guidance counselor 2.0 · episode 230
you belong in tech w/anna mcdougall
key takeaways
- learn technical skills through structured programs or frameworks like scrum sprints to mimic real development team workflows.
- network by asking questions, listening genuinely, taking notes on people, and showing up consistently over time instead of high-pressure pitches.
- customize applications with research, company names, and your unique background rather than sending hundreds of generic resumes.
- highlight skills from previous careers as strengths, not liabilities, showing why your diverse experience brings value to teams.
- say yes to opportunities and show up; most people count themselves out before trying, making consistency a competitive advantage.
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about this episode
how to transition into tech through learning skills, building community, and strategically applying to jobs rather than mass applications.
I am joined this morning by Anna McDougall who is out of Germany and we are going to talk about her book! Definitely going to be a great conversation and belonging in the tech ecosystem! Recruiter Against Recruiters - Click the Link Below For Job Postings, Newsletters & more!
Like what you hear? Connect with me - Website: www.vaco.com/taylor LinkedIn: Taylor Desseyn Tweet me: @tdesseyn Pics of the life, wife, daughter & dog: @tdesseyn
full transcript
auto-generated from the audio, so expect a few typos. the audio is the source of truth.
Hello, hello. Thanks for listening to Guidance Counselor 2.0. Listen, I want to give you a quick rundown of what this podcast is and what you're about to get into as you listen to these episodes. We had Guidance Counselors in middle school. We had Guidance Counselors in high school, but we didn't really have Guidance Counselors in college and now as professionals, we don't really have anybody to turn to to ask a quick question to learn something about the job search or to navigate your career. And so that is what I want this podcast to be for you. I want it to be a tool for you to navigate the job search and your career.
So that being said, I hope you enjoy this episode. And if you need to reach me, Taylor at vaco, VACO.com is how to get in touch with me old fashioned email social media at T D S and T D E S S E Y N. And finally, please rate and review this in the app store because I want this to be discoverable for others so they can navigate their careers. Hope you enjoy the episode. All right, so we are going to dive in. So Anna wrote a book. Now, you're probably going to be like, oh, great. We're going to push the book. No, we're not.
We're going to talk about it. But hopefully you buy it. So Anna, let's go and dive in. First off, sets of stages. People do not know you. Who are you? What are you? And then let's go ahead and dive into this. Yeah. I mean, I've got a really weird background story. But the short version is I coded a bit as a kid, left it behind in my kid years. And I actually studied like media communications, did some digital marketing kind of kept up a little bit with my HTML CSS through that. Then did my first major career change, became an opera singer for seven years, did my Masters of Music, moved to Germany.
I'm from Sydney originally, you might be able to tell from the accent. And then after that, I decided I needed another change. I had my first child, I gave birth to her, And I realized, OK, I don't want to keep going as an opera singer. I want something that's more challenging. I want somewhere that's got room for me to grow. And I ended up doing a certification in web and software development, which led to a job as a junior software engineer, and then got very quickly promoted to software engineer. And I then got headhunted and became director of product and engineering for Europe's largest media publisher, Axl Springer.
And just to give you an idea of how large that is, just one of our websites has about 3 million unique users per day. So we are huge and alongside that, of course, comes a lot of challenges. With me, if we have websites, of course, apps, video streaming, machine learning, data, text to speech, editorial tools for our journalists. So my job is basically to understand all of these things, both from the top down and the bottom up. And then I go around and I talk about it a lot and I also work on a lot of kind of career-based initiatives and diversity initiatives for our technical and product staff.
So that's the shortest version I can give you. That was a lot. So talk about the book, right? What made you, what prompted you to write this book? Yeah, so I mean obviously, opera to software engineering is not a standard career path to put it mildly. So when I was trying to make this change, I had the benefit that I already knew a little bit about HTML and CSS, but I mean very little. It would have been 16 years between coding, you know. So I needed what I was missing was like a step-by-step, right? So like not just like, oh, here's a free course here and a free course there.
