Photo by sydney Rae on Unsplash

How To Be More Confident

Mastering Mentorship with Doug Stewart

Doug Stewart
Nov 17, 2017 · 7 min read
Subscribe: iTunes |Google Play

When I was eight years old my favorite Disney movie was Robin Hood and all I wanted was a real bow and arrow. Not a compound bow, a simple bow & arrow just like Robin Hood.

One day, miracle happened and I talked my mom into buying me one. I should’ve known then that I had a future in sales. As I unpacked this beautiful green bow I realized that the arrows weren't quite what I expected. The arrows weren’t actually arrows. They had these big rubber tips on the end. It was like someone had replaced the tip of my arrow with a tennis ball. Frustrated, I went to my mom and made a case for real arrows. After all, these arrows were for little kids and I was not a little kid. I was eight years old.

Later that week, my mom took me to Walmart and got me two real arrows.

Now, before you start judging, you should know that we lived in the country and there were a lot of kids my age who already had their first rifle. So, the bow and arrow was actually pretty good purchase as far as we were concerned.

Not being able to contain my excitement, the second we got home I ran out into the yard with my bow and two new arrows.

I loaded the first arrow into the bow put it back and shut it directly into the tree about 20 feet away.

Dang, I’m good at this, I thought to myself. My confidence was sky high. As far as I was concerned, the skill of archery had been mastered.

So I loaded the next arrow into the bow put it back pointed straight up to the sky and let it go.

The second the arrow left my fingertips I lost it in the sun. Immediately, I regretted the decision and my confidence evacuated my body.

I wasn’t sure if I should stand still or run. I had no idea where the arrow was going to come down or how fast it would be traveling. My short eight years of life were flashing before my eyes. I decided to stay put and think thin.

A few moments later, I heard the greatest sound of all time. It was the sound of an arrow piercing the ground. I was alive!

I learned a valuable lesson that day,

Confidence isn’t a decision.

Confidence without competence is a delusion.

A few years after the bow and arrow incident, I found myself in middle school about to make a really big mistake.

The school I attended was pretty small, only about 300 kids from kindergarten through high school graduation. One day, Todd (an 11th grader) embarrassed me in front of my classmates.

Todd wasn’t a bully, he was one of those guys that was more than willing to put you in your place if you stepped out of line. Something else you should know about Todd, he wasn’t just an 11th grader. He was a grown man. Facial hair and all.

And me, I was a scrawny middle schooler that didn’t like to be embarrassed in front of my classmates. I was so furious that I decided the next day at school I would make Todd pay.

That night, my dad noticed I was angry about something. When he asked what was going on, I told him about what had happened. Then, I told him my plan for the next day.

Me: “Tomorrow I am going to fight Todd.”

Dad: “That’s a bad plan, Son.”

Me: “I’m not scared.”

Dad: “Son, you don’t have to be scared to get your ass kicked.”

The next day, I found out just how true that was.

I walked right up to Todd the next day and punched him square in the chest. I’m not sure what I thought would happen. Maybe I thought that he would just explode into a million pieces and that would be that. He did not explode. In fact, he barely moved. I immediately knew that I had made a huge mistake.

Before he could hit me back I turned and ran as fast as I could. As mentioned earlier, Todd was more than willing to put people in their place if they stepped out of line and clearly I had.

He chased me almost the entire length of the campus and finally caught me right in the middle of the gym. He grabbed me, threw me to the ground and proceeded to put me in the most epic Rick Flair Figure Four of all time.

I was sure that he was gonna break my leg off. Luckily, he didn’t break it completely off but it hurt a lot and it taught me another valuable lesson,

Confidence is something you have to prove to yourself.

Simply not being afraid isn’t the same as confidence. Blind confidence Will cripple you faster than a Rick Flair Figure Four.

So, if you can’t just decide to be more confident what can you do to become more confident?


Confidence is incremental. It happens slowly over time as we demonstrate our competency.

People ask me all the time how to get on the TEDx stage. When I asked them how many talks they’ve given this year most of them look at me in confusion. They don’t see the connection between giving 100 talks for free and being ready to give a talk on the stage as prestigious as the TEDx stage.

If you want to give a TEDx talk, the best thing to do is to give 100 talks for free before you ever apply to speak.

Contact your local YMCA, volunteer to give a talk at a church or social event, get a group of friends together and tell stories, anything, anywhere, just practice.

Hone your craft, earn the right, develop your skills and demonstrate your competency overtime.

In fact, one of my upcoming episodes will be a step-by-step guide of how I got picked to give my TEDx talk. It may surprise you just how simple it really is. Stay tuned for that.


What doesn’t kill you, makes you stronger.

I’ve always hated that quote. It seems like people say what doesn’t kill you only makes you stronger when they have nothing else to say. You go through a divorce, or someone you love passes away, or you unexpectedly get laid off and people think it’s encouraging to tell you,

Congratulations! You didn’t die.

As much as the saying irritates me, when it comes to developing confidence, it’s pretty good advice. When we put ourselves in a position to take calculated, non-fatal, risks we open ourselves up to real growth.

It’s like pruning a rosebush. If you never prove it, it never blossoms. If you cut it back too far or too deep it dies. But if you prune it back just a little bit on a consistent basis it will flourish.

The same is true with humans. That’s why, I coach people to always stay about 6 feet outside of their comfort zone.

If you stay in your comfort zone all the time, you never grow. If you go 100 miles outside of your comfort zone, you die. If you stay just a little bit outside of your comfort zone, you flourish.

So go ahead and take some risks. Do something that’s a little scary. Give a talk, do stand up or improv. Heck, just go to Starbucks and asked the barista for a discount. Whatever it takes to keep you just a few feet outside of your comfort zone.


A great mentor doesn’t see you as you are, they see you as you can be.

All great mentors have a few things in common:

They Meet you where you are.

They Encourage your growth

They Nudge you toward action

They Tackle tough issues

They Organize your thought process

They Realign your perspective

You may ask, how do I find someone like that? The answer is pretty simple. You don’t go looking for them. You do the things that attract great mentors.

It’s like fishing. If you jump in the lake and swim around in hopes of catching fish, not only will you not catch one, you probably won’t even see one.

On the other hand, if you do your work get a fishing rod and some bait and do it takes to attract the fish you want to catch, you are way more likely to have success.

The beat that attracts mentors are people who are curious, ask questions, and try new things.

The best mentors are attracted to people who are already doing their work.

So, if you want to be more confident, it’s time to stop wanting and to start earning the right by demonstrating competency, making non-fatal errors, and doing the things that attract the mentors that you would like to have.


Mastering Mentorship

Mentorship doesn’t happen in a straight line. It is more dynamic than that. In this publication, we will discover, and re-discover, the ins and outs of mentorship

Doug Stewart

Written by

Dale Carnegie instructor | TEDx Presenter | Coach | Podcaster | Storyteller — Lives in Raleigh, North Carolina

Mastering Mentorship

Mentorship doesn’t happen in a straight line. It is more dynamic than that. In this publication, we will discover, and re-discover, the ins and outs of mentorship

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade