How to Adopt a Winner’s Mindset (Even if You Feel Like a Loser)

The brutally honest truth about success

Some people are clearly and objectively not winning in life. They’re not bad people, but they didn’t make the correct moves. There are certain situations that simply aren’t ideal and the only conclusion you can draw from them is the fact that the person in them just didn’t play their cards right.

Again, let me add the little disclaimer that I have to add to almost every self-help post. I’m not talking about people caught in cycles of true poverty who were screwed from birth. It’s weird how people who aren’t personally in that situation always bring that up (coping mechanism).

If you grew up with a relatively normal upbringing and find yourself in a position you don’t want to be in…that’s not winning.

It’s obvious, we pretend like it isn’t, and we’re all collectively in this shared agreement where, as a society, we don’t discuss the fact that most people bullshit away the vast majority of their lives.

Why can’t we just be open and frank about this fact?

Why can’t you be open and frank about this fact with yourself? I did it. When my life was screwed up — depressed, drinking 7 nights a week, constant weed-smoking, arrested and put on felony probation, rarely had more than $100 to my name — it was difficult to view myself as a winner. Gee, I wonder why.

Self-care mantras, energy crystals, and affirmations didn’t help me change my life. I just got tired of being a loser. Maybe your situation isn’t bad, per se, but only you know whether you feel like a winner or not.

If you’re one of those people who scoff at the idea of success then stop reading this article. Why are you reading this article? Don’t you have some ‘contentment’ to get to or something? Go away.

Ok, for the rest of us honest folks, you have to be more objective and honest with yourself. Until you’re able to do this, you’ll always be stuck in the same spot — using your rationalizations and coping mechanisms to get by.

This doesn’t have so much to do with other people as much as it has to do with how you’re keeping track of your own internal scoreboard — the one you pretend doesn’t exist but exists nonetheless.

Maybe I’m wrong. Perhaps I will continue to rack of self-improvement points only to find I could’ve been happy and content with nothing. I’ll grant you that possibility. I’m still going to do it my way though.

I’ll tell you why.

Photo by Rob Wingate on Unsplash

“For I have a single definition of success: you look in the mirror every evening and wonder if you disappoint the person you were at 18, right before the age when people start getting corrupted by life. Let him be the only judge; […]If you do not feel ashamed you are successful.” Nassim Taleb

All I do with my self-improvement writing is project my worldview onto you. I don’t claim to be all-knowing. If you agree with me good — fall in line and start working. If you think I’m full of it? Equally good. You should be skeptical of people’s opinions, especially random bloggers on the internet and especially random self-improvement bloggers because, as a category, we are the most egregious peddlers of BS.

Before I share a message with you, I ask myself if there’s any modicum of BS in what I’m telling you. I always end up with the same conclusion. I keep coming back to winning. It’s hard for me to imagine someone not wanting to win.

Ask yourself…sincerely…don't you want to win? Don’t you secretly want to live up to the idealistic version of yourself you saw in your youth? If you thought you could pull it off, wouldn’t you do it?

I’m certain in saying that your 18-year-old self was right. What that person wanted is supposed to be you right now. And if it’s not you have some work to do.

If you want to successfully do the work, you have to adopt the mindset of a winner and understand that there is such a thing as living a low-quality life. Is the inherent worth of each individual equal? Yes. Are there outcomes and quality of life? Come on…

I come across as mean because it seems painfully obvious to me that this type of situation isn’t winning.

We all know it, too, but we’re in this culture where everyone is supposed to feel good about everything, all the time, for no reason. But still, people don’t like losing.

Deep down, you don’t like losing. So how do you fix it?

First, admit there are such things as winners and losers in life. You have to let go of the delusion that just because many other people live the way you do that it’s okay. It’s not okay.

Always be skeptical of any narrative society is trying to push your way. Never ascribe benevolence to your overlords. Why is the narrative of acceptance no matter what being pushed so hard? This participation trophy culture?

You’re easier to control when you have no incentives to improve your life. If you just give up, the only option you have is to do what your overlords say.

Equality stops at the inherent worth of human beings and the right to pursue your own happiness. Don’t take it an inch beyond that. In real life, outcomes are quite unequal. Some people are literally smarter than you — I can try to be Elon Musk all I want but, come on. Some people work harder than you. This is something you can fix. And yes, some people get lucky breaks.

