Entrepreneur Educator, Program Developer, Facilitator

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What would life be like if rejection didn’t hurt?

Don’t waste your wins

Last week, I got a huge win. A consulting client I had been chasing for months agreed to work with me and paid the entire project fee in advance. It basically meant that any money I make the rest of the year is pure profit.

How did I celebrate this achievement? Did I buy a new car? No. Did my partner and I blow a wad of cash at our favorite restaurant? Nope.  

After a big win, I am basking in a specific emotional state not unlike Mario when he eats a star. It’s a cocktail of joy, optimism, confidence, and forward momentum. This feeling is rare. I don’t want to squander it.

The best way to use the emotional momentum and warm fuzzies of this state is to take another shot. The window of “everything is great and the world is my oyster” is open. When “the window” is open, you’re playing with house money. Any rejections you face during this time are minimal because you’re already riding high. It’s the opposite of when you have failed five times in a row—those are times when it’s hard to imagine that life can go any other way.

Feels kind of like this

The best way to springboard your wins is to funnel that energy into taking aim at something even bigger. I’m an education entrepreneur who runs courses on how to be good on camera and make videos because I think it’s THE SKILL for the future of work. So what did I do after my big consulting win? I looked for other organizations that could give me a bigger stage to amplify my message. I shot my shot with Harvard Business School because working with them would be one hell of a megaphone.

Here’s how they responded:

The “creativity you have included included in this inquiry” refers to a personalized video I sent along with the email

So Harvard did not bite. But this rejection barely registered because I’m still flush from the win that preceded it. Water off a duck’s back.

Rejection Hits Twice as Hard

The psychological pain of losing hits twice as hard as the pleasure of winning. Studies show most individuals would feel more upset about losing $50 than they would feel happy about gaining $50. This concept has a name: loss aversion. Coined by researchers Daniel Kahneman and Amos Tversky, it paints a picture of how people make choices in situations involving risk.

If we follow our natural tendencies, we should try to avoid rejection and failure at all costs. We put up with a 9-5 to avoid entrepreneurial risks, commit to the friendzone because we’re too scared to ask our crush out, and allow fear of rejection to keep us from applying to our dream job.

If you don’t take the risk, you never have to face the pain of rejection. This is the playbook for most people’s lives, and it all ends the same: full of regrets. 

Fulfilled people know this is no way to live. A meaningful life—one filled with accomplishments we can be proud of, which ultimately drives life satisfaction—involves the risk of rejection and loss.

Using the momentum from one win to fuel taking another shot is the magic trick that sidesteps loss aversion. It’s how you insulate yourself when your big project turns into a dumpsterfire, your application gets rejected, or your love interest tells you they just want to be friends.  

Shots I’ve Taken While the Window Was Open

I was pretty excited when the University of Texas asked me to teach a class. Halfway through the semester, it became clear the course was a hit. I used that window to invite Matthew McConaghey as a guest speaker. He said no. But I didn’t care. That would have been icing on the cake, but the cake I was eating was so good it didn’t need icing.

I gave a talk about writing cold emails to a room of 250 entrepreneurs and I could tell they were eating out of my hand. The confidence from that experience gave me the idea for how an entrepreneur friend who makes leather jackets could make a connection with multi-platinum rockstar Jack White. It ended with Jack White wearing my friend’s brand on stage

Jump Through the Window

If you struggle to put yourself out there, remember the window the next time you have a win. By all means congratulate yourself and appreciate the positive outcome you created. But recognize that the positive emotional state you’re in is fleeting and rare. Why not cash  it in as propellant to create the conditions for another win? 

I just hit publish in this essay. Boom! That’s a win. Sure, I’ll pat myself on the back. But the real question is, “how will I use the momentum from this win while the window is open?”

I help people get wins from learning how to be on camera and creating videos. If you want to learn camera confidence, fundamentals of video production, and on camera storytelling, join my newsletter or claim your spot in my cohort-based course, Minimum Viable Video.

Thanks to: Rick Lewis, Mik, Elizabeth Edwards, Frank Corrigan, Fatima-Zahra Maelaininn, Chris Wong, Aurora Klæboe Berg