How to Win at Life

We all want to win, but each of us defines winning differently. How do you define success?
  1. Think about someone you know who has achieved something you would like to achieve one day. What qualities do they possess? How do they live their life?
  2. What holds people back from defining their win?
  3. Have you ever worked hard at something only to feel like you haven’t really succeeded? If yes, explain.
  4. When you’ve experienced success in the past, what did you have to give up in order to succeed? What kind of routines did you put in place?
  5. So, what’s your win? How do you define success in your relationships, career, and/or finances? What changes would you need to make to prioritize this win (or wins)?

NOTE: The following content is a raw transcript and has not been edited for grammar, punctuation, or word usage.

So today, I wanna talk about winning because winning is better than not winning.


Winning is better, thank you, than not winning. And I know this for a fact because I have been a "not-winner", okay. Being a "not-winner" started for me in the 8th Grade when I was trying out for 8th Grade basketball at Tucker High School, and I got cut at the last night. I told somebody this story, I honestly, I'm not exaggerating, I never tried out for anything again for the rest of my life to this very day. I have never ever entered any kind of competitive thing that I thought I could get cut from. It was so traumatic. 

Today, I wanna talk about winning, but personally I'm not really much of a competitor, I'm not, I'm not competitive. And maybe you aren't either, but I just wanted you to know that you're not the only one in the room. So I don't lose you on this topic.

Others of you are so competitive that you have lost respect for me. [laughter] Because you're so competitive, it's like, "You are such a loser, I mean winning what you know... " Because come on, you're so competitive, when you were a child, you were the one that wanted to finish all your food the fastest. And your parents are like, "Slow down." It's like, no, everything in your life has been a race, everything's a race, everything's competitive, you always have to win. Because in my mind, I hear a little voice, my little voice says this: "Hey, you can't win. So why try?" That's what I hear. What you hear is, "Winning is everything. Try anything. Winning is everything, try anything." So you rise to the challenge, you're willing to do new stuff. It's amazing, you scare me a little bit, but it's amazing and I understand this. I have three kids, and all three of my kids, they are not like me, they try everything. My sons are so competitive, and I wish I was more like that.

Regardless, winning is important, because winning is better than not winning, especially in the arena that matters most. And the arena that matters most, of course, is your life. Which leads me to a question that I wanna leave you with today, that I hope you'll wrestle with a little bit. For some of you, and I can attest to this because this is true for me, this could actually be a life-changing question. I'm not exaggerating, you'll see in just a minute. This is a question that I hope you'll wrestle with. This is a question that perhaps I hope you'll wrestle with for the rest of your life.

For those of you who are parents, I hope that at some point you can introduce this into your conversation with your kids. Because if you do not answer this for yourself, you will spend too much of your life to use a phrase that King Solomon would use in the book of Ecclesiastes. You will spend much of your life chasing the wind. Instead of winning, you'll spend your life chasing the wind. This is a question that most people never ask. Consequently, it's a question that most people never answer. And if you don't answer it, if you don't answer it, in some arena of your life, maybe not your whole life, but in some arena of life, life will begin to feel like a race that you feel the pressure to finish, but you're not sure where the course is, and the course doesn't seem to be laid out very well, and everybody else seems to be running with purpose and you're just running but you don't know how to run with purpose because you're just not sure where the race ends, but you feel the pressure to finish it.

And here's the question I wanna introduce and ask you to think about: What's the win? 

What's the win? It's difficult in any arena of life to know that you're winning if you've never identified the win. What's the win relationally? If you're in a relationship, what's the win for that relationship? Financially? All of us think about money, and we think about money all the time, every day, we're trying to make as much as we can and save some, but what's the win?  What's your win professionally? If you don't know what the win is professionally, did you know it could be... You'd be like somebody who's running a race, and you run past the finish line, and you just keep running, and you're exhausted, and everybody's like, "What's up with you, and what's going on, and why are you so driven, and why can't you relax, and why can't you enjoy life?" And you'll just feel like, "No, I gotta keep running." And you feel that, to some extent, because you never identified the win.

In the areas of life, in the areas of life that matter most, most people never define the win. And here's the real tragedy, and this is where some of you are right now. And I'm not being critical, this is why you're here, this is why you're listening, this is maybe why you're watching. If you don't define the win for yourself, you'll end up adopting somebody else's. You will date like everybody else dates. You will spend your money like everybody else spends their money, you will spend your time like everybody else spends their time, you will parent either like you were parented, or in reaction to how you were parented, or you'll simply take your parenting cues from everybody else around you.

