What It’s Really Like to be Married to a Successful Woman

Jenna Kutcher 

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March 16, 2020


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The term “gender roles” just makes me cringe a little right from the start. Suggesting that there is any role that any gender must fulfill is limiting and narrow-minded… But let’s talk about it. Let’s talk about what it means to bust out of traditional roles and what real men or real women should do.

I’m proud to be part of the shift in traditional gender roles. I’ve talked about it before, but my husband Drew is essentially retired… If retirement includes chasing our baby girl around and making sure I nourish myself after a marathon podcast recording session. We’re not only comfortable in these quote-unquote non-traditional gender roles, we own them.

But of course, we still occasionally encounter the curious or confused person who doesn’t quite understand why or how I’m the breadwinner. Their antiquated view of a “real man” doesn’t align with what they see in my husband. And while society as a whole is largely accepting and expecting of a working woman these days, it feels like the views of a “real man” are slower to evolve.

I love speaking with and for women on this podcast. But when I saw this man’s name land in my inbox, I knew it was the perfect opportunity to offer a different perspective on the show. This is a great discussion to hear together with your partner. Dave Hollis is COO of The Hollis Co. He’s also husband to one of my friends who you may know very well, Rachel Hollis. And in this episode we discuss what it’s like being the husband of that very successful woman. I ask him about gender roles, about imposter syndrome, and the lies men continue to believe about how a real man acts or feels. I can’t wait for you to hear this conversation.

Clinging to Status and Titles

Dave Hollis worked in the entertainment industry, everything from tour managing Destiny’s Child on a mall circuit to landing in a head sales position and President of Distribution at Walt Disney. Status was something he appreciated but that he ultimately let go of to join his wife Rachel Hollis at The Hollis Co.

“I left what I knew for what I needed,” Dave explained, “I was leaving something I was very comfortable in for the opportunity to pursue something that would make me uncomfortable on purpose.” The transition from a job he knew so well to something he was totally new at was a jarring change.

Dave found worth and enoughness in those status positions and in the stories he could tell about the people he worked with… And then he left those things in hopes of finding that same affirmation while also creating more impact.

Titles at the Hollis Co.

When Dave approached Rachel about the topic of “title”, he didn’t have the context he has now. Rachel founded her company (previously Chic Media) and spent 15 years building it into something massive enough to draw Dave away from his career at Walt Disney.

“And then I went to her and asked to be CEO of the thing she’d built and worked on,” Dave chuckled. He felt like he could justify his request at the time because he had the career experience and skills her company needed.

“But my ego was the thing that was asking for a title,” he explained. Dave said it took him a while to realize the “ridiculousness” of asking for that title in the first place. Rachel obliged because she knew the challenge it was for Dave to leave his former role, but they’ve since shifted his title to Chief Operating Officer.

“[Title] could not matter less to me now,” Dave reflected.

Working with Your Spouse

When your career coincides with the career of your spouse, and you’re both working in and on the same business, how do you define your professional relationship versus marriage? For Dave, he’s learned that how his love shows up for his wife in their marriage is not necessarily the same way it should show up as the COO in their business.

One day Rachel told him she wanted to be the host of a nationally syndicated television show. Dave thought it was his role to manage her expectations so he told her he felt it had a 3% chance of coming to fruition. Four months later, Rachel told Dave he had bought her a gift. Inside the box was a bracelet with the number 3% stamped on a charm. She had booked the TV show.

“One, I truly do believe my interests were to keep her from being surprised by the possibility of not achieving a goal and so I was trying to keep her from having to experience disappointment,” he explained. “But what I also said inadvertently was that I don’t believe that you’re strong enough to handle disappointment if this doesn’t come to pass.”

Dave learned in this experience that it wasn’t in her best interest to keep her from getting excited about things. Now in his role at Hollis Co, he reflects on that story. “My job is to operationalize the ideas…My job is to, in partnership, find solutions to the dreams that she’s able to have that, frankly, I’m not.”

Save also shared how they do and don’t create boundaries between work life and their marriage, and how their non-negotiable routines play into it. Press play to hear the full interview.

Writing a Book

“It was way harder than I thought it would be,” Dave laughed.

When Rachel published her first book, Dave remembers begging her not to release it into the world. The stories were vulnerable and raw while they’d spent so much time curating her image on social media. Some parts didn’t paint Dave in a great light. He did not want that book out there… Until he learned the power of sharing your story in it’s raw, real truth. That’s what connects people to it.

He was thankful for that lesson when he came to write his own book titled Get Out of Your Own Way. Dave dealt with a great deal of imposter syndrome as he wrote the book, wondering if he was good enough to put his words on paper, if people would compare his efforts to that of his wife.

More from this Episode

Dave’s thoughts on failure and failing publicly, more on his relationship with Rachel, and what he learned about himself in real time while writing his book. Press play above or tune in on your favorite podcast app to hear my full conversation with Dave Hollis.



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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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