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The following podcast is a Dear Media production. This week, I'm joined by the journalist and podcaster who inspires us to question everything, Danielle Robaix. Danielle has built her entire career by betting on herself, asking the right questions and creating her own lane from scratch. She breaks down exactly how curiosity, asking the right questions, and shooting your shot are the keys to getting exactly what you want want. Danielle, welcome to. She's so lucky.
B
First of all, I'm so excited to be here. I'm a huge fan and listener, so it's kind of surreal for me to be on the set with you. Thank you.
A
I have actually wanted to have you on the show for so long. It was just a matter of us being in the same place at the same time. So I feel like this episode was meant to be.
B
You and I share a lot of sensibilities, so I'm excited to get into the conversation so we could, like, go back and forth a little bit.
A
I know, but that was a note that I had to have for myself as I was getting ready for this was like, les, you can't let her interview you because I watch you. I watch when people interview you as well. And you do that.
B
That's hilarious. I do. I usually am more comfortable asking the questions than answering, but I'm actually practicing being a good interviewee.
A
Yep.
B
So I have some things prepared. No.
A
You're ready?
B
Yeah.
A
With your notes.
B
I'm ready. Let's do it.
A
So what we've been talking about on the show all month is this idea of how to get what you want. And so far this month, I've explored that in a few different areas. I did, like, a general solo episode talking about the attitude and belief of how to get what you want. Last week, we talked about how to get what you want from more of a spiritual perspective.
B
Cool.
A
But what I really admire about you is I think you are such a good example of somebody who has really created her own lane and found ways to thrive that are so unique and fitting to you.
B
Thank you. And I'm. I think it takes one to know one, but thank you for that. Thank you for seeing it.
A
Yeah. And I think that there's so much that our community can really learn from you about that.
B
Thank you.
A
First, before we get into that.
B
Yeah.
A
I want to bring it back to a question that I used to ask on the show that I haven't asked for a while, but I actually really want to ask you, which is, can you tell me about a time that you recently felt lucky?
B
So. Yes. And can I also give you a story that I've been wanting to tell you since your rebrand. Yes. Okay. So I feel lucky when I am with my parents. I think that I hit the lottery, and there's no work that goes into that. It's a lucky sperm club and lucky egg club. My parents are totally imperfect. It's not like it was all amazing. They gave me such a good foundation and allowed me to explore the imperfections and be upset and go to therapy and bring things back to them. I feel lucky when I'm with them.
A
That's really beautiful. I feel very similarly about having my parents, who I love, who I have a really good relationship with, who are imperfect, and I'm grateful for them both in a lot of different ways. When I in particular, think about my mom and the example that she has set for me as a woman, it's something that, like, I get really emotional about because I. I think a lot of girls and women have had experiences where their mom could potentially kind of be their first bully or kind of be their. Their first hater or their biggest hater. And my heart breaks for those people.
B
Don't you hear stories like that all the time? Yeah. Also, I'm curious. I won't interview you, but I am curious. When you say example, what you mean, because I can share that. My mom and I have almost opposite personalities, really. So, like, I'm kind of more demure than she is. She is a bulldog. Like, I'll never forget one time I was working in Chicago in a newsroom doing a morning show, and they moved the desks around, and the executive producer of the show, and I really did not get along. And he gave me. I was one of the hosts of the show. He gave me the worst desks, and he gave an intern a better desk than me. And I was fuming, like, I could not let it go. And the guy I was dating at the time called me and was like, you need to channel your mother. Would Deanna get the bad desk? I was like, my mom doesn't even show up to her office, and she has the corner office. She works from home. Like, you're right. I say that. All to say that the example of going after what you want was actually set. I just go about it in a different way than she does. Do you feel that?
A
Oh, absolutely.
B
Yeah.
A
My mom and I are also opposites in the sense of I'm very introverted, I am very reserved. If I could have made it through life not speaking speaking, I would. But unfortunately, that hasn't Worked out.
B
That's crazy that this is your profession.
A
I know it makes no sense, but my mom is the most extroverted person. She makes just rised up best friends everywhere. She always says, there's no such thing as strangers. It's friends you haven't met yet. And I'm like, no, ma', am, those are strangers. I don't want to be friends with everybody.
B
But she can't live in New York. It's dangerous here for her.
A
I know. Because she will just make friends with everybody. Something that I appreciate from her example was that I have never in my 30 something years of life.
B
Yeah.
A
Ever heard her say anything bad about another woman to make herself feel better or put down another woman to make herself feel better. She is so confident and self assured in who she is and has always been. From a very young age, she had me very young. And it's never had anything to do with putting down anybody else. And that has been the best example.
B
So my mom is the same way. And I actually always say she's really the only person I know that is like Samantha from Sex and the City in that, like, she always wants hot people around her. It doesn't make her feel less. It makes her feel better. Like with all my mom's friends, she'll be like, that doesn't look good on you. She wants them to be their best selves. You know, I think that probably has a lot to do with us being for the girls also. Yeah.
A
Well, in creating spaces where we can have conversations with other women and openly.
B
Hype them up, I will say what's been interesting for me is I grew up in a house with my brother and my dad were like dominant forces, I would say. I grew up in a boy house. When I went to college, I felt really anxious and nervous to rush a sorority. I didn't feel comfortable around a large group of women. I always had good friendships, one on one, but not like in big groups. And I could have said, like, if you throw me in a fraternity house, I'm good. I could talk to 20 men. I'm comfortable. A sorority. I didn't know how to act or what to say. College actually, like, changed that whole dynamic for me, which was cool.
A
In what way?
B
I was so against being in a sorority because if you know me, it's not me. I am not cheering. I'm not doing certain activities that you're making me do. I'm not dressing up for a party that like as a cheerleading party. Yeah. But my mom said to me, you have to find out, I went to Madison, Wisconsin. It's like 35,000 people. And she was like, you have to find a way to make it small, smaller. Even if you don't like sororities or Greek life, do it for a year or two and make it a smaller world. And meeting those people helped me really understand the power of girlhood in large groups. It was very cool.
