How to Sell Yourself -- And Anything Else You Believe In

By Frank Shines and Ajellon DeDeaux

October 29, 2023

I'm Frank Shines and this article will chronicle my life experiences, but it is written with the aid of insight and research from my nephew, Ajellon "AJ" DeDeaux.

Ah, the daunting realm of sales—a land where rejection reigns supreme and self-doubt is your constant companion. It’s a place many loathe to tread. And the paradox? Often, we detest selling as much as we do ourselves. But why is this so, and what on Earth can we do to navigate out of this mire?

Flashback to my salad days—a skinny Black kid from Oakland's gritty streets, suddenly plunged into the pristine hallways of an almost entirely white high school near Seattle. Amidst the monochrome, I was the colorful anomaly, weighing a mere 60 pounds when drenched. Dating? That was a laughable feat. Gymnastics competition? A pipe dream for a kid from the ghetto. Fast forward to the US Air Force Academy, competing against the progeny of high-ranking government officials, military brass, and business tycoons. I was the only freshman on the varsity gymnastics team. Imagine the imposter syndrome that danced in my head as a team strapped me into a military jet, whispering, “Are you truly worthy, Frank?”

It wasn’t just about selling products at Sears during high school, it was about selling myself—believing that I had as much right to thrive and succeed as anyone else. Each “no” was a hammer to my self-esteem, each doubt a chisel sculpting my fear of inadequacy. But then came the paradigm shift.

I stumbled upon a truth as bright and glaring as the sun—the realization of my own self-worth, and a product/service I was born to sell: solving intricate problems for others. This revelation dawned during my tenure with the USAF Management Engineering Team and burgeoned as I ventured into consulting roles at IBM, Ernst & Young, and Pilgrim Software.

Now, with 35 years of trial, error, and learning snug in my arsenal, I am here to fast-track your learning curve, shielding you from the mistakes that once tripped me. But before I share with you my findings, let me first offer a word of caution.

At the heart of every successful sale lies a product or service that exudes excellence, a team that stands united in its vision and values. Before you set out to sell anything—be it a product, a service, or your illustrious self—it's imperative that what you're selling resonates with your core values and ethics. The foundation of every enduring success in the sales arena is an unyielding allegiance to ethics and a relentless pursuit of excellence. When you align yourself with a product or service that stands as a paragon of quality and integrity, your sales journey doesn't just become smoother—it becomes meaningful and rewarding.

But what if you find yourself in cahoots with a subpar product or a company embroiled in legal or ethical quagmires? Well, no amount of self-esteem or adept sales tactics can salvage your endeavor. The bitter truth is, a tarnished product or a morally bankrupt team can turn your sales venture into a Sisyphean task. Moreover, each sale then becomes a dent to your conscience, a compromise on your values. It's akin to building a mansion on quicksand, no matter how grand, it’s bound to sink. Hence, it's not just about mastering the art of selling but aligning with a cause, a product or a team that epitomizes excellence, ethics, and evokes a sense of pride. This alignment is the wind beneath the wings of your sales aspirations, propelling you toward not just financial rewards, but a legacy marked by integrity and a trail of satisfied, loyal customers.

Now, diving into the psyche of sales and self-worth, we embarked on research going back 40 years to identify common themes and patterns. Employing AI tools like Google Bard, OpenAI ChatGPT 3.5, ChatGPT 4 (with and without Browser), Anthropic Claude 2, and Perplexity.AI , I scoured through the psychological maze of ‘hating sales’ and ‘self-loathing.’ Here’s a snippet of what I unearthed.

The task of selling oneself or a product is a multidimensional challenge that encapsulates not only the personal barriers one might face but also the systemic and interpersonal hurdles embedded within the buyer-seller dynamic, three broad thematic intersections emerge: Transparency, Value Proposition, and Relational Dynamics.

1. Transparency: Bridging the Trust Deficit

• Understanding the Landscape: At the intersection of buyer and seller complaints lies a common thread of transparency. Buyers are wary of misleading claims, hidden fees, and feeling manipulated, while sellers grapple with pricing pressures and shifting buyer expectations.
• Tangible Actions: Providing clear, honest information, avoiding high-pressure tactics, and ensuring a transparent pricing structure can alleviate some of the buyer's and seller's primary grievances. This transparency can also extend to acknowledging one's limitations, a trait that can differentiate an individual or organization in a marketplace often marred by overpromises.

2. Value Proposition: Beyond the Surface

• Self-Awareness and Authenticity: The data illuminates a lack of self-awareness as a core barrier to selling oneself effectively. Coupled with the psychological impediments like impostor syndrome and low self-esteem, the challenge of articulating a compelling value proposition becomes evident.
• Customization and Relevance: From the seller's perspective, the complaints about long sales cycles and ineffective prospecting reflect a disconnect in understanding the buyer's needs.

3. Relational Dynamics: Humanizing the Process

• Empathetic Engagement: Buyers' complaints about indifferent or pushy salespeople underscore a craving for a more humanized, empathetic sales process.
• Lifelong Learning: This ethos can be infused into the sales domain, promoting a culture of continuous feedback, learning, and adaptation to evolving buyer expectations and market dynamics. Consider the impact of Generative AI (like ChatGPT) on marketing and sales. It won't be long before top sales professionals willing to embrace this technology will supercharge their own success and increase the satisfaction of their customers, leaving their counterparts far behind.

Customers loathe high-pressure sales tactics, crave honesty, and yearn to feel valued rather than just another notch on the sales board. Sellers, on the other hand, are often shackled by rejection, long hours, unrealistic quotas, and the perennially lurking shadow of a negative stigma.

From the seller’s standpoint, the complexities of sales cycles, lack of quality leads, and pricing pressures are akin to Herculean challenges. Buyers despise a lack of transparency, high-pressure tactics, and post-sale neglect.

The enigma of self-sales is often tangled in a web of low self-esteem, fear of rejection, and a glaring lack of self-awareness. Perfectionism, poor communication, and a fixed mindset further exacerbate this quandary.

So, how do we morph from self-loathing to self-loving, from sales disdain to sales dynamism?

1. Values & Ethics: Be sure you are selling a product or service in which you truly believe.
2. Self-Appraisal: Delve deep within to recognize and appreciate your worth.
3. Continuous Learning: Embrace the beauty of learning from every no, every rejection -- and new technology like ChatGPT that can provide insights on customer expectations and future needs.
4. Genuine Engagement: Ensure your interactions are genuine, your promises real.
5. Master Your Craft: Know your product/service like the back of your hand.
6. Empathy: Step into your customers' shoes. Understand their needs, cater to their concerns.
7. Preparation: Be well-prepared to articulate your value proposition succinctly and effectively.

Let’s transmute our fear of rejection into a quest for reflection, our self-loathing into self-loving, and our disdain for sales into a passion for meaningful engagement. Together, let’s embark on a journey to sell not just products or services, but our unique, irreplaceable selves.