Annie Meyers-Shyer: Author and Creator of "This Oak House"

14 Sep 2026 · 55 min · 23 chapters

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In short

Annie Meyers-Shyer (creator of “This Oak House”) discusses her career pivots from fashion magazine editing to tech (MySpace fashion director) to Chanel PR, then her decision to renovate her mother-in-law’s Los Angeles home during motherhood, document it on Instagram, and turn the project into her debut book, This Oak House (out Sept 15).

Guest background

Double major in public communications and women’s studies; worked at InStyle (assistant to Hal Rubenstein, then market/assistant roles), then Harper’s Bazaar as associate accessories editor; later fashion director at MySpace (ran celebrity video series “The Fit”); then PR at Chanel for six years (West Coast office, celebrity dressing, LA events).

Key claims

She learned “what looks good on the page,” that interiors lacked transparency compared to fashion, and that architecture and room layout should drive design. She left Chanel when travel conflicted with parenting and felt guilty despite being at her career peak.

Notable examples

Lady Gaga shopping on “The Fit”; Chanel dressing Kristen Stewart; building an upstairs hallway to fix access issues; Pinterest boards per room; book format split into “House” and “Home,” with end-of-chapter takeaways (e.g., hot fudge recipe, tablescape).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Annie's Background and Career Journey

0:45 to 2:04

Annie shares her journey from fashion to interior design and launch of her book.

“Before embarking on her renovation journey and diving into all things interior design, Annie started her career in the fashion industry, first at InStyle Magazine and later at Harper's Bazaar.”

Early Career in Fashion

2:04 to 4:00

Annie discusses her education, early job hunt, and experiences at InStyle and Harper's Bazaar.

“We like to start this podcast at the beginning.”

Ambitions and Career Shifts

4:00 to 6:06

Annie reflects on her ambitions to become an editor and the challenges she faced.

“And he was always nice to me, always, always nice to me.”

Working at MySpace

6:06 to 8:04

Annie shares her experience as fashion director at MySpace during its transformation.

“I was hired by a really wonderful woman who had been at Vogue named Danya Unterhalter.”

Transition to Chanel

8:04 to 10:00

Annie discusses her transition from MySpace to PR at Chanel and the challenges of the role.

“I mean, I was called on my cell phone weekends, nights, it didn't matter.”

Life at Chanel and Personal Changes

10:00 to 14:00

Annie reflects on her six years at Chanel, balancing her career with personal life changes.

“And it just felt like things were changing.”

Working at Chanel: A PR Perspective

14:00 to 20:08

Explore the unique challenges and experiences of working in PR for Chanel, especially in celebrity dressing.

“that whatever was being drummed up in Paris.”

Balancing Work and Family Life

20:08 to 21:57

Annie shares her struggles with managing a demanding career at Chanel while raising young children.

“And that became hard for me, especially with little kids.”

The Decision to Renovate a Family Home

21:57 to 24:49

Learn about the decision-making process behind taking on a family home renovation during the pandemic.

“And I looked at my husband and I was like, I'm done.”

Documenting the Renovation Journey

24:49 to 26:46

Annie discusses how she began documenting her home renovation on Instagram and the unexpected community it built.

“Talk to me a little bit about what that process was like.”
Show all 23 chapters

Becoming an Accidental Influencer

26:46 to 28:00

Explore Annie's transformation into an influencer and her thoughts on transparency in the interior design space.

“So I want to talk about your decision to document the process on Instagram for your friends, right?”

The Journey of Home Design

28:00 to 29:31

Annie shares her initial experiences and motivations in home design.

“And I was DMing people and saying, I really love that mirror.”

Crafting a Personal Aesthetic

29:31 to 31:06

Annie discusses identifying her design aesthetic and working with an interior designer.

“So you write in your book, which we will get into in a minute, and I quote that your interest in design began in childhood and was shaped by formative experiences throughout my life and career.”

Renovation Process and Layout Changes

31:06 to 32:58

Annie explains the layout challenges and solutions during her home renovation.

“And I just brought that to this project.”

Designing Functional Spaces

32:58 to 34:32

Annie describes creating functional spaces in her home while removing unnecessary structures.

“So because this was a family home and I had spent so much time here, I knew what worked and what didn't work.”

The Creative Process and Book Development

34:32 to 36:40

Annie reflects on the creative process of turning her renovation into a book.

“Hire people smarter than you whose job it is to figure it out.”

Bringing the Book to Life

36:40 to 39:51

Annie discusses the challenges and joys of photographing her home for the book.

“Talk to me about the idea and the process of taking a renovation and an Instagram account and turning it into the most incredible book.”

Writing Experience and Tips for Renovation

39:51 to 42:00

Annie shares her experiences during the writing process and offers valuable tips.

“A digital experience is different from a print experience and I often want both.”

The Writing Process and Book Structure

42:00 to 45:00

Learn about Annie's writing process and how she structured her book.

“And so I would go in a completely silent room and write.”

Looking Forward: Tours and Collaborations

45:00 to 47:14

Discover Annie's excitement for her upcoming book tour and brand collaborations.

“Now that the renovation is finished, now that the book is almost out, I will be the annoying person who says, what are you working on now?”

Product Details: The Target Collection

47:14 to 50:00

Get insights into the specific products in Annie's Target collection.

“You know, I always tell my kids like, move towards the people that make you feel warm and stay away from the people that make you feel cold.”

Advice on Career Transitions

50:00 to 52:50

Hear Annie's insights on making career changes and believing in oneself.

“You can find something that's an amazing thing at any price point.”

Reflecting on Past Decisions

52:50 to 53:42

Annie shares reflections on past career decisions and lessons learned.

“My last question is my favorite question, which is, if you could get into a time machine and go back in time and give younger Annie some advice at any point in your career, what would you say?”
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Transcript

Automatic transcript. May contain errors.

0:05Hi, everyone. I'm Hilary Kerr, the co-founder and chief content officer of Who, What, Where, and this is Second Life, a podcast spotlighting women who have truly inspiring careers. We're talking about their work journeys, what they've learned from the process of setting aside their doubts or fears, and what happens when they embark on their second life. Today on the show, I'm joined by the creator of This Oak House, Annie Myers Shire. This Oak House is the name of a beloved Instagram account Annie created to share her home renovation process, and it's also the title of her debut book. Before embarking on her renovation journey and diving into all things interior design, Annie started her career in the fashion industry, first at InStyle Magazine and later at Harper's Bazaar.

