How I Built Up My Confidence After Years Of Self-Doubt

“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves, ‘Who am I to be brilliant, gorgeous, talented, fabulous?’ Actually, who are you not to be?” – Marianne Williams


I Need Confidence

It is my firm belief that the lack of confidence in our abilities and self is one of the most disabling things we suffer from. It acts like a virus that starts small but over time grows to hurt our thinking, our actions, and our feelings.

It starts with doubt. Doubt that we are good enough or that we lack something. Doubt leads to fear. Fear that an attempt may result in embarrassment because of what we lack. Fear leads to Reservation. Reservation prevents us from even attempting or being the presence of an opportunity that could cause fear due to what we lack. Over time, reservations can add up and start to impact the personality of an individual. It can result in personalities that are overly shy or afraid or reserved. If left unattended or unchallenged, a lack of confidence can alter a person’s life in the decisions they make, the people they surround themselves with and the level of interaction they have with society.

Our Society Punishes Failure And Rewards Perfectionism.

In my opinion, one of the biggest contributors to the way we feel about ourselves and our achievements stems from the way our society punishes failure and rewards perfectionism. There are medals for first place and ribbons for all other places. When we start out as kids we praise participation and effort, however, as we grow older, success and rewards is only given to those that are better than all others. Perfection (first place) becomes what everyone strives for and failure (last place) is not even considered as an option. People try to avoid failure or anything that is moving in that direction. Whenever we do anything that has a chance of failing or not being the best we abandon it. At any point, if an idea, business venture, race, or competition start to face failure or sub-optimal success we consider abandoning it.

Failure is a valuable learning tool. As important is it is to strive for success, by alienating ourselves from failure or perfectionism, we do not allow for the benefits of failure. We try to avoid it at all costs and put ourselves in a protective bubble where we become too afraid to try new things.

Most Of Us Hate The Way We Look

One major contributor to the root cause of doubt in our abilities or the lack thereof stems from a dissatisfaction of self-image. Simply put, we do not love ourselves enough and think we are beautiful. When we look at ourselves in the mirror we focus on our flaws, scars, birthmarks, skin color, eye shape, nose pointlessness, lip size…etc. We feel these imperfections need to be fixed or removed and until that happens we will not be happy with our appearance. We form this perfect image of appearance from actors, models, musicians. This fabricated image is constantly used as a comparison to ourselves. We are convinced a good appearance means an attractive face, an in-shape body, and expensive clothes/shoes/accessories.

This logic is flawed and destructive in so many ways. By fixating on the imperfections we disregard and ignore the good features of ourselves. We fail to see the great smile, bright eyes, adorable dimples, great cheekbones, thick forearms, big calves, symmetrical nose, well-sized ears…etc. Our appearance might lack some qualities but we should be grateful and appreciative for the good qualities we do have. Chasing after an ideal image of an actor or model causes us to lose our own identity. Not to mention this is a fool’s quest because these individuals have the top 1% of genetics, the power of makeup teams and photo editing masters. We can never hope to compete with forces like that. Not to mention, half of those people only look great because of all the makeup and editing that takes places. Some of them look no different than us.

Ways To Improve Your Self Confidence

Find A Boring Weekend. Make It Your Transformation Weekend.

The key to the transformation weekend that will boost your self-confidence is actually taking a weekend out of your schedule to make it happen. In order to effectively transform yourself and follow all of the steps, you are going to need a chunk of time that has no interruptions. This process needs to be done all at once. Starting and stopping will significantly diminish the effectiveness and could result in failure. This process cannot be half-hearted, it requires 100% commitment and conviction.

Find a weekend when you do not have any commitments or events. It is paramount you will not be disturbed or distracted by any pre-made plans or obligations. Make sure to double-down and inform your friends and family you are busy this weekend so no last-minute interventions happen.

I understand weekends are an important time to unwind and relax from the work week. However, something it is worth sacrificing some of this time for a lifetime of improved self-confidence. Think about the new opportunities, relationships, and victories you will get in return for taking out one weekend and focusing on yourself rather than relaxing.

