Don't be afraid to burn the boats

Sometimes you have to be willing to burn the boats, meaning in order to move forward, you have to let go of whatever's holding you back. And over the years, I found that to be true in relationships. I found it to be true in business decisions. I found it to be especially true in just your career as a whole. And I think the mistake that a lot of people make is they try and take a step forward while simultaneously keeping one foot in the old world. They hedge. And I'm not advocating for throwing caution to the wind. I am not that sort of person. Every time I've had to make a decision like this in my life and in my career, I did it very thoughtfully. I did it by first proving to myself, is this going to work the way that I think it's going to work? I find ways to reduce my risk. But at a certain point, I've also had to make the decision to leave something behind. And there have been a couple really specific moments in my career where I've had to do this. And at the time, it felt very risky. But in letting go of the old thing, that's what really allowed me to jump to the next level. So I wanted to share this with you because you might be thinking through a similar decision. You might be in a certain place looking at an opportunity, and you want to pursue it, but at the same time, you know, you don't want to leave the thing that's comfortable, and you don't want to remove whatever is currently giving you identity or money or community or whatever it is. Right. And again, whenever I've seen these giant leaps in my own career, they always came after making some sort of calculated bet where I had to leave the old world behind. So the first one is out of college, I worked at a small advertising agency downtown Chicago. I worked there for four years. My boss became a really close mentor to me. I played essentially every role you could play inside an agency. I started as an entry level copywriter, and I moved all the way up to editor in chief. And along the way, I did everything from work directly with clients and write all of their content to. I ended up moving into sales. This is like where I learned how to sell and land clients myself. I even learned how to manage my department and look at accounting. All of the skills that I inevitably would use as an entrepreneur, I basically just got to acquire them by working for someone else. And something that my boss and mentor always said was, you know, if you want to be entrepreneurial, the best way to learn is to work inside someone else's. Business where you have such little risk. You know, it's not your business, it's someone else's. But you get to learn a lot of the same skills and get paid to learn them without incurring all that risk at the beginning. And I always kept that frame and I stayed working there for four years. You know, I did not, I was not one of the, I go to college or I drop out of college and I start my first business. You know, I worked a full time job and in this ad agency for four years and I really viewed it as an exercise in accumulating all the skills that I wanted. And at a certain point, the question that I was left with, it wasn't, you know, I want to start my own thing or I want to go my own way. Like, yeah, I wanted to do those things, but I didn't leave until I felt like I had crossed a point where there was nothing else to learn. And this is a framework that has stuck with me over, over the past decade of being an entrepreneur. Is that every time I'm thinking about the next decision, my focusing question isn't is that going to make me money or how much money is it going to make me in the short term versus the long term? Yes, those things play into it, but the real focusing question is do I want to pursue this opportunity and what is it going to teach me? And I've always found that the best decisions I've ever made came from a place of I want to learn this thing or I want to build this skill. Not necessarily, oh, I think this will be lucrative and so I should just go do it. And so I really pushed working at this ad agency until I felt like the incremental return on my time and what I was learning was no longer worth it for me. And in order for me to learn the next batch of skills, I actually needed to take the risk myself. And so to hedge my bet, what I did was I started, I remember it was end of January, end of December, beginning of January in 2016. And at the very beginning of 2016 I said, I'm going to start tracking my side hustle income. And at the time I had written a couple ebooks on the Internet. I had a small following on Quora. Those ebooks were making me like a couple hundred bucks a month. And I was trying everything on the side to make extra money. I was trying to personal training because I was really into bodybuilding at the time. I was, I tried like creating social media strategies for like the restaurant down the street from me or like my friend's startup who needed help with something. I tried writing blog posts for companies as a freelance writer. You know, I tried everything. And every time I would land side hustle income, I would track it in an Excel sheet. And that was the same year I started writing for Inc. Magazine. And when I started writing Frank magazine, this was back in the day. They don't really have this model anymore. But what they would do is they would pay their highest performing writers a penny per page view. And in order to unlock that, you had to write a certain number of columns per month and you had to bring in a certain number of page views. And once I saw that that was a lever where, oh, if I go viral, my upside is essentially uncapped. Once I realized that, I started to experiment with, okay, well, what if I give this more and more time? And for months in a row, I basically just wrote and wrote and wrote Inc. Magazine columns. Like the average writer for Inc. Magazine was writing four to six columns per month. I wrote one a day. So I was writing upwards of 30 columns a month every single month. And inevitably, I became one of their top 10 most read columnists. I brought in some of the most page views of the entire publication, and I started generating, you know, 2, 3, 4, 5 grand a month from my Inc. Magazine column. And after I had sustained that for six months in a row, the question that I started asking myself is how much more could I make if I had eight more hours in the day? And that was really the thing that made me start to question, you know, is there a risk in leaving this job? Yes. It's also variable income. It's dependent on me performing. You know, I have to write lots of stuff and I have to go viral in order to make this money. But it started to open the door for me, and I was terrified to leave this job. But I did one day and I sat my boss down and said, you know, I think it's time for me to leave. And he was really sad, but he wished me well and that was it. And I remember at the time how much I felt like it was a burn the boats situation. And I really didn't want to leave my job thinking, you know, well, if this doesn't work, then I'll just go back. I really did not want. I didn't want to run into friction and then go back to where I was. I really set the goal for myself that I was going to do whatever it took in order to move things forward. And inevitably what happened was I Fell into ghostwriting thereafter. All of a sudden, I started landing clients. All of a sudden I, you know, double tripled my income. And then I started telling a friend, one of my closest friends, about what I was doing. And he was getting his MBA at the time, and he was like, we should turn this into a business. And this is the second big decision I had to make. And another sort of similar burn the boat situation was I showed him this opportunity with ghostwriting. He really wanted to build a business to apply all these new MBA skills. He was like, I'll talk to the clients, I'll do sales, you handle the writing. We'll build this into an agency. And at the time, even though he was excited about the idea, he was really afraid to leave his job too. And granted, I was still living in a studio apartment downtown Chicago. My rent was like 1,000 bucks a month. It was one room. If I sat in a swivel chair like this and just kicked my leg out, I could pretty much touch everything in my entire studio. Like, it was a very, very small, no air conditioning heater from the 1960s. Like, I was, I had just quit my job. Yeah, I had tripled my income, but I was hardly living it up, you know, and I haven't. I hadn't really upgraded my lifestyle yet. And. But because my expenses were so low, I was actually saving a lot of money very quickly. And so I saw a lot of potential in us building this agency together. And so what I did is I went to this friend of mine and I said, how about I remove all the risk for you and how about I start paying you a full time salary until we figure this out? And it was sort of jarring for him, and it was a huge bet for me because I was basically saying, you know, I just started making money. How about I take all of that margin and all of the excess income that I'm producing and I give it to one of my closest friends instead. So instead of padding my own bank account, instead of upgrading my own lifestyle, I was like, I'm just going to stay in this tiny little studio apartment and I'm going to give all my extra margin to my friend and then hopefully this works out. It was a huge bet at the time, and after a lot of conversations, he took it and he accepted. And it took us four months to figure out how to start landing ghostwriting clients through an agency offering. I really just had the same handful of ghostwriting clients that I had been working with. And I was working double time. I was working 1214 hours a day. And I was essentially paying for both of our lives. And I also had to fight the psychology of knowing that I was paying my friend a salary. And there were many days where he was like, sitting, sitting at home being like, boy, like, I don't know what else to do to land clients. And there were. It was very stressful. And then around the four month mark, he started experimenting with some new cold outreach methods. And we got our first client. And then like two days later, we landed two more clients. And then a week later we had a whole roster and both of us were making more than we had ever made in our lives. And it was a really exciting time, but it was a huge risk for me to take. And when I look back, you know, the reason I felt comfortable taking that risk was because I knew, like, worst case, if it doesn't work out well, I'll just keep doing what I'm doing, you know. But that decision is what propelled everything thereafter. That decision is what led to us building an agency. It led to us hiring people. It led to us working with hundreds of clients. It led to me accumulating a ton of credibility for the rest of my career. It, you know, that chapter of building that agency accelerated so many different things. And I don't think it ever would have happened had I not made that sort of bold decision. Now, do I think everyone should do something like that? Not necessarily. I think that when you're thinking through whether or not to take risks like that, I had another mentor explain it to me. Like the difference between one way doors and two way doors, you know, a one way door is you make the decision, you can't go back. You know, it's like choosing to get divorced, for example. A two way door is, well, I make the decision, if it doesn't work, I just go back, you know, and there's this almost cognitive dissonance where on the one hand it's like you want to burn the boats in the sense that you want to remove the option to go back to what's comfortable. But at the same time you want to recognize that a lot of the riskiest decisions that you make ultimately are two way doors. Like if they don't work, then it's fine. You just do what you were doing before, you know, and then you try again. You try again, you try again. Right. The third big moment, and this was probably the hardest one, was after building that agency for about three years, I realized a bunch of different things about that business. I realized that I, first of all, I Realized that me and my co founder were too similar. We are both, we were both very creative minded people. Neither one of us was really good at operations. And as a result, the operations of our business struggled a lot. And in order for the agency to keep growing, you know, once you cross a million bucks in revenue, $2 million in revenue, a lot of the game isn't really about ideas anymore, it's about operational complexity. And so I started looking forward in the business and realized, you know, we don't really have the skill sets in order to scale this thing. So that was the first big one. The second was we were both just so burned out. We had scaled the business so quickly. We went from me and him on the couch in his apartment to 23 full time employees, 80 plus clients at a time, 2 million bucks in top line revenue. And it happened all in 18 months. And looking back, one of the biggest mistakes that we made was we grew too quickly. And if I could go back, what I would have done is have paused at different levels and stayed there for a year or two years and really cleaned things up before moving on to the next level. And we never did that. We basically just kept reinvesting the profits every single month into hiring the next two people. Hiring the next two people. And as a result, we both didn't really take much money off the table. And so not only was there a lot of risk inside the business, but there was a lot of risk for us personally where, you know, we were doing 2 million bucks in revenue, but both of us had, you know, five grand in our personal savings. And so all of these things sort of swirled together. And I eventually reached a point where I realized this business is not going to get me to where I want to go. And this was a one way door decision, and this was another burn the boats decision. And the decision was I came back from a trip that I had taken, sort of get some distance and think, think through this. And me and my co founder basically decided, you know what, we're done. We're going to scale back this entire agency. We're going to fire every single employee on one zoom call. We're just going to rip the band aid off. We're going to fire 90% of our clients. It was a whole 180 going 100 miles an hour down the highway. And it was one of the hardest things I've ever done. But immediately after it was over, I felt like this weight had been lifted. And the hardest part about that decision, and I've talked to a lot of other entrepreneurs in my life about this, especially ones that are earlier in the journey or more aspiring, like they're working a job, but they want to be entrepreneurial. And over and over again, whenever I share that story or I talk about that experience, the thing that friends and other people around me often say back is, I can't believe you had the awareness to do that. Because the hardest part about that decision was that I didn't know what came next. I was basically just saying, I know this isn't working. I'm going to remove my identity as a startup founder. I'm going to remove this family that I had built for myself, you know, this company and all these people that I had invested time and money into, you know, and I had built relationships with and gotten close with. I'm going to remove the status component of I'm building this fast growing ghostwriting agency. We were the first ghostwriting agency to really use the term thought leadership marketing, to say we specialized working with CEOs and founders. Like all these things that were really cool and always got me a lot of validation and attention. And I basically said, I'm going to give all that up and I have no idea what's on the other side. And that was, I think that was probably the most important burn in the boats moment of my entire career. And if I hadn't made that decision, I would still be hacking away at that business today. And instead I made a really hard decision and I removed the option and I said, I don't know what comes next, but I'm gonna allow myself some space to figure it out. And what happened after was Covid hit six months later and I just spent a year and a half in Covid basically writing and journaling. And I wrote the art and business of online writing. And I worked with a couple ghostwriting clients to pay my bills and I stopped focusing on making money. And I just took a lot of time to myself to think through, you know, what did I learn from that 3 year experience and what do I want to do next? And by giving myself that space, two opportunities emerged. That's when I got connected with Dickie. A mutual friend introduced us and Dickie had this idea for a writing challenge. And that's also when I started Category Pirates. And both of those ended up becoming not only incredibly lucrative multi seven figure businesses, but a lot of fun and so much better suited for my skills as a writer. And for example with Dickie, Dickie is way more operational minded than I am. And so I actually found someone who better paired with my talents, which allowed me to do more. And it's like looking back, I can't believe how different my life would be if I hadn't given myself that space in order to explore other new opportunities. And so sometimes when you're in this burn the boat situation, you don't always know what comes next. Sometimes what comes next is you just need to give yourself some space and you need to figure out what you need to give yourself in order to attract the next opportunity. You don't always know what that is. And oftentimes, you know, a good metaphor is like being in a relationship with one person, knowing that you're unhappy, but not wanting to leave until you already have the next person lined up. Right. We all know that that's normally not how it works. How it works is you need to leave the relationship that isn't making you happy. You need to open up space in your life and then you need to attract something new and someone new. Right? And the same is true in your career and the decisions that you make. The fourth interesting burn the boat situation is that after we had built ship 30 to a multi seven figure writing program and after I had built Category Pirates into one of the biggest paid newsletters on Substack and we started doing category design deals with startups, we would get paid in equity, we would get paid in cash. And as a result, Category Pirates became a six figure paid newsletter, but a seven figure consulting business. And I reached this point where I really realized that I and I reached this point where I really realized that I couldn't do both. Both had the potential to be multi, multi seven figure, potentially eight figure businesses. But I had to pick one or the other. And the decision for me really came down to where do I feel like my skill set is better served, who do I feel like is a more reliable co founder and which business do I feel like has more long term scaling potential and is what I want to spend the most time doing? And after I sat with that question for a while, I knew that, you know, no shade to Category Pirates because it was an amazing business. But I knew that Dickie and I would accomplish more together. And so I made a really hard decision. And the decision that I had to make was I'm going to leave this other business that was really like my side hustle but was incredibly lucrative. And as a result, I'm going to take a 50% haircut on my personal income. So when I made this decision, I was basically saying I'm game to make half as much Money with the hope that me and Dickie can build something bigger together. And again, short term pain, long term upside. And I think the only reason why I was able to make that sort of decision and not freak out when the next month my income is down by 50% was because I had gone through these different experiences of sometimes you have to burn the boat, sometimes you have to burn the boats. And what happened was I exited category pirates. I doubled down on ship 30 with Dickie. We came up with the idea for Premium Ghost Trading Academy. And six months later, Premium Ghost Trading Academy had grown beyond what I was earning from category pirates. So again, you know, what do, what do a lot of people do when faced with that decision? They aren't brutally honest with themselves and they don't come to the conclusion I can only do one. What they do is they're afraid to let go of one and they go, I'll just add in a third. And what inevitably happens is that they all suffer. And you can't do that. I've learned this lesson so many times. Every successful entrepreneur I know, this is the same lesson they've had to learn over and over and over again. And so I wanted to share this with you today because if you're thinking through a decision or an opportunity, more and more the older I get, the more I learn you can really only pursue one thing at one time. And the moment that you try and go, well, I'll just do another thing, I'll just do another thing, you're not only adding more complexity, but you're decreasing the likelihood that any of them will be successful. And 99% of the time, the right decision to make is you gotta let go of one and you gotta not hedge your bet. You gotta burn the boats, you gotta say bye. You gotta exit, you gotta quit, you gotta remove the partnership. And that's a hard decision. So I just wanted to share those stories with you. I hope this helps. And don't be afraid to burn the boats.