Check out this email I got from a reader:

“Man I would love to have better confidence, I would love to get cultured, and I would love to find a cool hobby like motorcycle riding or something….If I had the confidence, I would wear my style and not be worried about what people said to me or the looks they gave me. I feel like having confidence is an essential part of finding your style.” – Lee

I’ve learned a lot about confidence over the years, especially transforming not only my client’s style but my own as well.

Today I want to share what I’ve learned and how you can become authentically confident in almost anything – whether it’s to have the confidence to wear a leather jacket for the first time, quit your job and start your own business, or even ask that one girl out.

I LOOKED LIKE SHIT IN HIGH SCHOOL

Oh, the horror

Even for growing up in the late 90s it was bad.

I wore glasses too tiny for my face. I went through a big plaid phase. And for some reason I rocked a parted ponytail.

Like most awkward looking guys, I dreamed of being able to go up my crush (hell, anyone really) and starting a conversation.

I imagined being that badass who just effortlessly walks up to a girl he likes and starts talking to her, not giving a fuck about looking stupid or being rejected.

To me, that level of confidence was unimaginable. It only existed in movies!

And anyone that possessed that kind of confidence must be a freak of nature – they had to be born with it.

If chubby pony-tailed Peter attempted to approach someone that was remotely attractive, his nose would start bleeding, and he’d immediately throw up all over them.

It wasn’t like I didn’t try to figure it out. But the advice I’d sometimes get from well-meaning people just didn’t make any sense to me.

“Just stop giving a fuck and do it. Be confident, go up to her and talk! And you get confident!” They’d tell me.

But how the hell am I supposed to talk to her to get confident, if I don’t have confidence to being with?

It was a huge catch-22.

WHAT MEN GET WRONG ABOUT CONFIDENCE

Photo by Kris Atomic

It wasn’t until I started working in fashion, surrounded by models, did I learn the truth about confidence.

The world didn’t end after I had conversations with these ridiculously attractive women.

It was nerve wracking at first, but I survived.

A comment about the weather here. A small chat about the latest episode of Family Guy there. Soon, we’d have full conversations about traveling, relationships, and art.

It finally clicked…

Confidence isn’t about “not giving a fuck” what happens and doing it anyway, confidence is being able to predict the outcome of a situation based on experience. And doing it again and again.

I didn’t throw up or die the last time I talked with a model, therefore, I won’t die the next time I talk to someone that looks like a model.

In other words, people have confidence backward.

You don’t need to start with confidence to take action, you build confidence by taking small actions.

That paralyzing feeling you attribute to a lack of confidence is your brain telling you “Holy shit, I don’t have enough experience to know what to expect if I do this…Hold on. Stop!”

You’re not confident in trying something new on the menu, like that lamb burger with feta cheese, because you’re not sure if you’d like it.

But those fish tacos you get so much the waiter doesn’t even need to hand you the menu anymore?

You’re pretty confident you’ll leave satisfied.

So what does this mean?

HOW TO BUILD NATURAL CONFIDENCE IN ANYTHING

What we need to do is start making outcomes more predictable, and you can do this using what I call “The Flywheel of Confidence.”

You take a small action on something you want to be confident in.

You gain a little experience with the outcome, build a small bit of confidence.

You, in turn, use that small bit of confidence to take more action.

Now the flywheel starts spinning, your confidence starts to build up to the point where it feels effortless.

This is what they call a feedback loop.

Think about when you first learned to drive a car, how unconfident you were getting behind the wheel that first week.

You’re fidgeting, adjusting your seat and mirrors.

You were pretty sure you were going to crash the first second you got into the freeway.

But after years behind the wheel, you don’t even think about things that once freaked out.

You’re listening to Spotify, checking Instagram stories while sipping your coffee cruising down the freeway.

Your Flywheel of Confidence is spinning like crazy.

Amazing, right?

Here’s how you can apply the flywheel today:

#1: KNOW THAT CONFIDENCE ISN’T ALWAYS TRANSFERABLE

Many of my past styling clients came to me frustrated that they couldn’t “figure it out” on their own.

These are really smart, savvy, successful men.

