Struggling with Imposter Syndrome After Making Over $1 Million Writing, and How to Conquer It

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This is really hard to admit, but I struggle to call myself a writer.

I don’t have an English or Literary degree.

I’ve never had a business card that proclaims “WRITER” in the title.

Until I got to college, I never had a decent English teacher. I spent more hours than I care to remember in my English 101 instructor’s office just to pass the class. I sucked at grammar and struggle with it to this day.

Please don’t laugh at me when I share this with you. I know that you’ll point to the evidence that runs absolutely contrary to the way that I feel.

  • I’ve made well over $1 million over the last 15 years writing a weekly newsletter in the mortgage industry.
  • I published my first sci-fi book a few years ago that averages over four stars.
  • My first short horror stories are now published in Literally Literary and The Junction here on Medium.

Yet, on some days, I still wonder if I am really a writer. Even on those days where I feel like I’m a writer, I question if I’m a successful writer.

Imposter syndrome or probably better titled, “imposter experience” is the feeling that you are unqualified for or unworthy of the success that you’ve achieved and a fear that others will expose you as a fraud.

And I, like an estimated 70% of the population, suffer from it at times.

I can already hear your response.

“Dude, you’ve made over a million dollars writing? How can you feel like a fraud or unqualified? Are you mental?”

Let me share that at times that it gets even worse.

Every week, for over 725 weeks now, I write a mortgage market commentary. I distill what’s happening in the secondary mortgage market to a few paragraphs. My goal is for an average person to be able to read those paragraphs and have a basic grasp of why mortgage rates behaved as they did last week and what might influence them this week.

My clients are primary loan officers, banks, and mortgage companies that send the newsletter to their referral sources. I know from talking to my clients that my words are distributed to thousands of people. I’ve heard many times how important my newsletter is in their marketing efforts.

And that makes the fear kick in even deeper.

I’m not an economist. I don’t have a degree in Economics. I left business school for a field that held more interest to me, and it wasn’t English. Plus, I’ve never worked on Wall Street or for a financial services company.

What the hell qualifies me to write about the secondary mortgage market?

The “What if” Nightmare

The core challenge of imposter experience is that we project ourselves into the future by asking the question, “what if?” and then generate the most unlikely worst-case scenarios stemming from that hypothetical question.

  • What if someone finds out I sucked at English in school?
  • What if someone finds out my novel hasn’t made buckets of money?
  • What if my clients discover that I don’t have a degree in Economics?

These fears, while existing almost exclusively in our minds, often shackle our capability to move forward. The chaining together of these terrible, imaginary consequences can feel completely overwhelming.

Our minds burrow deeper and deeper into the depths of the rabbit hole creating irrational fantasies.

  • Everything I’ve ever written will be completely invalidated and thrown away due to the discovery of my lack of good English grades
  • No one will ever read my book, any future book, or anything I ever write again because my first novel failed to hit the Amazon bestseller list
  • My business will fail because one person will tell everyone in the world that I’m not a real economist, and my customers will abandon me
  • People will laugh at me behind my back, make fun of me at parties, and I’ll end up homeless, living in a van down by the river!

One of the largest challenges with imposter experiences is that we negate our accomplishments through a false mental narrative that our successes might have been sheer luck or circumstances beyond us. In doing this, we emotionally build a barricade between the reality of what we’ve done and its ability to reinforce our own role in our own success.

Developing a Celebrity Attitude

Because imposter syndrome happens in our heads, we retain the option of imagining it however we want. There are all kinds of exercises, techniques, and methods for working with your impostor experiences. I want to suggest something completely different.

If it’s all in your head, why not take it to the absolute extreme?

Oftentimes, the imposter experience is more of a generalized emotional state, a notion that something might go in a direction that might cause us harm. It’s this feeling that someone, somewhere, somehow might find the “imagined goods” on us.

Rather than leaving it at that nebulous state, try imagining it actually happening. Let your mind generate an actual person, who confronts you directly, exposing that which you fear.

