How to Transform Failure to Fearlessness

Paramount to success is making the attempt, which requires risk to reap reward. Often, numerous attempts are necessary to equate to a “win” meaning (1) you have to lose to win, (2) the risks will sometimes lead to defeat and (3) the experience you receive and lessons you learn from those defeat will lead to defining response and reaction. I don’t care who you are: you cannot win every single time. Eventually, defeat of some magnitude will come, and learning from it and learning how to move forward will go a long way in determining your flavor of and chance of success.

Reggie Jackson, a.k.a. “Mr. October” is known for his triumphs in Major League Baseball postseason, winning 5 world championships and exhibiting clutch play. While this is what he’s known for, he also struck out more times than any batter in history.

Kobe Bryant, one of the greatest students of the game of basketball, winner of 5 NBA championships, is known for his success in the athletic realm. He missed more shots than anyone in NBA history to get there.

Cy Young, winningest pitcher in baseball history, lost more games than anyone.

Faced with the decision to put these infamous “losers” in the game in their era and arena, no one would think twice. Their names are synonymous with winning in spite of their losses. So how do we overcome life’s losses to come out on top?

(1) Recognize the reason(s) for failure. Ownership of our stake in the reason for the plight going awry is the first step; where exactly in the process did we take the detour? Was there something we should have done differently? Was there a specific step we missed, question we did not ask?

It could be a sales attempt that flat-lined just before signature where we can look back and identify something we left unsaid or unattended to. Perhaps it was a business relationship that crumbled because we did not nurture it, show progress, check in or provide communication. It could be a business venture sparked by a great idea but because of failed execution of vital steps, attention to the right details, accounting for all potential variables… or just sheer dumb luck, it failed to leave the station.

Sometimes the reason for failure is the short end of probability; you can be the best card shark in your circle of friends but there’s no foresight to cure being dealt a poor hand. This is where the failure begets the temperament to best approach the poor hand, patience to wait for the better hand and knowledge of what to do with it to best capitalize. Know your odds and, effectively, like Kenny Rogers said “when to hold ’em and when to fold ’em.”

(2) Make adjustments. Failure is not fun, but it can be a telling teacher. Furthermore, rather than altering your approach by a complete 180 degrees or having a drastic reaction in the face of defeat, examine the ways you could make small tweaks to improve your trajectory.

Think about it this way: too much or too little of any one ingredient can make a monumental difference in your recipe. You don’t have to scrap every ingredient or change the allocation of all of them – you may only need to alter the approach of one facet of your process. Repeated application of your process can help point to the faulty piece; determine where you failed or are failing and address that component. Don’t just change it once, fail again, and go back to the comfortable old way of failure – justify a change based on results and probability and apply a more effective approach consistently over time, all while continuing to self-analyze and hold yourself accountable.

(3) Get back in the game. Don’t dwell on the loss. It happened, it’s over, but you have to move forward past the current fear of history repeating itself lest you’ll never have a chance at what you set out to achieve to begin with. Sure, you may have a day or two where you slink into the shadows and disappear, but you have to emerge rejuvenated and recovered – ready to give it another go.

It’s fear that often prevents us from wanting to try again after falling off. We took a gamble and it did not pay off and sometimes the sting of defeat can make us skittish. The other side of the coin is that the stings hurt less with each encounter; we become a lot more adept at navigating through these setbacks to get to successes.

Everything comes down to probability; there was a reason we pursued the potential outcome we were after in the first place. Don’t let the loss you endured prevent you from going after the new endeavor, starting the new relationship, chasing more sales. You cannot win without playing the game and you will have to play more games than possibly anticipated to get the wins you seek.

(4) Don’t look past the current game. Athletes in interviews will speak to this all the time – when asked about potential future foes based on speculation around contests that haven’t even happened yet, they will deflect and rightfully not look past the current opponent no matter how tempting it is. You cannot weigh too many future possible scenarios in your current mix because they may never occur and they may distract from the current missive.

