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Ep: 193: How this HR Leader helps thousands fast track their remote careers with Madeline Mann

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In this week’s episode, I speak with Madeline Mann who is a Human Resources Leader and Career Strategist, known for her rapid-fire career advice videos on her channel “Self Made Millennial,” which has amassed hundreds of thousands of followers across platforms. 

Madeline transformed her experience as an HR & Recruiting leader into advice on how to empower ambitious professionals to fast-track their careers. 

Madeline’s work has been featured on Business Insider, Newsweek, and more. Mann was named a top 50 person to follow on LinkedIn, and a top 10 YouTube channel for job seekers.

Listen on to find out how Madeline has been able to help thousands land remote jobs. 

Listen Below:


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Hey everyone. Thank you so much for being here. I am really excited for today’s guess, Madeline. Hey, Madeline, how are you? 


Hi Debbie, great to be here. 


Thank you so much for joining us today. I am so excited to speak with you because you have so much valuable content that I want to talk about. But before we get to that, can you tell us about you and why you live an offbeat life? 



So I am a human resources professional. I was leading HR at a tech company. I was on the front lines of reading resumes, I was in the back room discussing who was going to get the promotion, and I realized that all of this information, all of these conversations, if only professionals knew what I was hearing they would make many different decisions in their career and they’d be able to propel themselves much faster in the direction that they want. 

And so I started helping people individually and kind of giving unprompted feedback to people who apply to jobs which ended up going terribly. It turned out people don’t actually like unprompted feedback.

So I started building content and I started on YouTube and building at my channel – Self-made Millennial. From there, I went to LinkedIn, TikTok, and really building my own website, building my own brand. 

Ultimately, it turned into this Self-made Millennial brand where I provide courses and coaching and helped thousands of job seekers with an audience of hundreds of thousands of people.


The content that you are creating is definitely pertaining to all of us especially right now during covid when people are losing jobs. They’re maybe losing their nine-to-fives and a lot of people are transitioning into remote work.

So what you’re doing is so much more important right now. I definitely found you because I was looking for experts who can help other people really transition into this a lot more smoothly. Because so many fears go along with it. So this has been, I’m sure, a really crazy time for you as well.


Yes. As soon as covid hit, I knew that this was a time for me to step up. I started going live more often, I don’t even think I’ve ever done a YouTube live despite having a YouTube channel for several years. 

I’ve never done it before covid because I realized this is a time to step forward. And what was really interesting is that I work in the HR function daily. So I’m not coming up with theoretical things about what I think is happening in the job market. I’m in it, seeing it every day.

And it’s been really helpful to just notice these trends and be able to translate that to jobseekers because a lot of the rules have changed. 


And we’re definitely going to talk into detail with all of the tips that you have, Madeline, on really creating a standout resume and also interview skills that people need to learn for our extended interview. So I’m really excited to dive deeper into that with you. 

So when you started really going into your own brand and making this change for yourself, what did you do to prepare? Because that takes a lot of time and energy and you also still had your nine-to-five. 


Yes. So the first thing I did was I sat in my bedroom and I just had a blank document and I thought, “Okay, if I’m going to go on this journey, if I’m going to build this content, let me just see what topics I come up with.” I think I locked myself in the room for hours and came back with 20 pages of content. And that was the first indicator to me that I find this fun. 

I think the first step is if you were going to build your own business, if you’re going to also have it as a side hustle, you better love it because you are exhausted by the end of a day and if this isn’t something that energizes you, it is going to drain you. So that was my first indicator of like, “Wow, this is really a great time.” 

And then I just enrolled in digital courses. I’m a digital course junkie. I think that they have just given me leaps and bounds forward in order to really understand what is the next step that I should take to learn from experts who have actually been there.

And then just really absorbing as much as I can and it’s just crazy how years later, I’m still picking up new courses on the same topics just because of the amount of information that I need to take in to get that advantage. It’s just like it’s constantly humbling. 


So what would you say are the best courses that you have picked up throughout all of these years of really diving into these different tools that have really helped you succeed and make your brand grow?


One of the things is, truly, podcasts are amazing. You just type in a keyword and you can find anything. That’s how I found Amy Porterfield who is amazing at online marketing and she has a great podcast and really getting into the swing of her.

Not only just taking courses and listening to podcasts but what’s really interesting is that when you’re building your own brand, a lot of it is the stuff that goes on set. Like, just the way you’re conducting this interview.

You don’t even have to do a podcast on how to conduct an interview but I can like read into, “Okay, why was that interview so successful? What is Debbie doing?” Really just like having these mentors.

Sunny Lenarduzzi was great for YouTube, I took her course and she has a lot of great wisdom there about really helping you wake up to what SEO, what keyword research. It’s just not something that I’m naturally good at.

