Why "Pass/Fail" Thinking Is Killing Your Momentum
Ever quit on a goal the moment it stopped feeling like a win? This week's episode breaks down why treating progress as pass/fail is the quiet reason so many goals stall out before they get traction. He unpacks the start-stop cycle: new goals always run into friction from commitments you already have, and pass/fail thinking punishes you for that friction instead of accounting for it. Using fitness as the example, Jesse shows how to build momentum differently, going from zero to one, chaining b...
Ever quit on a goal the moment it stopped feeling like a win? This week's episode breaks down why treating progress as pass/fail is the quiet reason so many goals stall out before they get traction.
He unpacks the start-stop cycle: new goals always run into friction from commitments you already have, and pass/fail thinking punishes you for that friction instead of accounting for it. Using fitness as the example, Jesse shows how to build momentum differently, going from zero to one, chaining back-to-back reps, hitting a three-time streak, and only then raising the bar. Small wins aren't consolation prizes. They're the mechanism.
Next Jesse introduces "bookends": instead of judging a goal week to week, you set a real time horizon and a single checkpoint down the road; like committing to a podcast for 12 months no matter what the download numbers say early on. That container is what lets you actually learn, build relationships, and stumble into upside you couldn't have planned for (Jesse points to finding his own voice as one example).
Lastly, Jesse closes on why this matters beyond the goal itself, framing success not around hitting a number, but around impact, using his own book as the example: if it helps even one person, it did its job.
00:00 Escape Win Lose Thinking
03:04 Celebrate Zero to One
06:07 Back to Back and Streaks
10:01 Feedback Loops Beat Perfection
12:20 Shift Two Bookends
15:54 Podcast Bookend Example
18:51 Discovering Your Voice
20:58 Impact Based Goals
23:05 Book Link and Share It
24:19 Wrap Up and Next Steps
Lets leave the Construction Industry Better than We Found It https://www.depthbuilder.com/construction-leadership-lab
Download the free PDF copy of Becoming the Promise You are Intended to Be
00:00 - Why Big Goals Stall Early
02:20 - The Trap Of Pass Fail Thinking
03:05 - Fitness Example And Hidden Friction
05:06 - Zero To One Back To Back Streaks
08:39 - Feedback Loops And Raising The Bar
12:19 - Bookends As A Time Horizon
14:57 - Podcast Lessons Beyond Download Counts
20:24 - Skill Growth Through Recording Yourself
21:43 - Impact Based Goals With The Book
24:45 - Share The Book And Get Templates
Why Big Goals Stall Early
SPEAKER_00It's either a win or a loss, period. And the problem with that is when you're starting a big goal, when you're trying to make big things happen, the first step, the first rep, the first iteration is rarely going to be a grand slam. It's just not. Why? Because it's new. When it comes to making big things happen, like our big giant goals, there's one hurdle that we all have to get over, and it happens in our thinking. So we're going to go over two shifts to build and maintain momentum on all of your big goals. Shift number one is past fail thinking, and shift number two is bookends. If you've been caught up in like the start-stop cycle of we'll start a new thing, and then you stop, we'll start a new thing, and then you stop when it comes to losing weight, when it comes to launching your side gig, your business idea, your project at the house, or just being a better you, you're gonna want to stick around for the rest of this conversation. I am Jesse, your selfish servant, and my mission is to leave the construction industry better than I found it. I cannot do it alone, and this is why I am putting in work to help you do the damn thing. And so if you are out there in the omniverse, drop your question, drop your insight. If you disagree with what I'm saying, drop it in the comments, man. You ain't gonna hurt my feeling. I ain't saying my way is the right way, I'm just saying this way works for me. Point number one, again, these things are all about what I use to get my thinking right so that I can actually execute, learn, grow, and deliver on the big ideas and the big goals that I have for myself. And I also got to warn you when you start doing them, your goals are gonna get bigger and scarier. Why? Because you build momentum, because you start building evidence that you can actually do the damn thing, and it gives you motivation, not only that, but it starts revealing to you more gifts and talents that you have that you can contribute in service to others, which is just this beautiful momentum
The Trap Of Pass Fail Thinking
SPEAKER_00machine. And so here's the the number one thing, like this one over and over that used to get in my way, and I've worked with hundreds of professionals out there that have massive influence, and the one thing that I see over and over and over and over and over again is pass fail thinking, right? Like it's either a win or a loss, period. And the problem with that is when you're starting a big goal, when you're trying to make big things happen, the first step, the first rep, the first iteration is rarely gonna be a grand slam. It's just not why, because it's new. Let's just keep
Fitness Example And Hidden Friction
