Win Today

#234 | How to Make 2026 Your Best Year: The WINS Goal-Setting Framework

• Season 6

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It's time to crush 2026! I break down the WINS Framework, a simple four-step system I’ve used for over 15 years to help high performers turn goals into daily execution, personal discipline, and long-term identity. You’ll hear my 2025 reflection letter and learn how to write a future-self letter to December 31, 2026 that creates clarity, accountability, and momentum before the year even begins. If you want 2026 to be your best year—personally, professionally, and mentally—this episode gives you the structure to make it happen.

Key Takeaways:

  • A 4-step goal-setting framework to plan, execute, and win in 2026
  • How future-self reflection letters increase focus, follow-through, and consistency
  • Why building systems and identity beats motivation every time

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SPEAKER_00:

Welcome to Win Today. This show is crafted for those who want to win in every aspect of their lives. Every week you will learn from a renowned thought leader that will share a piece of a winning playbook that you can incorporate into your life. If this show has a positive impact on you and you see value in it, please share it with somebody and leave a rating and review so we can help more people win. So happy that you're here. This is all about best practices for your goals in 2026 based off of years of experience from myself being on this journey since 2011 and what I've learned from others. So we're going to quickly go over how you can best set yourself up for success to achieve your goals in 2026 using four simple tips that I've written down. And I'm also going to share my annual reflection letter. This is something that I've been doing for four years, is at the end of each year, writing a letter about the year, my experience, and what the following year, so in this case, writing about 2025 as a reflection and setting the intention for what 2026 is going to deliver. I've been sharing that now publicly for a few years, and the intention behind that is to showcase a tool that I believe works well, as we do every week on this podcast, but showcase a tool that I believe works well and also perhaps give you a new tool that you can put into your arsenal. I've found that by writing letters in third person to yourself and then also claiming the future, you will surprise yourself in how much you can and will accomplish. A lot of what we create in reality, rather, I believe everything that we create in reality had to have occurred in your mind first. One of my mentors, Jerry, said this to me once great things happen twice in your mind first, and then in reality. And I believe that's so true. If you cannot conceptualize or visualize yourself achieving a certain goal or crossing a certain milestone, then is it actually going to take place in reality? So I believe that by writing a letter and claiming whatever it is that you want helps give you that evidence, that mental evidence first. And you can go ahead and go execute and surprise yourself when you look back at that letter and say, wow, I wrote that a year ago, and here we are. So with that, let's dive into our goals first. Now, last week I shared some reflection questions that you can ask so that you can help understand what it is that you really want in 2026, especially if this personal development or goal setting journey is new to you. I recommend go back and check that out. And even if you're experienced, I believe that it's important to not always seek knowledge and new resources, meaning that we don't need to buy a bunch of new books or take X new courses. We most of the time just need to ask ourselves either better questions, new questions, or questions more frequently. So go back and that will that will be a useful episode. This is intended to focus on you have your goals, you know what you want, or you're you're almost there. Now, what do you do? So I'm gonna give you four things before we read the letter. The first thing with your goals, assume that they are written or you're thinking about it is what I just said, they must be written. W. By the way, we're gonna spell out wins, wins, so it's easy. The first thing is your goals must be written, and I highly recommend that you write it down on paper, not type it in your phone. You can type it in your phone as a supplement, but actually physically writing it down, I believe gives you in your body and mind more of that evidence that hey, this is happening because now I'm taking it out of my brain and I'm physically, you're physically declaring it and writing it down, just like our founding fathers did. They're physically declaring that this is our nation. Here we are. So write your goals down. Why is this important? Studies show that just by writing down what you want, you are 42% more likely to accomplish that goal. 42% because now we've taken something out of the abundance of thoughts that we have and we've put it on paper and we can see it, our mind and body start to believe it. What's interesting about the mind is that it doesn't know fiction from truth, meaning that your body, your mind rather, doesn't know the difference between fiction and truth. That's why we can often hold on to limiting beliefs so much as if they are true. They are not, but our mind and bodies are convinced. So imagine we can hack that by writing down a meaningful goal, and then our mind and body then takes one step towards believing that oh yeah, that's possible, and we're doing this thing. And there's proven studies to show that it is useful. 