0:59She then transitioned into the tech space as the fashion director of MySpace, but she ultimately returned to the traditional fashion industry, working in PR at Chanel. After working at Chanel for six years, Annie left to focus her energy on being a mom full-time. However, when her mother-in-law decided to move out of her Los Angeles home, Annie jumped at the chance to take on the house and thus a huge renovation project. She decided to document her journey on Instagram for her friends to stay updated, and what began as a small, casual Instagram account blossomed into a community of over 200 ,000 followers.

1:42And today, Annie has taken her renovation journey and documented it in a beautiful book called This Oak House, which is out tomorrow. Annie is an incredible delight, and I can't wait for you to hear her story. Now, on Second Life, it's Annie Myers Shire. We like to start this podcast at the beginning. So, what did you study in school, and much more importantly, what did you think you were going to be when you grew up? So when I was in school, I was actually a double major in public communications and women's studies. And my last semester of school, I took a class in magazines. I mean, maybe by that point I already was grown up.

2:28I'm not sure. But at that point, I really thought this is the world I want to go to. I want to try the magazine world. And I had spent a summer in New York before I graduated. And so like I kind of had my eyes set on the big city and trying my hand at that. What was your initial post-grad job hunt like? So it was a very short job hunt. My parents knew the fashion director at InStyle Magazine, who was Hal Rubenstein. He had been a waiter of theirs when they were in New York City making Baby Boom. He was like an adorable, smart waiter. And they kind of just asked him a million questions and they became friends and they stayed in contact all these years later.

3:06And so I had an interview with him. I remember going to his office, sitting on his sofa. We started chatting and I would say 20 minutes into the meeting, he was like, hold on. And he went into sort of the bay where everyone works. And he said, who needs an assistant? And I left there with a job. I was Toby Tucker's assistant. It was really a fun time. And I was in my heels and my pencil skirt sitting at that desk, just like so happy to be there and working such long hours and not complaining at all. So what sorts of things were you working on at that time? What were your responsibilities? So when I worked for Hal, it was a lot of coordinating sort of his life.

3:44I was very much his assistant and booking cars and making sure his reservations were triple confirmed, making sure we had everything ready for fashion week, which when you work in fashion feels like every other week is a fashion week. I mean, It's insane. And the travel and, you know, coordinating his hotel and all the sort of specifics that go into it. So it was like very traditional assistant work, but all with sort of fun, meaty things that I enjoy doing and calling, you know, the George Sank and getting them on the phone and making sure he had what he needed when he got to his room. And he was always nice to me, always, always nice to me.

4:16Ask me my opinion, come in my office. What do you think of this? Like he was inclusive of me. And then when I worked for Toby, it was really fun because she was a young market editor. And so we were calling in, you know, all the sort of brands that we were always thinking about and looking at and all the fun sort of denim. And she did swim. We weren't really working on the sort of well stories, which are those big fashion spreads. It was such for the market story. So the brands that I was familiar with, and she was also inclusive of me and also asking me my opinion. And it was where I started to really learn about if something looks good to the naked eye versus on the page and how do you make something on the page look good and the editing process and all of that.

4:57And I loved working in style. And I also at some point then became sort of the intern coordinator. So I had a ton of interns who worked for me and I really enjoyed that. And some of my interns now have gone on to have big, massive jobs. So it was fun corralling those girls. At what point did you start to have ambition to do something additional? And how did you start thinking about what that would mean for your career ahead? I looked around at the landscape when I was at InStyle and I was like, I want to be an editor. That is definitely where I want to go. Nobody was leaving. Nobody was moving out of those jobs.

5:32So I knew that I didn't have the opportunity there to become an editor. And I had a girlfriend who was an assistant at Harper's Bazaar and she let me know that they were looking for an associate accessories editor. And I went in and I interviewed And that jump from assistant to editor feels like the impossible jump. You know, you really have to have someone who believes in you and see something in you. And I went through many rounds of interviews. Christina O 'Neill interviewed me. Glenda Bailey interviewed me. I mean, it was a lot of interviews. I landed that job at Harper's Bazaar as the associate accessories editor.

6:07I was hired by a really wonderful woman who had been at Vogue named Danya Unterhalter. and very quickly after getting this job at Harper's Bissart, she went back to vote. She was gone. I mean, in my mind, it's a matter of days. I'm sure it was more like a couple of weeks or months, but I was all of a sudden sort of thrust into something that I definitely was not a hundred percent ready for, but fake it till you make it. I figured it out. So how much did you know about accessories when you walked into that role? Well, I had been the assistant in the market department in style for long enough. And also this was a real interest of mine.

6:43So I knew enough. Also, when you work in these positions, who your advertisers are, it's very meaningful. And once you get that list of advertisers, and then you have the list of people that you know you want to work with, I think the high jewelry stuff took a minute and figuring out sort of who's important there, I knew a little bit less about. But pretty quickly, I assimilated. Yeah. There's a little bit of a cheat sheet. Yeah. It was very different. InStyle had so many also different editors and sections of the magazine, right? What we did at Bazaar was very sort of singular. It was just straight up fashion.

7:18But there was an energy at Bazaar, I felt, like we were sort of the younger sister trying to kind of keep up. So there was this culture of what's everybody else doing? And we have to get that look and it has to be this. And we would, you know, send an intern on an airplane to go pick up a pair of shoes that was ending in the Cayman Islands on a shoot for somebody else. I mean, it was like intense. I didn't feel the intensity when I was at InStyle. It was all a little bit easier, but we also didn't have to have the most important look from the show on our cover. You know, it wasn't like that. So when you think about some of the foundational skills that you were learning in these early magazine days and the early aughts, like what are some of the things that really stick with you?

8:03I think really like work habit, you know, how you're really always on. I mean, I was called on my cell phone weekends, nights, it didn't matter. And I never felt that that was out of bounds. It felt like I should be working late on a Friday night. Like my dinner plans didn't matter. And I wasn't mad about it. I wanted to be there for a long time. I also learned a lot about why something will look good on the page. What makes something look good? sort of going back to that Coco Chanel quote, like always take one thing off, you know, before you leave the house and why something is important, how colors work together.

