Six ways to build Confidence and Self-Esteem

With confidence and self-esteem the world is yours.

Almost anything is possible, puppy dogs & rainbows follow you everywhere and life is fantastic. Everybody loves you, your dog thinks you rock and you love and respect yourself.

Now, there are some people who are born confident and overflowing with high self-esteem.  They are naturals and always seem to look at ease in any situation.  Think Michael Jordan, Angelina Jolie and Tom Brady. They cruise through life seemingly without a care in the world and their hair always looks perfect. They look cool, sound cool and seem extraordinarily confident.

This guide is for the rest of us.

If you’re totally confident and overflowing with self-esteem, stop reading as this really isn’t for you. This is a confidence building, self-esteem game plan for non-supermodels and normal people.  This is for the flawed, the scared, the unsure and the ones who don’t look cool all of the time.  This is for people who have suffered through trauma, self-doubt, anxiety and could use a plan to build up confidence and self-esteem.  This is for you if you’ve ever:

  • Felt ashamed for being you
  • Thought you weren’t good enough/rich enough or just plain ‘enough’ enough
  • Felt like you didn’t matter at all in the world
  • Thought you were unloveable and undeserving
  • Felt abandoned and scared shitless

First, who am I and why should you listen to me?

Well, I’ve felt the same way and battled those same feelings. I’ve been exactly where you are today and I’m lucky to say I don’t live in that place anymore.

I am a perfectly flawed man, father, husband, entrepreneur, sexual abuse survivor and positive contributor to the world. I am strong, happy and very comfortable in my skin. I’m proud of the man I’ve become and feel confident in myself and my place in the world.  And now I want to help you get to the same place.

I wasn’t always like this.

I was a train wreck waiting to happen- using sex for power,  feeling ashamed and unworthy/unlovable most of my waking hours.  I was sexually abused by my uncle from when I was 10 until I was about 15 years old. I didn’t care whether I lived or died. That shitty experience could have ruined my life but luckily it didn’t.

Living as a sexual abuse survivor (I refuse to call myself a ‘victim’ and so should you- more on that later) has alternated my life in numerous ways.  In my 20s I thought sex was all about power, love didn’t exist and that I had to hide my secret. I lived in LA, slept around and really didn’t live a conscious life. I remember once I had sex with a Playboy Playmate (which had been a major goal of mine for some dumb reason) and afterwards all I felt was empty and hollow inside.

“Is this all there is?” I remember thinking.  I made a ton of money, had cool clothes, ate at the best restaurants and hated my life.

So that’s my story, thanks for listening, let’s get into the game plan.


This is a game plan to build confidence and self-esteem but it many ways it’s a game plan for life.  These are the steps, tools and methods I’ve used to turn my life around.  I’m not a therapist, scholar or guru so this isn’t theory.

In fact, I am living proof that you don’t need a guru to change your life, you need direction and action.  I put this game plan together to help you do just that.  This is all based on what worked for me- a regular guy with flaws and scars.

Let’s get rolling and let’s start with some undeniable truths and the theory of crossed wires as they relate to confidence and self-esteem.


•    Confidence is your belief in yourself. •    Self-esteem is how you view yourself. •    Confidence and self-esteem go hand-in-hand. You cannot have one without the other.  In many ways confidence is the result of high self-esteem. They are building blocks of each other, the more confident you are, the more self-esteem you have and vice-versa. •    Confidence and self-esteem can be built, you do not have to be born with them. •    Confidence and self-esteem are not set in stone. You CAN develop them even if you’re a shriveling mess right now (like I was). •    They do NOT have to be based on a crappy childhood or what people have told you. •     YOU are the only person who can build confidence and strong self-esteem in yourself. No one else can (or should).


To successfully build confidence and self-esteem you first need to understand the roots of low self-esteem and a lack of confidence.  They are usually the result of:

• Trauma/abuse • Bullying • Negative childhood/adolescent experiences

Notice what they are NOT the result of:

• Your value as a human being • Your abilities, skills and intelligence • Who you are as a person

They are the result of things that you’ve experienced, not who you are as a person.  It’s all in how you look at it. Consider the two statements:

“I fail all the time. I’ve failed in relationships, in business and in friendships. I must be a failure.” (Low confidence/self-esteem)


“Every time I fail, I learn something. Because of that I am a success.” (High confidence/high self-esteem)


So let’s get started with the game plan to build confidence and self-esteem. These are the six steps you need to build confidence and self-esteem.


The very first step in building self-esteem and confidence is to know the Captain.

On every ship, on every plane and every team there is a captain.  While everyone may work together there is only one person who is directly responsible for everyone else. That person is the Captain and the buck stops there.

In your life, the Captain is you.

