Win Today

#233 | The Playbook For A Strong 2026: Ask These Powerful Questions

Season 5

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If your life were a movie, what would the audience be yelling for you to do right now? In this final episode of 2025, we use a third-person lens to close the say–do gap, run an honest self-audit, and design a lean, focused plan for 2026 that trades overwhelm for ownership. We break down the five-and-three rule, the observer test, and a simple start-stop-continue framework so progress is visible, repeatable, and rooted in who you’re becoming—not just what you’re chasing. The result is a clear, compassionate playbook to drop the bricks that weigh you down and turn the next year into a plot twist you choose.

Key Takeaways

  • Limit your world to a few meaningful categories and concentrate ambition with the five-and-three rule.
  • Get brutally honest on paper about what worked, what didn’t, and why—then port winning tactics across life.
  • Define December 31, 2026 outcomes and identity, because character is the scaffolding that holds goals up.

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Your Life As A Movie

SPEAKER_00

If your life was a movie and you're the main character, what would the audience be yelling at you to do right now? So if 2025 was a movie, or if life right now in this moment is a movie, and there's people out watching it, there's people that love you, that are watching you, and they love you to death, and what what what would they be telling you to do right now? There are more people living in mental prisons in their minds than there are people living in actual prisons in the United States. What that means is there's a lot of people that are holding on to things that don't serve them and are either unaware or are not taking the inventory to become aware or make or not being willing to make the change to get it, to get rid of it. Thank you so much for tuning in. My name is Ryan Cass and I'm your host. My purpose in this world is to help push people further and harder than they believe possible and become unshakable in what matters most to them in their lives. Every week, you're gonna learn from either myself or a renowned expert in their field, and we're gonna unveil pieces of our playbook to help you win today. Please, if you love this show, subscribe and share it with somebody that will benefit from it. Let's dig in. Happy almost 2026. Last episode of 2025. Can't believe we're here. I'm sure you can't either, but the intention of this episode is to help you take an inventory of the prior year, or really current year, what will soon be prior year, and help set the tone for 2026. One thing I b one thing that I believe is that we have so much more answers and knowledge than we believe. We don't need to buy a new book, buy a new course, get a new guide so we feel ready. I often find, and and I've fallen in this bucket too, that we can hold ourselves back thinking that we need to seek more knowledge. Well, really we need to ask better questions and take more inventory and audit ourselves more frequently, take a personal inventory and audit before we go ahead and think to find the answer in another book, in another course, in another conversation. So the intent with this is that I'm gonna give some questions to help take personal inventory and audit. This is the same exercise that I will soon be doing before the end of the year to assess 2025 and set the tone and set the path for 2026. So, with that, let's jump right in. How can we audit 2025? And what is here's a process that I believe has worked well. One thing I'll say when we're looking back at our goals and our intentions is that there is no one right way. There are frameworks and methods that work well for others, and if and if something works well for me, maybe it'll work well for you, or maybe a piece of it will, but not the whole thing. The intention is that we provide at least one tool to one person every week. With goals, there is no run one right way, meaning that not everybody has to follow the SMART Goals framework, which I believe is one of the more popular ones out there. But I believe it is important that everybody understands or has connection, content, real meaning behind their goals versus just throwing something up on a paper that sounds cool. We'll dig more into that next week as I share my annual reflection and letter for 2026. But before that, here's what we should do. Here's what I recommend doing, and here's what I will be doing. I believe our goals should be broken up into categories. And I like to break mine into five different categories, which you can see behind me on my whiteboard, which is personal, fitness, giving, financial, and business. So the business outside of my corporate job. Now, those are the things that are most important to me that can be completely different for you. It doesn't have to be those exact five. It doesn't even have to be five, but I recommend just from an aesthetics perspective and also knowing that less equals more, I'll talk about that in a second perspective, that it's easy to see and keep track of goals that are broken down by category that are meaningful to you versus just one big list. Now, with that, it's also easier to go ahead and take inventory because it's broken out. So I believe it's important to break it out into categories and also that you don't have a million goals. One thing that I thought about goals before I would say got decent at them and to the point to where now I'm working that as a vocation, teaching people how to not just set goals, but ultimately establish a foundation for sustained success and building unshakable discipline so that you can accomplish more of your goals is this. I thought that more goals equals more success, more equals more. That couldn't be further from the truth. I don't like to go into a year-end review looking at my list of 35 goals and then getting mad that I only hit 11 of them. And within those 11, there are a lot of meaningful targets, but I'm completely ignoring the fact that I that I hit those and getting mad that I missed the other 24. I thought that the most ambitious people, when I started this journey in 2011, I thought the most ambitious people in the world, the most successful people in the world, they must have the most goals. That is not true. They actually have a few things and sometimes even one thing that they are obsessed with and focus on. So I've developed what I call my five and three rule is that with our goals, no more than five categories that are meaningful to you. And within that, no more than three things. And really, I would challenge you no more than even one to two per category. One thing that I've continued to do, and it's felt uncomfortable, but as the goals have gotten more challenging and bigger, I have continued to shrink the list and shrink the list and shrink the list. And I've found that it doesn't make me feel any less ambitious. It's actually creating more space and focus to do more things that are to do more of what is most meaningful versus a little of what you think, a little about a lot of things that you think are important when really it's probably no more than five things. So with that, I'm looking at each category and I'm asking myself this what worked well and why, what didn't work, and what did I learn? And now to do this right, I believe it's important to be brutally honest with yourself across the board, not just with what didn't work, but what worked and why. Be be very descriptive. Think about list out everything, don't leave any stone unturned. That's why I say and encourage to reserve a few hours to do this. Because I believe what you'll be able to do is not only sure break down what didn't work, but with the things that did work and why. If it worked in one area in one category, then it likely could work in another category and for another goal or a set of goals. And it's important that we understand that. The reason why it's important to ask these questions and really get it out of your brain and on papers because it can help you really establish clarity. We have so many thoughts throughout the day. We have literally 50,000, 80,000 thoughts per day. But I remember this stat I read a long time ago, American Psychological Association, I believe, the APA, published a study that shows we have 50,000, 80,000 thoughts. So the more that we get out of our mind and on paper, the more clarity we can create for ourselves. So with that, spend a few hours. But brutal honesty is key all the way across the board, especially with what didn't work well. And the reason why I say that is because all that's going to do, the more honest you are with yourselves, the more descriptive you are in this process, the more that you're going to A, understand and B, unlock for the future. So, with that, what's an example of brutal honesty? I've worked with a lot of people that have a goal or intention to lose weight, to become more fit, to hit a certain amount of workouts. And sometimes they don't get there. Being brutally honest about that, we've got to really list all of the reasons, other than, okay, why didn't you lose 25 pounds? Well, I didn't have time to go to the gym because I have my school and work and kids and everything. Okay. Is it just that, or is it we didn't create time, we didn't eat right, we didn't invest in resources to help us become more fit, healthier, we didn't hire a coach, all these things. Brutal honesty. Because then you can sit there and look at it, and then you get to decide am I going to change this? What am I going to do differently as a result of being where we are right now? So that 2026 and the years that proceed can be great. What did you learn? What are some lessons that that popped up in each category? All this is doing is again helping you give yourself evidence and understanding. And that's something that I have a binder of every goal that I've written since 2011. And then what follows that page is this review. And over the years, it has become lengthier and lengthier and lengthier because of just being more honest with okay, here's what really worked, and really dissecting that, because then that helps really fuel the playbook for the coming year. And then what didn't work, because then I know, okay, hey, there's just things to really stop doing, which we'll get to here in a second. So jumping into 2026 and some questions to ask yourself for the new year. And again, to help really create understanding and even tell yourself the things that somebody else would tell you. But in this case, you get to look at yourself as that third party, as that third person, and give yourself those answers in that perspective. Because we don't often, I believe we don't we haven't normalized taking personal inventory and creating a high sense of self-awareness across the board. This is one thing I'm sure many of you would love to see everybody do. And think about what this world would look like with people that are a population that the majority were highly self-aware, right? So, with that, what can we do? Uh, one thing that I love and and a piece of somebody else's playbook that I added into mine this year is from Sahill Bloom. Saw Hill is a an incredible author, and I'd call him more of a thought leader. Uh, he released his book, The Five Types of Wealth, at the beginning of the year, and we had the opportunity actually to host him on the podcast and with our book club, where he answered questions about the book and some of the thought processes, thought processes behind the chapters, and it was a really invigorating discussion. But one question that he poses that I believe helps really set the tone for the coming year. So think about your favorite movie or a movie you've you've you'll watch over and over again, and the first time you watched it, and the reason why you've watched it multiple times is probably because it excited you so much that first time. You really love that actor. It doesn't get old to you. And you know those movies where you're yelling at the main character, like, don't go to don't go right, the bad guy's there, like go left. Like you're you're clenching your fists, you know that there's a bad person behind the wall if they go right, and you want them to go left because they're they're your favorite character, you love them, it's your role model, it's your it's your crush, whatever. You're yelling at them to go left as if as if they can hear you. Here's the question that Saw Hill posed. If your life was a movie and you're the main character, what would the audience be yelling at you to do right now? So if 2025 was a movie, or if life right now in this moment is a movie, and there's people out watching it, there's people that love you that are watching you, and they love you to death. And and what what what would they be telling you to do right now? And think about this too. What would they tell you to keep doing? Hey, keep doing that thing, man. You're crushing it, you're crushing it, sis. You're crushing it, homie. What would they tell you? Hey, stop, get rid of these people. Why do you keep doing that? Why don't you launch this? Go launch that business. You've got all the tools you need. What would they be telling you to do? Looking at yourself from a from a third person perspective can help unlock and help you create a lot of things and and help you hear advice that again going back to the very beginning where I said you have you have a lot more answers and knowledge than you think. If you have, let's say, the goal of losing 25 pounds, and you buy a bag of Doritos from the store and you're eating them, you know internally that you shouldn't be doing that. You have that voice that is saying, hey, hey, brother, hey, sister, don't eat that freaking bag of Doritos. You've got the goal of losing 25 pounds, but nobody is physically present in that moment to say that to you. But if we think about this from, hey, we're there, there's a movie going on, and people are watching me right now. I'm the main character, the audience will be screaming at me, don't eat those freaking Doritos, throw them away. So that's why it's important we can look at ourselves from a from an outside point of view that can help us create that that clarity and give us those those answers, that path as we go into the new year. The next thing is going back to observations. And this is the say do gap. Another one that I actually got from Saw Hill's newsletter, the Curiosity Chronicle. The say do gap. If there was an observer in your life right now that was looking at your day and week and month, they were with you alongside you, or even for the year, how what would they say about the seriousness you have towards your goals? Would they say, man, you're the this this brother, this sister is totally locked in, they've got it. Or would they say, uh, yeah, they on on social media they're serious, but in the reality they're not? What would they say? What would a third party observer have to say about that? What evidence would you be giving them? So those questions are again intended to really help you create again some some a different a different perspective that only somebody else would be able to give you. But here, you know, we're sometimes we're we're we can be alone in our thoughts or in reflections. So it's you really looking at yourself and you're in the audience looking at you. What would what would you have to say? Now, one thing that will now going into first person and personal reflections, and this is something that has again worked really well for for me, and I will share more next week. But you may be asking, well, how do how do I set my goals for next year? What do I do? What's the what's the process I need to follow, et cetera? More to come there. But what I will say is a is a brief nugget is if we were to fast forward the clock right now to December 31st, 2026, what would you want to be able to say is true? Or what would you want to be able to say happened? You're looking back right now on 2025 and you're looking at the things that either A, they happened, they became true, or B, they they didn't. And we've got that separate inventory. But if we were to go all the way to December 31st, 2026, what would you want to say you accomplished? What would you want to say you did? And I'll leave a note here that I may be suggesting a lot of these goals as outcomes, meaning that I launched this business or I made X amount of money, I lost X amount of pounds, I ran X amount of miles, ran this marathon time, whatever. This is also a process of becoming and really an opportunity to look within. One thing I know is that it's and focus on now, especially as I as I get a little older, feel so old at 33, just turned 33. But I see so much value and importance and really focusing not just on the outcomes, but also your being in the inside. Who am I? If I look at the years, one thing that I've really been focused on is opening up my heart more. Sure, that's not so much of an outcome-based goal, meaning, yeah, open my heart six times. No, just be more present and to rather be more accepting and open to letting somebody in and being vulnerable with your heart, not holding on to previous experiences with relationships where I have had my my heart broken and have no longer trusted people. That doesn't apply to all of the women, every single woman in this world. And what about focusing on, hey, did I was I vulnerable this year? Did I was I accepting of of love? Was I did I hold on to limiting belief? Longer than than I should have. So when you think about your goals, you also I encourage you to think about who are you becoming? Are you becoming more disciplined? Are you again going back to are you becoming more accepting? Are you becoming more open, more curious? Whatever rings true for you or whatever speaks to you there, I encourage you to also look at it from that perspective. So that's one thing that you can do to help with setting your path for 2026. If you were to fast forward the clock, what would you want