Experience has a way of evolving our trepidation, our approach and certainly our response to negative outcomes. Simply put, the jitters or butterflies you felt when you stepped into the batters’ box your rookie season will not exist in the fifteenth season of your career as a seasoned professional – even if your game has eroded or you don’t have the pluck and passion you once did.  Experience can forge you into a more durable tool; it will help you weather storms that once made an impact and it makes you shrug off losses that once would have been devastating.

The first break-up’s you had, first time you lost a job, first time something excruciatingly unfair pinned you to the mat, your pain lasted longer and the time to get back up took longer. It took time to get over the disappointment after all the effort you put in. The hurdles you faced then were in the face of pending loss; now you lost, and your only hurdle is compartmentalizing that loss, understanding it and moving forward smarter and stronger. If you face similar decisions again, you can adapt. If you face similar repercussions again, you can heal and rebound quicker.

Fear and failure become fearlessness when you no longer question your motive and process, you can shake off the setbacks and losses and continue on in the face of adversity. When you can acknowledge that losses are part of life – and integral parts at that – and why you lost, adjust your process accordingly and evolve based on variables and factors necessary to success, you’ll find success. Nobody will focus on your loss column if you have the most wins.


Carson V. Heady has written a book entitled “Birth of a Salesman” and sequels “The Salesman Against the World” and “A Salesman Forever” which take the unique approach of serving as sales/leadership books inside of novels showing proven sales principles designed to birth you into the top producer you were born to be. If you would like to strengthen your sales skills, go to

Heady posts for “Consult Carson” serving as the “Dear Abby” of sales and sales leadership. You may post any question that puzzles you regarding sales and sales leadership careers: interviewing, the sales process, advancing and achieving.

Question submissions can be made via LinkedIn to Carson V. Heady, this Facebook page: , Twitter via @cvheady007 or e-mail at or you may post an anonymous comment as a reply to my WordPress blog at the bottom of this page:

About cvheady007

I am a Christian, Husband, Dad, workaholic and author. Biography Carson Vincent Heady was born in Cape Girardeau, MO, graduated from Southeast Missouri State University and moved to St. Louis in 2001. He has served in sales and leadership across Microsoft, AT&T, Verizon and T-Mobile. Carson is best-selling author of the Birth of a Salesman series, the first book of which was published by World Audience Inc. in 2010. He released The Salesman Against the World in 2014, A Salesman Forever in 2016 and Salesman on Fire in 2020. He is also featured in Scott Ingram’s B2B Sales Mentors: 20 Stories from 20 Top 1% Sales Professionals. Carson is a 7-time CEO/President’s Club winner across 5 roles at AT&T and Microsoft and National Verizon Rockstar winner. He has been recognized as a top social seller at Microsoft and is consistently ranked in the top 25 sales gurus in the world on Rise Global. He is included among the Top 50 sales authors on LinkedIn. With over 330K social followers, Carson has also been interviewed on over 30 sales and leadership podcasts, by such luminaries as Jeffrey & Jennifer Gitomer, Jeb Blount, Brandon Bornancin, Sam Dunning, Larry Levine, Darrell Amy, Scott Ingram, Thierry van Herwijnen, Jim Brown, Sam Jacobs, Luigi Prestinenzi, Donald Kelly, Marylou Tyler, George Leith, Pat Helmer, Eric Nelson, Ron Tunick, Jeff Arthur, Mary Ann Samedi, Jean Oursler, Andre Harrell, Marlene Chism, Bill Crespo, Matt Tanguay, Josh Wheeler and Chad Bostick. He has also co-hosted the Smart Biz Show on EG Marketing Radio. His articles have appeared in several noteworthy publications such as SalesGravy, Smash! Sales, Salesopedia and the Baylor Sports Department S3 Report. Carson lives in St. Louis, MO, with his wife Amy and daughters Madison, Sidonia and Charlotte.
This entry was posted in Uncategorized. Bookmark the permalink.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s