If I Knew Then What I Know Now

If you could sit down with your younger self, what would you say? In this episode of Second Wind, KR Henderson reflects on the lessons that only time, mistakes, faith, and experience can teach. From health and family to regret, forgiveness, and purpose, discover why wisdom isn't about looking back—it's about living forward.

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Transcript

SPEAKER_00 0:00

If you could sit down and have a conversation with a younger version of yourself, what would you tell him? I thought about this, and this is actually how I came up with this episode, episode 20, if I knew then what I know now. Would you tell him to take better care of his health, spend more time with his children, trust God sooner, start earlier, forgive faster, appreciate the moment while he was in it? I was thinking about a scene from Shell Shank Redemption where Morgan Freeman's character, Red, talks about wishing he could go back and talk to the younger version of himself, tell him how things really are. You remember the scene, talk some sense into him. But then he realized something he can't. That young man is gone. And maybe that's why so many men struggle with regret. Because we spend years wishing we could have a conversation with the man we used to be. When the real question is, what is the man we become going to do with what he knows now? As always, let me remind you, I'm K.R. Henderson, and this is Second Win. You're not late, you're assigned. A 22-year-old may have disappointments. I mean, I want you to think about it. A 50-year-old will have receipts, receipts from relationships, receipts from opportunities missed, receipts from decisions that look right at the time. And if we're honest, most of us have looked back and said, if I knew then what I know now. But here's the problem. Nobody gets to live life forward with hindsight. Life doesn't work that way. You don't get the wisdom before the lesson. And let me break the news to you. You get the lesson first, then the wisdom. This is where many men get stuck. Not in guilt, in regret. Guilt says, I did something wrong. Shame says I'm something wrong. But regret, oh man. I wish I had done something different. For the believer, conviction comes from God. Condemnation comes from the enemy. We know this. But regret, regret comes from us. It's the replay, it's the rewind. The mental movie we've watched a thousand times. And it goes something like, if only. I should have. Why didn't I? And here's the thing about receipts. In business, you file your receipts away, right? I mean, this is what your tax guy tells you to do. Always file them. We don't carry them around every day. We don't study them every morning. We don't even build our lives around them. We file them away. That's what we do. And why? Because receipts remind us of what we had to pay. Some receipts remind us what something costs financially, other receipts what it costs emotionally, others what it costs relationally. Not to mention what it costs spiritually. But the purpose of a receipt is not to make you relive the purchase. That's really not the objective. It's to remind you what you had to pay so you can make wiser decisions moving forward. Some of us, brothers, keep carrying receipts that should have been filed years ago. And this is why regret is such an important conversation, especially for Second Wind, because Second Wind, men usually are filled with guys who not a starting life, these are guys now who are evaluating life. We've got enough years behind us to look back, right? Enough experience, enough experience to connect the dots. I'm talking about existential experience now, not theory, enough wisdom to see what they could have been, basically. Or just enough wisdom to see what they couldn't see before. And if we're not careful, we can spend so much time reviewing the first half of our lives that we never get off the bench for the second halves of our lives. And I want to get in the game. I want to tell you a story, as always. I remember when my dad passed. And for a while, man, I'll be honest with you, I was angry with my dad. I was angry with him not because he passed. No, not because he died. I was angry because I believe he still had more life left to live. I really believe that. He was 75 years old, no cholesterol issues, no heart issues, no blood pressure, no diabetes, no major physical ailments, but he smoked cigarettes from the time he was 19 until probably 65. And for years, I wondered what did those cigarettes cost him. I mean, I want this to sit with you for a moment. What did it cost him? I wanted my children to know their grandfather. Taste his hot water cornbread, his dressing, his barbecue, his everything. I wanted them to see him, and I wanted him to see them grow up. I guess what I really wanted when I think back on it was more time. And for a long time I carried that frustration. Now, make no mistake about it. I understand God is sovereign. I believe that. He ultimately determines our days. But I also understand something else. Choices have consequences. Make no mistake. Smoking has consequences. Neglecting your health has consequences. Living under constant stress has consequences. Living in excess, that can have consequences too. Everything I believe has a receipt. This is one thing I know now that I didn't fully understand then. Every decision has a receipt. And I got a few. I got a few in my bag right here. As a matter of fact, you may not pay for it today. You may not even pay for it tomorrow, but eventually, life hands you the bill. It always comes due. This is why when you're 25, you can eat chili cheese fries at 11:30 at night and wake up feeling amazing, right? At 60, try it. Try it. You look at a chili cheese fry too long and you need prayer. Electrolytes