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Someone in our Premium Ghostwriting Academy asked me recently how my daily and weekly schedule has changed over the years. So what my schedule was like When I was 24 years old I was working a full time job and writing on the side versus when I was 26 I quit my job and I went all in on ghostwriting compared to when I was 27. I started scaling myself into a ghostwriting agency compared to when I was 28 and at that point I was managing 23 full time writers, editors, salespeople running a multi seven figure ghostwriting agency and then compared to when I started ship 30 with Dickie and then Typeshare and category pirates and now Premium Ghostwriting Academy and how today we manage a team of around 20 people that does around $7 million per year, has a portfolio of our different writing related businesses and so if I'm being totally honest, my routine has changed tremendously over the years. As I'll walk you through certain years had great rout routines and other years had horrible routines. And I'm going to end this video explaining some of the things that I've learned going through so many different seasons of life and business over the past 10 years. And real quick before we dive in, a meta concept I just want to share is the reason people obsess over routines so much is because fundamentally we all understand that we have the same number of hours in a day. You know, Jeff Bezos doesn't have more hours than you do. He just figured out how to get more out of his hours than you've figured out how to get out of your hours or I've figured out how to get out of my hours. So we all fundamentally have the same resource. That is time is the core resource. Which means a lot of success comes down to your ability to do three different things. One is know the right things to work on. Another is making the time to work on them because you might know what they are, but you're just not making the time to do it. And then third is working on the right things in the right order. And this is something that took me a very long time to understand. A mentor of mine used to say all the time, if you give 10 entrepreneurs the same resources, they might all start in the same place, but they will end up in radically different places and unlock completely different outcomes from each other. Five will go bankrupt, two will build okay businesses, two will build really incredible businesses, and one will become a billionaire. But they all started in the same place and they were all given the same resources. But because each person chooses to work on different things, and more importantly, chooses to work on things in a different order. That is what allows them to unlock outsized returns. And so whenever you hear people talking about what is the perfect routine, first of all, there is no perfect routine. Second of all, the routine that works for one person might not work for someone else. And third of all, the goal is actually not really to build a routine. The goal is to figure out those three things. What is the right thing to work on right now? How do I make sure that I create the time to work on it? And then what is the next correct thing? Am I doing these things in the right order? And the order matters. It matters more than speed. It matters more than anything else. And so I'm going to walk you through these different routines and schedules that I had over the past decade so that you'll start to see how things changed depending on what I felt was necessary or the priority at that time. So let's go back to age 24. So this was 2014. My schedule at the time was extremely rigid. So what it looked like was wake up around 6:30 in the morning, shower, get ready as quickly as possible. I was really into meditation at the time. So I would always try and do at least a 10 minute meditation every morning. That was, it was very important to me in that life chapter and I was really interested in it. I wanted to be sitting down and eating breakfast by 7am usually something very simple like a bowl of oatmeal took me two minutes to make. You know, at the time I didn't have Internet in my apartment. And the original reason why I didn't have Internet was because after I paid my rent, after I bought groceries, and after I bought my monthly train pass so I could commute to and from work, I literally couldn't afford it. I did not have an extra $70 a month to pay for Internet. So during breakfast and every other time I was in my apartment, I would just read. I would just read or write. And over time I got so used to that. And I started to realize how much more productive I was by actually not owning Internet for chapter of my life that I set a goal to myself saying I will not allow myself to get Internet until I publish my first book. And that's what I ended up doing. I didn't have Internet for four years and I ended up publishing my book four years later. And then I finally got Internet. So small little tidbit from that chapter. My goal was to be out the door by 7:20 in the morning so I could catch the 7:30am train. I would commute an hour to work both ways. So I'd leave around 7:30 and I'd get. I was living up north in Chicago and I had to commute all the way down in, into the middle of the city and then into the West Loop. Usually took an hour. So I'd get there around 8:30, get to work around 8:30, spend the first 30 minutes, you know, making coffee, organizing my stuff for the day, getting ready for whatever meeting I had at 9am with the team, that sort of stuff. And then I would work from 9am till about 5:30 or 6pm and all day. I mean I, I learned a lot in that job. I was working at an ad agency. It started to click for me. You know, I didn't enjoy it at first, but it started to click that I was getting paid to learn so many skills that I was ultimately going to need to know how to do. You know, I started out as a very entry level copywriter and I would proofread documents all day long and I hated it, it was so boring. But then I reframed it to myself and went, well, Cole, if you want to be a writer, you should probably get pretty good at editing and close reading. So treat this as practice. So that helped me, you know, have, have a more conscious relationship with my work. Then I started getting into social media. Content writing for clients. I hated it. I was doing content writing for like coconut water brands and random clients that I like, really was not interested in. But then I reminded myself, well, Cole, you want to make it as a writer and writers should probably know how to write on social platforms, right? So then I was like, okay, I might as well treat this like I'm acquiring a skill. I ended up playing just about every single role you could play at this small ad agency, talking to clients. I eventually did sales, client management, internal, like hiring, hiring documents. I ended up playing every single role. And every time in that moment I thought it was a waste of time and I was like, wow, spending all day, every day doing all this stuff that I'm really not interested in. I just want to write. And then I didn't realize that I was acquiring all the skills that I would later use to build all of the businesses that I've built since then. So I just. Little side note for you, whatever you're doing right now, you probably underestimate how many different skills you're acquiring and how you are