SPEAKER_00it simple, right? A lot of things that a bunch of us have dealt with, and and if you haven't dealt with it, it's very likely that you will deal with it again in the future, which is weight loss or physical fitness, right? So let's just say physical fitness. My goal for 2026, your goal, other people's goal, is to start working out every day of the week. Five days a week, I'm gonna hit the gym, I'm gonna run some miles, I'm gonna do whatever it is. What we don't take account for is the fact that we haven't had that as a priority in our life. So all of the other things that we have been committed to are still kind of pulling, not kind of, they're still pulling our attention, they're still pulling on our focus, they still expect the same level of contact with us. So that's friction that we don't see, and then we decide okay, I'm gonna have this brand new goal, this big idea, I'm gonna work out five days a week, and we don't know what how that's going to impact our environment. So day one comes, Monday comes, and for whatever reason, the sky falls down, you have an emergency at work, the kids get sick, you're sick, and you don't work out. And then what happens? Then we say, I suck, I'm giving up, right? Hopefully, you're not that doomy and gloomy, but that's past failed thinking. I said I was gonna do five days a week, I I missed the first day, so piss on it, I'll start again next year. I know that's a little extreme, but this is what we do with some of these big ideas and these big goals I have. We have we don't account for the friction it's going to take to put this new order of operations, this new way of functioning into action. It takes time, man. Like you're gonna have to learn. And so the way and more specifically, the the thinking or the mind games I play, the mental exercises I run is like, okay, I know that it's gonna be very difficult for me to just right out of the gate hit five days a week going to the gym or whatever your goal is.
Zero To One Back To Back Streaks
SPEAKER_00So I want to figure out how to celebrate small wins, and so the biggest win that we're like no when oh, we're not good at recognizing, is going from zero to one. And so if you're starting a little side gig, you're gonna launch a new, you're gonna start getting active on social media, like whatever it is. The idea is huge, exciting, and it's and all the things, the execution is a little harder, and so what we need to do, or what I do, this helps me a lot, is what I recommend. Is okay, I set the target, I have an idea, and when I take the first step, I went from zero to one, which is massive, and reason to celebrate. Yes, my goal is to eventually get to five days a week, but when I get my first workout in, I'm gonna celebrate. That's a big win. Why? Because it creates this feedback loop, it creates a little dopamine and starts building the momentum to do it again. And say week one, I only did it once. Okay, I didn't hit the five, but I'm not gonna judge it from a past fail perspective. I'm gonna celebrate that I went from zero to one, and so when I go to week two and I get a workout in again, guess what? Now I have a back-to-back situation, right? Because last year I wasn't doing the thing and now I've done it twice. That's a big, big deal. We don't give ourselves a credit. This is what I'm trying to tell you. Find an excuse to give yourself my more credit. My excuse is finding the small wins. Zero to one, huge thing to celebrate. When you do it two times, back to back, back to back, baby. That's a big, big deal. And if and when you do it three times in a row, let's say I only go to the gym one week one, one time week two, one time week three. Now I got a streak, right? For three weeks in a row, I made it to the gym. Yes, it was only one time, but that's a hell of a lot more than I did last month or last year. Now, here's where the little challenge comes and some account like personal internal accountability really comes into play, is because I don't give myself the out to just celebrate going once a week because my goal was five days a week. But if I had a streak of one day a week for three weeks, okay, now it's time to amplify and elevate. And so now I'm gonna go for two days a week. And the first time I hit two days, the cycle starts again, zero to one. All right. I did I went from one day a week to two days a week. That's a zero to one move. Reason to celebrate. When I get two weeks back to back of two days, three weeks back to back, now I have a streak, and it's just running that little cycle in my head to where I finally get to a point where I find myself doing the five days a week of working out or posting content or reading the books or working on the degree, working on the certificate, whatever your big goals are. If you're playing the past fail game, and actually I'll ask you right now, if you're out there in the omniverse and you get stuck with the past fail thinking, let me know in the comments because you don't have to stay stuck there. Oh, here we go. Miss Jackie is letting us know. Jackie says zero to one is a huge win, especially for things we have been putting off. Thanks for highlighting this, Jesse. Miss Jackie, you are welcome. And yes, like there's there's a
Feedback Loops And Raising The Bar