Okay, fine. I can do that with the Google search. But like, if I'm doing this course, what do I need to learn? What should I be paying paying attention to, how deep should I be going? And then after that, like how do I turn those skills into an actual job? Like how do I actually go from knowing this stuff to being hired? And I feel like there was an information gap there that I discovered through trial and error and ever since making my own career change, as you know, I post quite often on Twitter, not so much at the moment admittedly, I've gone off it a little bit, but nevertheless, usually I'm posting a lot on Twitter.
almost at 30k followers. And so I'm at the point like where I got asked the same questions over and over again from newbies. Like what language should I learn? How can I network? Like what are my options? Like is my CV okay? What should I be including in my portfolio? Like I was just getting a lot of same questions and I thought you know what, let's do this like a developer. Like let's take the easy root, let's stop repeating ourselves and instead just write a book where it's like everything I know, everything I've experienced, everything I've seen work in probably hundreds of career changes who I've spoken to over the years, let's just put it all into one place and then I can just like direct people there.
I love it, yeah. And say myself a little bit of time frankly. Yes, same. That's actually the why I put out content. The reason why I started putting out content is I, again, I talk about this. Recruiters can only help or can really only place 10% of the people we meet. So if you meet 500 people in a year, we only put about 50 of those people in jobs. So what am I doing with the other 450 people? And that's why I started to develop content. So I love that about you as well. Just that give back mentality is so important. So, so talk about maybe some, some, some main, main pointers of the book.
Yeah. So the basic overview of the book is that there's, in my mind, three steps to getting your first job to changing careers. Excuse me. I've got like, I'm halfway between a burp and it's like sitting there and I'm like, I'm not sure if it's going to happen or not. I'm like, I love it. Okay, I'll just drink some water. Let's try that. Hey, this is what I love about the show. It's just two friends. That's just me. I'm an open book. So, yeah, the basic idea is that there are three broad steps, right? First thing you have to do is learn the technical skills because you can't have a technical job without technical skills.
There's no way around it. The second step in general is creating some sort of network or finding a community or connecting with people who are either in a similar region to you, who have a similar tech stack to you, or maybe you have something else in common like a women in tech community, for example, I found a lot of great communities like that when I was learning. For me, it was Twitter. Like that was the main way that I found my community. It was also during the pandemic. So real world options weren't as available to me, but for lots of people it does involve meetups, does involve hackathons And just basically connecting to other people.
Yep. And part of that is also creating some sort of value proposition for yourself So finding where you are like what makes you different like what makes you unique? What's your unique selling point? What's your pitch? Like what do you bring right and then in the third step? It's the actual job application So how do you approach job applications? Should you spray and pray? Or should you be doing a lot of research? Yeah. I go with research and, you know, reaching out to people individually, asking questions and really finding the connection. So how do you write a cover letter? How do you write a CV?
What should be in your in your portfolio? All this kind of stuff. So those are the three basic things. Yeah. Learn the skills, create a network, apply to jobs. I love that. So let's break those down real fast. So learn the skills, right? I mean, I think I get these questions all the time. Yeah. Self-taught, boot camp, college, university, you know, and I've actually interviewed a lot of junior devs recently. I've kind of been on a little bit more of a kick on like kind of that mindset of going from zero to one and why I choose different things. And there's different reasons, right? I've had some junior developers that are like, I needed structure, like that's just who I am.
If I was a self-taught, I would never get it done. Do you have any thoughts on learning the tech and maybe things that have worked for you? So much. Yeah, structure is so important. I think one of the reasons I prefer personally, but also why I tend to suggest to people that they do some sort of program with other people, is because it creates a sense of accountability. That said, and also, sorry, not just accountability, it also proves that you can work with other people you can talk code with other people. Because one thing that a lot of juniors, especially those looking for their first job, they don't realize, hang on, I'm not actually sitting by myself in a room most of the time coding.
A lot of the time you're talking about code, you're talking about solutions, you're asking for help, your pair programming. It is actually a very sociable job in the end. And you have to know how to communicate those ideas. And that's very, very hard to do if you are sitting and learning by yourself. So that's it. Those These are the two big benefits of doing some sort of program, be it university, be it a bootcamp, be it some sort of online program like 100 devs by Leon Knoll. One of the benefits of those kinds of programs or the Oden project for that matter as well, which is how I started learning, is you have structure, but you also have people you're talking to about the projects who can help you if you get stuck.
And these are very similar to the skills you need in a job. If you must learn by yourself, be it because of life circumstances or you have some sort of social anxiety perhaps and you're struggling to get over that or get through it, I suppose that I think you ever really get over it, but you know what I mean? Then I think the key there is to create a structure. How do you create a structure for yourself when you have no idea of what you're learning or what you have to learn? So in my book, what I recommend is using some sort of framework, some sort of agile framework, such as scrum.