8:37Also really about like craftsmanship, the details of things. When we would go to Reese's at appointments, you would see something on the runway and then you'd get to touch it and see it and see how it's made. And also I think there was just like a love of design that was building within me at that time. The flip side of that was the culture there and the women who I was working with, I should probably not even say this, but they weren't living the life I wanted to live in my next phase. When I saw as an assistant that I wanted to be an editor, and then when I was an editor, I did not like where I was headed.

9:12It didn't feel like the life I wanted. I remember vividly being in the Prada show in Milan. I was sitting there and wishing I was in my room ordering room service. And I remember thinking like people would kill to be in this seat right now. And if I don't want to be here and I want to be in my bathrobe, what does that say? And that felt nerve wracking because I was starting to sort of establish myself and make a name. And I was like, I don't know that this is where I want to go. Yeah. It's like, what am I building for? I knew in order to be successful, like these amazing women I was working with, there were sacrifices I wasn't sure I was going to want to make.

9:46And that was a tricky time. At the same time, world was shifting. You were out there building who, what, where? I was like, huh, it seems like magazines might be tapering off. So there was like a culture shift happening sort of simultaneously. And it just felt like things were changing. And so it felt like to me, this might be a good time for me to think about something else. So on that note, you made a pivot moving from Bazaar to working at MySpace. I did. As their fashion director. I have so many questions about this. Let's start with just the basics. Like, how did you find out about that job?

10:22You teed us up nicely about what was going on environmentally and feeling the zeitgeist shift. But like, what made you think, oh, this might be something I want to explore? So the truth is I fell in love with somebody who was moving to LA and I was from LA. And so I thought, well, let's go back home. So we moved back to LA together. And as I'm sure you could imagine, he then promptly broke up with me and I was stuck in Los Angeles. And I was like, huh. I was the youngest editor at Harper's Bazaar. I had a great apartment. I've left it all behind. I'm living at my parents, not where I wanted things to go.

10:57But I had a friend who was working at MySpace at the time and she told me they were looking for a fashion director. So I interviewed for the job at MySpace, which at the time was a little unclear what this was going to be. It felt a little bit like maybe I could make it my own. And when I was hired there, it was being run by the original two, Tom and Chris. Wow. Tom was there walking around, looking just like that profile picture. And Crystal Wolf was there. And unfortunately, very similarly to what happened at InStyle, two new guys came in very quickly, Mike and Jason, to run MySpace. And MySpace was really at an inflection point.

11:38It didn't know what it was going to be. There were tons of all hands meetings, tons of layoffs, kind of like right as I got there. Fun. Yeah. And so there was this one thing that we worked on a lot and it was called The Fit. It was a video series where we would go shopping with a celebrity. And it was everyone from like Audrina to Lady Gaga. Amazing. Yeah, it was amazing. Lady Gaga and I went shopping together and we would film them shopping and then we would put it up on the platform. And MySpace was struggling when I was there, unfortunately. And so my time there was not long and we ended up like losing the lease of the building we were.

12:16I mean, things just kind of folded quickly. And then of course, the person who hired me was let go and then I was on my own again. And it was a tricky time. That's such an interesting thing that you've had to navigate a couple of times is like to be hired and then have your boss or the person more senior to you immediately leave the company. Which is awkward for a few reasons. One, because you felt like the person who believed in you has left. Yeah. You feel like you don't have cover. You don't have cover. But honestly, the place was starting to crumble a little bit when we got there. So I was not there very long, but I enjoyed it.

12:53So talk to me about your next move. How did you make the transition to working for Chanel? So I was at MySpace when the Chanel buzz hit me. And it was great because I realized that my time at Myspace was probably coming to an end, considering the whole place was a little bit coming to an end. Chanel was deciding to open their first West Coast office. Because I had been the accessories editor of Bazaar for so long, I had a major relationship with the PR girls there, most of whom are still there to this day. And they had said to me, do you know anyone who would be great for this job? And then through the series of conversations, I started to interview for it.

13:31And that was another difficult interview process. And I met with them many times. I flew to New York multiple times. It was really exciting. And it was the first time in my life that I was desperate for the job for a lot of reasons. I was going to be the only person out here. So I knew I could have some anonymity. I felt that if I was going to make the leap to PR, which when you're an editor, you don't really ever imagine doing that. You're sort of on the other side of things. But I knew that I was always going to feel so excited to be able to talk about this collection, that whatever was being drummed up in Paris.

14:07I had a very long interview process. I finally got it. And in the six years that I was at Chanel, I got married and had two kids, all while being there. So my life was changing in a major way. But for many years, I loved it. And I still love the people that I worked with. Obviously, you don't have a formal PR background, but I actually think there's a lot to be said for an editor working in a PR role because you understand stories and you understand storytelling and you understand brands sometimes want to communicate in one way that is not necessarily the most effective for press. So you really understand that.

14:44But the West Coast PR, that's a little bit of a different job. It was. You had to wear many hats. So there was the editorial hat in that there were shoots happening in LA, but I was not the one really coordinating that. That all happened through the New York office. So yes, things would come our way and we'd have to get shoes somewhere, but I was not the one really coordinating anything from an editorial perspective. I worked mostly on celebrity dressing and LA events. Those were sort of my big two lanes and celebrity dressing was 75 % of it, which was interesting for sure. And so I was really working with the stylist in the fittings and with Chanel, you know, I had to be the representative of my Paris office who wasn't there.

15:29And they were also asleep during my fitting because it's the middle of the night. So it was a lot of making sure that I was representing the brand correctly and how they wanted the pieces to be worn and working directly with the stylist and making sure that everything gets to where it needs to be and being at the fittings. And so that was a big, big part of it. And, you know, working with the stylist, events, You know, all the red carpet premieres, but then the big award shows, of course. And then we had many LA events throughout the year. We had a big Chanel Oscar dinner. There was always at least two or three other events here.

16:05And so coordinating those being sort of the on the ground person. And then, you know, always having to sort of manage or coordinate what shoots were happening in LA, which is always something. And making sure that, you know, the look gets where it needs to be and then back to where it needs to be. And, you know, they say PR is ER. So there's always something. So I can imagine that the events piece of it would probably come naturally to some extent because of like the level of background of coordination and all of the moving parts that go along with it. for the celebrity PR side of it and the celebrity fittings and the VIP piece of it, were you having to pitch like, I think we should dress this person?

