How to Raise Your Self Esteem (and Why It Matters)

A few years ago, I did the “Less Things, More Happiness” 7 Day Challenge, so now, I want to continue with a new challenge.

Nowadays, it feels like there’s so many things one can improve upon and spend their time on: fitness, health, focus, willpower, meditation, productivity … it’s overwhelming. For at least the next week, I’m going to take a step back and focus on improving self esteem and self love.

Why does self-esteem matter? You may be like, “What’s the big deal here? My self-esteem is fine.”

I think most of us think we’re fine, but we often don’t have the confidence or self-love when stuff hits the fan. When it’s time to approach or talk to a cute girl, we freeze or show a lack of confidence. When we continue to stop by the fast food joint on our way home from the gym even though we know we shouldn’t, we’re withholding self-love for our long-term future. When something bad happens in our life and we let slip a bunch of negative self-talk, like “I’m a piece of crap”, that’s a sign of low self-esteem.

Now, some people do not have a self-esteem issue. They have an arrogance issue. They think they are better than everyone when they are not. They demand more than they should. But one can argue even some of them can be arrogant in some moments, and then, have other moments when they have low self-esteem.

Why is low self esteem a danger?

Many of us:

  • Do not give ourselves enough credit for what we do.
  • Beat ourselves up and compare ourselves to people we shouldn’t compare ourselves to.
  • Lack the confidence to perform well in our careers or personal lives.
  • Feel like we deserve less, subconsciously communicate that to the world, and get less because of it.
  • Sweep any successes or achievements under the rug and do not celebrate them enough.
  • Let our past chain us down. The word of negative people who beat our self-esteem to the ground in the past still echo in our heads.
  • Still have people in our current environment who lower our self-esteem more than they should.
  • Buy into racial, gender, or some other stereotypes that make us demand less than we are worth.
  • Give up or let our past rejections and memories fuel our lack of confidence when the past is in the past and doesn’t need to be indicative of future performance.
  • Aren’t getting the results we want in life, so we continually think we need to be richer, stronger, more muscular, more charismatic, and so forth … going on an endless treadmill. Then, we look back at years of anguish only to see people who aren’t that rich, muscular, successful who got the results we want. Perhaps, we didn’t need all that to begin with.

These factors can lead to a lot of negative results. Examples include:

  • Not demanding the salary or benefits we deserve in work.
  • Not making friends with people we can because we don’t think we are good enough (when we are).
  • Not approaching or dating the women we are capable of dating.
  • Negative feelings and suffering, which may include depression, sadness, anguish, frustration, resentment, self-pity
  • Behaviors that aren’t ideal. For example, behaviors of self-harm, which aren’t limited to physical. This can include staying in toxic relationships, failing to ever talk to women, failing to ask for a promotion, failing to change your fashion, or self-sabotaging yourself out of great relationships and opportunities.

I was listening to a podcast episode of The Mating Grounds, and I heard an interesting story.

They had a friend who was an everyday, blue-collar worker who made an average salary. This man was dating a female Indian doctor. After a few weeks, he stopped the relationship. Even though everything was going well.

The man didn’t even noticed himself until he was prodded. Deep down, he did not think he was worthy. The difference in status held him back. Months later, this doctor married another blue-collar worker.

It seemed that she did not care about status and she liked a blue-collar type of man. This man lost out on a opportunity with a beautiful woman because of his own lack of self-worth.

The difference between self esteem and confidence

There’s a small definition difference between these two terms. I believe the former is something personal to you. The latter depends on the skill you’re talking about. Confidence is trust in your abilities. In the real world, you should have a realistic idea of your abilities. You don’t want to be overconfident. For example, if you think you are an Olympic runner when you have never run a day in your life, you are in for a rude wake-up call.

In the past, unrealistic confidence lead to death. Those who thought they could kill an animal they couldn’t died and failed to pass on their genetics.

Confidence can relate to anything and it’s domain specific. That means you can be confident at basketball but not confident at public speaking. As I mentioned in another article, confidence depends on competence. 

Now, self-confidence and self-esteem relate to you as a human in your daily everyday interactions with other people. These terms are often used interchangeably. They are very related but not the same thing:

Self-confidence is a trust in your ability with your interactions with other people (speaking, selling, forming friendships, etc.). Self-esteem is a trust in your own worth and self respect. 

Now, I also think self-respect is a very related but different term, but let’s not get too deep here. It doesn’t matter that much since everyone kind of uses them all the same because they don’t know any better. So the terms have all kind of morphed to mean the same thing.

I brought it up because I want to focus more on self-esteem than self-confidence. The focus of this challenge is on recognizing, celebrating, and rewarding my accomplishments and self-worth. 

I want to focus more on self-esteem rather than confidence because you could be confident in a skill (like starting a business or speaking to a stranger) but still lack respect at your own self-worth.

I think it’s more important to focus on yourself first since it’s someone you will be with 24 hours a day. And the concepts are so related that once you get self-esteem down, some of it will bleed into confidence in related areas.

B.S. Advice Online and What I Will Do

After searching online, there did not seem to be as much information I can trust as I want. There were plenty of opinions on how to boost self-esteem, but little information backed by science or people with evidence overcoming these obstacles.

There were some decent stuff I found that I have picked up though.

Here are the practices I will do and where I found them:

1. Mayo Clinic’s Self-Esteem Drills

I got this one from Mayo Clinic’s website. They are one of the world’s most respected medical facilities in the world. Their article is short but they cite the seven studies they got their information from.

2. The Jar of Awesome (from The Mating Grounds)

This one has no scientific backing but it’s so simple that it’s worth trying out and it’s obvious how it can help.