getting paid to acquire those skills. Which again is why I'm Such a big proponent of ghost writing because ghost writing allows you to practice and allows you to get paid to learn all of these skills. So then I'd work until you know, 5:36pm, usually around 4 or 4:30, I would grab my second cup of coffee. That was actually my halfway point in my day, which you will see. So I'd recaffeinate around 4pm Usually around 4:30 or 5, I would pull up a quick Quora question. I didn't have Internet in my apartment, so I would sit at the office around 5pm I would find a Quora question that I wanted to answer and then I would write an answer to it. And that's how I started writing on the Internet. I mean, started writing on the Internet after college. I mean I had been doing it since I was a teenager, but that was when I started to really take it seriously. I do that real quick. Then I'd try and catch the 5.30pm train, sometimes 6pm, another hour. So I wouldn't get home till like 7. While I was commuting the hour in the morning and the hour in the late afternoon, this is when I would read. And at 24 years old, 25 years old, this is when I started to read the most that I've ever read in my life because I had two hours a day where I was just sitting on a train. And so I just devoured books and I studied fiction in college and this was really the first time that I started reading nonfiction. I read a lot of business books, self help books, Simon Sinek. Start with why. Napoleon Hill, Think and Grow Rich, Dale Carnegie, how to Win Friends and Influence People. I just, I just went down the list and I was probably reading a book a week and so it was commuting time, you know, but I, I made it productive and so I, I did a tremendous amount of reading in those years. Then I'd, you know, get home around 7pm I'd eat a quick snack, I'd head to the gym. I was really into bodybuilding at this point. I was very into bodybuilding in college. I was like a year out of college at this point, just starting to get into the real world. And I still wanted to keep that habit. I was also in great shape and really healthy. And you know, it was important to me that I at least go to the gym for an hour, hour and a half a day. So I'd eat something real quick, go to the gym, be home and eating dinner by like 8:30. And then my goal every night was to be sitting down at my desk, either eating dinner or having just finished dinner by 9:00pm and then from 9:00pm till about 11:00pm, sometimes midnight if I was really fl, and sometimes only 10:00. You know, I'd only get an hour in if I was just exhausted from the day. But those last two or three hours of the day were the only hours that I really had fully to myself. Aside from going to the gym and just keeping my body working, those. Those were my only productive hours for anything that I wanted to work on. And I was living up north in Chicago. I was living in a very rundown apartment. I didn't have air conditioning. I didn't have really any furniture. I had a bed and a desk. And that was literally it. And very quickly after graduating and entering the real world, I started to realize that if I didn't reinvest that little bit of time into myself, my life was just going to be waking up, getting on a train for an hour, working all day, getting back on a train, coming home, having dinner, watching TV or YouTube, going to sleep and doing it all over again. And that was just not enough for me. And I felt really stuck in this position where I wanted to make more money, but I really didn't want to make more money doing something that I. That I didn't love. I was so determined to figure out how to build a life around writing. And yes, there was writing involved in my work, but really it was. I was showing up to a job and I, you know, I would bounce around and I would sometimes use writing, but I was just at the whim of whatever the agency needed. And it really wasn't the thing that was my true passion. So I had to figure out how to make my passion profitable. And that is a very hard thing. And the only conclusion that I could come to is I have the last two hours to myself, and I can either squander those hours or I can reinvest them very deliberately. And so this was essentially my schedule from age, you know, 23, 24, right out of college, 25, 26. I basically lived this way the whole time. And my whole goal, every single day, it was like I would wake up and the whole day was just, I have to get through this. I have to get through this. I have to get through this all the way until 9pm and then I could sit down and go, now I can do my writing. And at the time, just to show you how little I knew at the time, my writing, aside from starting to write on Quora and sort of doing that, you know, 20, 30 minutes a day right after work. The writing I was focused on was writing my first memoir called Confessions of a Teenage Gamer. And I had no idea what it looked like to make money as a writer. All I knew, and all I thought was that if you wrote something really great, if you wrote a masterpiece, somehow the world would reward you. And so I spent those four years deprioritizing everything else so that I could write this memoir, which, you know, in many ways I still stand by. I think it's the best piece of work in my library to date. And I wrote it a decade ago. I still think it's the best thing that I've ever written. But it required me to give up a lot in order to prioritize that time. And so I didn't really go out. I didn't really spend weekends with friends. I never went out on weekdays ever. Maybe once a quarter, once every six months, I would go do some sort of event. I'd go to a music festival or something. You know, maybe once or twice a year, I'd give up a weekend and I'd go visit my family or something. But for the most part, I really, really prioritize those last two hours of the day and my weekends. On weekends, I would just wake up first thing Saturday morning. I'd write for three hours. I'd go to the gym, break for lunch, come home, write another three hours, hang out the rest of the day. Sunday, I'd do it again. You know, my goal on the weekends was to double or triple however many hours I got of practice during the week. And so as a result, you know, I got. I got a lot better at writing very quickly because I was prioritizing it over everything. The cost was. I didn't really have much of a social life. I endured a lot of peers challenging me constantly. You know, like, people at work being like, come on, we're going out after work. It's Tuesday. Why don't we go get tacos, go get drinks. Let's go do something, you know, And I'm like, sorry, catching the train. I'm going to the gym, going home, getting my two hours writing in. And that was. That was the challenge of that life chapter. But four years later, I quit my job, I published my book, and, you know, the rest is history. So I think it was all necessary. But I am aware in hindsight that I was probably more rigid than I needed to. I could have taken a couple more weekends off. I could have prioritized friends, you know, 10% 20% more. Maybe I didn't need to be so, so strict with myself, but if I had to pick between the two, I'm glad that I did what I did. So that was, that was pretty much my, my weekly, my daily, my weekly, my monthly, my yearly routine at that age. And my schedule didn't really start to change until 2016 when I was 26 and I was getting ready