16:42Because to your point, everything has to run through Paris, but yet part of your responsibility is to know who the next new right person is and to be on the front lines of celebrity, which can really make or break a brand in so many ways. It's such an important part of the overall strategy. So how did you figure that piece of it? Well, you know, the interesting thing about Chanel also is it's not obvious, right? Nothing was obvious with them. The people that they choose to work with, you know, when I was there, we worked a lot with Kristen Stewart, right? And she's so gorgeous and so unique, but an interesting choice for Chanel, right?

17:17And so me being the eyes and ears here, it was a lot of keeping up with who's being cast and what, who sounds like they're up and coming, having relationships with stylists where they say, I've just signed this person. They're in this new Ridley Scott movie and doing a deep dive on them. It was also the rise of influencers. And so it was these young girls and those relationships were important. But I was very much online trying to figure out who's being cast and what, pitching people to Paris. And then it was also having those relationships with stylists where they would call you and say, so-and-so's nominated for best actress and we'd love to get dressed in Chanel.

17:55And then we wouldn't typically dress more than one or two people for an award show. So is that the person Chanel wants to dress and having those conversations? And oftentimes we would make something for somebody. And so what does that look like? Or we would iterate on something and having those fittings. But Chanel always, I felt, had a really unique perspective on things. It never felt automatic. I could never send an email off and say, so-and-so wants to be dressed for the Oscars. What do you think? And I never knew. It could be like, we love her, or it could be like, that's not a fit. I never knew.

18:32It was always a unique perspective, always thoughtful, always interesting, always kept me on my toes. I never could really figure out what was going to work and not. But before our fittings, I got very clear direction on here's how we want the look to be. And it was my responsibility to make sure that I did that correctly. What was a typical day like? Typical day was some meetings. Then we would be possibly working on a show. I would go to a lot of the shows. Who do we want to invite this year? Talking about that kind of thing. Then there was always some sort of coordinating of samples. Dresses come in.

19:06Has this look arrived? Calling WorldNet a million times. Where's the thing? You know, like all of that. When I would call the messenger, I'd be like, hi. They're like, hi, how was your doctor's appointment? Like they knew everything about my life. You're in the trenches. You're in it. So it was always some sort of level of like coordinating a sample, getting it to where it needs to be, figuring out how it needs to get to wherever it needs to be. And then it was oftentimes fittings, lots of conversations with stylists. Like I would get an email, like we would love these looks, 8, 12, 16, and then I'd have to figure out where is look 16.

19:36Oh, that's with Bazaar. And then I'd be like, I can get you the shoes to look for. Is that helpful? Yeah. I was like, does that work at all? I also might people to get you the tiara? Like, no, we need the look. And then we had a beautiful salon at Chanel. And so we would do fittings on site. And that was always fun. And sending photos then back to Paris. Here's my fitting. Here's what worked. We have this and alterations. Here are the 10 looks. What do you like? And coordinating that feedback. Then there was a lot of travel with my job, a lot of travel. And Chanel looked at travel like no big deal.

20:08I did not have the same perspective. It was far to get to Paris from LA. And that became hard for me, especially with little kids. Yeah. So as you mentioned, your personal life changed quite a lot while you were working for Chanel. At what point did you start to think the travel schedule while being a mom for young kids is just not lining up? I mean, a real moment was when I was pumping in Dallas, Texas at a fashion show. And I just was like having to get back out to where I needed to be and pumping and just try to figure out how to be what I needed to be for everybody. And I remember my mother-in-law sent me a video of my kid like laughing and I was not there and I just felt like I missed it.

20:51And the travel was ramping up. And I also felt like my priorities were just shifting. I was a little bit less in love with fashion and a little bit less in love with the allure of the whole thing. I just started to feel like I needed to focus on being home more. It got really hard for me. And so I remember being at an all-hands off-site and just feeling like very similar to the feeling I had when I was at the Prado show. I don't think this is where I'm meant to be. And it's such a wild feeling when you realize I am, in many ways, in the pinnacle of my career. I am in a peak situation. there are a million girls who would kill for this job and I'm lightly to moderately miserable.

21:38You also start to feel guilty, like you're taking this from someone who would really, really love it. And that's not a great feeling either. It is not. And also the job deserved more than I was willing to give at the end. And so I had my second and I was on maternity leave and I got an email about booking travel to Cuba for a fashion show. And I looked at my husband and I was like, I'm done. I can't do this anymore. Everybody was unbelievably understanding and kind. And I still have a great relationship with them. And it was my time to leave. And I felt absolutely, completely good about my decision.

22:17What was it like to stop? Honestly, it was great. I think I felt the weight of disappointing these people I adored was lifted from me. And I was really happy. I felt like I was exactly where I should be. I started to get into working out and doing things that I was enjoying and really just being with my kids. And then shortly after the pandemic hit, and then I was like, huh, I'm really with my kids. Yes. Can't get away from them. And around the same time, your mother-in-law decided to move from her home in Los Angeles to Montecito. And this LA home of hers was of particular interest to you. So tell me the story of deciding that you wanted to take on this home and turn it into a renovation and personal project.

23:08So my mother-in-law, Marcia, had had a weekend house in Montecito. And when the pandemic hit, we were like, you got to go. Get out of town. Go to Montecito. It just felt like the right thing. And after probably three or four months, she was so happy there. And so we've had this family conversation of, I think I'm going to stay in Montecito, but I don't want to sell the LA house, but I don't want to live in it. And my husband was really like, well, what do you think we should do? I was like, what do you think we should do? I know what we should do. We had been looking to move for quite a while.

23:38Our kids go to school sort of far away from where we live. And we wanted to get closer to that side of town. We also wanted to have more space. and that house hunt was just coming up empty. And so when this opportunity happened, I had always loved the house that my mother-in-law lived in. And luckily my husband did not grow up in this house. So he wasn't emotionally attached to it. So we had a lot of family discussions, like, does this make sense? Is this what we want? And my mother-in-law, Marcia's perspective was, it's going to be your house one day anyway. I would love to see you guys live in it.

