 Because not everybody needs to show up tomorrow wearing a suit in fact you can't because again That may not be the story that you want to tell that might not be the aesthetic that it's consistent with the kind of man That you are or the kind of man that you aspire to be There's a book that I just finished reading It's called how will you measure your life and one of the things that the author talks about is the difference between an Emergent and a deliberate approach to life and this is one of those things that I Obviously doing what I do I started thinking about it in a style context And I think that this applies really well So we'll talk about the difference between a developing style versus a deliberate style because one of the things It's so great about being in your 20s is that you don't have to be deliberate about everything right now How many of you guys had an idea of what you wanted to be in your head when you were five years old? How many of you guys are anywhere near that path? Right, I'm certainly not in fact as we dive a little bit deeper I'll tell you guys where I was when when I was your age And I'm not anywhere near there anymore because I was willing to take a developing approach to my life as opposed to Always being deliberate and always having to stick to what it was that I thought I knew now The first thing I'll tell you with this is when you're being when you're taking this developing approach Be willing to make mistakes. There's a lot of mistakes going on right in here So this is me about five years ago So this is right when I started the site and that's just like a whole vomit mess of me trying a whole bunch of Different things right bright blue trousers a dress belt that's old and crappy this awful mustache the stupid target trilogy It's just it's bad and I can look at that now And it's actually kind of one of those things that even debate about putting up here because in one way I could say well That affects my credibility But it doesn't because I'm willing to take this developing approach to my style and get better and better at it as opposed To having to double down all the time even if I've been proven that I'm wrong on something So don't be afraid to make any mistakes because you will make mistakes and it doesn't necessarily mean anything wrong is is wrong All right, so I'll give you a little bit of context about me and then how this worked with my developing style So this is from 1996. This is me right here up on a hike with my family And I can't tell you guys how excited I was to get these air walks Holy crap At that age I was just starting to get into the BMX world. I was 12 years old I was just starting to really kind of establish myself as someone separate from my parents And so it was becoming this big thing to start to dress in the way that my idols dress And so I got a pair of air walks and I was so thrilled to be able to have these But what's funny is obviously you move beyond that the sad thing is is I have guys with whom I'm friends You know, I'm 32 years old now. This is 20 years ago I have guys that I'm friends with who still dress this way Because they've been stuck in what they were when they decided they wanted to change their appearance when they were 12 years old. One of my best friends still looks like he did when we were 12 Albeit 20 pounds, 40 pounds heavier You know what I mean? Like it's just a refusal to change and a refusal to develop and grow Now I was kind of forced into this because when I was in fourth grade My parents took me and my siblings out of our public school that we were attending and they put us into a private school For me that was something that was really hard primarily because of the uniforms And it wasn't necessarily hard at school with the uniforms But it was hard at home because my friends in the neighborhood the kids that I went to church with They all got to wear whatever they wanted to cheer or they got to wear whatever they wanted to school And I would see them as I was coming home And I would get teased and I would get picked on because I'm this goody-two shoes preppy kid Who's wearing a uniform? You know and so for me that was when I first started to subconsciously realize that Just this little subtle thing was communicating that I'm them compared to their us I was now ex-tribe just because of what I was wearing and I started to get treated differently Even by these kids parents even though these were people that I had known for years There started to be this differentiation in our church group because we were the rich family which we weren't financially any better off than than Anybody else, but my parents just wanted us to attend the school And there's this whole thing that this division that started to happen And for me it was all focused on the clothing because that was the easiest way for the other kids to recognize it because they All went to different schools. They just all went to different public schools. They didn't have to wear uniforms So as you can imagine, I wanted to get out of that as quickly as possible We'll turn things forward a few years And I'm still the same guy or I was still the same guy that I was when I was 12 When I was your age, this is all I wanted to do I just wanted to professionally ride a BMX bike And so I dressed like that was all that my aspirations were skinny jeans a t-shirt skate shoes That was about it But I wasn't any good at it. I wasn't any good at it at all. I was terrible. I was afraid of falling I was afraid of failing I had friends who they could learn a trick in two hours and it would take me two months to learn it I just never got any good at it and I started to realize finally at the age of 22 Which is kind of embarrassing that I'm not going to be a professional BMX rider You know, it's like I have to be that far along in my life to realize it's like, okay This is not where I'm going so I have to change my path a little bit So I started to think about different things that I wanted to do take different approaches And one of the things that I was doing in between trying to figure out where I wanted to go was I got a job as a bank teller worked for a credit union all of a sudden I had to start wearing a shirt and a tie I Made the transition from working as a teller to working and doing loans when I was six months into the job so I was only about 23 at the time 22 23 and It's kind of a weird situation to be in when you're that young because you were Approving or denying loans for sometimes people who are twice or three times your age, you know, there's this inherent authority and power that comes from this position and I started to realize that if I'm wearing the same baggy shirt and The same too wide or too skinny tie that I was comfortable wearing before It started to affect the way that these adults would treat me and so instead I started to dress up a little bit more Yeah, I got a lot of grief from the other tellers and the other loan officers because it wasn't in the dress code that we Needed to wear a jacket