42% more likely. Now, quickly, if you are struggling with wanting to, if you're struggling with what to write down, how what gold do I want? I don't know what to do. Imagine if you fast forwarded the clock all the way to December 31st, 2026, and ask yourself one question. What would I want to say is true at the end of this year? So if you if you don't know it all, put yourself all the way in the future. What do I want to be able to say is true or what happened this year? And that can get you ruminating on a bunch of things. I want to say that I ran my first marathon, or I want to say that I lost 25 pounds. So, not to make it too complicated of an exercise. That's what you got to do. That's what I recommend you do, rather. Now we're on to the I. Okay, so the first thing, your goals must be written. I can't say that enough. I've been saying it for 14 years, 15 years now. Inform someone about your goals. Make sure somebody knows about your goals. At least one person. A lot of people that I see that don't reach their goals or they continue to struggle with the same thing is because the only person that knows about it is themselves. That means that there is no accountability in place. That means that they can more easily cheat themselves. And that also means that there's not somebody else that can help potentially open the exact door that you're going through because they already have the key. They've already been through it. Now let's go back to the studies. When you inform somebody or a group of people what your goals are, the odds of achieving them increase to 70%. 70%. Just because I know what it is that you want to accomplish. And I know and trust and believe that if you're listening to this podcast right now, you are an ambitious person. You're somebody that deeply cares about your development, making a positive difference in the community and your families and meaningful things that you value being a person of your word, meaning that whatever you write down, you're gonna go after it. You're not writing it down so it looks cool, and you can put it on social media. Here's my big goal, and then do nothing about it. I guess that would be telling somebody about it, technically, but make sure that somebody knows. And this is a great, great opportunity now at the beginning of the year to find one person to build a small army of support and make it and keep it simple. You don't have to do a million things or tell 5,000 people. One thing that I really look forward to on a monthly basis, I've got one of my good friends and accountability partners, Michael. Every month we go out to dinner at the end of the month, we pick a new restaurant and we talk about our goals and where we're at. And occasionally we'll spot check each other. So because I know what his goals are, he knows what mine are, he can pick any goal at any point in time and reach out to me. Now, I don't want to show up to these dinners flat footed and be the person saying, Yeah, I did nothing this month. So just because I know that one person knows, then that also from a daily and weekly standpoint will help keep you pushing forward because you don't want to be that person that, all right, I told the world this or I told this person that, and I did absolutely nothing. The next thing that you can do is look at accountability groups or masterminds. Now I will put in my plug for my mastermind group, the unshakable disciplined community. We meet every week on Tuesdays at from 6 p.m. to 7 p.m. virtually Eastern time, and the people, the members in our community are absolutely crushing it. In 2025, there were multiple first-time marathoners that had never run before or weren't runners before this. There are members that uh completed 365 workouts that they had been attempting to do that for years. Folks that created time that they didn't believe was possible with their families. So much more. And I believe a lot of that is because they've got an ecosystem where every week we're being intentional about where we're at, what are we doing, what are we struggling with, so that those roadblocks can be cleared, more doors can be opened, and it is just a powerful, powerful, powerful effect when you let somebody know, when you inform somebody of what you're going after in 2026. The next one, so we have written and inform. Written and inform somebody about your 2026 goals. The next one, make sure that your goals are noticeable, meaning, all right, you wrote them down, you told somebody about them. Now, I don't want you to not look at them again until December and then wonder, oh, what the heck is going on, man? Make sure that your goals are noticeable. So you can see right