You'll work like everybody else, you will settle for what my friend Adam Johnson calls "not-goals". You know what a "not-goal" is? A "not-goal" is, "Well, I'm not gonna be like him. I'm not gonna be like her. I'm not gonna do... I'm not, I'm not... " And you're gonna set "not-goals", and "not-goals" are not enough because "not-goals" are not wins. 

So, what's the win? What's the win? If you don't know what the win is, it's hard to tell if you're winning. And let me ask you this way, what's the win in this season? Because in every season of life, there are different wins. 

If you're a newly-wed, or you've been into marriage maybe two or three years, what's the win? Now, I'm gonna share what Sandra and I's marriage win is, and I don't want you to snicker, okay, because we came up with this early into marriage, alright, I just wanna let you know. So it's a little idealistic, it's a little corny. 

And I'm not suggesting you adopt it. I'm just suggesting if you're married, what's the win? The win isn't, "Well, we never got divorced." [laughter] Wow, in our culture, that's kind of a win, right? Right, [laughter] "We just gutted it out, you know? [laughter] I hate to see you're coming, but by God... " That's not the win, right? 



Nobody is gonna stand at the altar and say... Anyway, we kinda do "till death do us part." That's such an awful thing, "till death do us part." [laughter] It's like, "Wow, I'm looking forward to that." So anyway, [laughter] so here's our statement, okay? It's corny, we were young, foolish. Hey, we still talk in these terms. Our win, we decided, was to always want to be where the other person is.


Thank you, oh shucks. I know, and that's great. Yeah, we just decided. You know what, this isn't complicated. We didn't have a verse or a scripture or something from Psalms, nothing embroidered, it was just, "Hey, you know what, if at every season of our life, I wanna be where you are and you wanna be where I am, you know, that's a win." So what would happen is, from time to time, this is how I would ask Sandra how we were doing with our... I would say, "Hey, do you still like it when you hear my car pull in the driveway at the end of the day?" And sometimes she would say to me, "You know what, I still love it when I hear the garage door opening." And that was her way of saying, "You know what, I still like being with you." And then she would ask me this, she would say, "Hey Andy, do you still like being at home more than you like being at work? Do you like being at home? Do you still like being at home more than you like being at work?" 

So for us, we decided the win wasn't money. The win wasn't... The win was just, if 10 years in, 20 years in, 30 years in, I still wanna be where you are and you still wanna be where I am... You may come up with a better one, that's a pretty good one. The point is, you need one. Because in marriage, it's so complicated, it's so emotional, it's so busy, right? 

Hey, for those of you who are parents, what's your win for parenting? Let me tell you what it shouldn't be. And again, kind of sticking my nose in your business. And most parents don't ever write anything down. Once you're a parent, who has time to write anything down, right? You can't find anything. So the win for parenting for a lot of parents by default, because they don't think about it, is perfectly behaved kids. I just want my kids to behave, I just want my kids to behave. Now, you don't write that down, because when you write it down, it seems so shallow. I mean, we want our kids to be educated, we want them to behave. But just, if you would just spend some time as parents thinking,

"Okay, so when they're gone and we're looking back on this whole thing, what's the win?" Because you are, whether you know it or not, parents, you are parenting in a direction. You are.

So Sandra and I, we came up with the statement. And I know, again, you don't have to adopt ours. Andrew, our oldest was in a car seat. That's how young he was. And we're talking about, "Should we? What are we doing? What are we doing?" So we talked, and talked, and I loved the way her family acted with each other, her family was very family-centric. There were five of them, with three kids and parents. And they love to be together. And I love the fact that they love to be together. I loved it.

So here is the statement that we came up with. This was our goal for parenting. Again, I don't have a bible verse. This was just what we felt like the win was as parents. We wanted children who want to be with one another and with us when they no longer have to be. We wanted our kids, when they were older, to want to be with each other and with us when they were old enough that they didn't have to be. And we parented toward this north star. And I'm telling you, once you decide what the win is, whatever the win is, you will change your parenting style, and you will change the way you discipline and the way you talk when you realize, "What are we trying to get to?" This was an extraordinarily important part of our life and our parenting.

Now our kids are in their 20s and they don't have to do anything we tell them to do. And they love to be together, and we think they still love to be with us, at least they're faking it if they're not. [laughter]

Now, here's the deal, regardless of where you are on a faith journey, this isn't really even about a faith journey, we'll get to that in just a minute, regardless of where you are on a faith journey, or whether or not you're even on a faith journey, you need to spend some time identifying the win. 