So scrum is the one that I use as an example. For those who don't know if they're very, very new and they don't know like scrum white, like what is this? This is rugby terminology. I've never heard this before. It's basically the idea that you work in what are called sprints. You have like work periods of one week to one month is usually somewhere in there. And then you set goals at the beginning and then you work through sort of tickets or tasks during that time. And then at the end, you kind of review how much you got done and then you can kind of say what worked, what didn't work, how much did I learn compared to how much I thought I would learn.
And so I actually recommend using that as a framework for yourself, not only because it gives you structure, but also because it gets you used to how actual development teams work, because a lot of them are working within this sprint structure. I love that. I love that. And so let's talk about the second. What was the second bullet point again the second network network in community. I love it. I love that. So I mean, I listen, I know people roll their eyes. I because that's what I preach all the time. And the reason why I preach it is because when I moved up here from music myself to Nashville, I didn't know how to network and I truly believe I was not successful music because I did not know how to network.
So talk about maybe some of Anna's tips and tricks to networking. Sure. There are there are lots. I'm trying to like think about what the most important ones are. I would say the most important one is just to, I can swear here, right? It's just, it's just to give a shit about other people, right? Like I, because I think, I think a lot of people they see networking is, oh, I have to go in, like sell myself and I have to like, push, push, push. And actually that's not the best way to network. Like the, yeah. And I have a lot of people say, I don't know how to talk.
I don't have an like a pitch for 30 minutes and I'm like what expectation like who told you you had to have a pitch for 30 minutes like people are talking for more than three to five minutes yeah exactly no it's true but I mean this is the thing if it goes well like maybe you're talking for half an hour but by then it way past the pitch like sure it's gone yeah like it's gone um so yeah I would say definitely like go in asking questions more than giving statements. Like obviously I do think a pitch is very important, I've spoken about that before but I do think for the most part people don't go to events to listen to other people's pitches.
They go to events to like see what other people are doing, get a like feel for where other people are out to see like who's working on similar things to them, who can they talk to about different topics, who do they get along with well in general, like they see maybe helping them at the next hackathon, maybe they want to put a team together in advance or something. So like it doesn't have to be like this high pressure scenario, like you can literally just go in and like introduce yourself to one or two people and just say like this is me, I live here, I'm interested in this, tell me about you, what are you doing, are you working, like you know get them talking about themselves, really listen, like really try try to take a board, what like, what they're interested in and what they specialize in.
And if you need to, I've got a terrible memory. I go away, sometimes to the bathroom and I will take notes. I will write a spoke, I spoke to Taylor. He, he's really into Java and he thinks that, um, Kotlin is overrated and, you know, or whatever it is, like, I'll just take like two or three dot points. I love that. I have a terrible memory and I play, I just, I've accepted it. Like I'm not going to try to change who I am. I've accepted that I have a terrible memory. So I work with it, you know, and, and then later, if I see you again at another event, because let's face it, a lot of these local events, you'll see.
Yeah. Everyone kind of, yeah, mangles. I might make a note about like what you look like. I'll be like, I'll be like a K blonde hair, like red beard, glasses, and then I'll go to an next event. I see blonde hair, red, big glass. I'm like, oh, that's Taylor. Hey, Taylor. How's Java going? Have you converted to Kotlin yet? Like, you know, and that way we've got a starting point, you know, and hopefully I can remember it and I don't have to consult my phone, but of course often you do. And yeah, so I mean, that would be one of my, one of my big tips is don't be afraid to just like talk to one or two people, learn a few small facts about them, then be like, oh, I need to get a coffee or a pizza or whatever it is at the event.
I'll see you around. Yeah, like ditch if you need to like just ditch like if you're feeling that feeling that awkward feeling just oh I need to go to the bathroom go to the bathroom take your notes like whatever like you can you can bail whenever you want like it doesn't have to be a full high pressure thing but what you'll find is that if you do this kind of stuff consistently and you tell people who you are consistently and you say yes to opportunities which is one of the hardest things to do but puts you ahead of 95 of people if you can say yes to opportunities and turn up to those opportunities, you will honestly be amazed at how quickly you make contacts and how many people you find are willing to help you when the time comes.