A
There's a level of depth in genuine conversation and connections with women that you just can't really get anywhere else. And that's not to say anything, you know, bad about men. People can have friendships and all sorts of things. With men, that's fine. But I feel like there is just a level of depth with women that is so important to maintain and protect.
B
Well, it's like a lived experience that you understand. You know, when we talk, even though I don't see you every day, because we're both doing podcasts in a very similar way, there's so much that's understood that doesn't have to be spoken.
A
Yes.
B
And it feels like validation.
A
Exactly.
B
And like, I think being a woman talking to another woman just feels like validation.
A
Exactly. It's like there's just things that we get.
B
Yeah. Okay. Can I tell you my lucky story? Yes.
A
I want it.
B
So I had a very sort of fraught relationship with luck my whole life because I do believe in something. And I feel like when you achieve anything, there is a humility that comes along with believing in luck. And there's this interview with Obama that David Letterman did where they talk about luck, and Obama has so much humility, and I always love that. And it never quite sat well with me that our whole lives are just up to chance. I understood luck in a different way when I read a book called the Third Door by Alex Benayan. And he was a USC student, quit school after his freshman year, which killed his immigrant parents. And he went on to go interview the most successful people in the world and wrote a book about it. So he interviewed Maya Angelou and Jessica Alba and Lady Gaga and Warren Buffett, and he interviewed this guy Shilou, and he grew up in a very rural town outside of Shanghai, China, and it was so poor, they had, like, deformities because of malnutrition. At 27, he was making the most money he had ever made, which was $7 a week. Fast forward 20 years. He is the president of online services at Microsoft. And she is telling Alex his story, and Alex is in disbelief. And at the end is like, how much of your life do you think was luck or chance. And she said, the best thing about luck I have ever heard, which is luck is like a bus. There will always be another bus you can hop on, but you have to be at the bus station. Meaning, like, you have to be prepared. You have to be doing the work, otherwise you'll never jump on again. Another bus will come if you miss it, but you gotta be at the bus station for sure.
A
Putting yourself in the position to. To receive it or to hop on.
B
Yes.
A
Yeah.
B
Yeah.
A
I literally wrote a substack with a similar sentiment. I'll put it in the show notes. I was talking more so about increasing your odds for luck. And this whole idea of, like, dice. Like, when we were rebranding the show, my designer and I were taking inspiration from a lot of things that signified love. And dice was one of those things where the more you roll the dice, the more likely you are to get the outcome of the numbers you want. But you got to roll. You can't roll once and then get discouraged if you don't get the numbers you want. You got to keep rolling, and the more you roll, the more likely you are to get the numbers you want due to probability. And I think so much of that is kind of related to being at the bus stop of, like, where are you putting yourself? Are you putting in the reps? What is it that you're doing to make it so that luck can find you or increase your surface area for luck?
B
What you're saying is actually so deep because there's so many statistics about women who play poker and. And how their luck in their lives increase because they're willing to bet on themselves and take risks in a different way. My dad taught me how to play at a young age, and, like, it's something we do together. And I learned so much about life just from listening to him play. We actually just. We're in Panama. We go on a trip every year together, and I was at a casino, and he. He plays by the book. So, like, all by statistics. And he was like, the only way to win is when you play by statistics. And then those moments where you could increase your luck, you press up. And it's such a good metaphor for.
A
Life being really calculated about when it's time to push it, I think is very important, because if we're not, that's when we can burn ourselves out. That's when we get discouraged. That's when we come up against just the hard parts, which the hard parts happen anyway. But being as calculated as possible about how we Manage.
B
Does yours come from intuition, would you say?
A
I feel like almost everything I do at this point comes from intuition.
B
That's so cool.
A
It feels like. What about you?
B
Same. I'm not a numbers person. I don't know that I understood it as intuition growing up, but now I do.
A
Yeah. How does your intuition sound when it's speaking to you?
B
So mine actually shows up as curiosity. I notice that's actually how it shows up for a lot of people. They just don't recognize it. And so it's almost like a. You know how Oprah talks about whispers, and people will be like, no one's whispering to me. If you haven't heard the whisper, it doesn't have to be a voice. It can be this feeling of curiosity. Like, I wonder what it would feel like to be in that room. I wonder what it would be like to start a podcast like the. The. Hmm. What does that feel like? What would that be? I think that is intuition. Yeah.
A
And following that, curiosity.
B
Yeah.
A
How do you bridge the gap between, like, hearing the whisper and then actually doing something about it?
B
I am an executor. Am the eldest daughter, a firstborn from Chicago, and I'm Jewish, so I'm neurotic. I actually think that so much creativity is wasted because people don't take the next step to execute. If it's really bubbling in me, I'm an executor. Yeah, you are too.
A
I am, but I feel like I had to train that muscle. I wasn't when I was younger at all. And I had to really learn how to believe in myself enough to execute things. And that was really a lot of what my late teens, early 20s look like. And then once something clicked in my brain. Oh, I have the power to make things happen. Then it was like all bets were off.
B
Your ability to want to learn something, to plug in, and then execute is something that truly inspires me. And I don't use that word lightly. I think people throw it around. I actually. There's not a lot of people who inspire me.
A
That's such a compliment.
B
Yeah.
A
Thank you.
B
For instance, you've actually taught me a lot about money.
A
Ooh.
B
And I went to an accountant recently based on one of your videos.
A
Really?
B
Yes. Wait, I love that, because I was doing fine, but I was like, les is so right. Why have I not gone to an accountant to, like, deep dive? And you do the deep dive. Like, when you wanted to learn how to work out, you became a freaking trainer. Yeah. I think there's different versions. I'm Actually like a better generalist. And I'm trying to do what you're doing and go deep.