Here’s the fun part, as you hold this internal dialogue, you MUST be the most arrogant, obnoxious, offensive, and nasty character that you’ve ever imagined, and verbally express the successes that you’ve experienced. Even it feels unnatural, play the dialogue out. Be a totally sarcastic jerk to your imaginary antagonist.

“I remember you from high school English class. You couldn’t diagram a sentence to save your ass? You’re not really a writer, are you?”

“Back then, I couldn’t correctly diagram a sentence with more than three words. I hated grammar almost as much as I hated you. Cool thing is that while you made “manager” at that gas station, I built a million dollar business by writing, plus I wrote a novel and am now writing short stories for fun. And guess what? I’m also working on my second novel and have a project underway to write a non-fiction book. I still can’t diagram a sentence to save my ass, but hey, I’m sure diagramming sentences has massively helped your crappy career.”

“Oh so, you’re one of those people who wrote a book and it all but flopped. Doesn’t that suck? Guess you’re really not much of a writer.”

“Well, while you sat around doing little more than scratching your butt and watching soap operas, I wrote a damn good novel. Have you read it? No? Have you read the book reviews about my book? No? So, when was the last time that you read anything other than a supermarket tabloid? And, I didn’t write it just for money. It was about being a badass and doing something significant and meaningful. You know, more than being a brain-dead zombie glued to a TV.”

You may think that the whole idea feels funky. But each opportunity that you take to relish your success helps quell the feeling of being an imposter. If you’re really struggling, don’t just roleplay in your head, write the dialogue down and read it out loud. You’ll mentally reinforce your own role in your own achievements.

And guess what else it does?

It also improves your readiness for dealing with that real-life situation with that real-life person who questions your success.

Whoa! Back the truck up! I thought imposter experiences were all in your head?

It would be great if difficult situations only happened within the synapses in your cranium. While some people are never questioned about their successes in life, most people who find even a modicum of success will eventually be asked some variation of the questions that they fear.

Becoming The Celebrity

Don’t worry, I’m not recommending that you become that annoying jerk that you roleplayed. Just speak your truth. Once you’ve played that obnoxious role, and been that hotshot in your own mind, speaking the truth about yourself tends to be easier because you’ve practiced it.

The only caveat for the real-life situation is that you have to learn not to minimize or degrade what you’ve done. Share the facts, and let the cards fall where they may.

I vividly remember the first time that it happened to me. I’d been writing the newsletter for a number of years and answered the phone to converse with an inquisitive prospect.

“Okay, I understand how your newsletter service works. What I really want to know is what makes you qualified to write this newsletter?”

I paused for a moment. I dreaded this day’s arrival. I wanted to say something like, “Well, I received my Ph.D. in Economics from Oxford and my Ph.D. in English from Harvard. I cut my teeth working for the Federal Reserve Bank of New York, climbed the ladder at Goldman Sachs, and am now CEO of Redstone Capital, the largest private jumbo mortgage securitization firm in the county.”

Damn! That would have blown his mind.

Instead, I simply spoke the truth, “I owned a small mortgage brokerage and as a loan officer, I developed the newsletter. Another loan officer asked if I could make a newsletter for him, and this company was born. I’ve been studying and writing about the industry for a number of years, and the majority of my customers find the newsletter effective.”

He signed up, and I ran his credit card before we hung up the phone.

Enjoying the Celebrity Lifestyle

Once you’ve achieved a level of success in practically any pursuit, small or large, someone may materialize with a real desire to tear you down. When this happens, it’s time to do something very radical — rejoice that your imposter experience fears are finally manifesting in reality.

While you are now equipped with the sarcastic zingers to wiz back at them, you don’t need to do that. You certainly can if you want. Or you can just acknowledge that their desire, words, and actions are an awesome validation of the fact that you are successful.

As the social media saying goes, “haters gunna hate!”

You can either spend your time and energy worrying about those who resent and are jealous of your accomplishments or do what most successful celebrities do.

Ignore the haters, speak your truth, and carry on with being successful.