So I always say if you're thinking about networking at the job search, you're too late. Like you should be thinking about it from the beginning. And just time time and consistency and just showing up and saying yes, these things pay off and they pay off, I would say in a matter of, you know, six months to a year very, very easily. So one thing I want to add here, and I want to get a few comments here. So Ben comes in here, goes agree with this so much, community slash your network can even help you with structure too. Yeah. People really do want to help.
Yeah, I mean, listen, people, people, I love people want to hear themselves talk. So if you get them talking, they are going to be like, Oh, that was great. Let's see. I don't know what you're talking about Taylor. I hate talking. I don't know. Seriously, it's seriously Randall. It's great to see you buddy. Randall. So some of my buddy Brandon Arvey He actually got his doctorate in music Oh, wow And education and performance want to be an instructor and now he heads up on my content creation. He runs a content creation He runs a content creation Hey! So Brandon gets up. I think Michael speaking German.
What is this? Is that? That's me. Tell are you. Miegets, kanskut mieke, dan kazelle. There you go. I love that. I don't know what you said, but I love that. Alright, um, let's... Yeah, and then again, like, you know, Emmett's, you know, starting You know starting coder dads me shots Emmett with his community building. He has a slack channel where it's Lily Just a bunch of dads love that I love that and then Deb. I hate talking so much adheres So I want to add this to I love how Anna Like was said she would go and write it down actually to I was actually talking my wife It's funny.
You funny brought this up. I was talking my wife this weekend I'm going back to a pen and paper like I I Have like the notes app I use notes app use your minders app, but I told I told my wife this week I said, I said, my mind is able to flow when I write. And so I guess all that being said, try to try to try to take notes somehow. If it was an iPhone gray, I love what Anna said, but I want to say this too. What I realized when Twitter was down for me, it was a traumatic incident. Yeah, it's a way to this is going to there's no way to say this without it sounding weird.
It just is a way to touch people to drip on people. It's the worst analogy ever But like basically so so when Anna goes to meet up and says hey Taylor Java Kotlin yada yada And then goes away. That's the equivalent of me going on Twitter tweeting back and forth and a few times about something she tweeted Then we move on right and so you have to I think if you can combine both and I have to give a shot to dev here Right? I mean I think I think dev does if I can make content now we're people without talking but dev that's what I'm saying you could technically do that all online.
And that is one thing that I have found as an introvert, because Anna, you're an extrovert, right? Oh, no. No, no. No, I was like, I think you're an extrovert. I like the prime example of an extrovert. So like, so she thrives. For me, Deb, I think Deb, you and I are very close here. And that's one thing, like, I had to do a lot of self-reflection and basically be able to, I like this. It's a positivity troll. I love that. And so again, leverage social to be able to do that. I think it's huge. And so the last thing we talked about networking and applying talk about maybe your thoughts on that.
Yeah, so I have like, obviously I have like lots of strategies laid out in the book, but in general I'm very anti-spray and pray. So my flag goes up whenever I see newbies suggesting to other newbies, hey, like sometimes it takes 200 or 300 applications, just send them out every day as much as you can. Like eventually one of them will work. And I'm like, that's a lot of work. Like to me, I would rather send out like 20 epic applications that I've spent a lot of time researching. And you're playing more likely. Like changing your resume, adding your cover letter, like. Yeah, and here's the thing, like it's also about, it's about not hiding who you are.
So on the one hand, these are two extremes I say right for Korea changes specifically. On the one hand, I see people who try to erase their past. It's like it never happened. They've just got the focus on what they know technically. So you could have someone like me in the mid 30s whose resume, it looks like someone who's 17 because they've pretended that they have no other life, no other skills they've ever developed. That's one side of the extreme. The other side are these people who write like, Oh my God, I've seen those scenes. I'm sure you've seen worse. Yeah, but like it's like four or five paragraphs about like why they're so motivated and passionate.
And I'm like, OK, all right, let's see if we can find something in the middle where you you talk about your skills. You talk about what makes you unique. Like the fact that I used to be an opera singer is a very unique thing. I use that to my advantage. Like I spoke a lot about why I learnt from opera that made me a good program. I've got a YouTube video about it somewhere. You know, it's I think it's on my LinkedIn profile. So you can probably find it there. But I talk a lot about this. Like the fact that I believe music taught me a lot about programming, actually, how to think about programming.