Senior guys at their office. Accomplished athletes. Even a few guys that have founded multi-million dollar companies. (Even one co-founder of a multi-billion dollar company!)

If you’re feeling frustrated that you’re competent and confident at one area of your life but can’t figure another out, realize that this is PERFECTLY NORMAL.

Confidence in one area doesn’t necessarily mean confidence in another.

I’m pretty confident in my style knowledge and my ability to draw with a pencil.

But I’m not really confident in my tailoring skills, or my ability to paint with watercolors.

There is, of course, a few small exceptions.

I may be biased here, but improving your looks (losing weight, improving your style, or both!) DEFINITELY helps boost your confidence in dating and areas like public speaking.

(Kind of a no-brainer, but if you know you look good, you’re no longer paranoid about people judging your outside, that’s a huge relief and confidence booster.)

Action step: Don’t beat yourself up. Instead, remember what it was like when you first started something you’re good at.

When I first started drawing, I was ok, but was often too embarrassed to show people.

As I read drawing books, practiced, and took classes, I got better and better, and thus more confident in my drawing abilities. Now I sometimes do Livestream drawing sessions for fun.

Reframe “Why can’t I figure this out.” Say this instead:

“I know I can start something, get better and build up my confidence. I’ve done it in the past, so it’s ok if I suck or don’t feel confident about it now. I just have to take a tiny step.”

#2: WORK BACKWARDS FROM YOUR END GOAL TO FIND OUT WHERE TO START

The key to building confidence in something new is to start small.

And the best way to start small is to begin with your end goal, then work your way backward, step by step.

Let’s go back to the example of learning to drive a car.

Let’s say the end goal is to take a road trip across the United States.

It doesn’t matter if the end goal is lofty, so long as we can break it down phase by phase. Work our way back to a point where we would be comfortable starting at.

Let’s see what that looks like:

(GOAL) Road trip across the U.S. from New York to California ->
Drive to another state (From New York to Vermont) ->
Drive halfway across New York ->
Drive across town from Brooklyn to Queens ->
Drive around my block ->
Drive in an empty parking lot ->
(START) Sit in the car and learn all the components

Ok, what does that look like when it comes to improving your style?

Let’s say all you ever wear are t-shirts and jeans.

Your end goal is to confidently wear a full suit and tie for the first time in your life.

(GOAL) Wear a full suit and tie ->
Wear a sports coat, button-up shirt, and chinos ->
Wear a bomber jacket, button-up shirt, chinos ->
Wear a bomber jacket, t-shirt, chinos ->
(START) Bomber jacket, t-shirt, and Jeans

Action step: Write down your end goal, then work your way backwards, step-by-step. Break it down as much as you can, make each step easier and easier.

Ok, so you’ve broken it down. What’s next?

#3: THINK OF IT LIKE A VIDEO GAME AND LEVEL UP

We’ve all played a game where we breeze through the first few levels like pros, then hit that one that makes us feel like we’re Bill Murray in Groundhog Day, stuck, continually dying trying to figure it all out.

After a few more frustrating attempts, you have a breakthrough, and move on to the next level.

Now next time you load up the game, you can breeze through to later stages, just like you did the first few.

See where I’m going with this?

Think of each step as a video game level. The closer you are towards the final goal, you can expect it to get a bit more challenging.

Driving across town is more challenging than driving around your block. Driving across the state is more challenging than driving across town.

If we expect things to get more challenging instead of wondering why it’s not easier, you’ll feel less frustrated with yourself.

Instead of blaming yourself, you know that things will get more challenging as you progress.

The paradox is, the more you take action at each level, the more experience and confidence you build, the easier it is to move to further.

Action Step: Take a look your goal breakdown.

What’s a level you’re relatively comfortable starting at? Start there and take action.

If you can’t find a level you’re confident you can handle, it’s a sign you need to break things down further.

You might hit a few roadblocks along the way, internal and external.

Here’s what to do…

#4: BE CAREFUL WHO YOU LISTEN TO

Like dying a billion times on Super Mario World’s Haunted house level (ARGGGGGG), you’ll occasionally get an outcome you won’t like.

What should you do?