behind me if we've got the video available, if you're watching the video or a short clip, that I have a whiteboard with all of my goals written down for 2026 behind me. It is impossible for me to leave my house, walk downstairs without seeing this goal board. What that does is it's a one, it's a visual reminder to me and a mental download every day of what I am going after. One thing that's important with goals is that there is no guesswork. So if someone were to ask me my goals, I can rattle up boom, boom, boom, boom, here they are right here. If I ask you what your goals are, I don't want to see uh head scratching because you don't know what you wrote down because you haven't seen it in three weeks. Make sure that they are noticeable. And the other thing is here's another proven study fact. When you hit or when you cross off a goal, when you hit a check mark that you achieved XYZ, when you physically put that check mark next to that goal, studies show that you release just as much endorphins from that as you do from a workout. So a lot of why I share these studies is with the intention to, hey, not just convince you if you don't do this now, but also to encourage you that, hey, this is how we can we can hack life and create the best possible odds for success in our lives. And it is actually proven this is not just Ryan speaking from his experience, this is drawing from experts doing a lot of homework to understand what are truly the best practices and why you should do this thing. The number one motivator for humans is progress. That's from a Harvard Business Review study. People want to feel that they are making progress, even when you make your bed or clean something in the house. I imagine that you probably are thinking now about, yeah, that does feel pretty damn good. So when your goals are noticeable and you are able to look at them, literally touch them on a daily basis and check off the box that either you did that thing or that, hey, you ran some extra miles, whatever the case may be, something that is moving the needle forward, you get this feeling of progress. You are more motivated, and you are more likely to continue pushing towards that goal. So after I complete a workout, I always go to my goal board and it excites me when I erase the amount of workouts that I had completed for the year and then update it with the new number that we're at, in addition to how many miles have been ran throughout the year. So written, informed, noticeable. The last thing the S in wins is with your goals. Your goals are ultimately a desired outcome. What is important is that your goals have a clear system defined. So this has probably been one of the biggest unlocks that I've experienced as it relates to goal setting is that not looking at them as just purely goals or outcomes rather, but looking at them as journeys and asking the question who must I become? Who must you become in order to achieve goal XYZ? So a common one that I like to reference is the weight loss ones. There's a lot of folks that have a goal to lose a certain amount of weight. Let's pretend that the goal is to lose 20 pounds. Okay. Now, we could lose 20 pounds if we ran in a trash bag Monday through Friday this week. We could easily lose 20 pounds of water weight. I know this from my experience as a wrestler. It is not challenging to lose weight, but it is different to lose weight versus become somebody who has lost weight and has a system to keep it off. So if we went out right now with our trash bag and we're 160 pounds, we want to get down to 140, we could be there by Friday. But what didn't change is the system. So after Friday comes, you hit 140, and then what happens? Then the junk food. We didn't get rid of the junk food. We didn't build a real habit of working out, we didn't build a real true habit. We didn't become somebody who is disciplined. So who must we become if we're going to lose 20 pounds? We must become somebody who has a fitness routine. So somebody that goes to the gym a few days a week or runs, whatever the case may be. We must become somebody who is disciplined. So we're going to choose the lean grilled chicken over the fat nasties at McDonald's. Who must we become? So, with your goals to have the best possible odds of achieving them in 2026, make sure they are written. Make sure you inform somebody. Make sure that they are noticeable and make sure that they have a system behind it. Now, if this is something that you believe you could benefit from, that you could use help with, some assistance, some support, then please do reach out or check out the unshakable discipline mastermind community. It is a monthly membership and we are a tight pack of highly committed folks that are invested in ourselves, our communities, our families doing good. And we also get to hear from a lot of renowned experts around the world. So a lot of the focus this year is going to be bringing on a lot of guest speakers. And that's one thing that I've been fortunate enough with this podcast is to build a large network of guest speakers, or rather, amazing guests that will be coming in and imparting their knowledge. So highly recommend