Being Assertive Will Get You Shit

What separates the winners from the losers?

When I say winner, I mean people that get stuff they want.

What is Assertiveness?

When people hear the word “assertive,” they think of some juiced up bodybuilder dude, some obnoxious rich guy, or some aggressive asshole.


You don’t have to be loud or obnoxious to be assertive.

You just have to be willing to go for it and be prepared to face the rejection or failure. This is why people seem confident; they’ve done it over and over again, so they’re used to it. But, it’s that first initial attempt that’s the hardest.

It’s the same as fighting a boxing match. You could spend two years training until your first fight and think “ok, I think I’m finally ready to fight” or you go do it three months in. You may think it’s reckless doing a fight with three months of training, but if you’re determined to get stronger and better, you will do anything. That means competing in a real fight. That 9 minutes you spend in the ring, the experienced gained will be equivalent to a few months of training at the gym.

Who do you think will learn faster if you put two fighters starting their fighting career and with similar skills, with one taking a fight in three months time and the other one reading, studying, and practicing for three months.

Why Should You Be Aggressive?

Recently a friend of mine was at one of the lowest points in his life. He got demoted for a job he recently acquired – the first in 1.5 years. He’s been stuck in the same position in his life for the past year and a half – college drop-out, no job, nothing going on with his life, and nowhere closer to his life goal. Probably not the best time for jokes…, so this is what I told him:

“I want you to get find me 20 different marketing companies in your local area and get their email. I want you to draft me up an email telling these companies you want to work for them. Send me this draft by 4 pm tomorrow. If you don’t do this, you owe me $100.”

EmailAfter 1 week from sending out these emails, you know what happened? He got an interview and is mostly going to be offered this job position. From 1.5 years of doing nothing to changing his life in one week, this is what it means to be assertive.

Assertive people are the ones that take action and go for the things they want. They have the balls to handle the pain and failure that goes along with it.

NerdTake for example the skinny, dorky guys at the nightclub walking home with a hot blonde stunner. You would think the jacked up guys on the side of the dance floor would get them right? As sleazy as it sounds, it’s these skinny, dorky guys have the balls to talk to girls that are “out of their league.” They’re ready to face the rejections, failure, and the awkward stares from people. 99/100 girls would probably blow them off, but it’s that 1% he’s waiting for. If he approaches 100 girls, one girl will say yes. What about the jacked up guy in the corner? Though he’s got the body, he thinks girls will just go up to him. Sure, maybe girls will, but this is probably a 1% chance too.

You now have two guys now – the skinny, dorky guy that’s outcome independent, while the buff guy is outcome dependent.

Which one do you want to be?

The guy waiting for things to come to you? Or, do you want to be the guy that goes for the shit he wants?

Being Assertive by Saying No

Here’s a great example by my friend on assertiveness – He’s one of the most motivated and intelligent guy I have ever met. He knows what he wants and goes for it – the definition of assertiveness. Make sure to check out his blog.

I got on the plane. Oh, It’s my lucky day, I’m at the emergency exit row seats – this means more leg room for me. Fuck yeah.

One minute later, the person next to my seat sits down and says “hey, umm… sorry, but can you swap seats with my girlfriend? She’s terrified of flying.”

I think for a moment.

“Mmmmm… No.”

I like my seat too much.

He looked at me at disbelief. I could tell he was upset, but he didn’t say anything. He walked over to his girlfriend, chat for a bit and then walked back to his seat with his girlfriend trailing behind him. She stands there hovering over him, clearly trying to eye me out.

Jim carreyIt made me feel uncomfortable, but I don’t give a fuck, I don’t owe you this seat. It’s a good seat.

When you start saying no, it’s going to feel uncomfortable, but at the same time, it’s going to feel so fucking good.

You realize that most people’s power is just their ability to make you uncomfortable if you don’t oblige their request. So as soon as you stop obliging those requests, you really do achieve a much higher level of freedom.

You know that movie with Jim Carrey called “Yes Man”? You know what would be more inspirational? If it was instead called “No man.”

How to Be More Assertive in 6 Weeks

Goku flexI dare you to be assertive.

If you don’t think you have to be assertive to get things you want, then you are totally wrong. I challenge you to find one successful person who you wouldn’t describe as assertive.

How to be assertive?

Good question. I think the best way is to practice it every day. Even just a little bit. You will develop a habit that will eventually ingrain to your personality.

Here is my gift to you: a 6-week plan on how to be more assertive. I actually developed a 10-week plan myself, but I’m currently testing that out.

Week 1 – compounded for all weeks – Ask your boss one request. It doesn’t have to be something big, e.g., since you’re getting a cup of coffee, can you get me one too? – once a week

Week 2 – compounded for all weeks – Cold approach a random person and hold eye contact until they break – once a day

Week 3 – one-time thing – Disagree with something once a day, every day of the week. This is a bit hard to track but try your best.

Week 4 – one-time thing – Ask for a discount once a day when ordering something – e.g., Order Starbucks coffee and just ask for a discount.

Week 5 – one-time thing – Organize three events for the week – e.g., organize dinner, lunch, night out in town, etc

Week 6 – one-time thing – Order a meal/drink – get them to change the order once it arrives or to personalize the meal. E.g. It’s a chicken sandwich, ask them to change it to beef and with no tomato. – once a day, every day of the week.

Cat Wizard of Chiang Mai

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