One Question Friday: Where Did You Succeed Where Others Did Not?

Oh, Gaston, what's the Wi-Fi? I can't— no, I can't get in. Oh, it's ARGH. Connect your teams easier than connecting your Wi-Fi. HubSpot, grow better. All hands on deck. What's up, it's Sean, and it is One Question Friday, so we are taking one listener question and answering it on the spot. Hopefully 5 minutes, maybe 10 minutes. Let's see how this goes. I'm gonna play this audio recording that Ben sent to me. I haven't heard it yet. Let's hear it together. So I was having a cola the other day and I was thinking about this question. What do you do differently that allowed you to succeed that you think other people who had similar circumstances to you did not? Where did you succeed where they did not? Okay, good question. A very broad question, right? So we could take this a bunch of different ways. Here's how I want to take it. What are the common answers that you think people would give to a question like this? So, oh, what do you do differently that helps you succeed? Well, some people will say, yeah, let's break it into groups. There's the overly humble. The overly humble will say, you know, all credit to God. I've been blessed. I was really lucky. And, you know, I just kind of kept putting one foot in front of the other and worked hard. And, and I, uh, you know, I'm just fortunate to be born in this great place with all my, my limbs and my brain and all this, right? Okay, there's that path. All true things, but not that useful to somebody listening. So let's, let's kick that out. Also, that applies to many other people who didn't have the same result as you, so that certainly couldn't be it. Okay, second thing, hard work, right? Hard work is the next thing that people love to say. I I think because hard work feels like you earned it and it feels like you're not saying you're better than everybody else. It feels like you made better choices than others that were available to them too. And, um, who can argue with hard work? But the reality is I really don't work very hard. Um, or at least I don't feel that way. The thing I would say is I actually do work a lot, but I only work on stuff I like. And so I think hard workers, you know, like a janitor works hard. A line cook works hard, you know, um, a single mother works hard, you know. And so I, I don't really put— what I do has, you know, pretty much no physical strain, no emotional stress, a small emotional strain, I guess. And, um, you know, honestly, it's fun. Like, I do it because I enjoy it. I'm not doing it because I kind of feel like I have to do this in order to get what I want. That is not at all how I think about things. And there are many areas where I'm like, oh man, if I worked harder, I'd get a better result. And I can't bring myself to do it. I'm lazy in that way. Uh, the reason I work a bunch is because I really, uh, like, it feels like play to me. It's like watching somebody play a video game. You, you don't have to tell them, hey, sit down and focus on this for 3 hours. It's like, what are you talking about? This Call of Duty, of course I'll play this as long as I can. And so, um, it's not hard work. So what is it then? Well, you said something in your question, which was, What's different about you than like, uh, what did you do differently than like others like you in similar situations to you? Okay, that's a good way of asking the question. Let's take my college, right? Here I'm wearing the shirt. I went to Duke and there's a bunch of super smart people who went to Duke. In fact, at Duke I was a very mediocre student, um, middle of the pack, maybe slightly below average. And, um, you know, whatever, it's a good school, a lot of smart people, a lot of hard workers. Okay, I do think that I've had probably more success, you know, by kind of a traditional definition, but also just more fun than 99% of the other people who graduated in my class. Um, I could be wrong, no way to really know, but, uh, I believe that to be true from, from what I've seen. So what is different? What I would say is that most of my friends from college, most of the people I went to school with, played it quote unquote safe. And is it really safe? Uh, that's the question. And because to me, safe is good if you can get the outcome you want with the least risk possible. Safe is awesome, right? Like, I don't want to, you know, go to war because the outcome I want is to be alive. And like, I can just stay at home and that is way less risk than, um, going to war. But I also don't just stay at home and not drive places because I want to go see them. I want to go to a movie or I want to go to the grocery store, whatever. I have an outcome I want., but I'll take the least risk possible. I'm not gonna, you know, drive a motorcycle. I'll drive a car. You get the idea. So to me, safety is when you get the outcome you want with the least risk, uh, taken. What I saw was most of my friends from college took what was, what you would call a safe path if you wanted that outcome. The reality is that I definitely did not want the outcome that those jobs led to. So the jobs, the most popular tracks were doctor, um, kind of like lawyer, consultant, or banker. Those are like the kind of like high achiever paths that I would say most of the smartest people in, um, at my school did. And I guess the other one would just be like corporate manager of some kind. Okay, cool. So the problem with that is when I look at what success looks like for a doctor, for a lawyer, for a consultant, for a banker, or for a corporate manager. None of those by default would get me the outcome I wanted, right? I was like, dude, I wanna make tons of money. I wanna have fun every day. I wanna have action, creativity. I don't wanna just be doing the same thing over and over, right? Like I shadowed a doctor 'cause I was pre-med. I took the MCATs. I was planning to go to med school until I shadowed a doctor and I went to shadow him to figure out Can I do this? But by the end of it, the answer I walked away with was, I don't want to do this because it was extremely repetitive what was happening every day. And you're helping people, which is awesome, but I could not stand the repetitive nature of seeing patients and having the same, you know, as an orthopedic guy, oh, yep, you have a torn meniscus, you have a torn ligament, you have joint pain, and there's nothing we could do for you. That's what it was over and over and over again.. And so, um, I didn't want the winning path of that. Um, so financially, some, some paths I was like, oh man, you work how hard and you make how much? And like, is there a path here where I could have like, I don't know, $50 million? Like what if I want $50 million, right? You don't have to want it, but let's say I do want it cuz I do, right? And I'm not afraid to say it. I'm not ashamed of the things I wanted. I was like, ah, that sounds awesome. If I could choose between less money and more money, I'm choosing more money, right? That was very obvious to me at the time. And when I looked at how much you could make in a certain amount of time, the first, let's say, 10 years of your career, I was like, wow, okay, finance, I might be able to get there, but not really these other paths. Okay, maybe I can do it in finance or consulting, but what do I have to do to get there? Oh man, I got to grind 80, 90 hours a week, kind of as the low man on the totem pole. And I'm just like an Excel monkey. And I'm like, you know, I'm not building, I'm not creating anything new and I'm not building my own business. I'm like, just this kind of like middleman. That's what it felt like. Or corporate management. That's cool. But like, I got to go to an office every day, 9 to 5, wear a certain thing and talk a certain way and spend a bunch of my days doing, you know, like, you know, certain meetings that I didn't want to do, like, you know, talent calibration and like, you know, employee onboarding and all this bullshit, right? So I didn't find that fun. And I even saw people who were playing that game at a high level. So for example, when we got acquired by Twitch, I saw, well, what does the CEO of a multibillion-dollar company do every day? And what does, you know, the VP of product do? And what does the CTO do? What do these people do every day? If I look at their day and I don't want it, then why am I in this track? So I would say the first, the most important thing I did differently was get clear on what I actually wanted, how I wanted my life to go. And then I looked at the quote unquote safe tracks and I realized pretty quickly that those don't get me to that thing I want. So in that sense, they're not safe at all. They're extremely dangerous to my goals, right? Are you following that? Like, if you, if you look at what you want, if you have a clear picture of what you want, and then you look at the safe path and you say, does the safe path get me to what I want? And the answer is no, then it is not safe. It is extremely risky cuz it's putting my dream at risk. And, um, knowing what you want also takes a little bit of work. So take some time, take some imagining, take some sampling. I would go and, meet a bunch of people and be like, so what's your life like? You know, uh, okay, you have this much money. What, how does that work? You have this, uh, work schedule. How does that work? Oh, you never see your kids. Okay. That doesn't, that doesn't sound like a win, right? Like, uh, my buddy dated a girl in college. My roommate was dating a girl in college and her dad was a high, you know, whatever partner at whatever, Deloitte, Boston Consulting, whatever, whatever it was. And, you know, she was just like, yeah, growing up, like he was home Thursday through Sunday and then he would fly out Thursday through Saturday. He'd fly out Sunday and he'd be at a client site. From, you know, Sunday through Thursday every week. And then he'd fly back and he was super tired. And that was the first 18 years of my life. So I immediately could cross that safe path of consulting off because if that's how the, the top of the top do it in that field, then I don't want to do it. And of course there are outliers in every, in every industry, every track, there are some outliers. But then I'd have to be really clear that, hey, am I betting on being an outlier in that path? If so, then I gotta be willing to make that choice. So for example, I chose entrepreneurship. What I knew was that the day-to-day of an entrepreneur sounded really fun. I get to build a, a product, a create a product from scratch, maybe invent a new product. I get to sell it. That sounds interesting. Marketing, as I always found fun. And, you know, I get to go on this ride where I'm sometimes I'm pitching to investors, sometimes customers, sometimes I'm putting out a fire over here. That sounded really fun to me and I tried it out and I actually really enjoyed it. And I knew that, okay, most entrepreneurs don't make it, but I thought, well, if I really enjoy this, then I'm, I'm probably gonna be willing to do it for 10, 15 years. And what I saw was that most people would quote these statistics that 90% of businesses fail, or that this individual idea has a very low chance of, have a very low chance of success. And that is true. Most individual ideas and businesses do fail. And the way, uh, the quote I heard was that, yes, startups fail, but entrepreneurs don't. What that means is that if you look at any great entrepreneur, any entrepreneur who sticks with it, who really tries hard and actually has some skill, over a 10 to 15 year period, they all win, right? They tend to, they tend to win. The odds are in their favor that in a 10 to 15 year period they do have a win. And when they win, they win in an order of magnitude of millions and millions of dollars. Okay, great. So even the one idea that I'm doing this year might not have the highest odds of success. If I just keep at this for 10, 15 years, my odds of success go from individually very low to collectively over 10, 15 years, very high. So I loved that. I loved the size of the prize. I loved the likelihood of success, and I loved the day-to-day to get there, which told me I'll probably stick with it long enough to hit a win. And so that's how I chose what I wanted to do. So in summary, what I think I did differently was get clear on what I wanted. And then I, what I recognized was that the quote unquote safe paths weren't really so safe after all. Because they had a very low chance of getting me to that outcome that I wanted. And so in that sense, they were the riskiest paths of all. Whereas most people, I think, gravitated towards something that sounded good in theory, or sounded good to their parents, or sounded good to their aunts and uncles and their peers and their teachers and whoever. And they said, yep, this, this sounds good. And they got onto a track that actually won't lead them to a lifestyle that they want. Whereas I figured out the lifestyle I wanted first, and then I figured out, and then I looked at what tracks can get me there. And I chose the safest amongst those. All right, that's all. Hope that was helpful. Come on, I know that was helpful. Had to be helpful, right? I put my, I put my heart into that one. So I hope that it was helpful. I hope I might have took an idea that you already had and maybe put it a little differently or brought it to the front of your mind, and maybe it was buried in the back of your mind. That's, that's a win for me out of these. So One Question Friday in the books.