checking that out. Now, going into the letter for the year, and as I as I mentioned, the the reason for doing this is to serve as a reflection tool, but also these are things that I've kept every goal in and since I've written for 15 years now. I have a set of goals in this blue binder right here that go all the way back to 2011. It is fun to be able to measure your progress, see how you've evolved, see how your thought patterns have evolved as well. And I love the reflection to not just highlight, hey, here's here's what was great, here's where we need to. And not even need to. Here's where we're going to improve. Here's how we grew as a person. So this isn't so much just outcome focused, but I'm really looking at from deep from within. And then what's the intention for the coming year? So I write this in third person, write it to yourself. As you hear this, it's my intention again that what you hear is a structure or a framework that you can use for yourself. So with that, next next thing is this isn't just to highlight a bunch of things of here's everything that went well. It's also to give yourself an opportunity to be brutally honest with yourself. What do you need to, what can you do better? What do you need to stop doing? So what supplements this is a start-stop continue list, which I'm not going to share here, but I am happy to share with you all. So as we dive in to my wish that you hear something that you can take away for yourself and also something that you can use to set up your intention or declare your future in 2026. Here we go. Ryan, another year that feels like a five and one because of continued growth, more so from an internal perspective and improving your way of being. This year, you really learned how to simply be and strengthen your gratitude muscles greatly. This led to being more calm, understanding, and empathetic. You learned how to appreciate the environment much more, embracing silent walks, noticing more of the birds chirping, and smelling the roses, as you like to say. This is something to be proud of and continue expanding upon. You're learning how to still do a lot while also learning how to not do and really see from within. Physically, you put your body through a lot and definitely achieved your fitness goal of being at your strongest and most endurable state. Four marathons, including three world majors: Boston, Berlin, and Chicago, three 100 plus mile races, including the run across South Carolina, and making it to the end of the four-day Spartan Death Race. Amongst all of this are countless random morning marathons before work, quote, for fun and ultras. You also burnt yourself out a bit with several back-to-back events. Take note of that. There's a time to challenge yourself, and there's also a time to listen to your body and mind. Be a better listener in 2026 and go freaking hard. But freaking listen. Community was positively impacted by you in many ways, most notably with the unshakable discipline mastermind and breaking ribbons. Lives are being transformed. Don't forget to zoom out and see it. Members in the unshakable community absolutely crushed it in 2025, exceeding their fitness goals, making big career moves, and prioritizing their families. Seeing others achieve their goals and playing a role in it is a huge honor and a privilege. Continue to make waves in multiple communities in 2026 and take part in meaningful communities. One in particular that has made a tremendous impact on your life is Washed Up Coffee Club. What an incredible group of men and women who are injecting so much good into the world and pushing each other. It's infectious or contagious for a better word. The voice of your dreams continues to get louder, and the long-held dream of getting to the top of the corporate ladder is dimming. You have built a meaningful organization inside the walls at Boeing in the midst of tough times, and it's now benchmarked across the enterprise. Stop forgetting about the macro because you're so invested in the micro. Spend more time in the macro. That's a challenge for you in 2026 as you're used to being a doer that you can fail to see the journey. This is catching yourself, quote, living in the gap, a key from a favorite book, The Gap in the Gain. You're meant to fully live your dream and take your mastermind community, podcast, coaching, and speaking ventures full time. There's very real value here, but you cannot go at it alone. Zoom out and build a team to help you. The quality and value are both high and genuine, but the marketing is non-existent. Fix that once and for all. On the relationship side, a lot of growth and some turbulence here as well. There will always be some level of turbulence in any relationship, but what I do appreciate here is more of a desire to communicate effectively and respectfully. Going into the new year, you've now recognized how important it is for both parties not only to communicate, but clearly establish boundaries as well. This will be a future focus item. Now for the fun part. Opportunities, highlights, and an ode to 2026. Opportunities because failures don't exist. Build a team. You can no longer be the podcast