Becoming an Underdog in 3 Steps

A short article about rejection + my email exchange with Mark Cuban

“There are enough people in the world who are going to write you off. You don’t need to do that to yourself.” — Susan Boyle

My first ever email address and Internet user accounts were labeled: underdogqueen. When I was about eleven and getting more familiarized with the wide world of the Internet, this became my identifier for myself. One of the things my parents taught me growing up is that there are plenty of people who are expected to be successful at what they do. Then there are the underdogs who come in and rock those people’s world. And it’s way cooler to be the underdog.

(If you’re pressed for time or don’t want to hear about my personal life, scroll down to the three steps heading below. Although, you might miss some juicy stuff).

The Backstory (Yes, I’ve got Mark Cuban’s real email address):

I feel super blessed to my parents for the underdog mentality I was raised under. We are from a rural East Texas town where everybody knows everybody. Lots of cows. You get the idea. I knew I wasn’t a well-connected “city kid” (as we called them). I lived quite comfortably, but I didn’t know any adults that taught at the colleges I wanted to go to, I didn’t have an “in” at a big corporations for internships or jobs. If I wanted to do something with myself: I was going at it by myself. At that age, my thought process was gritty. I felt that I had an underhand when it came to a network. And looking back, that was the best thing for me.

Nobody was there to tell me it isn’t normal to apply for a job you aren’t qualified for or find Mark Cuban’s email addresses in the buried corners of the Internet and send him a business idea. When I was younger, I truly didn’t care if I was rejected-like: at all.

When I was barely seventeen, emailing Mark’s secretaries to pass me through because I had a “potential technology advancement” for him after looking for their email addresses online for eight hours. Lol. At least he replied.

When I submitted my debut novel to agents and publishers, I got over two hundred rejections. Hundreds of hours were spent sending the novel to professionals and I got plenty of disinterest back. I didn’t have an MFA or any professional writing published, which I knew the industry would see as a setback. It became my motivator to show that I could be a good writer without all of that. I just needed a chance.

Flashing forward to age twenty-six, I find myself feeling different. Now that I’ve had two novels published, became an independently published bestseller (more on that later), written for some magazines, and met a few industry professionals, my identity as an advancing writer feels so important to my being that it’s practically become a handicap. All of the connections and validation have technically bolstered a life closer to my bookish dreams. Yet, they’ve also made me soft.

In connection with upcoming novels, it feels like there’s more to lose because I’ve already built a place in the literary world. Maybe it’s a tiny studio space rather than that million-acre mansion. But hey, at least I’ve got a spot here? The battle of rejection starts to feel more threatening to my territory. My more favorable position just feels like more to lose. And that’s a problem.

Becoming An Underdog In Three Steps

I’m on a mission to reintegrate myself with the younger underdog in me. Here’s how:

1. Underdogs are not just fighting to win. They’re fighting for their honor.

A true underdog isn’t fighting tooth and nail for the win: they’re fighting for their honor. It’s personal, deep, and without ego. They don’t care if they look like an idiot in the eyes of the masses. All that matters is the respect they have for themselves. And they respect themselves the most by showing up in that arena (that they might even be under-qualified for) and putting up the fight of their lives. Even if it lands them the loser in the eyes of the world.

A person who honors themselves isn’t looking for a flash of the camera or counting the length of their autograph line. They are so obsessive about their developing their passion and potential that they refuse to put their potential into a box. Even if that box would make them king of the hill to their town, city, or country. They’re not playing to wear the winner’s belt, but to prove to themselves that they’re worthy of their dreams.

When you love yourself deeply enough to fight for your honor, you’ll fight tirelessly. When you fight because you crave the recognition of a win, you’ll fight scared.

2. Underdogs don’t pretend that they win all the time.

Nothing is more annoying than that person that pretends that they’re always winning. Especially when we are that person. You’ve been there, I’ve been there, and it’s always exhausting. This happens when were fighting for our image and not our honor.

In 2021, I decided to leave myself a review on my own book so it looked more popular than it was on a specific platform. Two years later, the review is still there: “Lindsey Lamar is an amazing writer. Truly incredible book.” — Review left by Lindsey Lamar. (I thought it’d be anonymous. You can laugh.)

When we worry too much about our image, we pretend to win all the time. Pretending to win all the time is a slippery slope. Suddenly, we fail to remember why we’re in this pursuit at all: is it to chase our dreams or is it to uphold an image of success that we want everyone to see us through? (An image that will inevitably crash and burn at some point). True underdogs are honest about their losses. They’d never hide from the challenge. That’s the whole reason they’re in the ring at all.

3. An underdog is grateful to others. They know it’s not a one-man band.

An underdog knows they aren’t going to get where they’re going all alone. They don’t turn their noses up at help. Instead, they’re honored when success does come because of the dark times it took to get there. And they always remember the ones that sat with them in the dark, the help they received along the way, and the love that supported them. No matter how obvious their “team” is in their win, they know they have one. And they don’t forget their names at the podium. Because sooner or later, they too will become the helping hand in someone else’s story.

Thanks for reading my first medium article! I plan to bring original content here soon about writing, mysteries, and reflections on life and entrepreneurship. Follow me here on Medium, on Substack, and Instagram.