and a nap. Life starts sending invoices. How you used to live, right? I mean, think about it, gentlemen. Have you ever looked at an old picture of yourself and got mad? I have. I mean, you remember saying, and I remember saying this, man, I need to lose some weight. Right? Fast forward 20 years later, and then you find a picture of yourself and say, you know what? I'd love to be that fat again. Right? Now you're regretting the body that you complained about. And I guess what I'm saying is regret really can and will distort your perspective. It's distorted mind. Now that's the lesson now, ain't it? Regret is often the pain of seeing the consequences clearly after the fact. The problem is many stop there and let regret become like an enemy. And that's a mistake, brother, because regret was never designed to be a prison. It was designed really to be a teacher. But there's another reason many men get trapped in regret. Guess what that is? And I had that t-shirt too. Forgiveness or unforgiveness. Sometimes we don't forgive other people. You remember earlier I told you I was upset with my dad? But it's hard to get to that side of forgiveness when you hadn't forgiven yourself. Because regret and forgiveness, they often are roommates. They're road dogs. They run together. You hear people say birds of a feather? That's regret and forgiveness. The other one refuses to release, right? And one keeps replaying the mistakes. And this is why some men never really learn from regret. We keep reliving it. I mean, you may have had a child, but you didn't plan for it. I get it. But you can't keep reliving that. We can't do that. We gotta learn how to move on and let that go. Which brings me to forgiveness. Because again, when you start talking about forgiveness, some men learn these lessons years ago. Right? But some never get it. My mentor used to say some get it early, some get it late, some never get it. Some men just never graduate. Why? Keep revisiting the mistake, replaying the conversation, reliving the decision, rehearsing the failure. And eventually regret stops being a lesson and starts becoming a sentence. This is when forgiveness becomes necessary because you cannot move forward while holding court in your own path. Sometimes, sometimes, the person standing on trial is us, is you. Waiting on somebody to acknowledge what they did. Waiting on somebody to make it right. Waiting on somebody to say, you know what? I was wrong. But what happens when the person you're waiting on is you. Some men have apologized to everybody except themselves. You made peace, we made peace with a divorce, right? Made peace with business failure. Maybe possibly made peace with an addiction or a mistake. But they still hadn't forgiven the man in the mirror. This is why regrets become dangerous. It's a dangerous, slippery slope. Because it keeps presenting itself. It keeps presenting evidence. It keeps reminding us what we paid. When all we do is review the receipt and we never apply any grace to it, then you spend the rest of your life really wrestling with something that God has already forgiven you for. Forgiveness doesn't change a receipt, it changes your relationship. You understand what I'm saying? Brothers, regret is really looking backwards. We talked about, and we say this, we're not late. We're a sign. A sign is moving forward. At 35, if you told me I was going to have a son at 50, adopt a son at 51, and have another one at 57, man, I would have rebuked you in the name of Jesus. I'd have said, that ain't God, that's confusion. At 35, I thought I was moving toward less responsibility, right? And God said, hmm, that's cute. I thought I was entering the fourth quarter of my life. And then God handed me a diaper bag. Some of you know what I'm talking about, right? Exactly what I'm talking about, right? You buying baby wipes and blood pressure medicine at the same register. But here's what I learned. There were seasons when I felt behind, when I wondered, had I missed my window. But looking back now, lay purpose was really preparation. Delay promotion was development. I can recall multiple times not being promoted. What I call a missed opportunity was often God preparing me, preparing you, preparing us for an assignment that maybe we weren't ready to carry yet. And I'll allude back to something that's always the overarching theme when we have conversations, whether it's mentioned or not. And that's working harder on yourself. Whoa. This is why it's imperative and it matters. Not yesterday, not ten years ago, right now, working harder on yourself matters. The past can teach you, the future can prepare you, but only today, this moment, this present can change you. That's why working harder on yourself has to happen consistently, often, and now, not later. We can't rewrite yesterday, gentlemen, but you can rewrite today, and today's decisions comes, it becomes a legacy for tomorrow. You remember when we first started the conversation, we were talking about Shawshank and the scene with Morgan Freeman, where he wanted to go back and talk to the younger version of himself to tell him how things really are, to talk some sense into him, but he couldn't, because that young man was gone. Guess what? My good man, so is yours. That young man is gone. The blessing isn't that you can come back or go back, the blessing is that you finally know. So, what is the man you become going to do with what he knows now? What's he going to do? I mean, your past can teach you, the future can prepare you. We know that, but only today, this moment, this present, can help you. Second win exists because life doesn't end after regret, it begins really after understanding it. Does that make sense? Thank you for taking time out, stopping by. And as always, you're not late, you're a sign.