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Swagger – Chapter One: Everyone Wants to Swagger

This is an exclusive chapter from 2logical’s new book, Swagger: The “Way of the Sway” to Sales and Life Success.  It is the first ever sales book that integrates Motivational Intelligence™ into the sales process.

With 19 seconds left on the clock and the score Utah 86, Chicago 85, Michael Jordan didn’t stand around questioning his ability to intercept the ball, drive it down the court and make the winning shot. He kept his eye on the ball, easily grabbed it from the Jazz player and in a few strides, crossed over his defender and sank a jumper for the win.


When Joe Montana trailed the Cincinnati Bengals in Super Bowl XXIII with just 3:10 left on the clock, he didn’t stop to doubt whether he could lead the San Francisco 49ers to victory. He started throwing one pass after another, grabbing first downs until the 49ers scored the winning touchdown in one of the biggest drives in NFL’s history: 92 yards in 11 plays. I was in the stands that day, and watched Montana and his team rip the win out of the grasp of the Bengals and leave the stadium with the victory.

When Steve Jobs returned to Apple after leaving in disgrace a few years before, he didn’t sit around nursing feelings of inadequacy and self-doubt. He got to work with his creative team and produced the iMac, introducing the candy-colored computers to a huge rally of loyal fans and placing Apple back in competition for the top computing company in the world.

When 26-year-old Audra MacDonald took the Broadway stage in her first major role as Carrie Pipperidge in Carousel, she did not let the fact that she was the first black woman in history to play the role “slow her roll.” Not only did she play Carrie with grace and musical skill, but she won the Tony Award for her efforts—the first of three Tonys she would collect in a scant five years.

When Leonardo DiCaprio was passed over for the Oscar for his performances in The Aviator and The Wolf of Wall Street, he did not give up on Hollywood or start giving lackluster performances. Instead, he took on the role of Hugh Glass in The Revenant, one of the most challenging and complex roles of his career—for which he finally won the Oscar.

In 1940 and 1941, when Nazi forces rained bombs down on 16 cities in England, Prime Minister Winston Churchill did not allow himself to become demoralized by the destruction. Even when London became the enemy’s prime target for 57 consecutive nights in September and October 1940, he maintained British production of weapons, kept the economy on track, and led the defense of England with skill and courage.

And when Martin Luther King, Jr., led more than 25,000 people on a march from Selma to Montgomery, Alabama in 1963 to protest discriminatory voting rights laws, he did not hesitate to stand on the steps of the state capitol to speak even when the threat of personal harm and violence was a clear and present danger.

It is not difficult to see that these icons from across vocations dance through life to a different beat…they move with Swagger! We can all see it, and we can all recognize it as we observe their massive life accomplishments:

  • – Michael Jordan became the single greatest NBA player of all time.
  • – Joe Montana was named Most Valuable Player twice by the Associated Press, was elected to eight Pro Bowls, and had the highest passer rating in the NFL in 1987 and 1989. In 2000, he was inducted into the Pro Football Hall of Fame.
  • – Steve Jobs led Apple to become the largest and most successful company in the world.
  • – Audra McDonald is a six-time Tony Award winner who can choose any role on stage or screen.
  • – Leo DiCaprio is heralded as one of the greatest actors of our time.
  • – Winston Churchill led England to victory in World War II.
  • – Martin Luther King, Jr. played a critical role in passage of the Civil Rights Act in 1964 and led a movement that changed the course of history.

There is no denying the results of those who walk amongst us with Swagger.

But can we define it? Can it be taught? Can everyone learn how to Swagger?

Swagger Defined

The simple truth is that everyone can walk life’s road, professionally and personally, with Swagger. Each of us can build a life fueled by dreams and the progressive realization of those dreams. However, to do so, we must understand the origin and ingredients to those that master the “way of the sway.”

What is Swagger?

Merriam-Webster’s Dictionary defines swagger as 1. To walk in a very confident way, to walk with swagger. 2. A way of walking or behaving that shows you have a lot of confidence. 3. Marked by elegance or showiness.

However, to some, the word Swagger can be defined with a negative connotation of cockiness, arrogance, or ostentatious display of bravado. Nevertheless, there is no denying that the results of those with Swagger are demonstrably greater than those who lack the ability to strut through life with Swagger.

I personally think the best definition of Swagger is found in the Urban Dictionary. It describes those with Swagger this way: “How one presents him or herself to the world. Swagger is shown from how a person handles a situation.”

To me, and to today’s millennial generation, this defines those with Swagger best because it is simple, vivid and results-based… meaning those with Swagger get bigger, better, stronger results in all of life’s endeavors. But why? Because of the way they act and react to life situations.


That, my friends, is the essence of what this book is about, and it is exactly what my friend and mentor, Randy, taught me at the age of 21.