to say is true? Not just from an outcomes perspective, but also internally. What is that? What does that look like? Another thing that I do, and this is why the first piece is very important to really dissect what went well, what didn't, what did you learn? Is because the next thing that I do is I make a start, stop, continue list. What do I need to start doing? What do I need to stop doing? What do I need to continue doing? What is working well? And I believe that that's a that follows the previous year inventory first. So if you haven't done that, don't skip straight to this step. I highly recommend going and doing that first before you go into your start, stop, continue. And again, this is also another thing that requires brutal honesty. If you're really serious and intent on where you want to go and creating your dream life, then this is absolutely essential and essential activity for 2026. Two more that I will offer is I believe that everybody in life, we're all wearing a theoretical backpack. I just had an amazing interview with Damon West, who will this this episode will release in a couple weeks. If you don't know Damon West, his brief backstory is he is a well-known author and speaker. His message is about how to be a coffee bean and change your environment around you in life. And that originates from his past. Damon was originally sentenced to a life to life in prison in Texas, was sentenced 65 years in 2009 for organized crimes due to his meth addiction. Damon never never hurt anyone or injured anyone physically, but he did rob a lot of homes and really threw his life away so that he could fund his drug addiction. The last piece of advice Damon was given before he was transferred from county jail to prison was be a coffee bean. And that means change the environment around you. Damon only served seven years of the 65 because of the transformation that he led in prison and changing the environment on death row of all places in this world. So think about the power that we actually have in our lives. If somebody can go in, a meth addict can go in and change a prison and then be released and now be a motivational speaker. But one thing that he shared with me in our discussion is that there are more people living in mental prisons in their minds than there are people living in actual prisons in the United States. What that means is there's a lot of people that are holding on to things that don't serve them and are either unaware or are not taking the inventory to become aware or make or not being willing to make the change to get it to get rid of it. So in these theoretical backpacks that we carry, we can either be carrying bricks of experiences that no longer serve us well, that we haven't extracted the lessons from and converted into feathers that that help us soar and and let us fly. And we ultimately can hold ourselves back without even realizing it. So I don't blame people when I see somebody that you know maybe fatigued or struggling or having some victim mentality. I really encourage them to open up the backpack. What are we holding on to? Are we holding on to a bunch of bricks? I can't imagine what my life would look like right now in this very moment if I was still carrying in my backpack the bricks of my childhood, where I was often the middleman between my parents. My father has struggled with alcohol, that alcoholism runs in my family and ultimately broke my parents apart. I couldn't imagine what my life would look like if I was carrying on the bricks where I would stay up till two, three, four o'clock in the morning resolving chaos between my parents because my dad would come home drunk from work and all hell break loose, sometimes answer the door to the police, where I would show up to school late, lie to teachers about why I was showing up late. I couldn't imagine still carrying that today and being mad at the world. That's something that has been converted into a feather that helps, I believe, helps me soar in that I get to teach people and be the inspiration for at least one person to be intentional about their lives, to establish a foundation for sustained success, to develop unshakable discipline, to become unshakable because of the bricks that were converted into feathers. Now, it doesn't mean that bricks no longer enter my backpack. Bricks will enter anybody's backpack, but it's important to know when they got in there because we're asking ourselves these questions. We're taking inventory, not just at the end of the year, folks. This is stuff that I recommend doing quarterly, if not more, to really become aware of what's going on. So what am I holding on to that isn't serving me well? Whether that's a limiting belief, whether that's an experience from the past, whether that's a breakup from a few years ago that now you're not allowing anybody to even get close to you. And and I've done that as well myself. What are you holding on to? And what lesson can you extract from it to look to lessen the load, to turn that into something that's going to help you soar in 2026? The last one is what's holding you back more than anything? And what will you do to remove it? What is stopping you from whatever it is that you ultimately desire? Whether it's a limiting belief, whether it is a whether it is it is something that somebody told you, whether it is a fear, what is holding you back, and what will you do to remove it? I believe that this inventory is critical. It's key. I know it's something that has helped me certainly get to where I where I am, but ultimately to to clear a lot of mental roadblocks and obstacles that I see get in a lot of people's way. So by taking inventory, being brutally honest with yourself, you can understand what opportunities lie ahead and ultimately set up 2026 to be an incredible year. Next week we're gonna share, again, the annual reflection that I do, more in-depth process behind what I shared today, as well as a letter that you can write to yourself to make 2026 an amazing year and win today. Thanks so much.