How To Properly Win In Life

Losing sucks. Everybody wants more winning in their lives. But for the aspiring Stoic, this poses a problem, a problem of interpretation. You want to win and you want to be a force of good at the same time, right? I ask: Can you be a winner and a good man at the same time? What about other people? Shouldn’t I care about them too? Let them win as well?

“Reject your sense of injury and the injury itself disappears.”
Marcus Aurelius

When you read quotes like this one above. You have to be careful with your interpretation. You could be dead wrong about it and still act on what you think is the ultimate truth. More often than you can imagine, it will not be the truth, in fact, it will never be the truth, you can only aspire to get closer and closer to it. Always, always meditate and come back to your teachings so that you can actualize your understanding of everything. Never, ever, close your eyes to ignorance. This is a topic in itself, onward. 

For a long time, when reading Marcus Aurelius, I thought that being a Stoic meant that I had to take the punches in and still be happy, like a cow in the rain, stoically taking it all in, while having a barn in front of me to cover from the rain. Although I wasn’t completely wrong because it’s true, you can train yourself to maintain a noble demeanor at all times, no matter what life throws at you, I wasn’t completely right either. I wasn’t completely right because I fell in a position in which I began to let myself be pushed around by other people in some tiny matters and others not so tiny while at the same time thinking I was acting morally. 

I thought that, because a Stoic man knows how to better deal with adversity, he should take more of it than others. You could translate this to: losing so that others could “win” more. In my wretched way of thinking and wrong interpretation, I thought that while I lost, I was winning.

I was dead wrong of course, thankfully.

Why? How do you properly win then?


First things first. A mindset is a frame from which you see the world. Whenever you read something, you need to think about the mindset you are reading it from as well, for the meaning of your reading will be different depending on the mindset you read it with. This is true for your relationship with others and with life in general. 


In my particular example, I saw the world as a place of winners and losers. A world of competition. Don’t get me wrong, a competitive mindset is neither good nor bad, it depends on the context. You are having a one on one basketball match? Then sure, go for competition, winning is literally defined by winning against someone else. But what happens when you take that mindset to everything else? Such as I did?

This is where it gets fun. A wrong mindset, like a wrong map, will take you nowhere. And it will not make only yourself lose, but everyone else as well. When you live life wanting to win against other people all the time, you might find yourself in a context where winning or losing against someone else will make bought of you lose. Ok, here goes an example.

Suppose you are having a hard time on your donuts business and you are making 0 sales. You arrange a meeting with your sales teams and partner to decide what you and your team should do. You have a great idea, but so does your partner. You and your partner have had an edgy week, so you are thinking that he’s an idiot, so he definitely should not make this call, so you want to impose your view against his, for the company’s well being. You exert yourself and manage to make a better argument. Everyone ends up supporting you, so you win. Only thing is, your partner knew much better about what he was talking about as he works directly in the sales department. So your idea actually bankrupts the business, you should’ve listened.

Let’s see, what was the goal here? Winning against your partner? Or getting more sales? A competitive mindset, in the wrong context, will blow out in your hands.

Now, let’s suppose that you are a Stoic or just a moral man in your eyes, and the same thing happens in your bakery. Just that now, you are the other partner, the one that lost previously. But in this case, you thought that you should let your partner have his way because it was important to him to win, so you, as the good moral man you are, let him win. You “lost to win”, at least morally.

What happened here? You bought ended up losing. The company still went bankrupt and now you are angry against yourself and as Nietzche would put it, your false morality, disguised as cowardice. 

This is how it goes in a world of winners and losers. In this world, there are only losers. You have to be careful, very, very careful and become able to catch the mindset you are working with.


What’s the way out then, if there is one?

The way out is maturity and collaboration. A world of winners, a world of winning properly. The world is not black and white. Unless you are playing a sport, winning and losing will always have a million shades of gray.

When you mature, you realize that you don’t want to win against other people, you want to win with other people, even if they are too childish or foolish to realize it. The truly stoic way of being is this one.

A mature person knows what he wants. In the bakery example, that was more sales, not winning against your partner. The mature person also knows that the other person has his own needs and as well and a completely different understanding of reality. So the only answer left if you want to win is collaboration.

With collaboration, there is always a better way, a way that can fit bought parties to reach their objectives or create better, entirely new objectives.

Collaboration implies maturity and creativity as well. In a complex world not fixed by the dichotomy of winning or losing, there can be many solutions, but you have to be creative enough to find them. 

You also need to be brave and compassionate at the same time. Brave because you need to know what is it that you want and speak it aloud, and compassionate because you have to listen and understand so that you can find the map that is the closest to reality.

In Buddhism, the Buddha speaks a lot about the middle way. But when he speaks about it. He does not refer to the middle of a line, but to the higher way, to the apex of a triangle. With collaboration, this is what you want to achieve, the higher way.

Day to day how to


Be careful with your interpretations. Think about your mind frame, your mindset when you read, interact or anything really.

About winning. Kow what you want, define what winning looks like to you.

“If a man knows not to which port he sails, no wind is favorable.”― Seneca the Younger


Listen. You need to understand how other people see the world so that you can understand what you are dealing with. It could be a better view than yours, or a worse one as well, but without a proper look and assessment on your part, your interpretation of other people’s reality will most likely be wrong.


Be creative and think abundantly. There are many, many solutions if you’d just put your mind to work. Once you know what you want, and you know what other people want. It’s time to put your mind to work.

Take this to your day. Think win-win. Be brave and compassionate at the same time. Choose a higher way.



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