Stare Yourself Down Until You Feel Comfortable

The first step to building your self-confidence is becoming comfortable and accepting of your body. The best way to do this is to get naked and stand in front of a mirror. Stare at every part of your body from every angle. At first this will be very difficult. You will immediately feel awkward, shy or embarrassed. You will want to look away because your eyes will only fixate on the imperfections. However, it is crucial to keep staring at yourself in the mirror. No matter how badly you want to look away keep staring. You need to stare at yourself for at least 10 minutes.

The first 5 minutes will be spent focusing on your imperfections and thinking about how much you want to change them or get rid of them. As time passes you will get bored and start to see some of the good qualities. You will start to notice you have a well-defined butt or good shoulders. Little by little you will start to now gain a new appreciation for the good parts of your body. By the end of the 10 minutes, you will have come to terms with your body and know exactly what it looks like. Staring at yourself in the mirror will not be difficult or foreign to you anymore because you have seen all there is to see and you have stared at it long enough to come to terms with the image. Those flaws that once scared you, no longer hold the same amount of fear because you have come to terms with them.

Before you can change, subtract or add to your appearance you need to build self-understanding. You need to stare down every flaw and imperfections to take the power away from them. You will realize your flaws are not as bad as you once thought. Because we shy away from imperfections they continue to haunt us. We imagine them to be much worse than they actually are. By staring them down, we take the power away from them and there is nothing left to the imagination. They might even be less obvious now that you have gotten a good look at them.

Build A Wardrobe Of Outfits. Not A Wardrobe Of Clothes

Now that you feel more comfortable with your body and have an appreciation for your good qualities, it is time to build your style. Style comes in many different ways but perhaps the most important is in the way you dress. Everyone’s body is a bit different and as such, you need to pick the correct clothes which fit your specific figure and look stylish. When picking out clothes it is important to find clothes that match, do not contain colors that clash and fit well. To make this process easier and more effective we should consult professionals whose job it is to mix and match outfits to well fit different body shapes.

Think about the last time you watched a Red Carpet Event. Do you remember even one celebrity that looked bad in the outfit they were wearing? Sure, people like Gal Gadot, Brad Pitt or Chris Evans may need little help because they would look good in an outfit but there are a lot of directors, producers, sound engineers who do not have great figures and they look just as good. The key behind this is expert stylists and tailors who know how to dress people of different sizes and shapes. Obviously, we cannot afford to have the stylists and tailors of the stars but we can consult the staff of high-end stores like Nordstom and Niemen Marcus. These stores offer personal shoppers who can help you pick out clothes or outfits that best fit you. What’s more, their stores are full of a diverse set of clothing so you can get help on a variety of different outfits. Their stores even have tailors who can help determine the best way to alter clothes to fit your body shape.

Start by going to Nordstrom or Niemen Marcus and ask to be paired up with one of their personal shoppers. Avoid peak times of the day because these individuals work on commission and you do not want to take away some prime commission and you want them to focus their attention on you rather than helping multiple people at the same time. Tell the personal shopper you would like to assemble a few different outfits for different occasions and seasons. You need outfits for a social party, a work party, date night, hang out with friends. Each of these occasions should come with a variation for summer and winter.



Social Party


Social Party


Work Party


Work Party


Date Night


Date Night


Hang Out


Hang Out


For each outfit make sure you try each out one in the mirror and capture: pictures, measurements, clothing styles (ex: long sleeve polo). You will need the pictures and details later but it is important to see how good you look in professional, high-quality outfits picked out by a professional. Ensure each outfit gets tailored to you and be sure to pay close attention and capture the tailoring measurements. If this is done behind the scenes be sure to ask for a transcript with them. You will need to remember how to tailor your outfits because moving forward these will be the measurements you will use.

Once you come home with these outfits the real task starts. The first step is to find similar pieces of these outfits online at cheaper stores like Macy’s, JCPenny, Zara, Jcrew, Express, and Uniqulo. It is important to note high-quality clothing at Nordstrom and Niemen Marcus will fit and look much better than the clothes you find at the cheaper stores, however, rest assured, a good tailor can help accommodate for the difference. There also might not be cheaper or comparable alternatives at the cheaper stores. In these cases, it is up to you to try and find a suitable alternative or keep the specific piece of clothing from Nordstrom or Niemen Marcus. The quality, customer service and tailoring of these clothes are sometimes worth the price.