SPEAKER_00super awesome quote. I don't know where it is, I read it a long, long time ago. Um, it's kind of a study around thermodynamics of it. Only takes one degree to change the physical state of water, and it's an explosive change to go from liquid to gas to get water to go from its liquid state by boiling it to turning into a gas, steam, it only takes one degree. If that one degree never happens, it will stay in its liquid state forever. But once it reaches the that one degree of change, explosive things happen. And so I know it's a little nerdy, but that's what this can be like for you. And so if you missed my little cheat sheet to go from plan uh past fail thinking and start building momentum, it really is just celebrate small wins, which is still kind of loose, right? So, what are the small wins when you're starting a new thing? Small win number one, going from zero to one, period. If it's the first time you did it, that's a reason for celebration. When you've done it two times in a row, guess what? That's a back-to-back celebration. And when you've done it three times in a row, now you got a streak. That's a streak celebration. So there's three excuses right there to celebrate. Why is that valuable? Because it's the feedback loops that we design or we work in that reinforce our decision making and our behavior change. And if your feedback loop is a hundred percent, a thousand million percent completion rate all the time, every time, that's really difficult because life happens. Life happens whether we like it or not, and there's a lot of things that are gonna get in the way of us making the big dramatic change or becoming the amazing human being that we know we can be, or learn the things, or whatever it is. There is a lot of friction that we have to overcome. And so, building the habit of celebrating the small wins is how to overcome the past fail thinking. So, okay, we talked about the shift number one to get over the number one hurdle when it comes to launching, um, embarking on big giant transformation, big goals, make big things happen, which is our thinking. One of those things is past fail thinking. If you're in a past fail thinking cycle, give yourself permission to celebrate. How do you celebrate? Zero to one is it is cause for celebration. Back to back, cause for celebration three times in a row. You got a streak, cause for celebration, and then like raise the bottom, right? Raise the bar. So if I did it once a week for three weeks, that's a streak. Now I'm gonna raise the bar and I'm gonna go for twice a week, and I'm gonna celebrate for zero to one, back to back, and the streak. And then I'm gonna raise the bar and I'm gonna go for three times a week. What you'll find is you don't have to go through every progression, is all of a sudden you're gonna go from one to two to four to five, like you'll make bigger leaps because the thinking, like your the games, the mental exercise that we're doing, or the thinking exercise that we're doing starts kind of changing, connecting these super cool neurons, and we already understand, like, okay, I got something to celebrate, I'm getting closer. And then when you're on the track, then it's like, all right, let's just keep on trucking. So, number one is shift away from past field thinking. If you're in a past failed thinking, be kind to yourself, give yourself grace, and find a reason to celebrate. So that's item number
Bookends As A Time Horizon
SPEAKER_00one. We're gonna get it to item number two or shift number two, which is bookends. I couldn't come up with a different word or frame, and this is just how I think about it. Whenever I start a new thing, and and Miss Megan Shapiro, if you're out there, she and I had a uh do the damn thing conversation yesterday, and um, a lot of what we were discussing was in my heart about this idea that I wanted to talk about today. And so, like, the question is this like, okay, when I'm gonna start a new thing, a perfect example, I want to do a triathlon. My goal, I'm sorry, I want to do an Iron Man, a full Iron Man triathlon. And I said I want to do it by the end of this year. Right now, it is very unlikely that I am going to do one by the end of this year for a lot of reasons. Um, namely because I started training too late, but I've learned that most of the ones that are at the end of the year are already booked, they're outside of the country. There's a lot of things, but my bookends for this Iron Man thing are three years. And so when I'm starting a big idea, a big goal, when I was gonna when I decided to launch the Learn Ins and Missteps podcast, I knew out of the gate that there was gonna be a whole lot of crap to learn, like stuff that I knew I had to learn, right? Uh, in terms of the re the little bit of research I did of listening to different people and how to start a podcast and all that crap, like there were things that I knew I had to learn, but I also know just from experience, there's a mazillion things that I know I'm gonna have to learn that I have no idea, there's no map for what I was doing necessarily, because I was, of course, I was gonna do it the way I wanted to do it. And so instead of setting these past fail goals or targets, meaning I'm gonna do it, and if I don't get 5,000 downloads by week two or month three
Podcast Lessons Beyond Download Counts
SPEAKER_00or month four, then I'm gonna quit. Um, I use bookends. And by bookends, I mean what's the time horizon, right? Because I know from my experience, anytime I start something new, there are I learn a massive amount of stuff. Not only do I learn like my knowledge and awareness, not only does that like exponentially grow, but my network, the people that I come into contact with, the relationships that I build as a result of taking on this new goal, this new idea, whatever it is, is also massive. And so, what does that mean? Like, if I zoom out, rather, when I zoom out and look at all of the crazy things that I've taken on and started, a lot of them I never met, I never met, I never hit the summit, right? A lot of them I didn't. But holy moly, the stuff that I learned about me, the stuff that I learned about other people, the relationships that I built, and