How Do You Build Confidence?

“How do you build more confidence?”

This is a question I received during a presentation about 3 years ago. It was from a teenager. I can’t remember how I answered that day but the question itself has stuck with me. I suppose that young man was a little bit in awe of how a person could grow up with little external evidence that he should value himself but, somehow, do so anyway. That’s the paradoxical nature of my journey. Bullied, introverted, overweight kid turns into freedom fighting, athletic, combat veteran… and now, motivational speaker… doesn’t compute , logically… or does it?

As I’ve thought about the question I’ve realized that developing confidence is a simple matter. In any process if you express the humility to learn continuously and the consistency to execute that learning repeatedly, over time, you will see incremental results which will give you confidence in your ability to tackle the challenge. I’m betting that the young man that asked me that question that day wanted to know more about general confidence. As in, “How do you develop the confidence to approach any challenge?” In my mind the answer is the same but you have to keep applying those principles to new challenges. The principles are learning and repetition.

  • How did I lose weight and develop the confidence to take on different physical challenges? Learning and Repetition
  • How did I pay my way out of debt, learn about 401k/Roth IRA’s, and now, Day Trading Stocks? Learning and Repetition
  • How did I learn how to swim at 25 years old when I was deathly afraid of the water? Learning and Repetition

Confidence is simple. What’s harder is the resilience to withstand the inevitable trails that come with the process and life itself. Lets take a look:

People have been getting their worlds rocked for the last 20 years:

  • The Dot Com Crash in 2000
  • 9/11
  • The Enron Collapse (I say this specifically because this was a company based in Houston where I was going to college when it happened. I met people personally that worked at Enron and suddenly had no job.)
  • Hurricane Katrina (I was actually supposed to go work in New Orleans for Shell Oil just before Katrina struck. I was allowed to work in Houston because I made a strong request to change assignments.)
  • The Housing Market Crash and follow on Recession of 2008
  • Healthcare and The Issue of Student Loans etc.

Given all these events and circumstances, I still think we live in the greatest time in history. Life will never be void of sudden challenge. Of course these are big events but what about the situations that pop up in our lives individually? You all know about the rough go I had with bullying in school. You may not know that while I was paying off all my debt and living a pretty spartan lifestyle in my military training… While I was overcoming my fear of the water and taking on physical and mental challenges like I never had while I was in Special Operations Training… My sister committed suicide. 2 years later my mother would then have to send her only child to combat. I was worried about how my mother would handle my going to Afghanistan. I was scarred for her. When I visited home just before deploying, she couldn’t have been more calm and reassuring. You lose one child to suicide and then you send the other off to war… You stay totally calm. My mother is confident in her ability to deal with what life throws at her. I also have that confidence. It comes from learning to execute when life has dealt you a blow. I mean, when I lost my sister I had a clear reason to fall apart. When I headed off to war, my mother had a good reason to be in tears daily. But, No. We show up. We learn. We execute. Repetition.

If you let life push you around then you don’t stay in things long enough to see results. When you don’t see results, your confidence that change is possible starts to shrink. Eventually, confidence that anything can change starts to dissolve. This is the fundamental challenge that people have with diet and exercise: They don’t get through enough failures to make the behavior change stick. Or, they change behavior for a short period of time and allow life to derail them. The inability to simply stay the course and keep fighting to implement small changes over time keeps one from building the psychological momentum needed to see long term change. Allowing ourselves to be derailed over and over starts to make the task feel impossible. People lose confidence:

  • “I’m just naturally big and that’s how I’ll always be.”
  • “I’ll never be able to stick to a budget.”
  • “I just can’t focus. I’ll never finish this online course.”


  • “I’m big because every time life gets stressful I stop moving all together and eat mostly takeout because it’s just easier.”
  • “I’m in debt because I use difficult times in life as a reason to splurge on unnecessary expenditures.”
  • “I am unwilling to sacrifice time on social media and Netflix in order to give my studies the attention they need.”

Accomplishing any significant goal or changing any long standing behavior will require significant time. With time will come challenge. Repetition solidify’s learning. If we use difficulties and stress as reasons to give up on the pursuit of certain freedoms in life, we will get better and better at quitting when things get hard. Repetition creates habit. If we learn to let difficulties and stress be the crucible by which solid habits are forged into our DNA, then we practice resilience and that resilience will lead to confidence… in any situation. Confidence will be shaken at times. However, the choice to ‘stay with it’ will rebuild confidence… newer and stronger.

Real Talk: Are you someone that allows life and the ‘uncontrollable’ to derail you from the processes that you know will improve the quality of your life? If yes, why? What are the new stories you need to create around adversity to help you respond with resolve?


Solve Problems. Build Resilience.

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