A
Yeah. What are some of the things you want to go deep in? Of money.
B
Money, for sure. I actually have worked for free, like all the time, and that's something I'm ending. It's because I've always loved what I do and I want to get better and, you know, and so valuing myself has. Has been a thing and that's associated with money. The biggest goal this year, actually also somewhat inspired by you, to be honest.
A
Oh my God.
B
To like make you feel weird. I've seen you really like step into your power as a thought leader and as a personality. And I've been a questioner my whole life and I really feel like I have an expertise in connection and relationships and questioning. And so I did this thing last year that I haven't talked about or executed on yet, But I read 40 books, listened to like 30 different TED talks, a bunch of different podcasts, and wrote down all of the things about. I basically like took myself to grad school in a way. And I'm gonna start trying to become more of a thought leader in that space and try to step into my own power a little bit more.
A
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B
That's really smart. And that's how you remember stuff.
A
Yeah, it is, it is. So I'm curious maybe what some of the top learnings you took away from your year of self study were.
B
I'm so excited I could really get into it. I'll start with a question to you is do. Because you're, you are an observer and a questioner, do you ever get people saying like that was personal, like in, not in workspaces or like that's kind of nosy or that's a lot or that was deep.
A
I don't, but I think it's because I've learned how to sneak it in there. I get a lot of like, oh, I've never said that to anybody before or I've never told anyone this, which I think is a version of that where people start getting more personal than maybe they think they're going to.
B
So that's phenomenal. Most people either are really good on the surface or go for the jugular. The most common thing that I hear from people is, okay, well how do I get more curious or how do I ask questions? And what I've learned is that children, preschoolers ask 300 questions a day. There are millions of Google searches per minute. Everybody is actually very curious. And systems in our society, education, corporate, when not done well, kind of beat it out of us. And so it's really about returning to our original curiosity. And I've gotten people telling me like that was a big question or that you, you ask a lot of questions. And my new response to them based on my learnings is like, questioning is actually a responsibility. I find that questioning is how we stay awake to things. It's how we challenge power and hierarchy and systems and, and it's how we claim authorship over our lives. And when I think about all of the brilliant people that have ever changed the world for the better, they ask questions. Martin Luther King questioned unjust laws and segregation. Gloria Steinem questioned control over women's bodies. Serena Williams, I think she questioned grace and anger and rage and authority. And Rihanna questioned who gets to be beautiful. And Taylor Swift questioned, like who gets to own art? Mohammed Youssef, who's lesser known. But he asked everybody, like, why can't poor people get loans if they pay them back on time? And microcredit started and millions of people started businesses. Sarah Blakely, Nelson Mandela, Oprah, James Cameron, like Reed Hastings, all the people's names that, you know. It literally started with a question, why can't something be different? Why can't it be? And so I'm just like really emboldened to not be called nosy and to ask deeper questions and to teach people how. Because it's literally just a practice. Like everybody has it. I'm 5:1. I'm never going to be in the WNBA. Like, even if that was my dream, not going to happen. There are no, like barriers to entry to ask questions.
A
Okay, that spawns a few more questions for me, naturally. First, I'm curious from your perspective if you've always been a questioner or if it has been your journalism training that has kind of brought that out of you as more of the personal question for you. Second question is more general. What types of questions are we collectively not asking that we should be asking?
B
I have always been curious. I grew up in a very conversational family and even my grandparents were professors and, and school teachers. And so like they were always asking me questions and it gave me confidence to give answers and ask myself questions. So I think I was lucky in the sense that systems in my life emboldened that. And that's not to say if systems in your life didn't that you can't cultivate it. It is very possible and you would be surprised how quickly you can do it. I do think that being a journalist and then being a podcaster has really honed asking questions like, I know how to ask certain things. To your point about like easing in. The why questions are what get people emotional. The why is the jugular. If you ask how, that's how you have a more ping pong conversation. Like, huh, how did you get to that perspective? How did you come to that? How did you feel in high school versus like, oh, why did you do that? You know, like, that just feels more intense. The number one thing I ask myself before I enter any interview is what can this person teach me that nobody else can? And it helps me craft where I'm headed. I actually think most people are not asking any questions and that is the problem. It's so much easier to not question. It is really hard, sometimes painful. It awakens something in you. It cultivates consciousness. Once you start asking yourself questions, you start questioning other people. You Start questioning the world and you realize that just because something is not a problem for you doesn't mean it's not a problem because you start wanting to do something about it. I don't want to paint the world's issues with a big brush saying questions are the answer, but I actually think they're a big fundamental solve that is really overlooked.
A
That makes a lot of sense, especially if more people felt comfortable asking questions to understand instead of asking questions to try to get a certain answer or belittle a certain answer. But to listen for understanding would be really helpful.
B
Outrage does really well online. And so there's a lot of podcasters, I have to say, most of them are men. But there's a lot of podcasters who I think ask questions to be controversial or to stoke a flame. And that's actually, like, not helpful, necessarily. Like asking questions about pseudoscience, unless you're questioning the validity of it, is not ethical or helpful in my mind.
A
And so much of it is to elicit an emotional response, to just generate engagement, all of the things.
B
Yes.
A
And I think that's why I want people, consumers, listeners, participants, to be really savvy and discerning about what they give their attention and energy to, a thousand percent.
B
And also the fun part of it is that I think wisdom comes from wonder. And so to follow the wonder and the whisper instead of the outrage and all that stuff is like. Is what makes questioning, like, really beautiful and add to your life rather than detract.
A
Definitely. Speaking of questions, I would love to talk a bit more about some of the questions that you ask yourself. I think that you have been somebody who has done a very great job of creating this really amazing lane for yourself. Thank you. Particularly from a work perspective. And I would love for our audience to hear more of your story about how you got to where you were and the different career transitions that you've made to create this really beautiful platform and lanes for yourself that you occupy, as well as what questions you asked yourself along the way to get there.
