The Role of Self-Esteem in the Pursuit of Callings

Despite all your doubts, self-esteem is what tells you, “You can do this!”

Posted Aug 23, 2019

I have a $10,000 bill taped to the Rolodex in my office. It was given to me by the 5-year-old son of some friends, who taught me a critical lesson in the economics of self-worth, and the part it plays in whether I say yes or no to what my life is calling for from me.

I first met Christopher at the front door of his house. Standing behind his father, he wore tiny, bright-red cowboy boots, a red baseball cap, and thick, round glasses. One hand was on his hip, a pose his dad described as “ready for action.”

During that first afternoon of our acquaintance, he showed me his secret hiding places, and we played baseball in the backyard. I let him win 15-7, even though I was hankering to slug a few balls over the roof, take him to task for making up rules in mid-game and running the bases in a half-hearted circle that barely extended beyond the pitcher’s mound.

Later, as I was saying goodbye to his parents in the kitchen, he ran in carrying an envelope stuffed with play money, sat down, and very exactingly filed through it with his fingers. He pulled out a $10,000 bill—the largest denomination he had—and handed it to me, saying, “Here. This is for you. For playing baseball with me, and being my friend.”

In the blur of self-consciousness that followed, I gave it back to him, mumbling something about it being only a baseball game, not worth ten grand, but thanks anyway. He looked puzzled, went back into the envelope, and pulled out two $100 bills and again handed them to me. These I accepted.

That night, as I was undressing for bed, I emptied my pants pockets and found the two $100 bills, and the first thing that went through my mind was, “Dammit. I could’ve had $10,000. How did I end up with only $200?”

I was keenly motivated to find out, because, within a few weeks, I had to put a price on my head for a writing project which had the potential to be the most lucrative of my career. But I'd never taken on a project like it before, didn’t know what I was worth, and the incident with Christopher didn’t feel like a very promising omen.

It was a call to think big, which is exactly what I needed at that moment, and I turned it down. And if I was declining the advances of a 5-year-old, I wondered what tactical blunders I might commit at the bigger bargaining table.

When it comes to all the reasons you have for saying no to yourself, to your passions and callings and yearnings, most of them pale in comparison with the issue of basic self-esteem, your core regard for yourself.

Sometimes it isn’t even that you consciously say no to desires and opportunities, but that you're just stuck in a position of negating yourself, and your calls are swallowed up in the same black hole as all of your soul’s other petitions. The very self that receives calls is injured, and often by the injured souls who raised you and their poor estimation of themselves. The central message you received was a "No" rather than a "Yes," and that’s what you carry.

But the beating heart of self-esteem is the feeling that you’re acceptable as you are, without having to earn it. It's what tells you that despite all your misgivings about yourself—and your callings—despite all the odds and obstacles, you know you can do this thing!

Ironically, it’s a function of self-esteem that you resist your calls. Resistance is about self-preservation. You’re protecting yourself from imagined harm, the threat of pain, the experience of feeling badly about yourself.

“It's love, not hate, that underlies self-defeating behavior,” writes Roy Baumeister in Escaping the Self. “Our love of self is so great that it becomes intolerable to let ourselves be seen in a bad light. When events threaten to cast us in a bad light, the first impulse is to turn the light off.”

The term self-esteem is tossed around with such cloying abandon these days that it's effectively been gutted of meaning and is often thought of as something you can turn on with the flick of a switch. But raising self-esteem requires courage and damned hard work.

And it can't begin if you don’t admit the ways in which your self-esteem is wounded, don’t do some self-scrutiny and carve some new furrows in your brain. (It's also important to understand that this isn't just your own hard work, but requires retooling some of the apparatuses of human relations: child-raising, education, the teaching of social and emotional skills. In other words, self-esteem isn't just individual work, but cultural work.)

The difference between saying "No" and saying "Yes" to yourself can be contained in a split-second decision—take the $10,000, or leave it—but arriving at the point of being able to make that decision can take a lifetime.

For instance, the question “What am I worth?” is far more than a financial question, and answering it demands far more than a cursory look at what the market will bear or what the competition is charging. The answer isn’t just a function of what your parents thought you should receive in your allowance, or what the fast-food joint you worked for in high school paid a hamburger-flipper.

The answer also depends entirely on who you ask. To a chemist, your bodily components, boiled and centrifuged, are worth a few bucks in trace minerals. But to a 5-year-old itching to play baseball in the backyard, and no one to play with, you'd suddenly attain Most Valuable Player status.

Christopher’s bountiful gesture was a way of saying that what's most valuable, what he was willing to pay top dollar for, is intrinsic—friendship and time spent. And he got me thinking along the same lines.

But first he tripped a wire inside me, and I was flooded with memories of other times I’d sold myself short. My decision to attend the college that offered me financial aid rather than the one I really wanted to go to; not quitting my job at the newspaper sooner; falling into relationships I didn’t want, because something seemed better than nothing; all the times I told myself, “I can’t afford it,” when I could; all the times I tried to win my parents' approval, or heaped regrets on myself for decisions that were over and done with, or clamped my hands over my ears when life was playing my song.

These experiences were a big part of what orchestrated my conduct with Christopher, which prompted me to turn from his friendly call and blackout to the possibilities it hinted at. It was also what lent tremendous performance anxiety to my deliberations about what to charge for that writing project.

The day before I faxed in my proposal, I was back at Christopher’s house. It was my birthday, and Christopher’s father, Dan, gave me that $10,000 bill which he knew had obsessed me ever since I let it slip out of my fingers. This time I accepted it.

I asked for five times the amount of money the company had hinted it was prepared to pay for the project and twice the amount of time.

I had a contract within a week.

To this day, I still have that $10,000 bill taped to my Rolodex, with the picture on it of an Indian chief with a great hooked nose, and though it says “Not Negotiable” across the top, it reminds me of a tender negotiation with myself that helped me most literally re-evaluate my life.

In retrospect, I’ve probably gotten more “value” from that play money than from most of the money I’ve earned in my life for services rendered. Certainly compared to the $250 check from a magazine that was in my mailbox the afternoon I returned from meeting Christopher—money that went right out the door to pay for an overdue phone bill.

I was able to spend that money, but not enjoy it, and so it didn’t seem any more real than Christopher’s. It was money that did nothing to remind me that I have a friend somewhere who would gladly show me his secret hiding places, who knows the true value of friendship, and who has money to burn.

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