Life is a game and it works just like many games — a fumble here, a stolen pass there, a deflected ball or two can change the entire trajectory of a season. Oh well, dude. Gotta keep playing until you win. Well, you don’t have to. You could remain a spectator.

I encourage you to try to win because if you don’t do something about your situation, it will get worse. Just look around at what you see. Look at how many adults look.

They used to be fresh, creative, ambitious, energetic — qualities they could’ve retained into their age by the way. But now they just look broken. If you want to win at life, you have to juxtapose yourself against these people and become terrified of being one of them.

Photo by Júnior Ferreira on Unsplash

If you’re in my age range (25–35) and you don’t do something about your situation now, odds are you never will. You can’t keep having ‘potential’ forever. One day, your soul will calcify and cement. For every Colonel Sanders who started at 60, there are thousands of…let’s call them ‘not winners.’

People get older and they simultaneously become more arrogant and less productive at the same time. Their life isn’t all that great but they think they know everything.

But, of course, this is the only conclusion you can make and feel sane, otherwise, you’d have to admit you wasted your life.

Speaking of wasting your life, the key to winning is realizing when you’re wasting your life. I’m so conscious of my time that it bothers me and I should probably let up a bit.

There are consequences to all actions, especially the pursuit of winning. You can lose a ton in the process. The choice of whether or not you want to do this is on you. Look at the case I presented here and decide for yourself.

I’ve decided to win as quickly and often as possible. After spending five years working on my own self-improvement I just want to get as much done now because I don’t know how much time I’ll have left.

If you just ‘get on with it,’ you’ll come to realize that putting a few years of work into something that matters to you isn’t that long of a timeframe at all.

You’ll build the disciplines, strategies, and habits it takes to be a winner.

Why does Tom Brady keep playing football? Why do Oprah and Ellen keep growing their media empires? Why does Warren Buffet keep investing?

All of them are filthy rich, at the top of their game, and have achieved legendary status without ever having to work again a single day in their life.


What’s a better alternative than winning?

As much as I love meditation and mindfulness — I’ve practiced both for the past five years — I’m not renouncing my possessions and moving to a cave to meditate in silence for ten hours a day because that would be boring.

Winning doesn’t make you happy. It really doesn’t. When you win the Superbowl all that happens is you get a Trophy and some confetti falls on your head. On a long enough time span, all accomplishments will be forgotten. So why try?

Just to see what’s possible. To grow in the pursuit of excellence. It’s not the championship itself you love, but remembering doing sprints until you puked, studying hours of film, and practicing basically every day of your life since you were eight years old to get here.

Seeing the fruits of your accumulated work is awesome, not because of the fruits, but because of the accumulated work. Success is the carrot you need to drive the part that matters, the pursuit. With nothing to pursue, you don’t do anything.

So go on your pursuit.

I will leave you with these parting thoughts. If you want to win, you must cease caring about the opinions of almost everyone. I used to care a lot when I first started writing. The mean comments did hurt and rejection does suck.

But as you grow on your own self-improvement journey, you come to realize the opinions of people who don’t work as hard as you are worthless. They don’t deserve to have an opinion on you because they are, again let’s be nice and call them ‘non-winners.’

Hell, a winner doesn’t have time to leave negative comments or reviews period — I’ve read shitty books before but I’m not a dork who leaves one-star reviews.

Why would you care about the opinion of someone who you wouldn’t want to trade lives with? Sure, deep down you do really what to be you, but you know what I’m talking about.

If Malcolm Gladwell or Ryan Holiday had some critiques on my writing I’d listen, but I don’t care for the opinions of 99.9% of people on this planet.

You shouldn’t either.

Why do you want to fit in so badly? Tall poppy gets cut down? Nah, not if it’s not even in the same field as the other poppies. Separate yourself from the infectious negativity of ‘non-winners’ and follow a mission that matters to you.

This is about how you view yourself. You want to see a winner, trust me. And you have everything it takes to become that person.

Whether or not you will? That’s on you.

Grab your free checklist here The Ultimate Guide to Discovering Your Natural Talents and Strengths. Wanna keep in touch online? Follow me on Instagram here.

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