B
Absolutely. I was in college and was a political science communications major and called my parents one day and I was like, I'm going to move to LA and I'm going to work on the Internet. And my dad almost had a heart attack. He was like, the Internet? What the fuck does that mean? Like, he had only known YouTube as, like, that person who was like, screaming, free Britney.
A
That's kind of what it was. It was early that you had that desire.
B
That is true. I love etymology and that word desire. Is so beautiful because the Latin root means from the stars. And so it actually means, it's not like about greed. It is that you feel something that is yours that is not within reach yet. It's like so beautiful. And I think it gets a bad sort of connotation for women in particular. I was gonna go into journalism. I had worked at local news stations and I, I didn't wanna move to the middle of nowhere. And I saw the Internet becoming something and I didn't know what it was, so I booked a one way ticket. I had $8,000 in my bank account, which could sound like a lot, but honestly after rent and parking tickets in Los Angeles, it goes very quickly. And oatmeal packets to eat. So moved into this garage in Santa Monica and it was free, which is why I moved there. And it was a true garage, not like a Brentwood back house. I ate oatmeal for every meal because it didn't have like a kitchen, it had a microwave. And I'd never been happier. I wanted to be in LA so badly. I wanted to be by the palm trees. I felt like it was my place. And I started sending out tapes that I had made in college and no one would reply to me. I had seen my mom growing up. She was a CPA and sold mortgages and she would send people gifts sometimes like thank you after they close their, their mortgage. And I thought, what if I send people stuff? So I took some of that $8,000 that I didn't have to budget on cookies and bamboo plants. And I did. And people started responding and they would be like, hi Danielle, like we don't have a job for you, but thank you for the cookies. And this was like not before anthrax. So it wasn't weird to receive cookies in the mail. So I would then email them and say like, no problem, if you ever have anything, let me know. And one day like three months later, a woman called me out of the blue at 2pm and said, Our host is sick. Can you be on the red carpet in three hours? And I said absolutely. And I got dressed and I thought I looked so good. And looking back, I looked so bad. Like I came from Chicago, I had no fashion sense and I was on the red carpet with these people who had full glam teams and had long legs and blonde hair. And I was like so, like so out of my element and didn't notice. Like that naivete is so beneficial when you're young. That lack of self awareness. Like I thought Giuliana rancic was my peer. You could not tell me otherwise. You know that Drake line, when your idols become your rivals? Juliana was my rival, and you could not tell me otherwise. So I did that red carpet and then sent tapes out again, like eight months later, and finally got a gig. I started working on the Internet, and I ended up working in entertainment news, Entertainment Tonight, online. It was not for me. I realized I didn't care about why someone was wearing something I didn't want to report on their life. But I still liked news and I liked entertainment. So I was very lost. I was working like 16 hours a day and quit cold turkey and was very broke. And you understand financial anxiety. It is brutal. And so it kind of like threw me into a mini depression for the first time, I would say.
A
And when was this? When you reached that point?
B
20, 15 or 16? Okay. I never thought I would get another job. I didn't have a resume. And nobody is on is on Indeed.com saying, like, we want a TV host. And so a friend of mine said, I can see you're really upset. I have a surprise for you. And, like, be in hair and makeup the next morning. I'm gonna pick you up. And I was like, okay. It's 7am so he takes me to Nate Niles, which is a diner in Beverly Hills. And I walk in and Larry King is sitting at this booth. And it was like an LA miracle, honestly. And I go and I sit down, and he asked me a million questions. I didn't have any time to ask him questions. And at the end, I was like, larry, can I come back tomorrow? I didn't get to ask you anything. And he said, well, don't you have a job? I was like, no. He goes, well, you are welcome here anytime. And it was always Larry with his childhood friends. And I think maybe the youngest person at the table was 65. And then it was me. And I started having breakfast with Larry. And he. He made me believe it was possible. I saw somebody make a life and a interesting, fruitful, financially successful life based on their curiosity. And I just was like, oh, I have that. I can do that. And he did it in a cerebral way. And I hadn't seen that because I was like, in entertainment news, which, no offense, it's like the gutter. Sorry, to my friends that are in it, you're not the gutter. For me, it was. I got a job in Chicago as a morning show host, and I was in love for the first time in la. And it was very hard to take the job. And I. A woman that I really respect who's a book agent, but I just like, knew her personally, called me and said, if he's the right guy, he'll be the right guy in two years, take this job. And I'm so glad she told me, because he was not the right guy. And that job changed the course of my life. I learned how to be live on TV two hours a day with no prompters when everything goes wrong, when you are out of your element and you have no script and you have to be quick on your feet. And I found out that my male co host was making a third more than me. And when I found that out, I it my. It was like kind of in. In line with my contract being up. And I went to my boss and I was like, I need to be paid properly. I've been. And this is my co host. And I talk about this. It's no shade to him. I was doing more work than him. I had more Instagram followers. Like, there was no reason for it. He had didn't have more experience than me. And they didn't give me a proper raise. And so I decided to quit. And we had a third co host who was a black woman, her name is Felicia. And I went to her and I said, do with this information what you will. Here's what I was making, here's what Jordan's making. And I left. Phylicia is one of my best friends to this day, and we've never talked about that. She ended up staying. She's now moved on in her career. But it was during the Me Too movement and I was pissed. I was riled up. And I looked at my mom at the time and she said, every time you've bet on yourself, it's worked out. You're unhappy, you're angry. Go, go do it again. You did it once, you can do it again. So I moved back to LA and I started working at IMDb and like the NBC station. And I was frustrated I still hadn't found my place, even though I enjoyed the people I was working with and I was learning and getting better. And I just felt like I was constantly trying to fit a square peg into a round hole. And I'd always wanted to work at E. There was this audition, it was right before COVID And so I did it. I got to the final round, they flew me to New York. I was like, this is the moment. And it wasn't the moment I didn't get the job. And I fell on this bed crying. And the Guy I was dating at the time in New York said, you can cry, cry for a day, cry for two days, and then go hire yourself. And I was like, you don't get it. I want to be on the Today Show. I want to be on Good Morning America. You can't hire yourself. And he was like, who do you love on the Today Show? And I said, the names. Who do you love on Good Morning America? I shared their names. And he goes, could they get fired tomorrow? And I was like, yeah. And he was like, so just because you admire them doesn't mean they don't have a job. I was like, you're right. And he was like, you see yourself differently than other people are perceiving you. Go make them see you the way you want. He changed my life because I. I never really had anybody who thought that way or believed in me in, like, in that. I never even considered going to create my own thing. And that's when I initially started the podcast and then eventually launched a card game and fast forward. The funniest things that ever happened were because of that, I ended up getting a job at E. And the woman hired me because she loved my podcast. I really wanted to work at hello Sunshine. And I pitched them, like, I'm a big believer that if you want something, you have to go get it. And there's always a way. There is a way. If it is for you, there is a way. And you can't just, like, sit around and hope that it comes to you. I mean, some people, like, you know, Channing Tatum was, like, found on walking on the street. Like, that's like, who does that happen to? I don't know. Not me.