As you spend time finding suitable matches at cheaper stores, it is important to try out the outfits. For the next few weeks try out each combination of the outfit (from head to toe) to get comfortable assembling and wearing them. You want to feel comfortable wearing these clothes and start to own them. The only way to do that is to wear them and let people associate them with your style. Keeping them on hangars locked away in your closet will defeat the whole purpose of this exercise.

When you have assembled your outfits with suitable matches from cheaper stores, you will want to store each outfit in your closet on one hanger. This will allow you to take the guesswork out of picking and re-assembling your outfits. You spent all this time and effort assembling outfits and the last thing you should be doing is splitting them apart in your closet. The sum of the clothes is greater than the parts of the whole. Label each hanger by the season and the type of outfit so you remember and can easily pick them out. Ex: Summer – Work Party.

Polish The Rough Edges With A Great Skincare Routine

With your stylish outfits ready it is time to focus on the last part of your appearance…your face. The face is the window to self-confidence. It is the first and last thing you and others will remember. A poorly maintained face with acne, wrinkles, dark circles or a messy haircut can really take away from any outfit and hamper your self-confidence.

Even if you have good skin and a good haircut, everyone can stand to improve the health and vitality of their skin. Better skin always has great benefit and will add to the style of your fashion.

Do Not Be This Guy

For the best advice on skincare and the routine, I follow everyday check out my article. If your hairstyle is a mess or you do not have one, consider going to a salon and consulting a barber. Show him/her the outfits you will be wearing and ask them to recommend a hairstyle that would complement those outfits. They are experts and will be able to recommend the best haircut to fit the shape of your face. The last thing you want is to copy a famous hairstyle from a magazine because everyone’s face is different and what works for George Clooney would look terrible for you.

You Are Your Own Brand. Advertise.

Now that you have great outfits for every occasion and a well-maintained face, it is time to go out and showcase your style. You need to start wearing the outfits and putting yourself in situations where you want to be noticed. The hard part is done, you look great, now comes the easy part of showcasing your personality. Without you, the clothes and hairstyles are just individual attributes. Your personality, charisma and attitude is the glue which binds them together to create one cohesive entity “style”.

The more you wear the outfits and make memories in them, the more they will be part of your life and identity. Part of building self-confidence is to feed on the compounding effect of positive feedback and energy feedback. You won’t get any of that feedback by keeping the clothes in your closet or only wearing them on rare occasions.

Why Is It Important To Have Self Confidence

Taking a weekend to identify your style will allow you ample time to get your look down from top to bottom. You can take your time to learn, purchase and try on the new look. If you can do this early in the year you can set yourself up for an entire year of looks. You will be able to go into each new season with a confident image and style. With each passing season, you will start to love yourself more and become comfortable in your skin. Staring at your body and taking in all of your imperfections will reprogram your mind to become more accepting of your flaws. You will recategorize them as features rather than defects. Doing this will allow you to love yourself on the inside. Once you have established love, the outfits and hairstyle will act as confidence sustainers and boosters throughout the year. In addition, all positive outcomes you experience as a result of looking and feeling better will only stand to further add to your confidence. At the end of the year, you will have developed a strong impression and image of yourself. With this powerful self-image, any situation you encounter will be met with limited doubt on your side. With limited doubt you will have reduced fear. With reduced fear, you will have fewer reservations. Fewer reservations will allow you to have the confidence to take on new challenges and things that once seemed impossible.

How Do You Overcome Self-Doubt?

What I’ve shared above are tactics and techniques that have worked for me, however, I am still constantly trying to overcome self-doubt and build confidence in new ways. I would love to hear what tactics or techniques have worked well for you. Feel free to comment below with an example or identify an area I might have missed. Please share so we can learn and possibly incorporate ourselves.

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