24:13It would make me so happy. and I don't want to live in it. And there became a point where we decided to take it on and she lived here alone. So the layout was perfect for a single woman, but it did not work for a family of four. So we had to do some like very basic reconfiguration. And once you sort of do one thing, it's really just then the next thing and the next thing and the next thing and the next thing. And what I thought was going to be sort of this modest renovation became a very large renovation. I did not add one inch of square footage to this house. We just reconfigured the inside. From my first email to the architect to move-in day was four years.

24:51Whoa. Yeah. That's wild. Long time. Talk to me a little bit about what that process was like. And also, what was your relationship to interiors? Well, it was interesting. So I moved into the house I lived in before this current house, four weeks before I gave birth to my first son. So I was like insanely pregnant. My mom and my mother-in-law moved us in. Wherever they put things, I basically left them. I fell right into motherhood and having a baby and I just never really spent the time. I don't know your mother-in-law, but your mom has some chops to put it mildly. Wherever she put it was good for me.

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25:31Totally. Like the legendary Nancy Meyers. Yeah. She was like, I have a coffee table in my garage. I was like, great, I'll take it. I mean, I was very happy to take everything. Like set dress me, I'm done. Totally. And I grew up in a way where interiors were very considered. I've always loved design just as a whole. It's always been something that's been interesting to me. So I would say I had a relationship where I was an appreciator of interiors. I cared a lot about my last house, but I got to a point in our last home, and I think a lot of people get to this point where we knew we were going to move.

26:08So then you just kind of let it go. You just kind of let it go. And also it was like the pandemic and like, we didn't eat on our sofas, but then we ended up having to because we couldn't leave the house. And so you sort of just let things go. And I was very excited about this new project. I didn't know when I began the project that I would fall in love with it. I didn't know when I began the project that I would find a new career and life in it. But I knew like a pilot light had been switched on and it was just brewing. And then through all that happened, that pilot light really took off. I'll say.

26:46Okay. So I want to talk about your decision to document the process on Instagram for your friends, right? Yeah. It just started as like an easy place to say like, this is what's happening. And then you became, as you call it, and I love this, an accidental influencer. I did. Talk to me about starting the account, This Oak House, and how it has blossomed into what it is today with a community of over 200 ,000 followers. So I knew I was about to start something interesting in my own personal life with this house and this renovation. I thought maybe my old coworkers in New York would want to follow along and help me pick a paint color.

27:26I definitely didn't think that much about it. I started the account one day when I was in the bathtub at my old house. I was just like, hey. I posted on my personal account. I said, I might post, I might not. Follow along. Could be fun. But what I really found as I entered into this deep dive of this house was in fashion and in everything I knew, there was so much transparency. Everybody tells you everything about what they're wearing, who makes their glasses, what nail polish color they have on. But in interiors, that just did not exist. There was gatekeeping and trade accounts and all kinds of, it felt like ironclad doors.

28:05And I was DMing people and saying, I really love that mirror. Where did it come from? And nobody responded. And so all of that was happening at the same time as I was starting to deep dive into this. And I know my own nature, which is to deep dive and to learn a lot about things. And when you're doing a house, it's very expensive. And these choices you make could last much longer than you will even last in the house. And so I wanted to make good choices. And I thought, well, this could be fun for people to see, like this sort of woman go on a journey to find the best color grouch or whatever it was that I was doing at the time.

28:43And I was posting in real time, sometimes with a spelling error. It was really very, very, very real and authentic. I was never motivated by free things or the financials of it all. I was motivated to share what I loved and my experience. And I think that's what people really appreciated. And I was sharing my sources and where I'd find something and here's the number of my tree trimmer or whatever it was. I was just trying to share my experience. And that's when really things started to shift. And I thought, oh, maybe there's something else here. This is seeming to really hit with people. And there was definitely a shift for me personally.

29:26I was starting to just realize that maybe there was a business brewing inside this. So you write in your book, which we will get into in a minute, and I quote that your interest in design began in childhood and was shaped by formative experiences throughout my life and career. Home for me has always been more than just a place to live. It's a reflection of identity and creativity. Talk to me about how you forged and then also understood and shaped your design sensibilities. How were you figuring out like, this is my aesthetic. I don't like this. How does it all come together? What was your process like for that?

30:05So I think all good design should be driven by the architecture, right? I think you have to really look at what the house tells you about itself. What's the style, but also the room, right? The room layout will tell you a lot about what it needs. So from a sort of macro perspective, I worked with an amazing interior designer, Mike Mosier, who I love, who's my friend, who was an incredible partner. I had a really specific vision for the house. And the way that vision was developed was I just spent time thinking about what I wanted. And so I made elaborate Pinterest boards per room. What is the energy of the room?

30:42What do I want it to feel like? I added freely. I looked at these big, long hundreds of images of boards and there were themes that started to emerge. Well, I really like this or I really like a yellow sofa, I guess, or whatever it was that started to emerge. So market. Yeah, exactly. Exactly. I have always had a very strong instinct about things, always. And I know if I like something, I know if I don't like something. And I just brought that to this project. And I would look at fabrics and immediately something would jump out to me. Oh, I love that. Oh, I really love that. Or I don't love that.

31:17Or that feels dark. Whatever it was, things would start to speak to me. And then Mike would teach me, okay, well, that print that you love has a lot of blue and yellow in it. So let's find some blue and yellow fabrics to pull for the rest of the room. And he and I would come up with a scheme and then I would sit on it and think about it. Then I'd go show it to my mom and she would give an opinion. And so we worked together to figure out how something that I loved, how can we make that into a space or into a room? And for me, my process is very much like once I know I love it, I'm done. I never think about it again.

31:49But to get to that point sometimes takes a while. I like to see all the options. Do you have any other yellows? Do you have a lighter yellow? I want to see it all. And then I will feel really good about moving forward. So I listened to my inner instinct. I went with my gut on most things. And I also waited until we had all the elements of the room before we would sign off. I did not do it in piecemeal. It was not like that. It was like we had the sofa, we had the rug, we had the lamps, we had every piece. And then we would sign off and move forward. We were able to do it that way because we didn't live here.

32:25So we could look at the room holistically. And I also think you just go back to your experiences and things that you learned and they're all sort of living inside of you. And so you pull on those things. We made a couple mistakes here and there, but I had a good checks and balances, right? It was me. It was Mike. It was my mom. I workshopped things until we felt really good about it. And then we just held our breath. So talk to me about the renovation, like the layout piece of it, because to your point, you didn't add square footage, but you completely reimagined how things work together. How was that piece for you?

