Part 2: Hello, Impostor Syndrome

Welcome to a multi-part series on creating my first online course. Check out Part 1 here.

With each passing year, I’ve become more confident as an entrepreneur. It’s become easier to spot monetization opportunities, I can write way faster, and the voodoo that is search engine optimization and digital marketing is starting to fade. Yet, I’m still terrified of one thing: asking people to pay me for something.

This ain’t Patreon

Yes, technically I’ve been monetizing RadReads for the past two years via Patreon. Each month, 194 Patrons kindly open their wallets to donate amounts ranging from $2 to $20, for a total of $20,000 each year. But there’s a difference between donations and a transaction.

Why is it so scary to engage in an economic transaction? After all, I spent 15 years at the center of high velocity (and soul crushing) transactions – Wall Street. The answer’s plain and simple: self doubt.

A first for everything

I have no idea how to create a digital product. Yes, I’ve read a bazillion blog posts on the topic and have even recorded podcasts on the topic. But the stakes feel higher. Digital products are a gnarly mix of teaching, storytelling, tech, design, marketing, and community. Yowza!

Enter the inner critic. First, it questions why I have the expertise to teach any topic, let alone one as nuanced as fulfillment and financial independence. Next, it equates my self worth to the financial outcome of said product. Said differently, if you can’t sell shit… you ain’t shit!

Beware of the snake oil

But the impostor syndrome actually goes beyond the fear of failure. There’s something about selling stuff on the Internet makes me feel like a slimy snake oil salesman.

Hissss….Buy my product…hisssss

This is exacerbated by the category that I play in, one that is rife with snake oil: the wellness industry. So I ask myself: Who am I to teach people what it means to live a fulfilled life? Am I just drinking my own Kool Aid? How much of this can be attributed to my own privilege and bank account?

My greatest insecurity about RadReads (and, by extension, this course) is to be perceived as a fraud. A hedge fund huckster who lures unsuspecting readers into the false promise of a happier and more fulfilled life. I’m always wondering if I’m naive to the fact that everything I write about is of limited value – or even worse, it’s dangerous thinking.

So I stalled. And stalled even more. But my time has come.

Slaying the impostor

You don’t ever slay impostor syndrome, you simply renegotiate your relationship to it. And to me this renegotiation was simple: I’m going to dedicate my heart and soul to this course. It’s gonna be so damn good, thorough and honest, that you guys will leave saying to yourselves “Damn, that was worth 5x what I paid for it.” And if they don’t feel that way, I’ll return the money – no questions asked. So here’s my rallying cry. Let’s do this!

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