to quit my full time job. So quick context here, just so you understand what was happening at the time. When I got ready to quit my job, I really didn't know how I was going to make that amount of money again. I didn't know how I was going to pay my rent. The context of what was happening at the time is that I had made a lot of traction on Quora. So I felt pretty confident in my ability to write and to write things that people wanted to read at this point, you know, it's not like I had some huge audience. I maybe had 8,000 followers or something, but I had racked up millions and millions of views. So I knew, and there was plenty of signals showing me, hey, there's some potential here. There's a lot of data trending in this direction. You would be smart to double down on it. The same day I quit my job. Also, coincidentally, I didn't really plan for this, but then as it started to line up, I thought, oh, this is pretty cool. But the day I quit my job. So my last day of work showing up to the office was the same day that I published my memoir, Confessions of a Teenage Gamer. I self published it, I hooked it up to my website, I had Stripe, I put it on Amazon. It was a very cool and exciting day. And so that also felt like a big loop in my life was getting closed and I felt ready for something else. I was ready to start a new project. And at the time I was making around a thousand, $2,000 per month writing columns for Inc. Magazine. And how that worked was I had had so many answers on Quora republished in Inc. That they offered to give me my own column. And at the time, they paid their top columnists per page view. It was something like a penny per page view. So it was very. You get compensated based on how much traffic you generate. And so I had gotten really good at generating traffic on Quora, you know, and originally they were like, can you write, you know, four or six, I forget what it was, columns for us per month. And I came back to them and said, could I write one per day? Because I had a Mechanism to make money. That was the first time I'd ever had a mechanism to make money from my own writing. They were like, you're crazy. But sure. And that's what I did. So every single day I would write a Quora or an Inc. Magazine column and I drove millions and millions of pages for them. And I didn't quit my job until I did that for about six months and proved to myself, you know, it's not just, oh, I went viral one month and I made $1,000, but then it goes to zero the next month. I wanted six months of data to prove to myself that I could generate that amount of income over and over and over again. And I could and I did. And so after six months of tracking that and finding that average, okay, on average I'm making 1500 bucks or whatever from Inc magazine. That was like 40% of what I was making from my full time job. So when I decided to quit, it was really a calculated bet saying to myself, well, I don't really know how I'm going to cover the other 60% of my income. I just assume if I had eight or ten more hours each day to reinvest in myself, I bet I can figure it out. And so that was really it. It was a risk, but it was a calculated risk and I trusted myself and my ability. And I had enough data at that point showing me, you know, I wasn't just closing my eyes and jumping off a cliff and hoping that it all worked out. I at least knew which direction I was going to run in. And I had enough under my feet to know I felt confident in my ability to figure it out. And then as the story goes, you know, if you've been following my content, you know, because I've told this a million times, but I fell into the world of ghost writing, landed one client, one led to two, two led to four, four led eight. All of a sudden I was making 20 grand a month doing ghost writing literally two months after I quit my full time job. And it was a very surreal thing. It happened very, very quickly. But something that I haven't talked a lot about and I haven't shared very much of is right around the same time this happened, like right before I decided to quit my, my full time job is I was lifting in the gym one day and just in the middle of an exercise I felt this pop in my neck. I ended up herniating a disc. And so when I quit my job and like going into that and then after quitting my job, basically I had to stop going to the gym. Um, I had this herniated disc. It was extremely painful. I was basically on painkillers for three plus months. Um, I would sit at work and just have like an ice pack on my neck the whole day. Um, it was one of those things where it wasn't severe enough to need surgery. So I basically just had to sit around and wait for months and months and months for it to heal on its own, but I couldn't lift. And the hardest part about that wasn't just that I was in pain. It was the fact that this, this vehicle for me going to the gym and really just my love for bodybuilding and lifting weights and everything just felt like it was being ripped away from me. And so I no longer had this, this vehicle for, you know, letting my stress out every day or even just like feeling the endorphins of going to the gym and all of the things that come with it. And so that's a really important part of this story because very quickly after I quit my job and I couldn't go to the gym, so I had this, you know, extra two hours every day. And at the same time I'm on painkillers and I'm, you know, struggling a little bit with depression and like, a lot of things were very challenging about that. And so my daily schedule basically became wake up, eat breakfast, immediately dive into emails, because now I have clients, you know, take calls, take client calls, ghostwrite more emails, make lunch more calls, ghostwrite more emails, and then write on Quora and then keep writing my columns for Inc. Magazine. And then maybe at night I would talk to my long distance girlfriend who's now my wife. You'll see that theme over the years. And then I'd go to bed and I'd wake up and I'd do it all over again. And so my entire life, you know, just to paint the picture very quickly, when I no longer go to the gym, so I don't have that outlet. I. I'm not going to the gym, so I'm not seeing my gym friends. So I don't have my, my literally the only thing even resembling a social life, I just quit my job. And so I don't have the accountability that comes from working with other people in a team and everything, you know, I. And so because I'm not showing up to an office, I also don't have the social life that comes with work when you do show up to an office. And so every single day was just me and my girlfriend at the Time was long distance. I was in Chicago, she was in Arizona. So every day was just me in this little studio apartment with no air conditioning, sitting at a 15 desk, ghost writing and talking to clients for 8, 10, 12 hours a day, making the most money I'd ever made before in my life, go to bed and do it all over again. And so, on one hand, you know, this chapter was extremely lonely for me. It was extremely taxing. I started to see my health take a toll. I. The only time I would leave my apartment was literally to walk across the street to get a coffee at the coffee shop or something. And I also lived in this perpetual state of fear because I had just quit my job, and this was the first time that I was ever 100% reliant on me. You know, my ability to go hunting