And I talk a lot about that. I don't deny the fact that that was part of my past. But I also talk about the work I did in project management, the work I did in digital marketing, why I feel like that makes me a better junior candidate than someone who's fresh out of university. Because I already know how to work with people. I know how to work in teams. I know how to communicate. I know how to guide others, mental others. Those are very specific things, right? And I think it back you up with what you said a lot of while watching this show write these cover letters and these resumes that are just just fluff.
It's glossiness. It's just it doesn't mean anything to anybody. Yeah. And also also the other thing is like a lot of people like, oh, if I just show I'm passionate enough, like they'll want to hire me. And I'm like, well, passion's good. It's not necessary. but it's good, but at the same time, you wanna show that you're passionate without sounding desperate. And this is the thing that I think, I think we lose a lot of people there, because they're crafting resumes being like, I'm so passionate, I just need this one opportunity to get my foot in the door. And it's like, hang on, like think about what recruiters and hiring managers are actually looking for.
They're looking for someone to provide value to their company. Let's think business here. Let's take away all the emotion for a second. What we're talking about here someone that can provide value to your company. Now, passion is one thing that can help provide value, but it is not the thing that can help provide value. And so you need to balance that with all the other reasons that make you unique and that mean that you bring something valuable. And what that means to different companies is going to be different. So spray and pray doesn't work because one company, they might value, let's say, diversity of thought and innovation.
And for them, you might want to focus on the fact that you've done volunteer work or you've worked with lots of different communities or that you come from a different country or something like that. But for another more, let's say more conservative old school company, they might be like, okay, we see value in numbers. And for them, you might wanna make your resume or you'll cover that a more number driven, right? But either way, the way you find that out is through their websites, through talking to their recruiters and to their hiring managers, talking to people on their teams, finding out what the vibe is like, and then adjusting your cover letter CV, et cetera, to fit that.
I love that. And any way you can, you use names. This is a big thing I'm also about. I'm like, if you know a single engineer who's working at that company, you use that name. You watch the YouTube video from the CEO, you talk about that YouTube video and the speech that they gave. You'd use as many names as you can. I call it the NNQ rule, names, numbers, quotes, names of people who work at that company. Love that. numbers of what you've achieved and quotes from people you used to work with recommendations, this kind of stuff. The, the director position that I got, I had my two page resume and then underneath it, I had a full page just of extracts of LinkedIn recommendations.
So it was just a page of like, I think it was like eight different quotes from people I had worked with being like, Oh, yeah, she's great. She's amazing. Like, she's so much fun to work with, or she does great work or whatever. I'm like, how can you deny that? Like, if a recruiter is looking a page of people saying that I'm great to work with. They can't turn around and be like, I know it's hard. Social proof. That's what we call it. Yes, exactly. Yes. You got it. As we wrap up here and again, thank you everybody who's chimed in. Randall comes in once I reframed networking from something selfish to reaching out to humans as a human networking became so much user-emmusement introvert.
There are people who need to hear some some of the things I know and it's my job. I love that, love that so much. Yeah, even if you're You love the Ramble. Junior or younger in your career, you still offer value, right? My team is composed of a lot of new young junior talent. I'm gonna tell you this, they think outside the box because they don't know any better. And so you probably have a really good thought on something. You just don't know it because you're not communicating it. So I love that. And then Katie comes in here as a fellow musician, turns off, you're fine.
You're so inspired. I think you can. Well, as a fellow musician. All right, we're lightning rounds. Also go buy our book. Go buy our book. Talking stuff. Um, three lightning round, three questions. First question, what is a piece of tech or trend in the market you're seeing tech-wise that people should look out for? Or that you're reading on or something like that? Yeah. Okay. So I would say actually this is something not quite what you're asking me, but I'm going to kind of take it for a different, a different route. is that I think there are two things or two careers in engineering that are under-studied by people at the moment and where there's going to be a lot of demand.
First is ARVR. If you can start getting into ARVR as a software engineer, there's going to be a lot more demand for that over the coming years. And the second thing is security engineering. There is such a huge demand for good security engineers and so few people who actually go out of their way to learn it. It is, I mean, I haven't learned it myself, but I obviously speak to security engineers. But they say like, you know, it's not that much harder than any other type of engineering to learn, you know, people get like, you know, security and they get a bit intimidated. Yeah. And there's a lot of scope there to make a lot of money and to find a really great job.