like the other uh rewards, byproducts of that experience were amazing. And I know I would not have had them had I not stayed on that path. And so the point is instead of setting up like the kindergarten metrics and saying I want 5,000 downloads within six months, which I could have like, and I get it, like if that's the way you do things, it's fine. Um, what I'm saying is this is the shift that I use that and and I recommend to everybody for having massive growth, massive impact, expanding your influence in a way where you're affecting people's lives, not just at work, not just at home, but in your community within the industry that you're in. And so, by thinking of it in terms of bookends, I put a time limit or check in it, if you will. And so when I launched the podcast, the Learnings and Missteps podcast, I said, I am going to do this for 12 months, period, whether I get a download or not. Because if I would have tied it to downloads, let me tell you, man, it'll humble you. It takes a lot of work for people to just know that you have a stupid podcast. And so when I set that up, I said, I'm gonna do this for a year, I'm gonna post a podcast interview every other week for the rest of the year, and at the end of the year, I am going to check and assess is this something I want to keep doing or not. Period. The point of the podcast back then, it's changed a little bit, was to highlight the men and women that are in the construction industry, which was a very thing to achieve. All I had to do was interview cool people that have been on their tools doing the building of our country and all the things. And so there were times when I wanted to quit because I wasn't getting downloads. There were times I wanted to quit because the audio was jacked up and the editing was hard, and like it was it was difficult. But again, the impact, every now and then I'd get a message, a review, a call about hey man, I listened to so-and-so's episode, and thanks for highlighting her or him because they're amazing, and we need more people and like young folks in out there to know that these we have this caliber of human being in our industry. Boom, my fire was lit and I kept going. When I got to the 12-month mark, the bookend, right? The bookends is the start and the checkpoint. So when I got to the checkpoint, the last bookend, after a year, I evaluated and said, okay, there's a lot of things I can be doing with my time. Is this being impactful? Is this adding value? Am I learning and developing new skills? Am I getting better? Yes, yes, yes, yes. Okay, then I'm just gonna keep going. And and that's that's what's happened. Now, specifically, I did not know this was gonna happen. And had I been hyper focused on getting 5,000 downloads an episode by six months, I would have adopted a lot of the conventional thinking, the conventional practices and advice that are out there that would have totally shifted the way I deliver a message more accurately. I never would have discovered my voice. I didn't know that. I wasn't starting a podcast to discover my voice, but I discovered my voice as a result of having the podcast. I didn't do it to establish credibility out there in the world, in the omniverse, but I discovered it as a result of doing the thing for a year because I was thinking in terms of bookends, not passfail, not simple metrics. And so, what do I mean by that? Like when, like for real, for real. If you've ever like I recommend this to everybody and anybody, record yourself sharing an idea, just talk to yourself, talk to the camera, or record yourself when you're having a conversation, doing a power presentation or whatever, and then re-watch it. Like, you don't have to have a podcast to have some massive growth from this thing. Now, what I was doing was every other week I was doing interviews, and then I was editing the damn thing. And when I was editing it, I could see why do I make that face? Why do I do that thing with my hands? Why do I stutter here? Why do I use that word? Why do I say it like that? That's not what I'm trying to say. I could say it a little clearer, and so week after week, or month after month after month, I was getting this feedback that helped me get clearer about what I wanted to say and how I wanted to say it, and how I wanted to, you know, pause and then elevate the energy
Skill Growth Through Recording Yourself
SPEAKER_00and get really excited. Like I started learning these things as a result of starting the podcast. That was not my goal. My main point here is because I was evaluating my big goal, the big project that I was launching, or the the limit was the measurement, was bookends time frame. I discovered these other uh peripheral, massively impactful benefits of doing the damn thing. The same thing with my book. I'm gonna tell you right now, writing a book, it's not that hard, it's a lot easier now with all the tools that are available. But I learned a lot, and then getting the book out there, and now another cheat code, this is a little bonus cheat code. I it's not to say that I don't set goals, I just think a little bit differently, right? Instead of passfail, I'm looking to build, design in some feedback loops with with the small wins, right? Back to back, zero to one, and streaks. Those are reasons to celebrate. Bookends, it's a time frame because I already know anything that I take on, I'm gonna have to learn more stuff, I'm gonna discover more stuff about myself, and I'm gonna meet people and expand my network, which is massively valuable, period. But when it comes to goals, the book, uh becoming the promise you're intended to be.
Impact Based Goals With The Book
SPEAKER_00I'm gonna tell you right now, it is very rare to become rich from writing a book. And may there may be a formula, I ain't figured it out, but my goal with the book was to impact one person. If my book impacted one person's life, it is a success in Jesse Land. And guess what? To date, I think it's been out two or three years, I've had at least a dozen people reach out to me directly to tell me how one of the little stories in the book impacted their life for themselves, or how one little story in the book they shared with somebody that was having the same struggles that I was talking about in that story, and it helped that person. I had one guy say, Jess, I read your book, I've been wrestling with addiction and substance abuse, and I am going to start right now. And I mean, I get chills now just thinking about it. So my goal was to impact one person. I've done more than that, right? And I'll I just tell myself that there's hundreds for everyone they call me, there's hundreds that have been impacted it in some way. And so, my main point there is when I'm setting goals, maybe this is a little extra bonus point here, is when I'm setting goals, I'm thinking of goals in terms of impact, not like money goals, like I need to, you know, I gotta make a living and all that crap. But when I'm thinking about what is the outcome that I want to have, what is the intended outcome of the initiative, I'm thinking in terms of impact. I'm trying to find what is the impact that I want to cause on another human being or human beings, and I'm looking for that because, like, for real, for real, if I'm doing that thing and it's not impacting other people in a in a positive way, what's the freaking point? Like, I've done that for 20 years and it was not a fun life to live. I didn't have the fulfillment that I have today, and so oh, we got a comic. Miss Jackie says, That's amazing hearing the impact, but why the heck haven't I read your book yet? Well, Jackie, there again, that's a failure on my part. I'm gonna send you a link. I'll drop a link in the comments, but I'll send you a link so you could download the P because you can buy the book, but you can also get a free PDF download from my website. So um, I'll drop a link in the chat and Jackie, I'll DM you specifically. That way you don't you ain't gotta spend no money, just get the book. And I have one request, not just for you, Jackie, for anybody else. When you get the book, whether it's the download or you go buy it, doesn't matter, share it with somebody. Because the whole purpose of the book is, or the book, the like the content of the book is for people that are struggling or caught in the trap of self-destructive behavior. And so if you're in that trap, if you're in that quicksand, please read the book. If you know somebody that is in that quicksand, give them a copy
Share The Book And Get Templates
SPEAKER_00of the book, please, please. The PDF, I don't care if they buy it, um, because it's it's my experience, it's of the dirty details of what I went through and how I got out of this the trap of self-destructive behavior. And so, folks, I super, super appreciate y'all being here. Uh, I I think I've said it. And if you don't know, no, I didn't say it. So I gotta say it. Um, I like to help people find the time, the focus, and the energy to invest in themselves so that they can cultivate their skills and talents so that they can better serve the people around them. One of the ways I do that is with the self-first time management system. And so if you want the tools, like the frameworks for that system, drop double D in the comments. I'll make sure you get a template of all the tools that I use for that. Um, again, it's all about you, it's all about figuring out it's the systems and frameworks to build the habit of putting yourself first. Um, and I'm here to give you permission to do that. So I appreciate y'all very much for showing up. Be kind to yourself, be cool, and we'll talk at you next time.
unknownPeace.