to find some clients, put some food on the table. And so I was terrified every day that that was going to go away. I was like, yeah, great, Cole, you made 20 grand this month. And then I would be afraid that the next month it would all just vanish. And so I lived in this perpetual state of fear and scarcity, thinking that this wasn't going to last, which made me feel like I had to work harder. But I was already working 8, 10, 12 hours a day by myself, not leaving my apartment, had no social life, wasn't going to the gym, wasn't taking care of myself, you know, was. Was losing weight because I wasn't prioritizing, really eating. I didn't have a reason to eat like I used to because I wasn't going to the gym. And it created this vicious cycle where for that year, it's like, I saw the number going up in my bank account because I was making more and more. But every aspect of my life was declining in. In health, in, you know, my relationship felt taxed. We were dating long distance, like I wasn't seeing friends. And this was really the beginning of. And you'll see over the next couple years, this was the beginning of things being really challenging because I. In hindsight, I can recognize that the root problem was I was constantly living in fear that all of this was going to go away. And until I addressed that fear, everything else was just a symptom of that. But unfortunately, it took a long time for me to figure that out. And so what happened was I continued scaling myself, and I became more and more successful on paper, but every other aspect of my life, except for the revenue of my business, which was going up, was going down, you know, health down, relationships down, social Life down, everything was going down. So then my schedule started to change the next year. You know, I was 26 years old when I quit my full time job. I was ghostwriting by myself. I was sort of going through this lonely phase. And then around when I turned 27, me and one of my closest friends decided I had stumbled onto something really interesting. And we thought we could scale this into an agency. And the plan was he would talk to the clients, he would do all the client facing stuff, and I would do the ghostwriting. And then we would scale by hiring ourselves out of those roles. So he would hire editors under him and he would train editors to talk to clients, I would train writers and I would teach them how to write and ghostwrite like I did. And then that's how we would scale the business. And we would both be responsible for sales and taking sales calls. And so that's what we did. You know, in the first 12 months, it went from just me and him playing this role of editor and ghostwriter to around a team of about 10 full time people and probably 30 or 40 clients at a given time. And we were doing over a million bucks a year in revenue as a ghostwriting agency. And at the time, the joke, I like to say is that my schedule at the time was basically wake up, good luck, go to sleep, do it all over again. And what I mean by good luck is there was no routine. I basically woke up every single day and just reacted. You know, I would wake up and one day it would be eight sales calls in a row. The next day it would be reading client pieces and playing quality control for writers. The next day it would. I would have two podcasts that I was talking on, or I would be getting on a plane to go fly to some other city to speak at an event, and then I'd fly back the next day. Some days I'd be interviewing potential people to hire. Other days I'd be training the people that we just hired. So every single day really didn't have rhyme or reason to it. It was just pure reactionary behavior. And of course, amidst all of this, the most taxing part was that we were growing so quickly that maintaining quality, especially for something like ghostwriting, is very hard when you're hiring new writers and you're growing as quickly as you are. Like there was, there was an eight, nine month stretch where we were hiring two to three to four full time people every month, month after month for eight, nine months in a row. And so you're never really stopping or pausing to Clean up things at each level. This is why, you know, I lived it. So whenever I'm helping other ghostwriters scale now, that's one of the first things I tell them. I'm like, you got to here, stop. Like, stop taking on clients. I don't care who offers you money. Pause. Because you need to clean things up at each level. And I unfortunately, learned that lesson the hard way. But the hardest part about this phase is that because we were growing so quickly, writers would come up with, you know, they would do the writing for clients, and then a client would come back and be unhappy with whatever the piece was. And so I would have to step in and basically rewrite the piece, which, again, in hindsight, huge mistake. Like, there was. There was a much deeper level problem that I should have solved. So what would happen is I would be there. Every day was basically a sprint between I'm on a sales call immediately after. I'm jumping onto, like, a team call immediately after. Clients unhappy. I have to step in. I have 30 minutes before my next call. I have to rewrite their whole piece in 30 minutes. Set the timer. Ready, go. Oh, I just finished. Okay, I'm jumping on the next sales call. Oh, wait, I'm interviewing the next person after that. Oh, another client is unhappy. I have to rewrite their piece. I only have 30 minutes. Set the timer. Boom. Go do that now. And so, you know, at the time, that was about as taxing as it gets in hindsight. I go, wow. I developed a superpower because I really. I got to the point where in 30 minutes or less, I could take a client that I had never go through anything for before ever. I could open up their file in 30 seconds. I could understand what their voice was, what how it needed to sound, how I needed to structure it. I could skim through the whole transcript in three minutes and go, oh, those are the main points. I've shelled the whole thing out in my brain. Got it. And I could write the whole thing in less than 30 minutes and then immediately jump onto my next call. And so I don't know that I would recommend that. I think that was a very taxing way of acquiring some of those skills. But it ended up becoming a superpower for me because that was my day every day for, like, two years, and it was brutal. And my health suffered. And, you know, I ended up getting so stressed that I ended up in the hospital with shingles. And that was one of those moments where I had to go, okay, something about this isn't working. Like, you have to chill out. I was also living in LA at the time, so I was on the west coast. And that meant I was always three hours behind. So I would wake up at 6am and immediately my phone would have 100 notifications and Slack messages and emails from clients and everything. I would frequently be taking calls starting at 7:00am, you know, but, and, but I worked until 10 or 11pm the night before. And so I, and I didn't have time for breakfast and I just, I became a caffeine addicted, just cliche entrepreneur. And it was a problem. And this is pretty much how things went through age 28 and 29. And in hindsight it was so unhealthy. And the biggest problem was that our agency kept growing. So on paper we were crushing it. You know, we were, we were growing, we were growing