A
The girls know I've been telling them to shoot their shot. If that's not a testimony for shooting your shot, I don't know what is.
B
Oh, shoot your shot in relationships. Shoot your shot with friends. Shoot your shot at work. It has never. I've never regretted. Has only paid off, like, this slight embarrassment you feel from being rejected, which I have been rejected a ton, both by men, by work, by all of it. I don't even remember that. I remember the wins. Yeah. Yeah.
A
I'm beginning to have a reframe around this, because I'm usually not a shoot your shot girl. I'm usually like a let things come to me girl.
B
Really?
A
Yeah. And over the past few months, I've had the realization that's not working for me fast enough and that I need to put myself out there more to get more of the things that I want. And so it's like a practice in real time. But what's helped me have a mindset shift around it is if I ask for what I want, it could be yes or it could be no. If I don't ask, it's absolutely a no.
B
Yeah.
A
So which is it gonna be? A possibility of a yes or not a yes at all? And that's what's been helping me get over myself.
B
It's brilliant, because to me, no means next option. Like you. If you. If I. If you give me the no faster, I know to move on to my next shot, as opposed to just wondering in my mind and ruminating at night, like, I wonder, if I did that, would they be interested? Would that happen? And I also think there's an element of planting seeds here. I've pitched people to come on my podcast, and it's a no. And. And three years later, it's a yes. And so. And you never know who you meet along the way. Like, I always say that trying is winning. You can't solve for winning. There is no way to have that sort of certainty. But if you're trying, you will have momentum and things will happen. And that's like, literally the basis of luck and getting on the bus.
A
Exactly, yeah. Increasing the odds.
B
What made you decide you were going to shoot your shot? I Was there a moment.
A
No, I mean, I just got tired of my own. And I'm tired of not having things that I feel like I deserve. I feel like I deserve more. And maybe also towards the end of the year, seeing the Tina Turner memes, where the reporter was like, do you think you deserve all this? And she goes, I think I deserve more.
B
Yeah.
A
And I was like, you know what? Me too, Tina. So I'm gonna start asking for it. And so it's only been, you know, a few weeks. It's still early in the year, so I can't say that I've, like, sort of scored any of these amazing things, but it's a form of trying and putting in the reps.
B
I'm really curious to see how you feel in December of 2026, because I think it takes time.
A
Yeah, it does. It needs to compound. And like you said, planting seeds, sometimes it takes time for things to come to fruition.
B
Yeah. Okay.
A
Let's be honest. Nothing is better than clothes that look luxe but don't come with a crazy price tag, which is why I have loved shopping at Quints for years now. Their pieces feel so effortless, but also help me feel put together. Like you could wear them to brunch or a meeting and still feel like your best self, like all winter long. I live in my quince cashmere sweaters. They're soft, they're flattering, and they're the perfect, perfect cozy thing to put on when you want to be warm but you still want to look put together. Quince is all about elevated essentials like Mongolian cashmere, 100% silk, Italian wool coats and denim that actually fits like it's supposed to. They aren't trendy throwaways. They're true wardrobe staples that are made to last and that you will want to keep. And the quality really shows. The stitching, the tailoring, the fabrics, they all hold up. It's the kind of stuff that makes your closet feel like a capsule wardrobe without being too restrictive. Plus, everything is made in ethical, trusted factories and they still price it all way below what you would pay at traditional luxury brands. So many of my everyday items are from quints, whether that is the clothes that I'm wearing, the bags that I carry, even my bedding. And I love how everything they sell is simple, high quality and built to last. So if you're ready to refresh your wardrobe without wrecking your budget, don't wait. Head to quince.com balanceless for free shipping and 365 day returns. Now available in Canada too. That's Q-U-I-N c e.com balancedless quince.com balanceless if you know me, you know I'm all about the small wins, those little decisions that add up but make you feel so much better. And one of the easiest small wins that I've added to my daily routine is R.W. knudsen juice. Whether it's a part of my slow morning routine or an afternoon pick me up, these juices just fit. They're 100% juice, have no added sugar, and they make the most basic moment feel like a wellness ritual. I've been loving the R.W. knudsen organic beet Juice in the mornings. Beets are known for supporting circulation and heart health, and it's just super refreshing. Refreshing after I do my morning workout or if I'm in the mood for something brighter, I'll grab the organic just pineapple. It's naturally sweet, it's refreshing. Makes me feel like I'm having a tropical moment even in the middle of winter. And pineapple is often associated with digestive health and immune support, which I think we all need this time of year. Plus, it just tastes like joy in a glass and of course, there's R.W. knudsen Organic just Cranberry Juice, which is my go to when I want to feel like I'm taking care of myself without overthinking it. Cranberries are known for supporting urinary tract, heart and gut health. And here's the thing. R.W. knudsen crushes only the best ingredients so that you can crush everything you do. You don't have to overhaul your life to feel good. It can start with what's in your glass. So go ahead and crush 100% of your day, morning, afternoon, evening, and all of the in between moments with 100% juice and no added sugar. Pick up a bottle of R.W. knutson at your local grocery store. On the podcast front, because I love your podcast.