You are in charge. You are in charge of how you feel, who you surround yourself with and what you think.  It’s your ship and the sooner you realize that, the better.

This is the crucial step in building self-esteem and confidence because it gives you power. If you have low self-esteem you often feel powerless, right? Ok, well then the first step is to gain some power in your life. That is the thing that will kick everything off and help you start building momentum.

Remember that no one is you. No one knows exactly how you’re feeling or exactly what you’re made of so why should anyone but you be in charge?

This is your DNA and yours alone.  You're the Captain, you’re driving the damn boat and don’t forget it.


A lack of self-esteem and confidence often occurs when you really don’t know who you are. If you don’t know who you are and what you believe in, how can you really feel good about yourself or confident in yourself since you don’t have anything to base it on?

Your beliefs are the foundation upon which everything else is built.

If you’re like many people, you’re probably not sure what you believe. That said it’s important to identify your core beliefs right away. Here are two things you can try right away to get started:

1. Get a journal and write in it everyday for 2 weeks. Write down the emotions you feel, what happened in your day and what you did, etc.  After two weeks read it and see if any themes pop out at you.

2. Make a list of things you believe about yourself. Some examples:

“I’m poor” “I’m rich” “Nobody loves me” “Money can’t make me happy” “Money can make me happy"

Your beliefs shape your self-esteem. If you think only money can buy happiness and you don’t have any then that’s going to lower your self-esteem.

You build your beliefs based on your experiences and observations.  They form the core of you for better or worse.  And the funny thing is your beliefs can change on a dime after powerful experience.  I had this happen to me about 16 years ago.

From Bacon to Fakin’: About 16 years ago I ate meat three times a day.  Breakfast meant bacon, lunch = turkey and dinner meant steak. I would accidentally eat a vegetable only if it was hidden in the chili. And then my girlfriend (my wife now) showed me a movie called The Witness, which was about factory farming.  After that movie and seeing the horrors that farm animals went through, my entire belief system changed completely. I decided that I could not support that industry and would not be a part of that world and so I decided to never eat meat again. Remember that at this point I ate meat 3 x day so this was quite a decision. It was extremely difficult at first because I hated vegetables but I was committed to my new belief.   And to this day, sixteen years later I still don’t love vegetables and I still don’t eat meat.

That is the power of belief.  Once your beliefs are ingrained in you and you can feel them at the cellular level, they’re a powerful source of confidence and self-esteem.  When I went through this I didn’t care who thought I was right/wrong or crazy, it didn’t matter.  The only thing that mattered to me is being true to my beliefs.  It has given me untold confidence and self-esteem over the past 16 years.


The drive to be perfect is one of things that crushes self-esteem. If you set perfection as the bar, you’re going to fall short. A lot.

Rather than shoot for perfection, shoot for success.  Success as a goal allows for failures and setbacks along the way. Perfection does not.  Plus, being perfect is boring as hell. Perfect people never have any good stories, cool scars and they usually don’t appreciate their success.

Stop setting such a high bar for yourself. Use success as your marker and don’t  worry if you’re not perfect along the way. Most, if not all, successful people brimming with confidence and high self-esteem aren’t perfect.  They’re ok with being imperfect.

Shoot for success and let the other guy kill himself to be perfect.


Clearly you won’t hear this in any textbook or typical self-help book but I firmly believe one of the keys to building confidence and self-esteem is to say ‘f*ck it’ more. Now, I don’t think you should walk around Target blurting this out but I do think this little two word phrase can be extremely powerful.  Here’s why:

It inspires action and inspires taking risks.

Action and taking risks are key components of building confidence and self-esteem. You cannot be something if you do nothing. You have to take calculated risks and you have to take action. You cannot raise your confidence and self-esteem without doing this.

Most people overthink everything (myself included) and don’t take action when we should. We wait. We think about it. We talk about it and we think about it some more.  By the time we’re ready to do something the opportunity has passed.

Using this phrase spurs us into action. It may sometimes get us into trouble too but probably far less than we think. Personally, the times I’ve just said, ‘f*ck it’ and moved from indecision to action have usually been successful.

Some examples:

•    “F*ck it, I’m moving to California” (1993, moved from New York to California, met my wife, had my daughters and built a life) •    “F*ck it, I’m quitting and starting my own company" (1998, quit Sprint and started my 1st company. That started me on my path to entrepreneurship which I remain on to this day). •    “F*ck it, it won’t kill me”. (2000, made the decision to challenge myself and run a marathon.  For a guy with a history of surgeries on my back and both knees running 26.2 miles didn’t seem like a great idea.  I did it anyway and it was one of the great accomplishments in my life)

So take some risks and say the magic phrase once in a while. Do’t be reckless, (“F*ck it, I’m driving home drunk tonight”) be smart and don’t be afraid of taking some calculated risks.  You will fail and get scars but the successes will be worth it. Besides life isn’t about being perfect, it’s about success.  Bringing us to the next point, which is:


People love giving unsolicited advice (hell, I do it all the time:) but that doesn’t mean you should listen to it.  If you want to build confidence and self-esteem you’re going to have to learn to press the Mute button.  You have to learn to ignore the noise that bombards you on a regular basis and just listen to yourself. Don’t fall prey to conventional wisdom or the tried and not-true, “we do it that way because we’ve always done it that way” BS.

Think for yourself and get used to trusting your own instincts and your own opinions. This is crucial to building your self-esteem up- you have to get used to pressing the Mute button on other people and just listen to yourself. And when I talk about other people I mean anyone who’s not in your close circle.

In your close circle you should have no more than 2-3 people.  For me it’s my wife, Kelly, my friends Jim Eagen and Scott Laing.  If any of them questioned something I was doing or thought I was going in the wrong direction, I’d seriously listen to them.  I might not change my mind but I would definitely listen.

In my career I’ve had to raise millions of dollars for my different companies.  I’ve pitched tons of investors and had plenty tell me my ideas were not good, albeit politely. I’ve had people question my skill set, my market knowledge and my team.  If I listen to every person who told me no or that I was wrong I’d be cooking french fries somewhere right now.

In fact, just about the only two people you should listen to outside your circle are your doctor and your lawyer. One can potentially keep you alive and the other can keep you out of jail. I’d listen to them.


One of the best ways to start building confidence is to create highlight reel of your past successes.  Not an actual highlight reel, mind you, but a list of 50-100 of your top successes in your life so far. These can be anything from running a marathon to graduating high-school.  We’re not judging on difficulty, we’re looking for quantity.  The idea here is that by doing this you’ll prove to yourself that you have a history of being successful. So here’s how to create it:

- Get a pad of paper and number it from 1 to 100 - Write down any/all success you’ve had that you can think of - Don’t include the birth of your children or getting married/meeting your partner- those don’t count on this - Don’t judge your list, just write down anything you can think of that you successfully did. The first 20-30 will be easy, the rest will require some thought

When I did this, the first 20 were obvious (ran a marathon, started a business, learned how to surf, for example).  After that it got tougher and I had to dig back to high school and college.

I remembered that I was elected to the student council freshman year in high school, won 'Poem of the week' in my poetry class in college, and started a band in college. Other things like my team won the SuperBowl in my football league a few years ago and my business won an award given by a local non-profit.

You will be surprised by what you remember and put on your list.  So now you have your list and you can see that you have a pattern of success. By referring to this list often you start changing the view of yourself.  you start thinking, “Hey, maybe they were wrong, I’m not loser and a total failure because I’ve done all of these things”. It is extremely hard to think something (I suck) when there is a ton of concrete evidence (your list) proving otherwise.

Now once you’re done with your list think back to each moment of success you had.  How did it feel?

Before you go into any challenging situation run your highlight reel back through your mind. Remember those moments of success.  Where were you? What time of day was it? Were you outside, inside?

My example:

As you may know (since I talk about it constantly)  I play in a football league for guys over 35.  Although it’s touch football it’s very competitive and at the end of the season the two best teams play in the Superbowl. Two seasons ago we played in the Superbowl and were heavy underdogs.  No one watching the game game us any chance to win.  The other team was dominant and we also had a couple of our guys injured.

Long story short, we beat them and won the championship.

I played well, scored 3 TD’s and made a bunch of plays on defense.  I distinctly remember each of those touchdowns and they are all on my personal highlight reel. I know what part of the field I was on (right sideline) and what route I ran (stop & go). I remember that it was sunny and cool out and that it wasn’t too hot.

So now when I play any sports whether it’s pick up hoops, football, softball or surfing, I think of that game and how well I played. I play that highlight reel in my mind and it pumps me up.  It gives me additional confidence because it proves to me that while I might be the oldest, shortest guy on the court I have a history of success and a history of exceeding expectations.

That is what my highlight reel does for me and that’s what it can do for you.


One of the best things you can do to build confidence and self-esteem is to buy a journal and write in it every day.  Even if you’re not a writer this simple daily habit will force you to see your greatness and inspire you in many untold ways.  I’ll have more on this in a subsequent post but for now, head out to Staples and get a journal and start writing in it.

All in all, having self-confidence and high self-esteem will serve to make you happier and more successful.  Even if you think you can’t do it, try these steps and email me and let me know how it goes.  I’m here to help and read and respond to every email I get.  I’ve been in your shoes and I was able to make it work so I know you can do it too. And if that sounds a little ‘ rah rah’ for you, I get it but please know that I believe it.

Good luck!