so quickly that we could have applied for whatever Forbes or Inc. Magazines like fastest growing companies each year. And we contemplated it because we were like, well, we meet all the criteria. We're growing like crazy. And so on paper I looked like a quote unquote successful entrepreneur, which is so stupid to look back on. But really everything else in my life was a net negative. I had lost all the muscle that I built after seven years of bodybuilding, which killed me. I was completely addicted to caffeine. I couldn't survive the day without two or three cups of coffee, morning, afternoon and into the evening. I never prioritized getting help on my shoulder or my, you know, where I had this herniated disc. I lived in a constant state of just mild pain. And it was such a weird feeling to sit with because I should have been proud of myself, but I really wasn't. I was just stressed all the time. And again, like I said, my entire life was just wake up, react to whatever's happening, eat dinner, go to sleep, do it all over again. And unfortunately, this didn't really change until the end of 2019. So right before I turned 30 years old and basically after building and running this agency for two and a half, three years, my co founder and I just realized we needed to scale things back. We had grown way too quickly in many ways. We sort of felt like it wasn't salvageable. We could have maybe cut the team in half and tried to go back to a smaller scale, but we were, we were so burned out that we just thought if we're going to ever do something like this again, we almost need to start over. And so very hard decision. But we, we decided that we were going to let the whole team go and essentially fire 90% of our clients, which very weirdly ended up being, I think, the right decision, because five months later, covet hit, and that would have had just a massively negative impact on our business. And so that's when I started to prioritize myself again. I said, I'm. I'm not going to focus on really making money in this chapter. I'm going to reel things back. I'm going to get back to the basics. I'm going to build a new routine. So all through Covid, I basically would go straight for a couple clients in the morning. Just enough for me and my co founder at the time to pay our rent and save a little bit of money. In the afternoon, I got back to my own writing. So I started working on my next book, the Art and Business of Online Writing. And then I'd go to the gym and start to prioritize my health again, hang out with my girlfriend. We had just moved in together, and that was it. It was very simple. This. This chapter of life, especially going into Covid, was really not about making money or scaling my earnings. What it was really about was getting back to a place where I wasn't in a constant state of stress and anxiety and fear and feeling like I had to keep growing this business, even though every time it would grow further, it was a net negative on my life. And so that's what I did. And for that whole year, year and a half, I basically just deprioritized business goals and got back to my own writing. And this was really the beginning of, I think, you know, the second act and everything that came after this. So around the end of 2020, so right around me turning 31, that's when I started to ramp things up again. So at the beginning of 2021, I started two new businesses. One is Ship 30 for 30 with Dickie, and another was Category Pirates with Christopher and Eddie. And if I'm being completely honest, I was very apprehensive about doing both of these projects. I saw potential. They both excited. They both excited me, clearly, because I ended up doing them. But there was a part of me that really felt it was almost like PTSD from my first business. And I really felt like if I was going to do it again, I wanted to be very careful not to make the same mistakes. And so even though both of these businesses grew very quickly, at the time, I felt like I was taking it slow because my biggest problem building my agency was that it was like I understood how to grow things and So I just grew to infinity. I just kept growing as fast as possible. So I really, this was one of those moments where I really had to slow down and reflect on the mistakes that I had made and tell myself, okay, if you're going to do this again, you have to do things differently and you have to have a different North Star, a different compass, so that you're not driven by the same things which required, you know, a lot of reflection, a lot of journaling, a lot of therapy. I'm a huge proponent of therapy. I've been in weekly therapy for 12 years. And so if I look at what happened from there, so much of it wasn't really business insight. It was really personal and life insight and realizing, you know, what did I need to feel good? What was inspiring to me, what was sustainable for me, what was. What were the things that I could do day after day after day and not get burned out by them? What sort of businesses did I want to build? And so as I went into both of those ventures, I didn't really know where they were going to go. I just felt like as long as I was enjoying the journey, I was game to work the next day on it. And that first year, I had no big expectations for either one. I just kept spending time on them, kept enjoying the time I was spending, kept seeing them grow, didn't feel like the growth was costing me and, and making me have to give things up where that would put me in an unhealthy spot again. So I would keep working on them and then they would keep growing. And it was, it was a very, very natural process. But I was still ghostwriting at the time, you know, because that's how I was paying, paying my bills in the beginning. And ship 30, you know, wasn't making any money. Month one, month two, month three, you know, category pirates wasn't making any money for the first couple months. So really I was ghost writing and then doing these other bets and just saying, well, we'll see how they pan out. And so I would ghost write usually for one or two clients each morning. And then in the afternoon about three days per week I'd work on ship 30, and the other two days per week I'd work on category pirates. And then I would just keep prioritizing, like getting back to the gym slowly but surely, you know, usually every day around 5, 6pm and that worked really well for, for a while. Uh, again, I was not making a ton of money in the beginning, but a year later, you know, those slow and steady habits built ship 30 into the fastest growing writing community and challenge on the Internet. We did over a million dollars in revenue by the end of that first year. And category pirates, you know, again, slow to start, but a year later was a Top 5 business paid newsletter on Substack. And it wasn't making as much as ship 30, but it was trending in an interesting direction. And then, you know, like, over the course of that year, as things ramped up, my weekends, I started working more on weekends. I had finished the art and business of online writing. I published that book, I started working on the next one. You know, I. I just, I. I began to feel more comfortable and confident pushing myself again, but within reason and sort of learning all of these things that I had learned. But as you'll notice, I mean, a lot of these quote unquote schedules are very simple. And the whole