all the big stuff but forget about that human life behind the accolades, the numbers, the Instagram feed. So before I answer that question, I want to ask you a question because I think it’s important to address this first: are you afraid of success? I was recently at a conference as a keynote speaker and I was in a room of women and I asked the question: who here is afraid of actually making it… of becoming “someone” and finding success?

I wasn’t shocked when almost half of the rooms hands went up as these women admitted this struggle of wanting success and ultimately fearing it. I think if we’re honest, a lot of us actually feel that way: what would happen if I really did make it? Could I handle all that would come with it? Am I ready to sacrifice things just to be successful? To be honest, I think the fear of becoming a success can be as strong as the fear of being a failure. So back to the question: what has becoming successful cost me? Well, it’s honestly cost me, personally, a lot and if I’m being SUPER frank, I’ve been doing a lot of inner work to figure out how I landed to where I am today.

I went from being a highly extroverted person who loved to be out and seen and known, to someone who struggles to want to leave the house. I’ve become a person who has a really hard time trusting people because so much is asked of her daily. I’m now a woman who has very few friends by choice and would rather stay in than go out. Truth be told, I’ve turned very inward and have built up a lot of walls to protect me, my heart, and my business over the years.

One of my mastermind girls said to me the other day, “You have the best boundaries of anyone I’ve ever met.” And I smiled because I used to have no boundaries, I was highly accessible, I was the “yes” girl, and the girl who never said “no” because I was a people pleaser to my core. In time I learned that if I’m pleasing everyone else, I’m not pleasing myself and all of those “yeses” were adding up to equal “nos” in my life for the things that really mattered most to me.

Boundaries? I’ve got them. Big time. I don’t hand out my phone number or address, I don’t post things in real time to protect my location, I schedule my time so that I don’t end the day or week totally drained… I’ve learned that I have a certain amount of energy every day and it’s up to me to choose where I allow it to be spent. Do I really want to change the world? Yes, I do. If that’s true for me, then I need to create boundaries that protect the carrying out of that mission which for me looks like really making sure that what and who I am letting into my life helps support my bigger goals.

Success and Relationships

Honestly, not too much has changed with my family. They’ve been with me since the beginning and if anything, becoming more introverted and prioritizing my relationships was part of the reason that we moved home to be closer to family. My family is really close, the kind of family that group texts almost daily, and while people might have been skeptical about my decision to become an entrepreneur (looking at you, mom and dad) my family has had a front row seat to watch this business really grow — even if my dad still doesn’t really understand what I do for a living.

Both my mom and sister have worked in my business so they get to see the big picture, the goal, the impact and dreams of mine and I think all of this has actually made me closer to my family because I realize that they will be with me no matter what and at the end of the day I’d choose them over anyone else. You might notice that I don’t post or tag a lot of photos of my family, but I learned pretty quickly that it’s my responsibility to protect the people I love and while I opted in for this life, others didn’t. So my feed is 95% me and Drew and I try not to rope others, especially my family, into the madness. I mean, someone tracked down my parents address online and sent me a gift to their home, my parents have gotten chased down in an airport by a fan, and so things like that I just want to protect them from because this isn’t a life they chose, but I did.

As far as friends go, when I look at people who knew me before all of the madness, it can go one of two ways: they either claim that we were best friends when we spoke maybe once or twice before or the relationships have only gotten deeper. I am still really close with 3 of my college roommates and those girls have been with me since 2006 and have walked a lot of life with me, those are the friendships that I wouldn’t trade for the world. We’ve walked through dating, marriages, miscarriages, babies, and so much more together and I love it.

I also get a kick out of people from high school or who I knew when I was younger claiming things about me, because that happens a lot now and I think it’s hilarious. I recently ran into an old college swim teammate who was 4 years older than me and his wife was a big fan of mine and he acted like we were best buddies when really he was a senior and I was a measly freshman and he probably didn’t even know my name when I was on the team. I’ve had people track down my hairdresser and ask her “what I’m really like” after I get my haircut or people stalk my friends and ask them if I’m really the same person I am online… so I’ve become very careful with how I share anyone else in my feed.