32:59So because this was a family home and I had spent so much time here, I knew what worked and what didn't work. So from a very simple, basic place, there are three bedrooms in the second floor of this house. You were only able to access two of them from the staircase, meaning the third one, you had to go through another bedroom. So a logistic standpoint, if one kid wanted to see the other kid, they'd have to come through my bedroom. That was never going to work. So immediately we were like, how do we access that room? And our architect said, we need a hallway. We just have to build a hallway that gets all the rooms connected.

33:33We sort of took what the problem was and had to come up with the solution. When we created that upstairs hallway that connected all the rooms, what we no longer needed was the back staircase of the house because now we could access everything from the main staircase. So when you remove that staircase, then we had all this new space and what are we going to do with that? And we really just looked at the house from a perspective of here are the rooms we want to have, which are the obvious and then some not so obvious. And how do we want the flow to feel? And we just simplified things. And I didn't realize that by doing what we were going to do, we had to take the entire house down to the studs.

34:11I mean, the entire thing. But one thing leads to the next. And I knew another thing that I wanted in addition to the kids' rooms and our room all being accessible to one another was I cook a lot and I wanted my family to be nearby. So we really wanted to create a larger kitchen and family room. And by removing that staircase, we were able to do that. And so I think the best thing to do is know what you want to happen and then don't offer the solution. Hire people smarter than you whose job it is to figure it out. And so let somebody else who knows this better than you figure it out. Interesting.

34:46What were some of the surprising easy points about this project? And what were some of the complexities? The complexities came from the things that you don't foresee in a remodel, right? Where you're working and adding millwork to a room, but the room's not level. And so now your Wayne Scott's going to be off. And how do you fix that? It's the things that you don't know until you get into a project that you don't have when you do a new build. So finding out that the floor is not level or finding out that, oh, under this room is concrete and we can't get an HVAC system in there or whatever it is, those sort of things that you don't know until you're in.

35:21That was the hardest part. I am always a problem solver. I don't like to sit in the mess. I want to get to the solution very quickly. So that was the stuff that was hard. And when you're doing a remodel, there's a lot of that. The stuff that came easy, I don't know if anything came easy, but I found a lot of joy in the design process, the seeing our ideas come to life, you know, when we'd work on our cabinetry and then it would arrive or the day that the lighting went in, like all the things that you work so hard in. And there are these sort of like pipe dreams and things that you think about, but then they arrive and they come and they're the right size and they look great.

36:00And like, that is the joy. That is so fun to see sort of all the hard work come to fruition or all the paint color choices. And then the whole room gets painted. You're like, it's even better than I thought. And then in some cases, this is terrible. We need to repaint. You know, it goes both ways. So I also want to talk about your gorgeous book that I am so lucky to have. I'm so happy you have it. I thought it would be good because I know you. And I thought it would be good because I have been following the story from the beginning. I didn't realize it would be this good. Oh, that's so nice, Hillary.

36:34Thank you. It's inspiring and there's so much utility in it. It's unbelievable. It's coming out on September 15th. Talk to me about the idea and the process of taking a renovation and an Instagram account and turning it into the most incredible book. Thank you. So a lot of people had been asking me like, what are you going to do next? What are you going to do when the house is done? And I didn't have that answer. And anytime someone asked me, it basically freaked me out. And I got an email from a publisher, from an editor and said, are you free for Zoom? And as soon as the email landed in my inbox, I thought to myself, oh, this is the next thing.

37:14This is it. Got on a Zoom. I liked her right away. She was like, I think there's a book in here. I hung up the Zoom and I thought to myself, this is how I'm going to put the punctuation mark on this chapter. I just felt like this is the right next thing. And she said, come back to me with a book proposal. And she gave me some examples of book proposals and it felt really daunting, really daunting. And I sat with it and I sat with it. And then an idea hit me of how to format the book. And the second that that hit me on how to format it, the whole thing flew out of me. It was a legitimate light bulb moment in my life.

37:50And the format of the book, which you know, is part one is called house and part two is called home. And what I really, really wanted was I wanted my book to feel like the extension of my Instagram, which I think is part utility and helpful and tips and tricks and all those little sort of nitty gritty things that I learned, the what to expect when you're expecting renovation guide. And then the second part, I wanted to be like a traditional beautiful coffee table book with all the photos that you would see in a traditional editorial spread. But then I had this real desire that I wanted to make sure it was a book for anybody, not just someone doing a renovation.

38:27And so I was very insistent on this part that there will be things that anybody could use. There's a book that I love that I dog ear and I go back to and I look at it and I reference a thing in it. And I wanted my book to be that, that thing that people reference. So there are things in part two, at the end of every chapter, there's a takeaway for anybody. It's my family's hot fudge recipe. It's a tablescape. It's how to style a bookshelf. So it's totally independent of renovation. It's just something that I think could be useful for anyone who has a home or loves home. And furthermore, I wanted the voice of the book to feel very much me.

39:04And so when they first liked you, want someone to help you write it? I said, I think let me try. I wanted it to be voicey and to feel like me. And anyone who's been following me, I think for a long time will read through it and think, this is her, this is it. And it hopefully feels like the fuller, more expanded version of everything that has lived on my Instagram. And then I've taken all these people along on this journey and they haven't seen my house. And so now they get to see every nook and cranny, which by the way, when I signed on to do the book, we didn't live here. And so the idea that I was going to literally photograph every inch of it and I didn't know what it was going to look like, there was a big pressure I felt.

39:40I wanted to deliver. and I worked with an incredible team on my book and my photographer and the stylist. I think that we delivered something I hope my followers will feel really happy about. A digital experience is different from a print experience and I often want both. Like I want the luxury of seeing the big, beautiful image on a page. Talk to me about the shoot. What was it like shooting the house? Because I also was like getting glimpses of that from social. The shoot of the house was hard. It was eight straight days, basically. I think we took a day off between day five and day six. I moved my family out of the house.

40:18I moved them into my mom's. I mean, I just did because our rooms were set. We were ready. I couldn't then have them jumping on the sofa. And so having the house really set and ready for my photographer and stylist was great. I worked with Roger Davies and Anita Sarcetti. And I met with a lot of photographers and a lot of stylists. As soon as I met with both of them, I knew I had the dream team. What they both were able to do for my house was make it the best version of itself rather than make it something it's not. There's a lot of interior photography these days that are very moody and very brown and very kind of the sepia feeling around everything.

