A secret to winning

We all want to win in our relationships, investments, love. But winning is often counterintuitive. And we can sum it up like this.

To win, you must be willing to lose.

You see, in relationships, we want to be right or argue our point or make people see our way, our hurts, our pain, our truths. But if you’ve been around the block and have some experience, you know that doesn’t work. In fact, it only poisons relationships. Making people see what you see isn’t a way to create intimacy. To go deeper with people, you have to lose that need to be known first and, instead, try to understand others before being understood, empathize with them, feel their pain. When you do that, you will likely deepen your relationships. Of course, you want to find people where this “losing” is mutual. They are willing to “lose” for you and you for them. But sometimes, it takes someone to initiate it. And if you do, you will not find yourself without friends and loved ones.

Who doesn’t want more money? Of course, we all do. I’m just keeping it real here. But, what we aren’t real about is how to win in this area. In investing, winning is also about losing. Maybe you’ve lost money trying to invest, and you don’t want to touch the stock market. But I think there’s a reason for that. It’s the fact that you’re trying too hard to win. I know that sounds confusing. But let me explain. When I lost money in the market, often it happened because I was too afraid to lose money: anytime my stock or investment started losing money, I would sell. Then that investment would recover and appreciate, and I would feel terrible because I felt like I was missing out. So then I would buy back into that stock when the price was higher. Then it would go down again, and I would sell again because I was losing money. And that cycle kept happening. In short, I would try so hard to win that, at any moment when I was losing, I would try to save myself by getting out of the market out of fear of losing more money. Maybe you can relate. After reading books and reflecting on my countless mistakes, I realized that I needed to just buy and hold. But to do that, I had to get my head right. I had to be willing to lose my money, all of it if necessary, if I had a high conviction about a company. That’s when I started making money. To make money, you have to be willing to lose it.

Love is complex. And I don’t want to say that to make romantic relationships work, you just have to lose, because that’s not necessarily true. But it does help. I’ve seen it in my marriage. When I’m willing to die to myself for my wife, our relationship goes better. And, when I say “die to myself,” what I mean is that I’m willing to set my agenda, preferences, desires, etc. aside and let hers be higher, more important. That’s losing. And if you do that, you will win. Your love will grow. Now, I don’t mean for you to get abused. No, marriage or romantic relationship is a two-way street. So you need to tell the other person to treat you better if they are treating you like crap. But often, to engender love, love will feel like a one-way street. And you might be the roadkill sometimes. But your relationship will likely flourish.

And, in general, too many of us care too much. We live like we have something to lose. We strive to upgrade our cars, houses, jobs. And we are terrified of getting them taken away from us. But what we don’t see is that this race robs us of joy. When we care so much about our stuff and titles and money, keeping up with the Jones, we just end up living poorer lives. We lose.

It’s when we stop caring so much that we begin to live more richly. When we stop trying to make another buck, sacrificing time with loved ones, and start making sure they feel loved, we are richer. I mean, have you ever seen someone who seems to live so effortlessly, who doesn’t seem to have a care in the world? I don’t mean that they are careless. They just are not that burdened. They may not be the wealthiest person, but they have something money can’t buy. They are free. I’m not saying we should all become homeless people. But we all burden ourselves with things that just don’t matter that much. If that’s you, stop worrying about winning. In fact, be more willing to lose.

If you do, you’ll become a real winner.


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