My team often jokes about how we need to make a secret password for people who actually know me personally, because of the type of brand I’ve built and how personal it is, people often feel like they know me when they don’t know me beyond their screen or their earbuds so it’s nearly impossible to decipher if someone is really my best friend, a devoted follower, or a total stranger. It can be really hard for my team to figure out how to respond to every email, request, and inquiry in a way that is personal while still protective. I know of times where close friends of mine got a generic autoresponder or email template and I also know when total strangers convince my team that they really know me well and that I should see their email. So maybe 2019 will be the year that I implement a secret password but it’s definitely added a new layer of our communication because of the volume of emails and DMs we get every single day.

How has my relationship with my husband, Drew, changed amidst all this success? You’ll have to press play on the player above for the full episode.

Creating New Relationships

One of the most beautiful things that success has brought me is the ability to connect with other successful women on a new level. This podcast right here? It gives me an opportunity to interview some of the most powerful, successful, impactful women on planet earth and for that I am so thankful. I recognize that without my own journey, I likely wouldn’t be given the opportunity to connect with incredible women like the guests we’ve had on the show.

I also have created some of the deepest relationships with people I’ve met on the internet — some of which, I still haven’t met in real life. Isn’t that crazy? When I look at the people I talk to on an average day, a lot of them are friends from the internet that live hundreds of miles away. One of the hard things about what I do is that no one in our town or even the nearest city fully understands my business, what I do, and the scope of my work. It can be highly isolating being an industry that feels like an island and so I’ve found that sometimes the best friendships I can forge are with people who “get it.”

Since I work from home, my team is remote, and I don’t get a lot of face to face with people in my industry, things like text messages, voice texts, even sliding into each others DMs has been such a huge thing for me! Just to feel like I am in contact with other women who are chasing their big dreams, who tackle obstacles, face critics, and manage teams… that’s been a huge bonus.

On the adverse side: creating new relationships has been really hard for me. I wish that everyone could scroll through my DMs just for a few minutes to see what I get daily. I get hundreds of DMs. There are some really sweet and encouraging messages sprinkled in the mix, but so many of them are requests and hidden agendas that I have to get through to see the true and sweet messages. This also pains the heck out of me because of the mass amount of content we share for free and the fact that I know if the majority of these people took an hour to go through my blog, the podcast, or my feed, they would likely get the answers they are seeking.

It also just breaks my heart because I actually WANT to help and respond and point people in the right direction but if I spent time doing that, it would take away from the time it takes to make the resources I create that can reach the masses. So one of the biggest changes I’ve had to make is to really center myself on my one mission: get good, free education to the masses and then I have to measure everything up to that goal. Does spending hours in my DM’s get me closer to that? No. I’ll be honest but I’ve had to create a huge system just to protect my heart from all of the demands.

Big Picture Thoughts

I know, I know, this is all kind of weird and complex and you might be judging me for all the things I’m saying but at the end of the day I think an important question to ask myself is this: would you do it all over again if you knew it’d be like this? The answer is always yes. I believe that my platform and business has touched hundreds of thousands if not millions of lives and that because of who I am, I’ve been able to inspire and educate so many others and have paved a way for those I am trying to reach. Sure, there are some downfalls, sure it’s not always easy, sure, some days I wish no one knew who I was and I could just blend into the background but at the same point, when I meet someone and they tell me that I’ve changed their life, it’s worth it.

Just looking into ONE person’s eyes knowing that I played a tiny part in their big picture takes breath my breath away and so what if it’s hard for me to trust people or hard for me to find new friends? I’m pretty content with my simple life that has my husband, my baby, my family, and a few friendships that have been with me over a decade. I like it that way. I wouldn’t change it but I DO want you to know what this all can mean and it’s a decision only you can make if you’re wondering if it would be worth it to you. I’ve changed a LOT on this journey but I think those changes have helped me to change the world, I think they’ve protected my heart in hard seasons, they’ve equipped me to run a giant business, and they allow me to change lives. It’s absolutely been worth it, without a doubt.

For the full episode, press play on the player above or tune in with your favorite podcast app at goaldiggerlisten.com.

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  1. Sandra says:

    A simple life, husband, baby, family and a few close friends. Sounds perfect and beautiful Jenna. Living your life to the fullest on your terms. Keep doing you girl!


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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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