goal and what I ended up learning is that the simpler the schedule, the more progress you can make. You know, you want to work on fewer things. And so after this year, this was one of the big decisions that I had to make, is that I was starting to feel like I was getting pulled in different directions. So then in 2022, I moved to Miami so that Dickie and I could work together in person. And 2022 was really the year that I started to dial in my schedule. Um, I was working very hard and I was juggling a lot, but I was also starting to feel really healthy again. And it was the first time that I was starting to feel like myself in my body again ever since that injury. Um, and I was beginning to learn how I could do both, how I could push myself in business and with my writing very hard, but I could still prioritize my health and, and feeling good and having, you know, healthy, sustainable relationships and having somewhat of a social life. And like, this was the first time that I really felt like I was finding balance. Even though I wasn't chilling, I was still pushing very hard. And so for almost that entire year, I had the same schedule. I would basically wake up, have breakfast, meet up with Dickie in the morning. There was a period in Miami where we were getting together every single day. Then we would, you know, spend all day building something new in ship 30 and. Or we would be building while running a cohort, which was taxing in its own way. I'd work until around 4pm and then that's when I would go to the gym. And this is. This was the moment I decided to make a really big investment in my health. So when I moved to Miami. I hired a personal trainer, a physical therapist, and I got stem cells injected in my shoulder to help heal a bunch of the torn, you know, I had a torn labrum and a bunch of other things that happened as a result of herniating this disc. And just to be fully transparent here, you know, these were, you know, they weren't massive, but they were sizable investments in my health. And at the time, it's not like I was making crazy money. I felt these investments in my health. I just had gotten to a point where I realized that the return on investing in my health was so much higher than whatever it would have given me or made me if I had taken that extra thousand bucks a month or whatever it was and put it into Apple stock or something. And this was the first time really in my life where I made that sort of decision. All before this, I just erred on the side of I'm not going to take care of myself and I'm going to take the extra thousand bucks a month and say, oh wow, I'm saving an extra thousand dollars a month. And it was all about money and making money and saving money and investing money. And it took me a long time to realize that, you know, you are the most valuable part of your business and your health is really what allows you to work A the hardest and B, the most productively. And so, you know, at the time this felt like a big investment. And a year later, it completely changed my life. It was, I finally was starting to feel strong again. I finally starting to feel healthy again. Physical therapy helped me completely fix my shoulder, which had been in pain for seven years. Stem cells healed the torn labrum, like really, really insane progress happened in that year. But it required me to prioritize it not just from a time perspective from, but also from a financial perspective. And no surprise, it made me way happier. It made me a lot more productive and it ultimately allowed me to make way more money. So it was a significantly ROI positive decision. But at the time it felt like a risk, which just seems so silly in hindsight. Then I, so I'd go, I'd. I really prioritized, you know, 4pm every single day I was taking care of my health. Get home around 5:30 or 6pm I'd close loops for the day so I'd be on Slack from 6 to 7pm roughly. I'd sit down for dinner around 7pm with my dog and fiance who's now my wife. And then from 8pm to 10pm usually most nights I would work on Category Pirates and, and then on the weekends I'd, you know, get ahead on ship 30 things. I'd do personal writing or I'd catch up on Category Pirate stuff that had, you know, gotten deprioritized throughout the week because ship 30 was definitely the number one priority. And then category Pirates was like the number two fun side hustle thing that I had going on on the side. And all of that led up to in 2023, I basically realized that I had to make a decision. So at this point, ship 30 had grown to several million dollars in revenue, but Category Pirates had also grown in revenue. And Category Pirates had a really unique model where we had a paid newsletter as the engine. You know, people would subscribe to, read Category Pirates. Then we created other revenue streams by republishing all of our paid newsletters into books on Amazon. And then people would read the paid newsletter and read the books. And usually it'd be an entrepreneur or business owner or CEO or someone. And they would go, I love your content. Can you help us with our category design? And this is the world that Christopher and Eddie both came from. They came from the world of consulting and advising. I had had a good amount of experience doing that when I was living in la. I was an advisor on I can't tell you how many different crypto projects and companies would give me equity in exchange for helping them with their messaging and stuff like that. So I wasn't new to the model, but they had significantly more credibility than I did. They had just been doing it longer and they had been doing it with way bigger companies. And we started doing a couple deals. Some were equity, some were in cash. And we would help companies with their category design. And these were really big deals. You know, these were not like, pay me 10 grand and I'll help you with your cash. Category design. This was, you know, give us a million bucks worth of equity or give us 2 million bucks worth of cash and then, then we will go do this for you. And it became clear to me that I couldn't do both. I could not scale ship 30 and scale that business with Dickey and scale this consulting business with Christopher and Eddie. And to make a long story short, essentially I had to make a decision. I. I don't think that there was really a right or wrong answer. I think both businesses were very lucrative at the time and could have extremely lucrative. It really came down to who I wanted to work with and what type of work I wanted to do. And as I thought about it, I mean A the synergy between Dickie and I, and me, Dickie and Daniel, and now our whole team is just unlike anything I've really ever had before. And I just knew I was never going to give that up. But then on top of that, I was just really not interested in doing services and consulting like that. I knew it. Both businesses have different problems. It's just a question of, which bag of problems do you want? And I much preferred the bag of problems that we had building digital products than the bag of problems that come with working with, you know, CEOs and consulting and telling them how to run their company. The short answer of why is because with our businesses, I can take all the things I know and just deploy them into our businesses. When you're consulting for other people, you can, you know what the right answer is, and you know what they should do, but that doesn't mean they're going to listen. And so, so much of the work is you telling them, hey, if you go do this, this will work, and you will be successful. And then them giving you every reason why they don't want to listen to you. And so you just have to tolerate that. And a lot of times, they don't even do anything with the strategy that you give them. I was like, I don't want to make money that way. That's annoying. So I made the hard decision, and I told Christopher and Eddie, you know, I have to pick. I want to build ship 30 and what I've got going on with Dickie. And so I exited that business. Christopher, Nettie bought me out. I hired someone to replace me in that business to take over the writing of the newsletter. And at the time, just to be transparent, you know, choosing and making that decision meant taking a 30% haircut on my monthly earnings because category pirates was paying me a decent amount of money. And so by me choosing to exit the business, that fundamentally meant that I had to take one step back in order to take two steps forward. And as a small side note, that decision is something that I find a lot of people struggle with. Whenever I was talking through this decision at the time, you know, as I was thinking, you know, how do I do this? And, oh, my income's going to go down by 30, 40% overnight. I don't want to do that. I'm going to have to, you know, eat gravel for the next six months until ship 30 and our business sort of grows to the next level. Like, there was a lot about that decision that was hard. And whenever I would talk with entrepreneurial friends about it, the vast majority all pushed back and said, cole, you don't have to pick. You can do both. You can do both. And I have learned over the years that you can do both is the biggest fallacy in, not just in business, but just in anything you want to make meaningful progress on. And also all of the people that were telling me to do both, when I looked at their lives and their businesses, they were trying to do multiple things and they were all stuck and they were all struggling with it. Meanwhile, the entrepreneurs in my network that I would talk to that were way more successful than me, they all understood the decision and they all agreed. So, you know, the entrepreneur doing a million bucks a year was like, Cole, you can do both. The entrepreneur doing $100 million a year was like, Cole, that's the right decision. It's going to suck in the short term, but it's the right one in the long run. And so just observing that gave me the answer. And so I exited the business. I doubled down on building with Dickie, and I just accepted that my income was going to go down in the short term. But six months later, we, I mean, right after that is when we built pga. And six months later, PGA had completely eclipsed what I was doing with category pirates, and it had eclipsed what Ship 30 was doing. And PGA became our core business. So it was the right decision. It just required taking a step back to take two steps forward. And I find that, broadly speaking, when you're looking at routines and you're looking at how to optimize your life, that that decision is the thing that people struggle with. They really, really struggle with the short term loss for longer term gain. And oftentimes it's not even as long as you think. You know, it's not like you have to wait six years for things to change. It's like six months or less, you know, but there's discomfort in that. And, and if you want to continue leveling up in anything that's entrepreneurial, that is part of what's necessary. And so my daily routine since then, you know, since the beginning of 2023 has basically been the same. I, I wake up around 6:30am I'm at my desk by 8 most days. Now I batch all of my calls in the mornings, so I'll have calls from 8am to 10am or 11am, quick break for lunch, and then my goal is to do deep work from noon to about 4pm If I can get those deep work chunks in four hours a day, I can make really meaningful progress in the business. And in the mornings, you know, we have a larger team now. We have a team of like 20 people. So I just have to have calls. And that's just part of running a business at that size that keeps growing. Then I'll break around 4pm I'll go to the gym and or physical therapy. I've been keeping that as a habit even though I don't technically need it anymore. I just keep it. You know, I go get scraped or I go get cupping on my shoulder or I get dry needled just to stay healthy and stay proactive. Then I'm home by 6. I'll close loops from, you know, 6 to 7pm I'll go through Slack, any lingering emails, make sure I'm not the bottleneck for anybody. Dinner around 7 and then I'd say about half the days in a given week after I eat dinner, I will go back to work. So I'll spend another two hours before bed working on something. Um, it's especially weeks where I am call heavy and I don't get in as much deep work. Sometimes it just means I got to prioritize it elsewhere, you know, so I'll have calls all day talking with people and then 8 to 10pm is when I make serious progress on a new curriculum or a new digital product or something. The other half the days I just, I'm too exhausted from the day and I'll just, you know, zone out after dinner and just hang out with my wife and recharge. And then weekends, almost every weekend I work. So Saturdays I will usually reserve for some sort of personal writing, whether that's, you know, my own social content or that's working on a new book or some other side project I have percolating in the back of my brain. Maybe outlining a new digital product for us that I think would be really great, you know, three months from now or six months from now. And then Sundays I'll usually spend two or three hours just reflecting on the week and prepping for the next week, doing some light scripting and writing out notes for YouTube videos and podcasts like this one. I really, I feel very strongly that those two or three hours on Sunday are important for really getting the week started on the right foot. I find that whenever I don't do that, Mondays just feel way too overwhelming. And that's basically been my schedule. And it is a really, really nice blend of work hard but work smart and what I've learned, you know, and I just to share a couple takeaways for you. As I've gone through these different life chapters and built different businesses and taken them to different levels and all of these different things, my routine has changed, but the fundamental lessons haven't, and these will probably continue to be true as businesses progress from here. So the first one is working on the right thing is much more important than working hard. So said differently, it's better to move slowly in the right direction than move quickly in the wrong direction. And so much of where I went wrong in my mid to late twenties was I was so focused on measuring success by effort. So I felt like because I was working so hard and I was working 8 hours a day, 10 hours a day, 12 hours a day, every weekend, you know, I was working at night, I was waking up early. It disguised the problem. And I thought, I'm, I'm moving so quickly that that means I'm making progress, not realizing that I was moving quickly in the wrong direction. Very different than where I am now, which is I feel like I move a little bit slower on a day to day