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Every College Dude’s Experience Ever

Fellas, we are about to visualize a situation as old as time.

You’re a 21 year old college student in the US of A. Life is good: dollar drinks, no real responsibilities, living with your best friends, and surrounded by pretty girls. So like any other weekend night in college, you and your friends go to your favorite bar.

Then a girl catches your eye. You’d seen her around campus before. Maybe you were at the same party a few weeks ago. Maybe she was in your stats class. It doesn’t matter. She’s gorgeous, and you can’t keep your eyes off of her. You want to go talk to her, to go get her attention. But she’s so far out of your league that you have no idea what to say.

You walk towards her and almost say hey. But your mind freezes, so you continue walking right past her to the bar behind her. Then you glance back and think, “Dammit, just go talk to her.”

You walk right back by, but you still can’t muster the courage to say hello. Because nothing is as terrifying as approaching a new girl out of the blue. So you go back to the corner with your friends and do your usual bar shenanigans for the rest of the night. You keep glancing at the girl. She’s having a blast, hanging with her friends, probably waiting for someone like you to go say hey. But you never go.

Then the next weekend comes around. And it’s Groundhog Day.

You’re a 21 year old college student in the US of A. Life is good: dollar drinks, no real responsibilities, living with your best friends, and surrounded by pretty girls. So like any other weekend in college, you and your friends go to your favorite bar.

And that same girl catches your eye. And you want to say hey, but you can’t bring yourself to do it. You walk towards her and almost say hello. But your mind freezes, so you continue walking right past her to the bar behind her. Then you glance back and think, “Dammit, just go talk to her.”

But this time is different. You finally muster the courage to say hey, and you turn around to do just that. Except now you see some other guy walking her to the bar with his arm around her waist.

You had plenty of opportunities to say hey. To catch her attention. To at least get rejected. But you didn’t shoot your shot, and some other guy did.

Good game kid. Try again next time.

What Does This Have to Do with Careers?

Quite a bit, actually. Besides being hopelessly consumed by missed opportunities in my own life (just kidding. maybe), I tell this story because this dynamic constantly appears in our professional lives. Replace approaching that girl at the bar with applying for a new job. Or asking about a promotion. Or leading a project at work.

You want to go for it, but you can’t get out of your own head.

“What if they ask me to demonstrate a skillset in the interview, and I look like an idiot?”

“What if my manager thinks that I’m less qualified than other applicants?”

“What if I screw up the presentation in front of my director?”

So you play out every possible scenario in your head, because you are terrified to fail. You plan, and plan, and plan some more. Because you want to be prepared for every possible outcome. And then you plan so much, that you never take action in the first place.

That girl in the bar? She appears in your professional life every single day.

From Planning to Procrastinating

Don’t get me wrong, planning is important. At least in the early innings. Blindly attacking any problem without any sort of plan is a recipe for disaster. But there comes a point where you have to transition from planning to doing. If you don’t take action, “planning” is no longer productive. It is procrastination.

There is a small window to take action. It opens once you have fully assessed the problem at hand and closes when the opportunity is gone. The problem is that you never know when that window is going to close.

It’s tricky, because planning feels productive. You can spend all day thinking about how you would handle hypothetical scenarios. But once you have a solid understanding of the task at hand, you have to go do. Once you start doing, you'll notice two things:

• Half of the stuff you planned for never happened

• Half of the stuff that happened never could have been planned for

Understand the basics, then get to work.

Someone Else Will

Over-planning is a double-edged sword. First, more time spent planning means less time available to take action. Second, more time spent planning increases the likelihood that someone else takes action before you.

When I was 16, twelve of my high school teammates and I attended a three-day football camp at Mercer University (ironically, where I ended up playing college ball). There were several hundred kids in attendance. Each night, the coaches would hold 1 on 1 competitions. Receivers and tight ends (me) would line up across from defensive backs and linebackers. The quarterback would tell the receiver a route, and then it was a 1 on 1 battle against the defensive player. My goal? Catch the ball. The defenders goal? Don’t let me catch it.

