Take More Calculated Risks!

Sean argues that avoiding decisions is itself a risk, and successful people thrive by taking calculated risks with high upside and minimal downside. He shares how Amazon turned a cost center into AWS, how he quit Walmart in 2012 to start a failed business before landing at Apple, and outlines five steps: failure planning, clarifying your contribution, identifying win scenarios, defining outcomes, and evaluating opportunity costs.
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Most people don't take risks because it seems like it's not a risk. And in reality, we deal with risks every day. Not making a decision is taking a risk, as is changing everything that you're doing. The people and companies that succeed are masters of taking calculated risks or risks that have high upsides and low to zero downsides. You can take Amazon as an example. One of the riskiest and bold business moves they made was turning a cost center for running their website, which is basically computers and servers and data centers, and turned it into a revenue stream using aws, Amazon Web Services, which is what runs a good chunk of the Internet. You take a look at people like Thomas Edison, who was awarded over a thousand patents in the US in his life across a wide variety of technologies. But he's credited to saying that it took him 9,999 tries before he perfected the light, which is he took risk 99 or nearly 10,000 times before he was able to get that perfect product that changed the world. And when we get comfortable in our careers, in our relationships with life in general, we have our risk profile change. And it gets skewed towards not rocking the boat, not going out there, taking bold action towards our visions for more in our lives, for our dreams. And it's not awesome, right? Because if you never change, the world will and you'll be left behind. If you are someone that's worried about AI taking your job because you're in a creative field or software and you're worried that this new tool is going to replace you, so you resist learning the new tool, you're going to be left behind. If you are someone who thinks that their current job is always going to be there and it's always going to be just smooth sailing time and time again with the list of companies that have dominated their industries and fail, that's not going to be the case. So we really need to be taking more calculated risks in our careers, in our relationships and health and being. Because it's these calculated risks that help us progress, that give us a shot to have your mind fricking blown by the results that you can get in life. So story that I have personally on this is in 2012, I left my first corporate job after college, right? I was working at Walmart Information or the ISD Information Systems division. And I remember not feeling like I was contributing in the way that I wanted to or feeling connected to the work that I was doing. And I was comfortable there. I had that figured out. I didn't really feel Like, I was getting paid market rate for my education and the skills that I had. And took me years and years to really plan out an exit from that first job. And it was excruciating, right? There's a lot of fear in quitting a job or changing careers or making a jump that goes into that decision for anybody. And it came down to learning a couple things that I'll share with you here in a moment to really help me find the path forward. And essentially, that's what happened. I left that job. I started a business. That business, for all intents and purposes, failed. But those that decision to leave, that decision to work on that business led to a job at whole and successful career there before I jumped again to run my coaching business. And the moment where I made that decision to take a bet on myself to see if I could make this business work, not knowing if it would or not, but knowing that if I started a business and moved to San Francisco, where the texting was happening and hot in 2012, that if I failed, I'd have a backup at this huge ecosystem of companies that were doing cool things. And so that calculated risk of, okay, I'm gonna try this, take a bet, I think I can make this work, and if not, then I have an out ultimately helped me leave that job, and it changed my life, and that's what I want for y'. All. So you are wondering, like, how can I take that jump from being a professional, working for a company, starting a business myself, or how do I get myself out more to ask more people out on dates or to go on more dates, or how do I figure out how to take more of these calculated risks? So I live a life where I feel like I'm at the helm of, you know, I'm the helm of what I want. I'm creating. I'm designing and creating the life that I want, and I'm getting after it. Then we got these tips for you. And before we go into it, as a coach, I've learned that so much of taking calculated risks is dealing with fear, right? We have these underlying fears of not being enough, not being confident enough, having the skills needed to succeed. And more times than not, we are way more prepared, way more capable, and way more willing to take these chances on ourselves to live an extraordinary life. And so I do that as a coach day in and day out. And if you are someone that's been thinking about, I need to take more calculated risks. I need to get out in the world more. I need to make my difference and dent in the world, but I don't know how or I'm getting stuck or I feel like I'm not able to take that next step, then maybe talking to a coach is great for you. And I have a link below this video if you're watching this on YouTube where you can sign up for a free one hour high performance strategy session which I walk you through the high performance curriculum at a high level to build you a personalized plan for you to get clear on your vision, to develop the plan to handle those risks, those fears, those situations where you're like that happens, then I'm sunk. And so that's why I can't take that next step towards my great life. And I want you to have a great life. I have this high performance process. We build you a plan custom to you and then if we like that call, we both think it's, we could work well together. Then we take that next step and we jump into a coaching relationship. But if not, you're walking away with high performance strategies. You're walking away with a personalized plan. You're walking away with actionable things to improve your life, to help you get to your next level. Because ultimately that's what I do as a coach and I love doing that. This is something very pertinent to this topic, is very pertinent to what I do on my coaching side. But here are five things that can help you take more calculated risks in your life. Okay. And I just want to say too that everyone has their own tolerance for risk or in different phases of their life. So this isn't saying that you should just take risks and that it'll all work out because it's called a risk for a reason. There's probability involved, your ability to be dedicated and consistent and motivated. There's a factor of luck in a lot of things. I don't know the right mix for you, but I do know that if you think through these next five things, you will have a clearer picture on whether you should take that jump to start that business or switch careers or make the change that you want or not. Okay. So I just wanted to throw that out. Okay. First thing is something I learned from Tim Ferriss, which is really helpful and I'm just going to call it failure planning. Right? So if you say I'm going to quit my job, which means I'm, I'm going to start a business or go to this, this new place, right, Think of all of the things that could go wrong and write a list of them Right. So if I leave my job at Walmart, I'm not going to be able to pay my student loans, I'm going to go bankrupt and be embarrassed. I'm going to be seen as a failure in my family and social circles and nobody will talk to me. I'm going to and on. Right. And these are things I felt when I was considering leaving the particular job. And then the job is, once you have that list out, one, you'll feel better because it's not bouncing around in your head, negative energy. But two, you get to do the second part of failure planning, meaning what can you do to mitigate each of those items? Right. So if I quit my job and start a business and it fails, I'm not gonna be able to pay my student ones. That was a huge fear for me. But again, from the story of leaving it, like, I figured that if I moved to a part of the country that had tons of options and jobs in technology as a software engineer with a master's in information systems, I figured I could find something if I really needed to get cash quick to move forward. Right. Second point of that is, oh, if I save 30 grand from stocks or I can find that money, have a little bit of a nest egg to figure out for a year if I can make this business run, that'll also help. And so you start to go through that list of, oh, everyone's going to think that I'm, you know, I'm a loser and a failure and nobody will talk to me. What are you going to do if you fail? Right. For me it was, I actually think, if I'm honest, most people don't take risks. Most people don't chase their dreams. And that act of boldness. Boldness will actually be admirable. Right. People might say, yeah, you really screwed up, but I admire you for having a vision and jumping on it. And what I found when I announced that I was leaving that job is so many of my co workers and family and friends were extra supportive. They're like, hey, that sounds like you have a clear idea. And I had one guy that I worked with, he's, everyone wants to do what you're doing, but nobody has the moxie to go and do it. And I felt very seen there. And part of it was that hypothesis, but also it was talking with friends and family and finding out how supportive they were to be like, no, we would. We're going to love you no matter what. We'll still talk to you even if this blows up in your face. But we got your back, right? And so that mitigated that fear enough to where that wasn't an issue when I made failure. Planning is key to taking these calculated risks because if you can imagine the worst case scenarios and plan for it, maybe you never have to initiate those plans or maybe something gets thrown at you that you don't even know, but it is, you'll feel confident when you make that decision that you can handle almost anything that comes your way. So second thing to do when you are thinking about I need to take this career risk or relationship risk to ask people out or stand up and set boundaries or whatever it is for you. Second thing to do is to clarify your contribution, right? So focus on and not get the story. If I quit this job, I'm going to have a chance to feel more fulfilled. I'm going to have some time free up that isn't spent totally focused on this day job that's all consuming. I'm going to the chance to have better rewards for my skills, better compensated, more abundance financially, those types of things. If that business works really well, my family's set financially, but I'm also, because I was a business helping people with student debt. The world's going to be better because there'll be less people stressed out like I was about my student loans. And that's something worth fighting for. And so being very clear on what you're fighting for when you make that change and how it's actually going to improve people's lives, yourself, the people you love around you and the world is a really great way to be. Like what ends up happening is when you have fear or you're like, maybe this isn't worth it. If you can't clearly state that this is going to help all these people in this way, you're not going to follow through and it's not probably going to work out. But if you have that guiding, why that can help motivate you when it's hard, when you're not feeling like getting up and doing the work, when you are freaking out that you made a choice and you're not sure you made the right choice. Right? That's the chance to be like, no, this is why I'm doing this. And it's worth the shot of great things and doing this and making a debt in the world. And I found that in my coaching practice that the people when they take that shot on themselves are for themselves and for that grand idea that maybe it doesn't work out the exact way that you want, but it Works out in a way probably greater than you could expect. It was my case getting a job at Apple when that business didn't work out and then starting my dream business as a coach. So. And it all is based on that decision to take that risk at that time in my life. So super interesting, super important to clarify the contributions, know your why and why it's worth taking the risk. Third thing to consider is when scenarios like Amazon that I was talking about earlier in the video, what is the opportunity you can realize from failure or for from a weakness, right? So like Amazon, that took a cost center and that was a huge risk to invest in that. Right. Spend millions and millions of dollars on all this computer processing power to run their website. And then what if you overdo it? What's the risk there? Like you're spending a bunch of money for stuff you're not using. But the risk to not do that is your website completely crashes because you don't have enough processing power to fulfill all of the Amazon prime orders during the day. And by mitigating, right. And finding the win scenario is if we build extra capacity and we can sell it to other people that might need to do websites, we can turn this thing that is burning tons of cash and make it the reason why we can offer low prices on our goods instead of Walmart because we have this new business that we can leverage. Right. So that's the win scenario. It could be in my story also when I said that, hey, I'm going to move to the San Francisco Bay area where there's a lot of tech companies, I have tech skills, I have master's degree, and if this thing doesn't work out, at least I'll be in the place in the country where I'll have a great chance of getting hired in another technical position. And that's what ended up happening. And it happened in a way that was again, like Apple was the dream job. And I felt super helpful there. I felt like I contributed a lot of good work there while I was there. And so it's creating these win scenarios that can help reduce the impact of the risk billionaires that do big investments are really great at. If the market does this, I'll make money. If the market goes the exact opposite, I'll still have this other method to make not as much money. Right. But it's still moving forward. It's still not hamstering yourself by thinking about how I can make this win no matter what happens. Okay, the fourth thing to consider is to clarify your outcomes and your Total risks. Right? And really this is summed up in the question, what are you measuring for success? Is it just raw cash money? Millions? Is it time with your family? Is it how healthy you are? Is it a factor of all these? Because if you're like, I'm going to quit this job, in my case, so that I can make my first million dollars and that's all that matters. And that's all you focus on. The opportunity cost of spending 120 hours a week building a business to make that dream happen is that you're not meeting people that you could potentially get in an over relationship and marry. You're not spending time with friends. You're neglecting your health by working and not going out in the sun, ever. Working vampire hours where you're in the office before the sun comes up, you leave the office before the sun goes down, eating convenience foods. And so sometimes having a calculated risk and taking it properly is being very clear on, yes, I might shift careers and take a job that pays half of what I have right now, but I'll be able to spend time with my kids as they grow up. And that's important to me and that's worth taking that risk of a hit of some financial resources right now. Or it could be that I'm going to go all in on my health and the risk is I never have anyone around me to enjoy that health with later. And so how do you really make sure that you're hitting all the different areas of your life that are important, that make you successful? Right? Because oftentimes we can get so fixated on the one thing that we forget that there's other areas of our life that suffer by that focus. And so I also, here's an example. I had a client who loved her job and was doing really great things, but wanted to volunteer more at her daughter's schools and wanted to be more part of her education. And she shifted jobs a little bit before starting out on her own to have a company that eventually turned into helping schools that had trauma and inherent in just the student body. So you're talking about like things like schools that have lots of violence and crime and stuff like that are really tough and how it not only traumatizes the students in those situations, but a lot of times the staff and teachers and really making that difference there. But her opportunity cost was, I need to get out of this job that is taking up all my time, not allowing me to live the life that I want in order to maybe take a little bit of hit on Money. Think about moving from the Bay Area to another place where the money would go a little bit longer so she could spend more time with her dog, right? So that's the outcomes that are time with family, it was having a bigger house and not a commute and so some quality of life things, that's what anyways. So clarify your outcomes and total risks. And then the final thing, and I mentioned this in passing, is to consider your opportunity costs. So many times, like I said at the top of the video, we think that not taking a risk is without risk. But that's not always the case. Sometimes when we don't adopt the new tool, when we don't change the way we operate, we don't try to reach different markets in our businesses, we stagnate and ultimately fail. Right? If you think of Kodak not shifting into digital photography, they were high technology and killing it at their height, but where are they now? That's all because of the opportunity cost of changing how they did business. Getting out of developing film and creating cameras and shifting the medium that ultimately got them so they chose not to add. And the risk was that the world would reject the digital technology which ultimately did it and they failed. So what are you giving up for by not demanding change for yourself right now? If you have that call to adventure in your heart, for greater contribution, for a greater shift in your life for yourself, for your family, for your communities, what is the cost of not heating that? And how long can you ignore it and not experience pain? Right? If you want to start a business, if you want to work at that prestigious firm, if you want to spend more time with your family, whenever, again, that is for you. What are you giving up by not changing right now? And write that down in a journal and really keep that on top of mind. Because sometimes, again we d. We don't consider the risk of an action and sometimes when we put out all of the opportunity, all the trade offs that we're doing, making calculated risk isn't actually as risky as we thought. It's. We're going to gain more no matter what by making this choice. And there's some things that are uncertain that we'll have to work on. But ultimately it's up to us to make it happen. Right? And to take that step. And that's what I'm here to cheer you on. Again, if you are wondering how can I figure out how to take action towards those calculated risks in your life, then hit the link below for that free strategy session. Otherwise, again, most people again, don't take risks because it seems like it's not risky to do, but there is tons of trade offs that we're just not acknowledging. So again, do your failure planning, clarify your contribution, consider your win scenarios. When you take action, clarify those outcomes and consider opportunity costs. And I know you will figure out the right decision for you. If you need someone to talk her over again, hit the link below to sign up for that strategy session. That said guys, go out there, live with more joy, with more personal growth and more impact in your communities. This is Sean but signing. Sat.