B
Thank you.
A
And you also rebranded your podcast, and I would love to talk a little bit more about that because I remember when it was Pretty Smart.
B
Yeah.
A
And it has evolved to Question Everything, which matches your card game. And I know that you also have aspirations to really turn Question Everything into a broader brand. So I'd love to talk more about what made you want to make that switch and then also what your ideal future state of Question Everything is.
B
Thank you for asking that. Nobody's ever asked me about the rebrand.
A
Really?
B
Yeah. And I listened to your episode on off the Record about your rebrand, and I loved how intentional you were about every. Like, you really thought through. You asked yourself a lot of questions. Mine came actually kind of sporadically. I loved the name Pretty Smart. I always had. The original name came from this book I read called beauty sick. And Dr. Renee Engeln, the psychologist that wrote it, has this wild statistic at the top. She asked her class every year at Northwestern, would you rather be hit by a car or considered fat? And 54% of women each year would raise their hand and say, like, how fast is the car going? Or is it a truck or a Prius? And when I read that stat, my stomach sunk, because if you asked me that question in high school, I think I probably would have said the same thing. And I had since healed a lot of my food stuff. And I thought, that is so true. And also, like, no matter what a woman is in America, she has to be pretty. And the prettiest women I know have bumps and bruises and scars. So the name came from putting. Wanting to put a new spin on pretty. Like, pretty bold, pretty witty, pretty strong, pretty smart. And then I did that for, I think, three and a half years. And I interviewed the woman who started SoulCycle. And she was. She's great with product, and she was touching my card game. And she was like, someone sent this to me as a gift. I have this on my coffee table. I love it. And I was really touched by that. And she goes, what is Pretty Smart? Like, everything needs to be Question Everything. I want to wear a shirt that says question Everything. I want to. It's like a religion. It's a movement. I don't want to wear anything that says Pretty Smart. And it feels gendered. And I was so annoyed because I knew she was right.
A
That's always how it happens when it hits a nerve and you're like, damn it.
B
And it's so expensive to rebrand. It is to do it well.
A
Yeah.
B
I invested in Pretty Smart. And all my old footage said pretty Smart. I just knew she was right. And I also think that culture had shifted. I really hate when I look at brands and I'm like, that is so 2014.
A
Like, you can tell when they came up with it.
B
Yes. And I felt like, Question Everything could stand the test of time. And it really is my ethos in life. Susie Welch has this question that she asks people whose life looks good to you and then why and why not, like, take the parts you like and take the parts you don't? And I listed all these people whose life looked good and why, and I realized that everyone I really admire is somebody who's trying to change culture in their own way. And so I think Question Everything really delivers on that idea. More so than Pretty Smart. At this moment in time, I consider.
A
You, like, the queen of questions. Truly, it's hard to ask good questions, and to be a thoughtful, active participant in conversation is really hard.
B
Yeah.
A
I know something that I have struggled with, and I've kind of alluded to this a little bit on the podcast about my relationships with religion being a little bit touchy. And a lot of that is because in the religious spaces that I grew up in, questions were not encouraged.
B
Yes.
A
Was actually like, a bad thing. It was seen as a sign of disbelief and was like a means of punishment if you had any sort of question, even just to understand. And so I think a lot of people have experienced that and have a hard relationship with questions and with different things because it's something that they could be kind of punished for or seen as a bad thing. And getting more people to embrace questioning is so important now more than ever.
B
You're so brilliant for bringing that up, that I actually think that's a huge part of questioning. That nobody thinks of because we actually are a very religious country. Millennials are the least religious in six decades, but we are still a religious country. And I agree with you. That is what is taught. I have always felt like questioning actually means you have faith. You are in pursuit of the truth and answers, and it's because you care. It is because you have faith. And I know that's contradictory to some faiths, but that's my personal belief.
A
Yeah, I love that reframe, though. I love that reframe. And I think coming back to this idea of how to get what you want, we have to ask questions to get what we want. We have to ask questions of ourselves and of the world around us to even understand where we are, where we're going, where our feet are.
B
Yeah, we have to.
A
It's essential.
B
I think, like, the biggest barrier is where do you start? Right. Like, if you're not like a. A typical questioner, I always say that the best place to start is with people who are paid to talk to you. So I know that sounds funny, but truly, like, with servers at restaurants or baristas or if you're like, in Pop line at Potbelly's, they have to ask you questions. And I think part of the nervousness with questions is it's actually like an invitation. And so you could be turned down. Someone could turn down your invitation. And talking to people who are paid to talk to you takes that out of the equation. And then as you practice it more, you become more confident. It is literally a muscle the way, like, your glutes or your thighs would be building in the gym.
A
It's true. So for everybody who's scared of conversation, asking questions.
B
Yeah.
A
Go to Trader Joe's.
B
And while truly checking out, yes.
A
Ask some questions, because they'll answer.
B
And it can be super surface. Like. Like, do you like sweet or salty? I think one really good one when you meet somebody new is people introduce themselves and they love talking about, first of all, themselves. There's a ton of studies that have shown that when people talk about themselves, it triggers the same part of your brain as sugar and sexual. And so you are literally giving them a mental orgasm. Like, they love talking about themselves, so don't feel like you're probing. And then I always ask the origin of somebody's name. Like, I'm like, what? Les. That's such a. That is really a unique name. Like, I've met Leslie's. I haven't met a lot of Les's. Where does your name come from?