So what I wanna do with the rest of our time is, I wanna show you A win statement from the New Testament by a gentleman who has influenced all of our lives, either directly or indirectly, certainly indirectly in that we don't know him. But in terms of his literature, he really did shape all of our lives because of his words and because of his letters. And of course, I'm talking specifically about... Well, he showed up in history as Saul of Tarsus, and then he became a Jesus follower and started using his Roman name, and so we know him as Paul or the Apostle Paul. And the Apostle Paul's win... He's gonna give us his statement in 1 Corinthians, his win, and maybe you can relate to this, and this should be encouraging, his win, what he decided the win was for his life, was actually a response to a failure.

It was actually a response to a loss in his life because he steps into history as someone who has decided to put out of business a Nazarene sect or a Nazarene cult that sort of revolved around this Nazarene rabbi named Jesus. He decided, "I'm gonna put that out of business because it's disturbing the world order between the Jews and the Romans, and we can't let that happen. So we gotta put this thing out of business." So he started rounding up all the Christians and having them arrested. He had some of them tortured. People were maimed. And so, he had a track record of being very violent, but he thought he was serving God. He thought he was doing the right thing.

And then he meets the resurrected Jesus. Uh-oh! And he realizes, "Oh, no. I thought I was doing something for God. I was actually working against God." And then now, he’s got all of that in his past and he feels so guilty and he feels so terrible and for the rest of his life, he's gonna run into people. It's like, "Oh, yeah. I... Saul of Tarsus, yeah, yeah, yeah. Did you know you had my brother arrested and he's not been able to walk since. The rest of his life, he would run into people whose families he destroyed because of his zealousness to do something for God even though he was misinformed.

So he steps into history as that person. In fact, here's how he says it, because he became an apostle, a follower of Jesus. But here's his words. He said, "For I am the least of the apostles." He's talking about Andrew and Matthew and John and all the guys that followed Jesus. He says, "I'm the least of these guys. I don't even deserve to be called an apostle." Why, Paul? "Because I persecuted the church of God. But by the grace of God," I love this little phrase, "I am what I am. In other words, I can't change the past. I can't go back and undo what I've done. I am who I am with all that baggage and with all that stuff. I am what I am, and God's grace to me was not without effect. In other words, God did not waste His time coming after me. God did not waste His time revealing Himself to me. God did not waste His time. Now, I work harder than all the rest of them. In other words, you know Matthew and you know John and James and Bartholomew. I mean, those guys are great, but I'm outworking all of them, and I feel like I need to outwork all of them because of what I did in the past."

And sure enough, the letters that he wrote to the churches around the Mediterranean rim, they shaped and continue to shape Western civilization. It's amazing. He's the one that introduced Jesus to the non-Jewish world. And in 1 Corinthians, he explains what the win for his life is. Now, let me... I'm gonna show it to you, but here's my point; my point is not that you would adopt or adapt his win, my point is showing you his win is what he says afterwards. So here's his win statement followed by the motivation or his approach afterward. So here's what he says, I'll hit this quick. He says, "Though I am free and belong to no one, I have made myself a slave to everyone to win as many as possible." 

"So Paul, what's your win?" He would say, "My win is to win people. I wanna convince Jewish people that Jesus is their Messiah, and I wanna convince Gentile people that God has done something in the world on their behalf, and through the person of Jesus." He says, "So here's what I did; to the Jews, I became like a Jew to win the Jews." To which we would say, "What do you mean you became like a Jew? You are a Jew." Paul would say, "Oh no. Let me tell you what I mean. I mean, when I'm with Jewish people, I'm like a better Jew than any of them, like I amp up the Jewishness. Why? He said, "Because I wanna influence them. I want them to recognize, 'Wow, you're like a great Jewish person. I mean, I thought I was doing well. You're doing better than me.'"

And he says, "Because I want influence with these people. I wanna win the Jews. To those under the law, I became like one under the law, though I myself am not under the law," talking about the Jewish law, "so as to win those under the law. "To those not having the law," like us Gentiles, "I became one. I became like one not having the law, (though I am not free from God's law, but I am under Christ's law)." I'll come back to that in a second. In this top statement, here's what he's saying, "When I'm with the Gentiles, I eat like a Gentile. I drink like a Gentile. I dress like a Gentile. I walk like an Egyptian, and talk like... And wherever I am, I can get along with anybody. I can become whatever I need to become. Why? Well, because I have a North Star. I have a win that defines my life. I want everyone to know what God has done in the world by sending Jesus."