If it’s a bad result after you took some action, like hitting a parked car riding around your block, you need to do some reflection. Analyze what went wrong and make adjustments for the next attempt.

Other times you might find roadblocks that come out of nowhere, like criticism or unwanted feedback. These can come from of strangers, friends, even loved ones like your wife or family members.

One of my business mentors, Ramit Sethi, has a great saying:

“The world wants you to be vanilla.”

That is, the world wants you to stay the same.

Clients I’ve worked with in the past have sometimes been afraid to try a specific look because “My friends don’t dress up and they’d make fun of me.”

I recently hired a trainer to get in shape for my wedding. Some of my friends, hell some of my family members told me “You’re losing too much weight. You look fine! Have a drink!”

Here’s what I tell my clients.

Action Step: When someone gives you criticism, often thinly veiled as a concern, take a step back and look at who’s giving you the feedback.

Are they someone who you’d aspire to when it comes to that goal?

For example, If they’re making fun of your new style, examine their style.

Are they someone you’d consider stylish? Are they someone that you would want to dress and look like?

With fitness, is the person telling you ”You look fine!” in a shape you’d like to be?

The answer is almost always no.

What people say and how people react often says more about them than you.

It’s important to get feedback as long it’s from the right people.

Want to insulate yourself from roadblocks further and reach your goal faster?

#5: GET EXPERT HELP (PREFERABLY FROM PEOPLE THAT ARE WHERE YOU WANT TO BE)

One of the most valuable lessons I learned as I got older is that the HUGE impact of paying more to save time.

It all started a few years ago when I went to visit the famous Cedar Point Amusement Park, paying $100 for a “Fast Pass,” which is roughly 2x the cost of a regular ticket.

The Fast Pass let us skip to the front of the line of rides, saving us from waiting sometimes HOURS in the sun for the more popular coasters. It was so good we actually blasted through the rides too fast, we ended up riding our favorites a multiple times.

It was a revelation.

While most people look to squeeze out as much of a discount as they could, I looked for opportunities that saved me huge chunks of time, stress, and frustration.

Like the two times I went to Coachella, paying for the VIP pass, which had a fenced off area void of annoying college kids along with their own food stalls and luxe bathrooms with no line.

And let’s not forget my most recent investment – hiring John Romaniello as my personal trainer to get me looking good for my wedding.

I swear I know how to tie a bow tie

Working with John got me in better shape in 10 weeks than I got in the previous 14 months trying to do it myself.

Getting to your goal faster is awesome, but biggest benefit by far was the peace of mind.

I knew I wouldn’t miss any amazing rides at Cedar Point. I could relax and enjoy the music knowing I wouldn’t be dealing with annoying lines to the bathroom.

I was confident I would look amazing for my wedding because John’s helped hundreds of people before me look sexy.

Working with John was just like cutting the line at Cedar Point, except instead of feeling nauseous at the end, I have a nicer jawline and 2 out of 6 abs poking through.

IF BUILDING CONFIDENCE IS LIKE PLAYING A VIDEO GAME, HIRING AN EXPERT IS LIKE THE CHEAT CODE

This is precisely what my private clients have told me after working together.

The best part was not stressing whether or not they were wasting hundreds, even thousands of dollars in clothes they’d never wear.

They were confident whatever they threw on from their new wardrobe would just work and look good.

It’s like magic.

Action Step: Think about your goal. Are there any experts in helping people achieving that goal you can learn from?

For example, fitness trainers for weight loss. Swim instructors. Personal stylists (hint, hint).

Even if you can’t invest in hiring them, many will have resources that can help you skip a few level or two. Think about their courses, books, blog posts, podcast. Even hiring one of them for an hour or two consultation can save you MONTHS of time doing it on your own.

I WANT TO HEAR FROM YOU

What is something you’d like to get confident in?

It can be dating, public speaking, or dressing better.

Leave a comment below with your goal and break it down into steps.

peter@theessentialman.com'
Author

Hi, I'm Peter. I spent 11 years as a menswear designer here in NYC. Now, I help some of the most successful men look really good as a Private Personal Stylist and writer of The Essential Man. You can learn more about what I do by clicking here