Win Without Pitching®: Thinking

Share on twitter
Share on facebook
Share on linkedin

I once played a first game of chess with a friend in which he destroyed me with his opening move. In the very first second of the game he had me panicked – robbed of my ability to think clearly. The only thing that was clear at that moment was that he would beat me quickly, with much humiliation. The prophecy did indeed did come to pass.

It wasn’t the move itself that rocked me (it was 1. e4 or P4K – the most conventional opening in chess), but the manner in which he did it. The confidence with which he grabbed the piece and thrust it two squares forward served me notice that he was about to eat me for lunch. It was just a hand moving a piece on a chess board in an conventional opening, and yet, in that moment I was unmasked as a pretender playing against a master.

The odds of me winning the game were always poor. My opponent was an accomplished player and I was trading on distant memories of having once been better than most of my childhood peers and my usual overconfidence in my ability to get myself out of sticky situations. Going into the game, I was confident that I had at least an outside chance – a long shot. In the few games I had played as an adult I had surprised better opponents before. I thought that with a combination of my basic skill, intelligence and luck, an opportunity might present itself for me to steal this game too. With the confidence of his first move, however, he robbed me of mine and I quickly crumbled.

In that game, each of us demonstrated one of the two levels of confidence that we see every day: that of the salesperson and that of the expert.

Level One: The Salesperson's Confidence

The best salespeople are able to muster and maintain confidence in situations where they are largely faking it. Indeed, “Fake it 'til you make it” is advice I often give to owners and employees of newly positioned firms and to those just going out on their own. This acting skill is invaluable in the early days but it is a transitional skill that should eventually be replaced with the gold-backed confidence of someone who knows his subject matter better than anyone else on the planet, or at least in the room.

Level Two: The Expert's Confidence

I went into that chess game having played it for a few years in my youth. It wasn't foreign to me, but where I had basic knowledge and the confidence of a salesperson just at the edge of his limits, my opponent was a skilled and schooled expert. He had played more chess in his life than I had played all strategy games combined. His confidence was real, built on years of playing. He had benefited from repetition and variance – playing the same game, the same openings, the same defenses, in different situations over and over and over again.

You cannot be good at chess without hours and hours of repeated observation and execution. His thousands of hours of accumulated knowledge shone through in a way I would have previously claimed was impossible simply by picking up a wooden figurine and moving it two inches. The deft and assured movement of his hand brought the lightening bolt of realization that this man knew what he was doing and I, in comparison, was faking it.

The Bond of Creative People and Salespeople

Salespeople and creative people share in common the ability to think on their feet. This gives them confidence going into pitches, presentations, sales calls and other arenas where they might barely know their subject matter or their audience. This skill is a valuable one, most important early in one's career before one can reasonably expect to amass any real expertise. But after amassing a few thousand hours in a narrow enough field, real expertise takes hold and the need to “sell it” with a salesperson's confidence diminishes. The confidence of truly knowing the subject matter better than others trumps all other forms.

This skill comes at a cost, however: the inability to focus (see The Cost of Creativity), and thus, too many creative professionals find themselves at a point in their careers where, when they should be operating with an expert's confidence, they remain at the salesperson's level, relying on that mixture of some basic knowledge and an ability to fake the rest.

The Opportunity Lost

To rely on brass balls well into one’s career is to admit that one has never progressed to the next level of confidence – has never become the expert. It might not feel like a crime of lost opportunity ten or fifteen years into a career, but by 20 years in, anyone still trading on a salesperson's confidence will have the costs tallied and presented. They include humiliating unmasking moments when caught trying to fake expertise in front of real experts (see Slaughter on the Chess Board, above), lost profit and with it the ability to retire in luxury, and an empty personal balance sheet when one realizes that despite many years of work, little meaningful knowledge has been accumulated. (I am grateful to have been confronted with this terrifying realization after only ten years in advertising.)

Career Games

Well before you’ve logged 20 years at your craft you should be seen by your peers, clients and prospects as a leading expert in your field. If you're not, it's only because you've chosen too broad a field. Like me, you chose to learn and play a wide variety of games instead of focusing on just one. There would be little real harm in such an approach if we were just talking about games instead of businesses and careers. The trap for creative professionals and for anyone else earning a living from their passion, however, is that the first third of a career or a business can feel like a game.

In the final third of a career, it's only true experts – those with the deep confidence rooted in strong personal and financial balance sheets – that have the luxury of playing games.

Blair Enns
Blair Enns is the Win Without Pitching founder and CEO and the author of The Win Without Pitching Manifesto and Pricing Creativity: A guide to Profit Beyond the Billable Hour.
We help agencies close more business the Win Without Pitching Way

You will get a curated collection of Blair’s best writing, videos, and podcast episodes immediately after signing up.

Then, you’ll receive Blair’s latest work as it’s published.

Sign up to get our best advice delivered straight to your inbox

Recent Thinking

Getting Paid

There are three keys to getting paid: start with new standards for new clients, summon the resolve to enforce your new standards the moment client behavior starts to slip, and be willing to walk away from clients that don’t honor their commitments.

The Five Levels of Pricing Success

In this post I lay out the five levels of pricing success and ask you to do an assessment of where you are now. Then I identify the best resources to help you move up from your current level.