And then I love this phrase, "Though I am free from... I'm not free from God's law," talking about the Sinai Code, "but I'm under Christ's law." Now, this is a really important distinction. I don't... We won't spend a lot of time on, but do you know what Christ's law is? Now, when the Apostle Paul talks about Christ's law, he's talking about the single command that Jesus gave on the night of His last Passover when He said, "I'm gonna give you a new command, and here it is. You don't need 10, you just need one. As I've loved you, so you are to love one another." That was Christ's single law, not the Ten Commandments though, one commandment.

And Paul said, "I am under that command." That's why he gave up violence as a means to an end to further his cause. He said, "I'm under Christ's law, so as to win those not having the law." Then he finishes up, "To the weak, I had became weak to win the weak. I became all things to all people. Why? So that by all possible means." I mean, this guy was focused, wasn't he? "By all possible means, which means, I thought it through. I ordered and organized my life so that by all possible means, I might save some." His win was to win people.

But what comes next is for you and for me. What comes next is for you whether you're a Christ follower or not, and what comes next is really for all of us, because the Apostle Paul knew what we know intuitively: It is not enough to wish. It's not enough to want. It's not enough to desire. And so, he now dips into this sports metaphor that the people in his context understood and that we understand to some extent. He goes right into this after saying, "This is the win, that to win people, I'll do anything it takes to win people." And then he goes right into this next topic. It looks like he changes the subject.

He says, "Do you not know... " He asked these questions all the time. "Do you not know that in a race all the runners run, but only one gets the prize?" To which we're like, "Yes. Paul, thank you. We know how a race works. Everybody lines up. Everybody runs. One person finishes first, and that person gets the prize. So yes, so... But why are you saying that?" And let me tell you why he's saying it and then I'll show you how he says it. Here's the point he's about to make, this is so powerful; imagine if we lived this way. He said, in an athletic competition, the competition is obvious. In an athletic competition, the competition is obvious. In a race, they are lined up right beside you. You always know how you're doing in relationship to the competition. On the football field, they are lined up right in front of you. You always know how you're doing against the competition.

But when it comes to winning in life, when it comes to winning in your marriage, when it comes to winning with your kids, when it comes to winning financially or dating or whatever, it's hard to tell, isn't it? It's just not as obvious. Consequently, we lack urgency. There's no scoreboard. There are no fans. There's no clock. It's hard to tell how we're doing. So listen to what he says to us next. He says, "Hey, run in such a way as to get the prize." Implication: Live your life with the same urgency, with the same focus, with the same order that you would bring to a race or a competition to where there was a clock, where there were fans, where you knew who the competition was and you knew how you were doing against the competition. Live in such a way that you win. Pay the price you have to pay to make sure you're prepared to win, right? Because in an athletic competition, there's always a price to pay to win, right? And in the arenas of life that matter most to you, I don't even know you, but we know this about each other, right? The person on your left and your right, isn't this true of us? In the areas that matter most to win, there is a price to be paid.

The same is true in every single arena of life that matters to us. "Everyone who competes in the game," he says, he goes on, "Everyone who competes in the game," and he's talking about these games that took place right outside of Corinth. It was a famous place that for over 700 years, they had sort of these miniature Olympic games. Everybody knew what he was talking about. He said, "Everyone who competes in the games goes into strict training. Why? Because they want to win. Everybody who wants to win knows you have to say no to some things in order to say yes to prepare yourself to win." They do it to get a crown that will not last. And then he speaks to those of you who are Jesus followers, and he speaks to me as a Jesus follower. He says, "Come on. Think about the competition you're in. Think about what's at stake. But we," he includes us, "but we," in terms of competing and winning in life, he says, "we do it to get a crown that will last forever. And therefore," he says... This is so powerful. He says... Look up here. He says, "Because of what's at stake, because I don't wanna get to the end of my life and wonder if I won, because I don't wanna get to the end of my life and wonder how did I do," he says, "even though I can't see necessarily my competition; they're not lined up beside me or in front of me or waiting in line behind me, I run as if I can see them." He says, "Therefore I do not run like someone running aimlessly."

He says, "I do not run like someone running aimlessly. I do not fight like a boxer just beating the air." He says, "No, I strike a blow to my body and I make it my slave." "Why, Paul?" Paul would say, "Well, of course, I'm gonna do this because I know what I'm about. I have defined, I've identified the win for my life and I'm gonna order my life, my time, and discipline myself to make sure at the end of the day, even though I have to say no to me to get there, I wanna get there and it's worth saying no to me in order to get there."