host, scheduler, editor, mastermind host, admin, editor, and everything else on top of your corporate job. If you're really serious about building and designing a dream, treat it as such. Be more clear and less apologetic about boundaries. This applies to many things and isn't exclusive to a relationship. To be treated as you deserve and protect what matters most, you've got to be more clear here. Narrow list and sharpen focus. Recognize the limited time you have. Less equals more. Let every open opportunity be about improving, refining, and growing the dream hustle. Continue to really dial in on less and get help. Big stride this year in passing off active management of your retirement accounts to a professional. You managed it well, but that's a big thing for a dedicated professional to focus on. You can focus more on your dreams. Your life and circle will infinitely improve as a result of defining boundaries. Get this done early. Don't overwhelm yourself to where distractions pose as outlets. Keep dialing in. Highlights. Creating a massive impact for families who need it most and have someone currently battling cancer. Over$20,000 was raised and five families blessed through breaking ribbons in 2025. Running across South Carolina, surpassing your longest distance PR by 44 miles at 194 miles. Dozens of wins by members and the unshakable discipline mastermind. New PRs, first-time marathoners, business wins, family wins, and giving back in their communities. Spartan Death Race, you lasted all four days, 70 hours nonstop. Brutal experience. Win Today podcast is now ranked top 2% globally, one step closer. 10 day solo European trip to Amsterdam, Berlin, Prague, Copenhagen, keep exploring. More time in nature and solitude, which helped you grow. Moving further along in your faith and spiritual journey, creating meaningful experiences with family, flying mom to Miami, creating continuing new MLB ballpark tour with dad watching the Yankees, and sisters engagement plus 30th birthday festivities. Leading the first advanced training center at Boeing, South Carolina, making several new deep and meaningful friend connections. Continuing to give back unconditionally through my heart, time, and financial blessings. This continues to be the greatest reward. Weekly podcast streak surpassing 150 weeks in a row every Monday. Learning how to comfortably say no and create more time. Still a ways to go here, but big steps including stepping down from a nonprofit board, turning 2025s from 2024 opportunities into highlights. Now an ode to 2026. It's time to really lock in on less and go back to refining your old school systems, old school approach of crafting meaningful systems. This is what you help others do so well. When you reflect back on this in December of 2026, here's what will be true. You built a team and ran your business like a business. This freed up capacity, which led to more mastermind group members, coaching clients, podcast growth like never before, and paid speaking opportunities. You continued to raise the bar on giving back unconditionally. You grew more than you ever have spiritually and through your way of being. You focused on less but went extremely deep. You earned sponsorships and brand recognition that has helped elevate your mission. You created countless firsts in the lives of others and have helped them push themselves further and harder than they've been. You created love you haven't felt before. You watched your sister get married and gave the best dinner blessing of all time. Lock in, be obedient to the mission, hyper obedient. That's your word for 2026. Obedient. This will be a game-changing year. As always, never forget where you came from, do things bigger than you, and continue creating ripples of positivity, growth, and community. Love you. So that's what that's it. That's the letter. It's a great opportunity to allow yourself to see how the previous year went and guide yourself for the following year. So you notice that a couple times where I say zoom out, one thing that I do see a lot of ambitious folks, which I understand that's the listening, the listener base here, the audience, ambitious people can sometimes get so invested in the micro in the moment and forget all the steps that you took to even be where you are right now, to arrive at the very place that you are right now. And we can sometimes be continuing to check chase the next goalpost and forget the goalpost that we just reached. I understand that about myself, that there's even more opportunity to slow down and be and recognize what it took to get to this very moment. And I'm intent on that. And I know throughout as the years go by, again, that's that's one of the things I'm guilty of. So putting that in there is just another reminder, but also a guide for 2026. Enjoy the journey, witness the journey, see the journey. So it's my wish that by providing this, these best practices and this reflection, that it can help you see more of you and set a great course for twenty twenty-six and win today. Let's go.

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Ryan Cass

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