Simply explained, people that exude Swagger in all that they dream, attempt and ultimately do in life do not have the same thoughts and beliefs about themselves, others, or their propensity to achieve results in life.

People with Swagger have a different mindset. I call it a Swagger- Set, a set of core governing beliefs from which they operate. As such, the way they act, react and interface with others and the world as a whole is different from the overwhelming majority of people in equal or similar roles in life.

Whether it is a career role in sales, leadership and management, operations, customer service, or a life role as a parent, friend, coach, teacher…those who learn to walk with Swagger in each respective role dramatically outperform those who never learn how.

The Road Less Traveled

Whether your vocation is in sports, the arts, public service, or professional sales, it is a well-known fact that the road less traveled is the one defined by those who become the best that they can be— versus opting out for a life defined by mediocrity and often less than average performance. I do not state this observation with a judge’s robe on, and the fact is I have met some people who truly are content to take life as it simply comes to them.

However, I have met far more people who want to live a world of career and life abundance, but truly do not know where or how to begin to build it.

As a sales trainer and the CEO and President of an internationally well-known and recognized workforce development company, I can assure you that most business leaders and people as a whole want to compete in their career and the game of life to win—and to win big!

Yet they are imprisoned in a collective mindset by a world that breeds mediocrity. Again, I do not state this fact in a judgmental or preaching kind of way. I simply state it as an observation I have made through the mental prism I adopted when I learned to Swagger as a young man and professional in sales.

The Greatest Sale You Will Ever Learn to Make…

The greatest sale you will ever learn to make is the one you make to yourself first—to be the best you can be at whatever role you commit to in life.

These are the words that succinctly summarize and illuminate the journey you must take if you wish to learn how to live life with Swagger!

These 32 words embody the core philosophy of those who seek to Swagger Sell in their career and in life. They are easy words to say, yet difficult to embrace—because few are helped to see exactly how to subscribe to a life of Swagger.

Henry David Thoreau said it best: “The mass of men live lives of quiet desperation, and go to the grave with the song still in them.”

This simple statement by Thoreau back in 1854 still bears truth for far too many of those we all know today.

We do not need to search long and hard to bear witness to the mediocrity we see that has become the norm in countless pockets of society’s great institutions: It permeates our K-12 education system, it exists throughout our local, state and federal government, and it is easily observable in the deterioration of the family structure and unit.

I share this not to depress you and me. I share this to help crystallize the fact that building your sales career and life with Swagger is truly the road less traveled.

Jack-of-All-Trades, Master of None

Most people in professional sales become the Jack-Of-All-Trades, and the master of none.

What I mean is simply this: The overwhelming amount of people in professional sales invest 30-plus years in this awesome career, and yet never master the fundamental selling skills and process that will make them great!


To bring our discussion back to center stage—meaning you and your sales career—the point I am making is that mediocrity is prevalent and commonplace throughout our society. You have no doubt witnessed this, and by default perhaps have lived it yourself to date in your sales career.

Most people never master the core fundamentals of how to consistently prospect (capture referrals, develop centers of in uences), and they never become lethal at executing each stage of the sales process:

    • – Build rapport 
    • – Perfect the transition from rapport to the qualify, through mastery of a Transitional Success Story 
    • – Qualify—logically and emotionally
    • – Perfect a presentation that dances from start to finish
    • – Close and consistently convert objections into deals

It is not hard to imagine an individual in your and my vocation of professional sales that has 10, 20, 30-plus years of experience, but can’t close…or does not consistently referral-prospect or qualify. It is not hard to imagine, because as a consultant, I see it everywhere I go, and you do, too. In fact, what I am describing may very well be what you personify to date in your sales career. And you know what? I am here to tell you: It does not matter!

What I mean is this: It is not good, it is not bad; it simply is. All that matters is what you do about it. It is never too early and never too late to begin your journey to professional and personal excellence. It is never too early or too late to get your Swagger on!

The Price of Mediocrity

Is there a price to pay for settling for mediocrity in sales and in life? You bet there is.

But is there a price to pay for learning to swagger your way through life? You bet there is!

However, I want to assure you that price in terms of energy, effort, time, and financial resources is almost the same, meaning this: It takes just as much time, energy, effort and concentration to build and live a life of mediocrity, because of the opportunity cost debited daily to our life performance, or lack thereof, by not becoming the best. But besides the opportunity cost, let’s face it: It takes just as much energy and effort to make up excuses for underperformance, and for the energy to hide and not apply ourselves, as it does to simply commit and apply oneself to becoming the best you can be.

Here’s the bottom line: Although the costs in terms of effort and emotion are similar, the results in terms of respect, opportunity, satisfaction and financial gain for those who learn to Swagger are profoundly different from the results for those who do not!

So do you want to learn how to Swagger? Do you want to learn and master the “way of the sway?” If so, I implore you to read on. You will not be disappointed.

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