Basically, you write notes about any small little awesome thing you did and put it in a jar. At the end of the day, you read these out to yourself so you are reminded and you don’t forget about your accomplishments without celebrating them.

I saw the YouTuber Swoozie do something similar with YouTube comments. Avoid social media numbers if you do it though because that’s a never-ending chase. Try writing it down rather than saving it on a computer because writing helps burn it into your subconscious more. 

3. The Self-Love Practices from Vishen Lakhiani (from his book)

Vishen is the CEO of a 100 million dollar self-development and meditation education online business. I was reading his new book Code of the Extraordinary Mind and he shared some awesome practices on improving self-love and self-esteem.

I wrote an article about those practices and will be using them in my 5 day challenge.

4. Helping Those Less Fortunate and Not Believing What Others Say

I got this advice from the billionaire John Paul DeJoria. He recommends helping those less fortunate than you when you are ever feeling rejected or insecure.

John volunteered at homeless shelters when he had nothing to give and no money to his name. It’s a lesson that you always have something to give.

He says this works because you feel so empowered when you help someone who needs help. I don’t like the word “empowered” because it implies that you are seeking fame or prestige and it might make you focus on chasing something power over others.

I think a better way of saying it is you feel valued when you help someone in need. Watch the video below to hear his own words on the subject:

He also mentions in the video that he was humiliated as a child and told he would never amount to anything. Rather than believe it, he chose to say, “What does he know?”

It’s a great lesson in realizing it’s okay to not agree to what someone else tells you. Sometimes, they’re wrong. Many people who have low self-esteem bought into a way of looking at the world that isn’t true and never considered questioning it (or never could).

A great example is Katherine Graham of the Washington Post and author of Personal History. One day, her husband died unexpectedly and she because the 100% owner of his company.

She was born in an era where everyone told her men were better than women. She believed it and so she wanted to give up the company and give away control. Warren Buffett came in and talked her out of it. Over the next decade, she ended up building the company into a globally recognized icon (and a very profitable one).

Buffett has said in interviews that Graham never fully gave herself credit for what The Washington Post accomplished. One could argue that too many years of conditioning from society were too much to negate.

Having said that, the world is making great strides. The highest paid MMA fighter is a female: Rhonda Rousey and Jennifer Lawrence recently came out to refuse to work unless she was paid as much as men.

5. Take care of yourself: Dress well, eat well, and groom yourself

I have heard this from personal development leaders like Brian Tracy, Zig Ziglar, Napoleon Hill, and Leo Babauta.

They say you should not buy into the idea that “it’s superficial to care about your looks.” That has been a crutch for me to remain lazy and dress like garbage. And I’m not the only one. A lot of people use this as an excuse.

In reality, people look at you differently when you dress better because it shows that you have good mental health, care how you present yourself to others, and care about staying clean.

Women are genetically wired to look for signs of ill health or STD’s. So do it.

I have heard this advice for years but I guess it was never presented in the right way for me to understand its importance so I never did it. Another part of it was not understanding men’s fashion well. Even when I spent my money on clothing, I would look sloppy because I did not know the foundations of fashion (fit, fabric, and function).

After taking a few months to study men’s fashion in my free time, I have a great grasp of it and can do much better now. A few hours of research is worth more than blindly buying clothes. I was blind but now I see. 

I have written a comprehensive article on the main things you need to know if you’re a busy person. But if that’s not enough, there is plenty of fashion advice online for free.

Finally, I just want to emphasize grooming. Dressing well is important but grooming is another important factor.

Let’s say you tell yourself, “I’m not superficial. I look beyond the surface.” I bet whether you want to or not, you will naturally give someone more of a chance if they have a clean haircut and a white teeth versus dirt on their face, hair sticking out everywhere, and smudges on their eye glasses.

When you look awesome, you feel awesome. And you attract more awesome people and events into your life. 

Bonus: Write and Read Affirmations

I wrote out several unique, reasonable traits about myself that make me an attractive, unique person. I will read these off my phone every day to remind myself why I’m worthy. From friends and dating coaches, I’ve come to discover this technique. It’s easy to forget about why I’m worthy if I’m just living my life. But taking intentional effort to realize the unique, cool things I’ve done can put me out of my “I’m just an average nerd who’s going to get rejected” mindset that I need to break free from.

One of my favorite affirmations is that “I am able to travel the USA as I work, something I wanted to do more of for years and found a way to accomplish.” But it’s not always the flashy stuff that I like the most. Another affirmation is “I am a kind, empathetic, hard working soul.”

Get Ready

Get ready to join me along this journey. It will last 5 days. I will continue to do this for this week and post my progress updates in the comments.

P.S. if you know of any credible self-esteem building advice, articles, sites, books, or other resources, let me know  in the comments below. I would love to find more. I am only looking for the best stuff though.

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By Will Chou

I am the the founder of this site and I am grateful you are here to be part of this awesome community. I help hard-working Asian American Millennials get rich doing work they love.


  1. Day 1 – I read the Mayo Clinic page, well, skimmed it. I was too busy to read every word since it’s somewhat long. But I got the major points. It’s a bit of common sense but common sense isn’t common. I will keep these tips in mind as I go through my day. I generally have a positive day unless a big interaction affects me, say I’m at the gym or somewhere and there’s a lot of fear or self-talk because a hot woman is there. We’ll see what happens today using these tips

  2. This article is just wow, I have often faced low self esteem since childhood due to some issues but this article is really well written!

    1. Thanks! I’m so glad you found value and relevance. I don’t often get comments on blogs, let alone positive ones. Thank yoou! I try also not to correlate my self esteem to social media / internet results; that’s another tip – people with flippant demeanors/self worths often make that mistake. That said, thank you! I think the article could be better but I’m glad it’s good for you

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