So I'd say those are two things I think are kind of trending ways and are so, so necessary, especially with hacking attacks, you know, malware, all this kind of stuff like we need security people and Alviar I think is an area that's gonna keep growing. Obviously I need security people for Twitter so there we go. Second question favorite holiday movie so if you and the family are at home and you're feeling very holiday-ish what's going on the TV right? Oh my gosh very holiday-ish oh my gosh you've really put me on the spot with this one. I know I know. I can talk programming all day.
I know. I know. I know. I know. I know. I know. I'd become an introvert suddenly. I don't know. So, okay, I don't really have one, but I'm gonna tell you any story, which is that I met a guy from, I think, I think, Uzbekistan. I was studying with him, and he was like, oh yeah, like we're all gonna watch Home Alone this Christmas. And I was like, is that a thing that you watch Christmas? He's like, well, it's like the Christmas movie. And I'm like, wait, like the Christmas movie? He's like, yeah, yeah, obviously everyone watches Home Alone at Christmas. And I was like, is this a thing he said in Uzbekistan?
It is like the movie that's always on every Christmas. That's hilarious. That's hilarious. It's just Home Alone. So like the first thing that popped into my head was Home Alone because he mentioned it, but we had this whole debate where he was like, yeah, he was very like pro home alone. And I was like, I would say my favorite, I would say is it's a toss up. So because I have just two more episodes, you and one more, I'll list two. I think Santa Claus with Tim Allen is probably like my number one. And I think number two, I think it's very special. It's very just vibey.
It's a wonderful life. Black and white, just classic. That's, I was thinking about that one to be honest. Like it is a classic, yeah, for sure. Good choice. All right, last question as we wrap up today and again, for those of you who are tuning, thank you so much. go connect with Ann on Twitter and LinkedIn. Because we had guidance, so this guidance counselor question, guidance counselor is a middle school high school college, not anymore. I know you came on recently. I don't even know what you were, I don't remember what you said for your biggest piece of career advice, but what would you tell your younger self from a career perspective?
Yeah, look, I'm pretty happy with how my career's went, to be honest. So I guess I'll just give the same advice that my mom gave me that I always followed, which is do what you, try to find something that you love and that you're good at. If you can find something that combines what you love and what you're good at, so not just one, but both, then you'll have a really great life in general. And so that can change over time as it did with me, and that's fine. The other thing that I often say to people is this say yes show up. Like that's a huge motto of mine, say yes show up.
If you can do that again, you're ahead of 95% of people because a lot of people will say yes and not show up. a lot of people just say no and count themselves out before they even try. If you can be someone who goes out and just tries, like when I was approached for this director position, I was like, I've been a software engineer for a year. Why would I be a director of anything? Right? But I said, you know what? Sure. Let's talk. Like, let's have a conversation. And now here I am, like living my best life. And I have a job that I love and where I get to work with amazing people that somehow combines these three careers I've had in some sort of magical combination.
So, you know, you just have to say yes and show up. And I think that's a huge, huge part of success. I love that so much. Awesome. Well, y'all hope y'all have a great Monday. I will be solo tomorrow on the show, talking about just some, I probably do a general Q&A. For those of you who want some general Q&A, I'll do that tomorrow. Wednesday, I have an internal recruiter, Adam, from Polygonon, Thursday, Unicorn Finders, and then we will be done for the month. Anna, thank you. Kayla, thank you. I agree. Yeah, it's been a real pleasure. So I say I can stay by to you.
But you all have a great one. I'll see you all tomorrow. Peace. Hey, you did it. You listened to an entire episode. And I am very grateful. Because you know why? There's a lot of podcasts out there. There's a lot of episodes. And I myself rarely finished an entire episode. So I appreciate you so, so much for listening. Quick reminder, please rate and review this podcast in the App Store. I want this to be discoverable to others and the only way that happens is if you take the time right now and rate and review it. Please, like, right now. Unless you're driving, then don't do it.
So, thank you again. If you need to reach out to me, tailor at vaco.com or at Tdastin on all social media handles. And I hope you have a fantastic day.