basis and I have a bit more balance in my life, but I am so much more aware of the right things to work on that as a result, our businesses grow faster. And so that's sort of the irony. You hear it, you hear it from people all the time, where they go, work smart, not hard. The problem is people don't know what that means. And that's a, it's a very rhetorical way of saying, you know, you have to work on the right things. And that is more important than working quickly and hard on the wrong things. The second is you are your business's most valuable asset. So if you build a business that requires you to destroy yourself, you know, destroy your health, destroy your sleep, sacrifice your relationships, et cetera, the business might be making money, but that doesn't mean it's a very good business. And it's much better. And this is what took me so long to understand, it's much better to start from a place of what do I want my life to look like? What are the non negotiables in my life? Like for me, getting to the gym three to four days a week is non negotiable because I would like to be able to walk later in life. You know, I would like to not have back problems when I'm 50. Hopefully that doesn't happen. And so that is very, really important to me. Which means if I build a business that requires me to give that up, that's not a very good Business, right? And so you have to start with these non negotiables in your life and then build a business around those things. And you know, it goes back to, I love great, you know, rhetoric pieces like this. But it's like as you work on the business, the business works on you. And what that means is that businesses are great vehicles for examining the decisions that you make in your life. And so often entrepreneurs that are overly stressed out, I'm saying this to the previous version of myself. Entrepreneurs that are so stressed out don't realize, you know, that they are their own worst enemy because they, they built the thing that is stressing them out. They built the thing that is making them have to compromise every other aspect of their lives. And so you have to view business as a mirror for yourself. And if you are unhappy with your situation, you have to take radical accountability and recognize you're the one who built it, and you're the one who built it that way. And it doesn't have to be that way because for every stressed out entrepreneur is someone else who does the exact same thing but is really happy and loves what they do. And so you have to figure out where, where are you making the wrong decisions going back to that little list, you know, where are you working on the wrong things that are causing you to build a business that requires you to have to give up so much of yourself? And then third, I feel like the biggest thing is that most businesses, no matter what size they are, really don't have daily routines. So you can't measure success on a day to day basis. You have to extend the time horizon. Most businesses and most entrepreneurs don't have daily rout, they have weekly routines. Because it's very rare that you will do the same thing every day, you know, especially as businesses grow and as responsibilities change. And like the business we have now is a great example. You know, I'm not managing one person, I'm managing 10 or I'm managing 20. Right. So fundamentally, could I meet with all 20 people in one day? No. I have to spread those meetings out across the week. Right. Which means I don't have a daily routine. I have a weekly routine. And so the same goes for whatever type of business you have or even if you're a solopreneur. Ghostwriting is a great example. Some days you batch all your calls together. Some days you only have client calls. Other days you only have sales calls. Some days you have no calls. And all you do is the ghostwriting. You know, if you set a goal of doing a hundred cold outreach messages per week. You could do 20 each morning or you could do all 100 every Friday. So it doesn't really matter what the daily routine is. What matters is the weekly routine. And are you able to get all of these things done over the course of five days or seven days? This is the biggest thing that has had to change for me over the years because I used to get really, really frustrated when I wouldn't get my personal writing time in every single day. And it took me so long to realize, Cole, if you want to build these businesses and you want to do a lot of different things and you want to have work life balance and you want to, you know, if you want the best of all worlds, you can't expect that you will do everything every single day. Which is why even today, my personal writing doesn't happen necessarily every single day. It might happen three days a week, you know, but I go, I want it to happen every Saturday. Okay? That's the goal. Great. Might not happen every Saturday, but that's the goal. And so you have to extend the time horizon and not judge yourself on a 24 hour clock, but instead over the course of five to seven days, that's how you slot all of these things in. And then the last thing that I want to leave you with is that if you're growing, your routine and your priority list will and it should change if it stays the same, fundamentally that means you aren't growing. So the goal isn't really to build a routine that never changes. The goal is to have the awareness of what is the right thing to work on, what is the effort and the amount of effort I need to deploy in order to make progress on that thing and in what order do I need to do them? You know, is this the priority today or is this the priority after I do those three things over, over there? And the priority list will continue to evolve. And you have to have the awareness to know what is the next priority for today or for this week or for this month. And it is the person who, who continues to work on the right things, AKA the next bottleneck in the business that makes the most progress, even if they're not the one working 12 hours a day. And I, if you take nothing else away from all of this, it's that effort is not the measure for success. It's are you working on the right thing again? It's better to move slowly in the right direction rather than quickly in the wrong direction. And you know, you will have periods. I still go through this, you will have periods where you need to work really, really hard for a day or really, really hard for a week or for one week. You go, I guess I'm not going to the gym this week because this is the priority, and we just got to get it done. And so you can do that for short sprints, and I would encourage you to do it when it's necessary. But recognize that those are deliberate decisions. And as long as that doesn't become your baseline, and that's not the. In order for my business to work, I have to sacrifice myself every single day, it's okay. The problem is when all of those bad habits create your baseline, and then you have no control over your life, and you are just reacting to everything. So I hope this was helpful for you. Um, it was really interesting, too, for me to retrace the past decade and how these different routines have changed. Um, but the. Again, the big thing is that the perfect daily and weekly routine doesn't exist. You have to figure out what that looks like for you. And the most important thing is that you're working on the right things.