And so really just having these people who have honed their craft and being honest guys to myself is like, there like, “Oh,  I still have  so much more to learn.” 


And also when you listen to Madeline and you watch her video, she has such incredible information and your videos are not super long either. They’re short and sweet but they’re super informative.

And I was telling Madeline before we got into this interview, “I found you through TikTok,” just a few seconds and she packed it on in such a short amount of time. How do you make sure that your content is really something that’s super valuable even though you don’t have a lot of time to really put it out there?


So when I was thinking about building content in the very beginning, the reason that really gave me the push was I looked at the people who were building content out there in my niche, in career development. 

I noticed a lot of it was very theoretical and it would take them a while to say things and they would give you the idea that you should do. I kind of kept getting off the videos and like, “Okay, but if someone got off this video would they know exactly the first step to take?” And the answer kept coming as a no.

There are people who are truly doing it but my learning style is: skip the bluff, give me the information. And so I wanted to create content for people like me and I realized it’s kind of one of my talents.

And so by doing all of that content on YouTube, I’ve spoken so much about these topics that by the time I got to TikTok which has a limit of 60 seconds to convey an idea. I even talked about the stuff for years so I was able to crystallize the things that I had said in a short amount of time on YouTube to even a short amount of time on TikTok.


And it really works for you. You have thousands and thousands of people watching you, learning from you, and you’re making an impact on so many people’s lives which is incredible especially during times like this where everyone’s kind of in a panic in some way. So probably listening to you has been like a lifesaver for a lot of people. 


It’s been actually overwhelming. I actually have to stop keeping track because it got too much. I started keeping track of how many success stories of people landing jobs during covid that I got.

It was up to like 300 something or 400. There are just so many coming in at this point that I can’t keep track of each one. And it’s been really amazing to see that these people who thought they wouldn’t be able to get employed during this time actually have had life-changing results.


When you got that type of response, how do you make sure that you keep on giving your audience fresh ideas? Because a lot of times people will be like, “Well, I don’t know if this is gonna be relevant still. I’ve been doing this for so many years and what if I’m not giving them enough information anymore?” 

How do you make sure that you keep up with what you’re doing and making that success even bigger or growing?


That voice for sure is talking in my head. It’s like, “Yeah, this is going to be good enough. Everyone has a video on the question: tell me about yourself. This is nothing.” You hear those voices for sure. 

I would say that what I realized is, by working in the Human Resources profession everyday, especially this is really noticeable during covid, all come out with things if you’re like, “Hey, here’s what I’m seeing. Here’s what I think.” 

The big indicator to me is the number of career coaches who say, “Okay, I’m gonna use this material now. Thank you for explaining that to me.” I’m like, “Whoa! This is your full-time job to be a career coach and I’m actually giving you information that is breaking news to you.” 

And so that is really confirming to be like, “Wow. Okay, I’m not only impacting people who are listening, maybe I’ve never really thought about this, but like the people who are in our profession, they are really grateful as well. 

I did a video the other day on TikTok about how to get a job without applying, without networking, without doing anything. My most recent job, I got it completely from just someone finding me on LinkedIn. To me, that’s a very natural, normal thing.

Most of my interviews in the past few years are just me not reaching out to anyone and companies coming to me. Ideas like that, I can’t take those for granted because that video on TikTok did really well. People are like, “Holy cow. I could actually never apply for a job again if I have a really great LinkedIn profile.” 

And so things like that. I just need to step back and realize I need to meet people where they’re at and not take my expertise for granted since I’m in it everyday. 


Well, with you, Madeline, it’s just that you are doing attraction marketing, right? You don’t really need to do too many things because your content is just so good that people just find you. And then they binge-watch everything that you do which is incredible and that’s what we all want – for people to keep coming back. 

Because everything that you’re saying makes sense, it’s realistic, it’s really what we need to learn. How are you able to make sure that you are really standing out from the crowd? Because like you said, there are so many people out there that are doing things that are similar to you.


I would say that I do have a little bit of a brand that is kind of round. My little motto is you have to be odd to be number one. And I really kind of thrive on being a bit odd, right? I really kind of try to add my own flavor, my own sense of humor into it and I think it turns some people off. 

A really important thing about content creation is that you should not be afraid to repel people. Because if you’re repelling some people that means you’re really attracting others. And it really helps you instead of being really generic. And so that has been fun for me. 

If you look at my LinkedIn profile it is bright orange everywhere. I had never seen anyone put emojis next to their name on LinkedIn before I did it. I got a lot of people raising eyebrows and be like, “That’s so unprofessional.” 

And yet now, anytime you’re scrolling through LinkedIn you see the oranges everywhere. It became like an endearment for my audience. And so just really kind of being bold. Experimenting, doing stuff that people will say, “Oh, that’s so silly,” but just seeing the results. 

And now, I have seen so many people put emojis in their headlines and their names. That was really confirming to me like, “Uh! See? I wasn’t this crazy person.”


It’s really inspiring when you see someone like you who doesn’t listen to what everyone else is doing. You’re experimenting and you’re not afraid to fail because I think what a lot of people are afraid of is making a mistake and like, “My goodness. What if this happens and that happens?” And you’re just like, “Hey, whatever. If it doesn’t go well, at least I know I’ve tried.”


Exactly. Yeah, there’s plenty of things that I throw away aside. But yeah, it’s been a fun experiment.


Now, we all have that what now moment when we start our new brand, our new company, leaving our nine-to-five. I definitely had that when I left mine. What was yours, like Madeline? 


I still work a nine-to-five. 


So what about when you created your own brand and you were like, “Oh my goodness. What if I start this and that it doesn’t go well,” did you have that moment of questioning whether you were doing the right thing? 


Not really. I didn’t really have anything to lose.  I can sometimes be bold. I’m actually pretty prudent. And so I think that I stepped on a ledge and I thought if I really felt this like, “I’m no one.” When I started, no one knew who the heck I was. 

And so I think that feeling is extremely liberating if you’re like, “Go out there,” and you try this new thing and then yeah, maybe you’re 2,000 friends on Facebook or Instagram or whatever may be noticed that you did something. And you kind of went away but that doesn’t matter, it really doesn’t matter. 

And so I think just kind of realizing that no one really cares. Like just go for it and the cost of failure really isn’t as bad as the upside of winning. I found that over time now people notice what I do and I’m a bit more under a microscope. So I am a little bit more afraid of making the wrong move. 

But yeah, I think just kind of just going for it and is realizing life is short. 


So for your nine-to-five that you currently have, is it always remote, or do you do this in the office? 


I wasn’t remote before this. The interesting thing about having a nine-to-five and the reason why I have a nine-to-five is because I absolutely found the career of my dreams.  I really do love working in human resources. But then my business is so complimentary to that. 

I read the 4-Hour Work Week and all that stuff of, “How do I multiply my efforts in a way where I’m not sitting in the work constantly. That I’m making money while I sleep.” And then I’m putting things out.

I’m pretty strict about things that impact maybe one person or a group of 10 people. Like, I don’t typically take on a lot of those things because if I only have so many hours in a day, I’m going to make a YouTube video that can help thousands and thousands of people versus you paying me a certain amount of money to meet with a few people. 

I’m always trying to think of how I can 10x my impact and how I can do things where it’s automated or I have helped.


You are definitely a rare breed, Madeline, because a lot of people do not love their nine-to-five and I love sharing stories like yours where you actually really enjoy it and it’s your dream job. And I also want to emphasize that just because you have nine-to-five doesn’t mean it’s a bad one. 

A lot of people actually also love their nine-to-five and there’s a purpose for it. So it’s amazing when people actually do that and it works out for them. 


It’s really trippy because I think even the word nine-to-five, there’s a connotation of like, “Yeah, you’re on the conveyor belt. You have a boss,” – all that stuff. For me, it’s like, “I am at work. I do only what I’m best at,” which when you are a business owner, you are the chief everything officer.

But when you have that balance, if you do actually love your nine-to-five, then you have that one thing you do when you have all these resources and you are really focused on your strengths. And then you go home and you have your side business and you get to have so much more creativity and freedom.

And so I think you lose the other with the other that you might lose. I think for me, personally, it’s been a really great balance. 


Yes. I say this all the time: not a lot of people are meant to have their own businesses. Some people just like to have freelance work, nine-to-five, or remote nine-to-five because you can have that too.

It just depends on what you are really into, what you’re good at, and what you’re passionate about. And if you’re not wanting to start an online business, that’s fine, too. I think that having a job that you really enjoy can be just as fulfilling. 


Absolutely. Yeah, I think that if you can become a business owner and just love it and in and kill it – that’s amazing. You’re actually very talented. 

So many of my clients and students of my programs find that they love the nine-to-five. That is a really tricky part – not that many people can say that they’ve done.


So talking about your brand and the program that you’ve created, how did you actually land your first client? Because that’s one of the first things that we’re all curious about, right? 

“How do I do this? How do I actually start creating money from this?” 


I would say that I started creating content before I started asking people for money. And the great thing about that is people get a sampler of what’s your style like. The fact that I do video and you don’t have to do video. I have a close friend and a really great career coach, Austin Bell, he does, almost exclusively, articles and he still gets amazing traction with clients.

Since I do video, I’ve noticed that when people ask to work with me, there isn’t a lot of vetting of me because they see me, they see me talking. They see me interacting with the camera. And so there is a powerful element to video where people feel like they already know you by the time they want to hire you which I found dramatically helped to my advantage. 

I think also one thing that people are really hesitant about is to just claim it. Like saying what your offerings are. Make them extremely clear and don’t make them too broad. So putting on your LinkedIn profile and putting it on your website.

I do interview prep, I do a review of your resume and LinkedIn, and then I do a job search audit of your networking or something like that. You just have the three things and people feel really clear and just really making sure that you have a very clear value that you add.

 ‘Cause I think sometimes we’re multi-passionate we might convolute things and say we do multiple things and then ultimately feels like if you’re good at everything, you’re good at that, you’re great at nothing. 

Those are some of the things that really helped me get those first clients. 


Yeah, you’re right. ‘Cause you’re pretty much creating all of these different useful content already and most of the time probably people just reach out to you and be like, “Madeline, how do I do this? Can you help me? I’ll pay you I swear.” 


Exactly. So they could get comfortable and kind of understand what I’m all about. 


So have there been any big setbacks that you have encountered as you created your brand and how do you usually deal with them? 


I definitely got burned out at a certain point. People tell me, “How the heck do you create so much content?” Truly I do work a lot. 

And there was one moment where I was going so strong. Like a YouTube video a week, all these different content on LinkedIn, I have a new piece of content or maybe not surely new but I post everyday on LinkedIn – all that stuff. 

And I had just gotten married and I was going on my honeymoon and it was on a cruise to Alaska and I was like, “This is gonna be relaxing. I’m going to get some good work done.” And my husband was like, “Wait, you’re going to work on this cruise?” 

I was like, “Yeah, honey. We’re gonna be at sea for several days. It’s gonna be so fun to get ahead on some things.”  And he was like, “Madeline, we just got married. We’re going to completely unplug.” And I was like, “I don’t know what that means.”

So we ultimately ended up taking a week off and it was probably one of the best weeks of my life. It was so amazing and it just made me realize how much I had been pushing myself and how I didn’t really give myself permission to take… 

I think  I only took two weeks off because I got, hello, married. Like, one of the biggest moments of my life. And guess what, nothing happened. Like, nothing was impacted, people completely respected that I was out of pocket.

And it was just a lesson for me. I was like, “Wow!” Step back and think about what’s most important and you don’t have to be grinding all the time.


It’s really hard to learn how to turn things off, right? Oh my goodness, it’s such a hard thing to do especially when you are creating something. But you’re right, the world keeps turning round and round even if we’re not there.

So it’s a good and unnerving thing at the same time. But if you appreciate that at all, it’ll be a positive thing.


Absolutely. I learned a valuable lesson. 


So Madeline, let’s fast-forward to 40 to 50 years from now and you’re looking back at your life, what legacy would you like to leave and what do you want to be remembered for? 


I want to feel like I helped people find jobs and just have a really fulfilling career. I love to work and  I want people to feel that too. There’s the Maya Angelou quote: People will never remember what you said. They’ll never remember what you did but they’ll always remember the way you made them feel. 

And I hope that the way the people feel is that they laughed, that they were uplifted, that they were motivated. When people look back and they see the little oranges and tangerines that are on everything and they remember Madeline from way back when or what and then they go, “Wow,  she really put a smile on my face.”


The biggest thing that we can ask is touching people’s lives and how you’re making them feel in the long run. That is such a good thing to be able to do. 

Are you working on anything currently that is really exciting to you? 


I have two digital courses. One of them is Standout Resume where I really help people make sure that they have a killer resume that opens doors. And then I have my course, LinkedIn For Thought Leaders, which is how to grow a massive following on LinkedIn and really get opportunities coming your way, get clients.

And both of those have been so fun because before I was doing digital courses, I was just putting up a digital course and hoping people liked it. But now I have communities associated with them, private communities.

I love doing this. Being in there talking to everyone and giving them feedback. I always want to do things on a larger level versus just want to want it. Like, really helping people at scale. 

And I think that that has been a really cool change that I’ve made in my business that has been really fulfilling and I’m driving towards doing a lot more of that in the future. 


Those are so many exciting things and we’re definitely going to add links to that on our website because a lot of our listeners will be really interested in doing this especially if you’re doing a transition to remote work. 

So if our listeners want to know more about you, where can they find you? 


You can visit my website: I also encourage you to check out my YouTube channel which is and absolutely follow me on LinkedIn:


Perfect. Thank you so much, Madeline, for sharing with us all of these different tips and tricks. We are really appreciative of it. Thank you so much. 


Thank you, Debbie.

Listen to Madeline’s extended interview where she shares how to perfect your resume and interview skills to land a remote job.

What you’ll find:

In this episode, Madeline will show us how to craft the perfect resume and back it up with interview skills to help you land that remote job.

Follow Madeline:

Show Credits:

Audio Engineer: Ben Smith

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