in fact I remember our VP of sales showed up one Friday was a casual Friday And he was wearing this awful polo shirt and these triple pleated khakis and just looked awful And I'm there in a three-piece suit and he started to give me grief about it Which now I understand is more this just kind of signaling and him feeling threatened by it But people started to treat me a little bit differently And while there was a price for that that came with the way that my co-workers treated me It paid off in spades with my clients or with the people with whom I was actually working So at this point I'm in school. I decide that I want to do broadcast journalism I'm a political guy and as I'm sure you can probably imagine. I like to talk That's why public speaking. This is a high for me as opposed to something I get terrified of And I decide that I want to be the young libertarian version of somebody like Limbaugh or Glenn Beck And so I decide that I'm gonna get a degree in broadcast journalism I go through school. I get everything finished and I graduate in 2010 Which is right at the bottom of the economic crisis No jobs available to me. I had worked for a radio station for a year I'd been putting in 80-hour weeks between working at the bank going to school and doing weekend overnight shifts with this radio station They didn't have anything for me. It just wasn't meant to pan out And so what I decided to do was continue to write And so it was a way for me to sharpen my voice and hopefully hopefully allow myself to be able to Get into a better career from where I wanted to be so I started to write Political blogs I started to write a few different things and they got too heavy and so that's when I started masculine style So I start this style blog not really knowing what I'm doing but having spent a lot of time reading blogs in between clients at the bank and I start to Create this thing that is now snowballed into something that's so much more So what does all that whole story have to do with style? What does that mean to go from the guy on the skate on the on the BMX bike to a guy who last year? I was all over a few different men's magazines after attending a show in Florence It's quite the transition right and if you would have told me the little airwalk kid That my career and the son and the thing that I was going to be most fulfilled by Would not have had anything to do with biking or punk music But would have had to do with clothing especially suiting like dressed-up clothing I would have said no way But because I took a developing approach and made each one of those transitions throughout my career Then I was able to get somewhere where now I can look back and see all the things that I wanted to be fulfilled By a professional career as a BMX biker or in a music or in a band are fulfilled by what I get to do now So I haven't betrayed any of those core principles. I've just found a better manifestation for them as I've grown Now what you'll notice is that if we go backwards My style is grown with that, right? It's all just a little bit different as far as how I dress and I didn't go from that I didn't turn into that from an immediate start with being the little kid wearing the The two tall ankle saw or the tube socks and the air walks. It was a transition It was a developing approach And that's the thing that you guys need to be able to do is understand that it's okay to take a Developing approach. In fact, that's the right way to do it because one of the things that people will do as you start to dress Better is they will treat you differently That's one of the biggest strengths and the biggest weaknesses of changing your style Because it's the easiest thing to do if you want to start a new chapter of your life You can go to the mall You can pick up a few outfits for a couple hundred bucks and you can be an entirely different person To a stranger than you were the day before but the people who you know are going to resent that Because one of the things we value most is people is consistency We value it in ourselves and we certainly value it in others. We're threatened by change We're threatened by inconsistency and we almost always treat it like it's hypocrisy as opposed to growth And so a lot of times it ends up being more detrimental than positive for you guys to make a too quick change Into something that's an aspiration of yours even if it's an aesthetic aspiration That's why it's oftentimes a lot better to do it gradually one step at a time I have a brother-in-law who we went and did and this is probably four years ago we went out and did a whole day kind of helping him get some new clothes and it was Something that was different completely different than anything you'd been wearing before and what it did is it told a different story Told a different story to his family to his friends to all these different people and it put him in a pretty unique And a pretty tough position and it'll do the same thing for you if you're if you're up for it Then it's a good thing to do and to do it quickly and more drastically if you're not up for it Then you're better off doing it more gradually and more slowly because what it did is it raised the level of Expectations that not only everybody else had for him, but the level of expectations that he had for himself so if those Expectations rise and you can use that as a catalyst for other much more important aspects of self-improvement Because as important as this is this isn't super and this isn't integrity. This isn't your moral compass This isn't your your relationship with your family This can just facilitate this But if you can handle a drastic change in the way that people treat you differently because your expectations are raised when you start To dress better make a drastic change and live up to those expectations and my brother-in-law wasn't quite ready for that and so he started to fall back to the way that he used to dress Because he was comfortable with the way people treated him based on the way that he used to dress So if you're not quite at that point and you know that you still want to improve Which you wouldn't be here if you didn't want to improve then just do it gradually do it step by step and take that developing approach And then at the point when you start to figure out what you want to do That's when you flip the switch and you go into a deliberate approach Now I know what I want to do for a career I've known that for three and a half years and I've been able to double down I don't have to think about what would happen if I were in a different company or if I were in a different industry Or if I were doing something different because now I know where I am and what I want to do I can take a deliberate approach and I can double down on it and the same thing happens with your appearance Once you know the general direction in which you want to head then you can double down You can start to get more deliberate and that's when you can really really start to dress well So how do you do that?