40:58And as beautiful as that is, that's not what my house is. And I needed to work with someone who's going to see what it was and just make it its best version. And Anita, our stylist, who's such a pro and she has been around for such a long time, She didn't want to remove the things that made it uniquely mine. She kept those and she was able to add this little bit of magic to every image. And Roger's an amazing photographer. So it was exhausting. It was exciting. It also put an enormous pressure on me to get art up on the wall and get everything ready for them because we were shooting. And sometimes a house takes a while to come together and I didn't have that luxury.

41:38We had to get the shot. And so it was a bit of a pressure cooker for me for a little while. How long did the writing process take? Writing process was about eight months. I wrote the first part in real time. So I wrote all of that while we were still in construction. And then I couldn't write part two till we lived here because it was about the home itself and how we're using the spaces. So that was nice. I kind of delivered part one and then I delivered part two. But it took about eight months. I really enjoyed the writing process. I love being alone. It's my happy place. And so I would go in a completely silent room and write.

42:12And I was like, this is good. I also grew up around writers. So I had a bit of a sense of how serious they took that process and what that looked like. And I really tried to give myself that. I worked like it was a job. I went in the morning and I sat and I wrote and I had lunch and I'd come back and I'd have goals for myself. I want to try to get to this by the end of this. And for me, coming up with the format of the book allowed me to write easily. If I didn't have the format, I'm not sure I could have done any of it. So as you spoke to, like you have these amazing additional pieces of information as well.

42:46It's so jammed with tips and tricks too. And I mean that in the best possible way. How did you decide what extra details to include and what didn't make it? So I wanted to include all of the things I wish I had known during my renovation. So that's all in part one, sort of all the things I learned. I worked with a paint consultant, the tips he taught me, or the things I learned from my millwork or all the tips and tricks. I knew that I wanted to put that in part one. And then when I thought about part two, I just wanted to make sure that there were things for anybody who's loved following me or loves home or wants to figure out how to make their house feel more like their home, how to make it feel more like them.

43:25And so I really thought about in each room, what is something that's a takeaway for anybody? What would I want to know from somebody else. And that's how I approach a lot of things that I do. I remember when I was working on my gift guide last year, I didn't want to see one more collage with like, you know, stocking stuffers under 30. And so somebody said to me, what would you like in a gift guide? I said, I want to know what Lauren Santo Domingo's giving. Like, that's what I want. And so they said, do that. And I DM'd her. I said, hi, Lauren, what are you giving this year? And then I ended up DMing, you know, people that I admired and figured out what they were giving for the holidays.

43:59So I often put myself in the end user's seat. What do they want? What will they want from this? And then I try to work backwards into that. And that's how I tried to come up with all the extra stuff. And then I knew that sort of the ethos of me was that I give all my sources. So that had to be in there. And one of the things that I was so excited about was that we had a scheme and we had fabrics and they lived in a pouch and that pouch became a full room of my house. And how can I show that to the reader. So we did these wonderful flat lays with all the fabrics, very much an editorial thing that I learned when I was at the magazine with the camera above and how are we going to lay it out?

44:40And then you see that flat lay and you flip the page and you see it in a room. And so I think it gives people an understanding of how a floral fabric becomes a pillow. You know, it's not the whole thing. And how does that all work together? And so building on my experiences, they were all like little building blocks that added into this bigger story. Well, I'm so impressed. Like the execution is just amazing. Now that the renovation is finished, now that the book is almost out, I will be the annoying person who says, what are you working on now? Because I know we have some things to discuss, but I'm curious about as an accidental influencer turned very purposeful author and subject matter expert.

45:24What are you excited about as you look forward? So I am excited to go on tour, which is going to be really fun. I'm going all around the country, which I'm very excited about. I'm excited to meet people and talk about the book. I'm excited for the book to be out. I also am really excited about my brand collaborations that I have coming up. And so I've worked really hard to think about what are the things that are missing in my life that I wish were out there and more accessible. So I have a collection with Target that I suppose by the time someone's listening to this will be out, which is unbelievable.

46:00I am not a vision board girl, but it was a vision board moment for me, Target, and having my collection in Target. And they just sent me what the end cap is going to look like. I mean, you know, Hilary, you've had your things in Target. It feels surreal. But more than anything, the pieces that we designed feel exactly as I wanted them to feel, which is such a big accomplishment. And we shot them in my house, which was something I was really insistent upon because I think that in order to really understand how to live with a product, you have to see it in someone's home. You have to understand how something can work.

46:36and it was an amazing process. I loved working with Target. I'm so proud of the collection. As we're recording this, it's not out yet. And I almost feel, and this is great, like I don't want to post online because I feel like I'm going to spill the secret. Like I am bubbling to tell people. I am ready to post. I think we're posting a teaser at the end of the week, but I am so excited. I am like that meme of Elsa who like is jittering, you know, I can't wait for people to You know, like that's how I feel. I'm very excited for it to get out there. And then looking further, I have other brand collaborations coming and working with brands that really make sense for me and are authentic.

47:14You know, I always tell my kids like, move towards the people that make you feel warm and stay away from the people that make you feel cold. And that's exactly how I'm operating. I'm moving towards the brands and the relationships that feel warm and feel good. And I'm so excited. Working on this collection has sparked a creativity inside of me that I did not think was still there. Really? Yeah. And then getting the samples and looking at them and saying, this color is not right. Let's make it like this. This needs to be taller. It's just like, I'm an editor all over again. I feel excited about it.

47:48I think the biggest thing is I'm proud. I feel very proud of what we designed and I am so excited to see it in people's homes. Can you talk a little bit about what the collection includes? So we have hurricanes, which I am obsessed with. And I knew from our first meeting, I was like, we have to have glass hurricanes, please, please, please. Because I think they're so easy to decorate with. And I think they look good on a coffee table. They look good outside. They look good on your entryway. They look good anywhere. We have some pieces that are made from natural materials, which I love. We have a gorgeous tray, a beautiful sculptural vase.

