A Story of Self-Confidence


When I was in college, I used to run Study Sessions for my fellow classmates before big finals. I prepared and taught a 4-hour crash course in everything they’d need to know. For my time, they each paid me a fee. Many of the attendees specifically credited these sessions with an improved grade in their course. This became common knowledge and by the time I graduated, people would seek me out to beg me to run a Study Session they could attend!

This is the type of story you read about as the start of a long and successful career. This is the story of young entrepreneur finding a need and meeting it. This is a story of success born of hard work and skill put to good use.

This is not the story I want to tell.

What I’ve told you so far is the end of the story. I showed you a successful Study Session and the happy students who benefited from it. I didn’t show you how I got there.

By now, you must be thinking that I ran several other Study Sessions that went really poorly. That I used this failure to fuel my drive to be better and make the Study Sessions the students wanted, needed, and demanded! But that’s not a part of this story, either.

Every Study Session I ran, from the very first to the very last, was well run and highly successful.

So if I don’t want to tell you about my successes and this story has no real failures to speak of, what do I want to talk about?

Today, I want to tell you a story of Self-Confidence.

First, let me give you a bit of background. I have always done very well at school; both in high school and college I graduated at the top of my class. And in both high school and college, I tutored other students and friends.

Despite this background, I didn’t start out with the intention to run Study Sessions. Rather, a group of my friends asked me to take a day to tutor them en masse. I was working to pay my way through college and told them I could do that if they could cover my lost wages for the day. They agreed and my first Study Session was born.

Why am I telling you this? Why am I starting the (real) story here? Because I want you to understand that whether or not I could actually run a Study Session was never in question. I had done it before and, more than that, knew that I could present the material in a way that they’d understand.

As a part of this agreement, one of my friends talked me into opening this session up to other students in our class. She argued that if she’d benefit from it, so would others and I’d have a nice additional revenue stream to enjoy.

Logically, I agreed. I knew I could provide value.  I even reasoned that if my friends were willing to pay me, other students probably would, too. I also reasoned that it couldn’t hurt to ask.

And yet, it took me an hour to write and send an email to my class offering this service. Actually, let me correct that. It took me 10 minutes to write and 50 minutes to hit that “send” button. I sat in my chair at my desk in my room, just staring at the screen, afraid of what would happen if I hit that button.

I was nervous about how the email would be received. Would they think less of me for being so presumptuous as to charge for a session when we’re in the same class? Would they laugh me off as someone who thinks he knows more than he does? Would there be any response at all?

You see, I had great confidence in the service I was providing. About the service provider, though, I wasn’t so sure. It wasn’t rational. These kinds of thoughts rarely are. But for 50 long minutes I hesitated as those thoughts swirled around in my head.

And then I did it. I pressed that button.

Now, you might think the story stops here. That some small group of students saw my email and jumped at the chance to join my Study Session. And you’d almost be right.

It started out that way. The very next day I had TWO people who’d signed up! One who I knew from class and another I didn’t know at all! It was very exciting. I was almost able to shelve my concerns and Self-Doubt.

Then, I got a third email. Someone in my class very pointedly (and quite rudely) asked why she would ever take a Study Session from someone who is in her class. She demanded to know what credentials I had that justified charging for this service. In other words, she literally threw every fear I had about doing this back in my face.

To make matters worse, I realized that I hadn’t actually made it clear that I was a fellow student in my initial email to my class. Had I misrepresented myself to the students who already agreed to show up?

I immediately responded to the email stating that I was in fact a student in her class and that no I didn’t have outside experience in the topic to bring to the session. She did not reply nor did she attend my session.

I then replied to both students who had already responded ensuring that they knew I was just a student. Both of them, fortunately, said they were aware of this and were still willing to come.

Over the next week, four additional students signed up.Everyone who signed up, actually attended the Session. And everyone who attended was pleased with the result.

With that, we have reached the end of my tale. I love to think of this story from time to time. I love to transport myself back to that chair, that desk, and that unsent email. I love to think about how hard it was to hit that button and yet how glad I was that I did. I love to think about facing the worst response I could imagine and how I got through it. I love that I have this story to fall back upon.

Because this keeps coming up.

A lack of Self-Confidence doesn’t magically go away with a single good outcome. Nor would I expect it to. In my experience, Self-Confidence isn’t really about outcome at all. It’s about pressing the button because it’s important to you, even if you don’t think it will go well. It’s about controlling what you can and letting go of what you can’t.

And it isn’t easy. Maybe one day it will be. But until then I’ll keep pressing buttons, even if it takes me 50 minutes to do so.

See you at the finish line.

-The Jack of Spades


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