A
Well, do you want me to tell you? Yeah, for real. So my name is Lestrandra. That's my full name, first name.
B
See, I didn't know that.
A
I don't put it out there a lot because it's very unique. And I try to generally keep people out of my business. So, like, people don't need to know how it's spelled or any of that. But looking for her Social Security number. But where that came from is it was made up. So when my mom was pregnant with me, I was supposed to be a boy. They thought that I was a boy the whole time. But while she was pregnant, she had a dream that she was pushing a stroller that had a baby girl in it. And the baby girl's name was Lestrandra. And she thought that that sounded really interesting. And so she, like, woke up, wrote the name down, went back to sleep, and didn't think much of it. Cause they had a boy name picked out for me, which they ended up later giving to my brother. And when I was born and I was not a boy, then that's the name that they gave me.
B
See, that is such a cool story because first of all, now I have so many follow ups. Like, is your mom a person who is spiritual? Does she have, like, premonitions in her dreams or this was just a particular moment?
A
I think it was a particular moment, but she is pretty intuitive, so maybe she does and she just doesn't tell me. I don't know.
B
And do you think that you lived into your name in terms of, like, the uniqueness of it? Did you always feel different in a good way because of it?
A
I think so. I mean, what's interesting is even going by Less was something that started when I was an adult on the Internet. Again, just more of, like, the privacy. I don't know. The earlier days of the Internet, I was like, I'm scared.
B
Do you know that I also have. I did that. Yeah. Yeah. My Robay is my middle name. Mm, interesting. See?
A
Yeah, we gotta, like, you know, keep it. Keep it cute. Keep it tight. Yeah. But growing up, I always went by my first name. Teachers at school, my friends. I mean, I have some family nicknames. For the most part, everybody called me by my full name. And people who are, like, really close to me still do. Less is more of almost like a stage name, like an Internet thing.
B
Less is more.
A
It is. It is.
B
Not that I tried to get you in any way, but Less. Look at the conversation we just had because of that one question. Yeah. I feel so much closer to You. I know about your mom. I know your real name. Yeah. Think that it could take, like, it's a quick little spark and it changes the whole temperature of the room.
A
Exactly. Yeah. And it's not something that's so invasive where someone's gonna be like, oh, that's. You know, you just asked me about my third divorce. I don't know. I don't know why that was the invasive thing I just thought of, but it is something that people could easily talk about.
B
Yeah. And you're right. Like, you can ask about divorce right away. You have to. You might want to warm people up.
A
You go there.
B
Exactly.
A
Especially if it's fresh. Yes. I would love to do a little rapid fire with you that are around just some of, like, the questions that we ask ourselves or the different ways that we can kind of reflect within ourselves. Because I think you're such a reflective person, and I'm just excited to hear kind of how you answer these. So this is a mix of questions and stuff, statements that I just want you to respond instinctively here. A desire that you admitted to yourself before anyone else.
B
Feels vulnerable to say, but I want it all. I want a family and a big career. And when I say big career, I mean really big career. It was hard to admit and still is, because I think we've heard a lot of women and women I admire say, like, you can't have it all or you can have it all. Not at the same time. Maybe that's true. I'm gonna find out. The systems in the world have changed, and I'm starting to see women who are, like five and 10 years older than us figure it out. I don't know them personally. I don't know if their inner lives are a mess, but tbd, no.
A
I love that, though. Have it all bigger. I'm always gonna push people for bigger.
B
Yeah.
A
A version of success you outgrew working for free. You know, I like that.
B
Yes.
A
The smartest risk you ever took.
B
It was a bet on the desire that whisper, the curiosity, the intuition. And every risk I have ever taken has been the best. They've all paid off. Even the ones where I lost. They all compound that quote. You either win or you learn is 100% true. I actually took a big L yesterday, and I was licking my wounds. It takes a lot to really get me. I was in bed for three hours, like, replaying all of it, and I learned such a good lesson. So is what it is.
A
Yeah. Worth it? Yeah, it's worth it. Something you stopped pretending to want I've.
B
Never pretended to want anything. What do people usually say to that?
A
I've never asked anybody that. I can tell you what I think.
B
Yeah, tell me.
A
Accepting partnership from average people. Accepting partnership rooted in mediocrity.
B
Wow. That's big and deep. And it's complicated. Like, it's not. It's not for rapid fire.
A
Yeah, it's not rapid.
B
Yes.
A
Where in your life you feel most authentic.
B
Being really honest with myself about that allowed me to be fully authentic because I could just live into what I really am. And so my insides match my outsides.
A
Yeah, I love that. And then the last one. For those of us who are seeking to get what we want.
B
Yes.
A
What question should we ask ourselves in that pursuit that you think we avoid but actually need to ask?
B
The question is, picture yourself at your 85th birthday. Close your eyes, think about where you are, who's around you, what would make you absolutely cry of sadness that you did not do. And the reason I think this is important, especially for women in their 30s and 40s. Have you ever seen Saturday Night Fever? It's a movie from the 70s, way back.
A
Is that John Travolta?
B
Yes.
A
Yeah.
B
All he wants to do is dance. And he works at this store and on the weekends he dances. And he goes into the store one day and his boss, who's probably twice his age, is like, you could probably save a little bit more and save for the future. And John Travolta goes, fuck the future. And the guy goes, no, you can't fuck the future. The future fucks you. And if it will catch up to you, the future will fuck you. And I remember seeing that movie as a kid and having this deep understanding that you cannot fuck the future. The future fucks you. And so the reason that question, I think is so important is we don't often work backwards. And in your 30s and 40s are like your 20s, you're still figuring stuff out. You're asking a lot of questions. In your 30s and 40s, you are building for the 80s and 90s. And so if you are not working towards your financial goals and saving, they're not just going to come. Most likely. Maybe you are pretty lucky if you're not like, I want a family. I'm 35. I don't know that I did a great job at this one. Like, I gotta figure out how to put energy and time into dating so that I can try to get lucky and make that happen. I think that question is, like, so clarifying.