48:21Then we have two ceramic pieces, which are vases, which are just beautiful. We have the coziest, most scrumptious blanket that is like absolutely delicious. My sister was here yesterday and I had an extra one. She was like, I'm taking it. And I was like, you can't. I only have two of them. She left with it. It's gone. It's in her house. And then we have a pillow in a very specific shape that I have in my house that we couldn't find when we were doing our house. It's a 12 by 20. And it is sort of the perfect layering piece with your standard 20 by 20s or your 22 by 22s. And so we custom made them and now they're readily available.

48:58And I've done them in a beautiful yellow because I love yellow and blue and brown. And then we did a really cool print pillow, which was inspired by some fabrics that I have around my house. And it's exciting. And the pieces are very usable, very easy, can layer into what you already have. And my whole philosophy behind it is just like beautiful things for everyday living. That is my guiding principle. We can have beautiful things at any price point. And that's how I live my life, by the way. That's one of the things that's magical is that you're like, this is vintage and this is custom and this is from Target.

49:33This is literally a basket from Target and you've always been like that. And that's how I dress also. I think good design has nothing to do with a price point. If I love the thing, I love the thing. You're like, this is Chanel and this is Gap. A hundred percent. Or like, I think about the Land's End sheets that you discovered and then I have used, They're now on every single bed in my family's home. I've even given them to my parents. And I would never in a trillion years have guessed that these lands and sheets would be the be-all end-all, but they're perfect. They are. And that's the great thing, right?

50:07You can find something that's an amazing thing at any price point. And so that was really what I kept reminding myself and the ethos behind what this collection could be. I cannot wait for it to get out and for people to have it. Okay, so final three questions. We asked the same ones of everyone who comes on the pod. The first one is about mistakes because everyone makes them over the course of their career, but we don't always talk about it. And I think it's really important to be upfront because I think everyone needs examples of resiliency and to understand that like a setback does not mean forever.

50:42So I'm hoping that you can tell me about a mistake that you've made at any point in your career and what you've learned from it. I think the biggest mistakes I've made was staying longer than I should have after I knew it was time to go. I ended up not giving my best self to a few of my jobs because I had checked out mentally. I should have left earlier. But it was hard and it's hard to make those big decisions. So ultimately, I'm not mad at myself about it. But I think when you know something is over, whether it's a relationship or a job, your body knows, your gut knows. I wish I had listened to that a little bit sooner.

51:21I felt that I ended up sometimes leaving a job not with my best foot forward, and that didn't feel great. So I would say that's the mistake that I made, staying too long. A lot of the folks who listen to this podcast are in their first lives, and they know they want to transition into something else. Maybe they want to go from one side of an industry to another, as you have done, or maybe they want to change industries altogether, but they're nervous. What advice would you give someone who's thinking about making a leap, but just hasn't done it quite yet. So I was listening to Ina Garten on the interview on the Daily Podcast over the weekend.

51:55And she said that she wrote her first cookbook in her 50s. And I literally like put the brakes on my car. I thought to myself, this woman wrote her first cookbook in her 50s and she's Ina Garten? Like, I couldn't believe it. I really will say like anything is possible. Anything is possible. Had I not just on a whim decided to start an Instagram account, this book would not exist. The collection target wouldn't exist. I wouldn't be on this podcast. I think what I would say, honestly, honestly, honestly, is bet on yourself. Just bet on yourself. I don't think I knew this was coming in any way, but I bet on myself and I just followed what felt good.

52:34I stayed close to what felt warm. I only went towards the thing that felt good. And by the way, during this process, a lot of opportunities came my way and they could have been really meaningful, but if it didn't feel right, I just let it go. And so I'd say bet on yourself. Literally anything is possible. Okay. My last question is my favorite question, which is, if you could get into a time machine and go back in time and give younger Annie some advice at any point in your career, what would you say? I would say, I mean, I was going to say break up with that guy that broke your heart. That's what I was going to say.

53:09I think the advice I would say is like, it's all going to be just fine. Because there were a few points where I just wasn't sure when I was working and not sure if I wanted to be an editor and I was leaving Chanel and not sure what was next. There was a lot of times where I felt like I was in a position that other people really wanted to be in, but it wasn't feeling good to me. And having sort of the inner knowing that it's all going to be okay, I wish I would be able to tell myself that. Sometimes people say things like, you left Chanel? I'd be like, I did. I'm happy I did. So it's all going to be okay.

53:42Well, Annie, I can very much agree. It's all going to be okay. Thank you. Thank you so much for taking the time. Hillary, thank you so much for having me. I am such a fan of your podcast. You're so excellent at this. And I've listened to you for so long. And you're always just smart and interesting. And I'm having a second life. And so I'm very grateful to be on your podcast. I really mean it.

54:11That was the author and creator of This Oak House, Annie Myers Shire. For more inspiring interviews with women like Annie, head on over to secondlifepod.com, where we have so many more for you to peruse. If you like today's show, please subscribe on Apple Podcasts or Spotify or wherever you get your podcasts. and don't forget to rate and review us. We love seeing you spread the word on social and now you can tag us in your posts. We are at Second Life Pod on Instagram, Twitter, and Facebook. We always want to know who you're interested in hearing from on the show. So send in your requests to hello at secondlifepod.com or you can DM us on Instagram.

54:53I'm at Hilary Kerr. The show is at Second Life Pod. Our DMs are always open. I'm Hilary Kerr and you've been listening to Second Life This episode was produced by Hilary Kerr, Summer Hammeris, and Natalie Thurman Our production assistant is Grace Ingram Our audio engineers are at Treehouse Recording in Los Angeles, California And our music is by Jonathan Leahy

From the publisher

Annie Meyers-Shyer is the creator of the social media phenomenon and book This Oak House. However, before embarking on a renovation project that would turn her into an "accidental influencer," Meyers-Shyer started her career in the fashion industry. She first worked for InStyle magazine and then Harper's Bazaar. For a period, she transitioned into the tech space as the fashion director of MySpace, but she soon returned to the traditional fashion space, working in PR at Chanel. After working at Chanel for six years, she left to focus on being a mom full-time. When her mother-in-law moved out of her Los Angeles home, Meyers-Shyer decided she wanted to take on the home and, thus, a renovation project. She documented her journey on Instagram for her friends to stay updated, and what began as a small, casual account blossomed into a community of over 200,000 followers. Today, she has taken her renovation journey and documented it in a book called This Oak House, which releases tomorrow.

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