Well some of these kids were good. Really good. And I didn’t want to get toasted in front of the college coaches. So I lurked near the back of the line the first night. Meanwhile, a tight end from another school jumped up front.

And he promptly got dunked on on his first play. He almost secured the catch, but the linebacker ripped it out of his hands for an interception on the way down. The defensive players and coaches were hyped.

And then something strange happened. This other tight end went five more times that night. And he had five catches. Including one ridiculously athletic snag on the sideline, and another acrobatic catch over a defender. This guy got clowned on his first rep. He dominated the next five. After the practice session was over, Mercer’s offensive coordinator was asking for his contact information.

No one beat me on any reps that night! But I didn’t win any reps either. Because I didn’t participate. How many coaches talked to me after practice? 0.

While I was worried about getting beat on a play, someone else was getting as many reps as possible. While you were scared to approach the girl, someone else did. While you were thinking about applying for a job, someone else landed an interview. When you hesitated to lead the project, someone else took the reins.

All of the planning in the world is worthless if someone else beats you to the punch.

The Only Way to Improve

You won’t become a good shooter by watching Steph Curry highlights. You won’t become a great writer by reading good books. You won’t master a foreign language by thinking about Spanish all day.

You have to do it. Again and again. 

And you are probably going to suck at it for a while. And you’ll probably get rejected and fail early on. But you’ll get better. Because all of those little failures come with little lessons. And they compound.

Maybe the girl shot you down, but you gained confidence. Maybe you struggled through a conversation in Spanish, but you picked up a few new words. Maybe your project at work was a bust, but you figured out a process to change moving forward. Maybe the first article that you published online sucked, but your next one will read much better.

And these minor improvements compound.

A bias to action is oftentimes a bias to failure. But these failures are necessary to help you build towards success.

Everyone who has succeeded at anything had to, at some point, try that thing. Meanwhile, everyone who didn’t try, never succeeded. See the Venn diagram below for an illustration of this amazing concept.

Considering that 100% of successes come from those who try, and 100% of people who don’t try don’t succeed, trying stuff seems to make a lot more sense than the alternative.

Rejection > What If

A few weeks ago, I wrote about the “Creator Economy.” In one section of that article, I talked about why people are often so hesitant to bet on themselves. To quote myself:

“We take solace in the “what ifs” because they let us envision the idea of success while avoiding the harsh reality of failure. Ironically, the biggest failure is never taking those risks in the first place.”

We see this all the time. We don’t apply for jobs or graduate schools that appear out of reach, or ask about promotions that we feel unqualified for, or take any long-shots because we fear rejection. We want to play it conservative. So we live in the career purgatory of “what ifs”.

But it’s the “what ifs” that haunt us.

Back to the girl at the bar scenario. As a red-blooded American male, I have experienced both the cold, cold pain of rejection and the frustration of “what if” several times. I promise you the latter is harder to move past.

No one likes rejection. But rejection brings closure and finality. You took your shot and missed, but you still took your shot.

Didn’t get the job? Fine.

Denied from that school? That’s okay.

At least you know.

“What if?” That’s the one that never goes away. The one that you think about days, weeks, months, even years later. Because you just don’t know. What if you had just interviewed for that job, where would your career be now? What if you had applied to that graduate program? You may have been accepted. What if you had taken on that project lead? You may have been promoted as a result.

But you didn’t interview for that job. Or apply to that graduate program. Or offer to lead the project. And someone else did. And now you’ll never know. A bias towards action inevitably means that you will fail some. You may fail a lot. But failure is infinitely better than not knowing what would have happened.

The other benefit of failure? You learn from it.

Failure yields feedback. Feedback is how you determine why you failed, and improve in your future efforts. Like I said earlier, these improvements compound.

Go do stuff. And screw up stuff. And fail stuff. And get rejected from stuff. Because all of those things help you succeed at later stuff.

More taking action. Less “What if?”

Let’s have a great week 🤝 - Jack

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