Now, isn't that true for you in the areas of life that matter most? I know it is, because many of you have already achieved extraordinary things. You already know what it means to focus. You already know what it means to say no to you to accomplish what you've already accomplished. But in the areas of life that matter most, have you defined the win? In his case, this is what he feared. I don't know what you fear. Here's what he feared, he said, "I have to do this so that after I have preached to others, I myself will not be disqualified for the prize." So here's his bottom line, and then I wanna talk about us for a minute, his bottom line is simply this, "I am going to prepare and compete as if my competition was lined up beside me or standing in front of me. I'm gonna live my life with the same focus and the same energy, as if I could actually see my competition, because I don't wanna get to the end of my life and be disqualified because I wasn't prepared to go the distance and I wasn't prepared to win."

I think he would say to us what to some extent we already know: You don't win by wishing. You don't win by hoping. You don't even win by just praying. You win by preparing to win. You win by preparing to win. You win by saying no to you so that you can win. But you'll never say no to you with the urgency you must say no to you until you have identified the win. So, come on, what's the win? Relationally, financially, academically, professionally, what's the win? Are you preparing to win? Singles, let me just say something. If you're single or maybe even if you're single again, hey, if the win for you is marriage, then you can't date like most people date. If you want a marriage that's unlike most marriages, then you can't date like most people date.

This is why every once in a while I say I say, "Look, you need to take this one-year-off challenge. You need to step off the playing field for a year. So you can decide, 'Okay, when I step back on that playing field with all that crazy competition, what is the win for me?'" And the win isn't just a date, and the win isn't just an experience. The win is bigger than that. What is the win? Before I decide I'm gonna play, I'm gonna decide what the win is. 

For parents, let me just tell you, okay, now on the other side of maybe where some of you are, you're gonna have to say no to some things to achieve your parenting goal, once you decide what it is. Once you know what the win is... In fact, Sandra and I said this a thousand times. Here's what we would say, "No for now, but not forever. No for now, but not forever. 

And here's the thing, and you know this, you will find it so much easier to say no to you when you know what the win is. And until you know what the win is, you will find no compelling reason to say no to you. There's just not the urgency. 

Now, I'm almost done. At the risk of being a little bit overdramatic, okay, you only get one season. You only get to be in your 20s one time. You don't get to come back next fall and do your 20s again. You only get to do your 30s one time. You only get one first marriage. You only get to raise each of those kids one time, and the clock is running, and you have to decide. You have to decide what life is gonna look like for you and what you want the win to be. And if you don't decide, life and culture and the people around you are going to decide for you.

And remember this, and you know this. Remember though, when you win, when you win in the arenas of life that matter most, you're not the only person that wins, the people closest to you win as well. And when you lose, they lose as well. Now, if you're not a Christian or not a Jesus follower, I hope this has been helpful, you know. I hope this has been inspiring. I hope that you'll go home and come up with some wins and you can, because again, this isn't a Christian thing. This is just a thing-thing. We just found a model or an example in the New Testament. But if you're a Christian, if you're a Jesus follower like me, you're someone who said, "I have decided to follow Jesus. I don't get it perfect. Sometimes it kinda looks like this, but I'm doing my best to follow Jesus," this isn't just meant to be inspiring.

This isn't optional, because we have something in common with the Apostle Paul, right? He said, "Everyone who competes, everyone who competes in the games, goes into strict training. They do it for a crown that will not last." But if Jesus was correct, and I think He was. If Jesus was correct, our lives are not book-ended by a birth certificate and a death certificate. There's more to this life. There's more to life. If Paul was correct, and Paul lived his life as if he believed there was life beyond this life, then there's so much at stake for us.

So, to leverage Paul's words, as we close, I just wanna say this to those of you who are Jesus followers, and I'm saying it to myself as well, when it comes to the areas of life that matter most, and you know what those are, don't run like somebody running aimlessly anymore. Decide what is the win. Don't fight like a boxer who's just swinging their arms in the air. Decide what the win is, and order your life accordingly, and make your body your slave. And in doing so, let your life, your parenting, your money, your profession, your relationships, your dating, your marriage, your all of it, let your life, let your light shine in such a way that people would catch a glimpse of your Father in Heaven. Because at the end of the day, that's a win. At the end of the day, that kind of Christian living changed the world once. But in the meantime, for all of us, what's the win? What's the win? After all, winning is better than not winning.