A
So, so good.
B
Yeah.
A
Such a good like mic drop.
B
Did you have an initial instinct?
A
My initial instinct and I. I talked about this a little bit in the solo episode at the beginning of the series. What do you want that's not influenced by other people?
B
Yeah.
A
That's not what everyone else wants for you. That's not what you see people on the Internet doing. That's not what your family says, what your church says. If none of that was a factor, like, what would you actually want?
B
Yeah.
A
And I don't think enough of us really explore that.
B
How do you think we figure that out and, like, get rid of the noise.
A
Self discovery, reflection, stripping it away, asking questions, no pun intended, but asking ourselves questions. And when we get those pings, those gut instincts, actually following it and not just doing what we think we're supposed to do.
B
I think some of it for me has been not failing, but sort of trying things on that don't fit. Like, I remember when Instagram first started kind of got popular, and I would, like, take photos in the mirror of my outfit and post it because, like, that's what people were doing. And I always felt so uncomfortable. Like, it never. People that I grew up with were probably making fun of me. Like, it just never felt right to me. But I think I had to try that on to get to the place where I was like, how can I make this work for me?
A
Yeah.
B
Maybe like trying on stuff that doesn't.
A
A willingness to try.
B
Yeah, I guess. Yeah. Trying is winning.
A
Yeah. That's like a good takeaway. Like a last little takeaway for the audience.
B
Yeah. That trying is winning. Yeah. There's nothing else to do. No. Yeah.
A
Try. Take the information. Try in a different direction. If it doesn't work.
B
Yeah. Are you ever scared to try?
A
Not anymore. I used to be, but I feel like once you get one or two good big tries and put yourself out there, then it just becomes less scary.
B
What would you say was the biggest try? Like, what was the first or second one that was like, ooh, just being.
A
Out on the Internet, putting myself out there on the Internet in the early aughts when no one was looking. That's the thing. We get so scared to put ourselves out there. But when you first get started, nobody's checking for you. It's actually so freeing. When you first create a podcast, nobody's listening to it, and that's when it's the most fun.
B
Yeah.
A
So when you think of it that way, it actually becomes less scary. But leading up to it, you think it's scarier than it is.
B
I never Thought about that. Yeah.
A
The most fun that I had podcasting was my first couple of episodes when no one listened and there were no expectations and it sounded horrible, but I could just say and do whatever I wanted.
B
Do you feel like when you're interviewing people, sometimes they give the same answers? Like, do all of them sort of run into each other?
A
No, actually, I feel like everybody kind of has their own interpretation of things, and I feel like we do get a good variety of answers. What about you?
B
I've interviewed a lot of highly successful people in different industries, and one thing I've noticed is most of them, and I'm not interviewing a ton of tech people, but most of them are, like, not. Like, their IQ is not so far away from everyone else's. Their vision is, like, not unbelievable. There are outliers. Right. But I find that they just believe that they can.
A
Yeah.
B
And that's been a big takeaway for me in podcasting is like, I think 90% of going after what you want and getting it is just believing you can truly.
A
Yeah. And then continuing to persist even in those moments where something doesn't work out the way you think it would.
B
The Resilience Olympics.
A
Yes. Danielle, thank you so much for being here.
B
Thank you, Les.
A
I loved this conversation.
B
I loved it more. I'm so grateful to be on your pod. Thank you for having me.
A
I'm so grateful that you are here. Please let the Clovers, the girlies, know where they can find you.
B
It's so weird because I'm a clover. Yeah. So, fellow Clovers, I'm R, O B A Y on everything and I can't wait for you to come on my podcast.
A
Yes.
B
We're gonna do a swap.
A
I'm so excited.
B
Absolutely. Thank you, thank you, Thank you for.
A
Tuning in to this week's episode of she's so Lucky. If you're ready to create your own luck, hit that subscribe button wherever you get your podcasts or on YouTube so you don't miss an episode and head to to the show notes for resources, links, and discount codes. And if you are really feeling lucky, we would appreciate your rating and your review. It really helps us be able to improve the show, to get great guests and to understand what you want to hear more of. Thank you for tuning in and I'll see you next week.
B
Hey, guys. I am Brioni Bass, a Pilates teacher and the founder of Pilates by Bryony. I started my podcast beyond the Mat after having some of the most moving conversations with people on the mat. Expect full disclosure moments, Life hacks to level up your life and stories that activate your dreams with no gatekeeping allowed. Listen to beyond the Mat every Thursday wherever you podcast.
A
Please note that this episode may contain paid endorsements and advertisements for products and services. Individuals on the show may have a direct or indirect financial interest in products or services referred to in this episode.
Host: Les Alfred
Guest: Danielle Robay, Journalist & Podcaster
Date: February 17, 2026
In this episode, Les Alfred sits down with journalist and podcaster Danielle Robay to unpack how women can proactively create opportunities and “get what you want without waiting to be chosen.” They delve into the mindset shifts, actionable habits, and personal anecdotes that have shaped Danielle’s career, touching on themes of luck, curiosity, intuition, self-advocacy, and the art of asking better questions. The conversation is an honest, dynamic exploration of ambition, resilience, and the importance of betting on oneself.
The episode is candid, inspiring, and conversational, characterized by mutual respect, humor, and the willingness to probe hard questions. Both women offer actionable wisdom rooted in personal experience, with a focus on empowering listeners to take charge of their own narratives.
Anyone looking to build confidence, learn how to advocate for themselves, or inject more curiosity and intentionality into their career and life decisions—especially women hoping to “create their own luck” and stop waiting for external validation or permission.
Find Danielle Robay:
@ROBAY (across socials)
Find the full episode wherever you listen to "She's So Lucky" or visit the show's website for additional resources.