We are always appraising the world around us. People, circumstances, risk, opportunities . . . the ability to accurately appraise a situation is necessary to life. And yet, we are so prone to drawing the wrong conclusions.

What happens?

Here’s a story of successful appraisal that I love. My sister and her family frequent estate sales and vintage and antique shops. It’s a hobby that has also turned into a side hustle because they’re great at finding deals. My sister resells dish and glassware, books, furniture, and other items in her Etsy shop.

A few weeks ago, my niece, age 6, found a Shopkin toy on sale for $2. Later that afternoon, her older siblings researched it online and discovered it was rare and worth a lot more. They sold it for $100. That’s a 500 percent mark-up and a pretty great appraisal of value.

Whether you are a painter or a president, a real estate broker or a baker, your ability to appraise your market is essential. The goal is to be able to draw accurate conclusions about more and more diverse challenges, and then add your insights to curating the creative landscape, connecting to the right people, or determining which way to go.

I love stories. The past few weeks I’ve binged on several mind-boggling and devastating stories about the staggering degree to which people can draw the wrong conclusions or take highly inaccurate appraisals. If this paragraph sounds like hyperbole because of all the adjectives, I assure you, it’s not.

The HBO subscribers might have also watched the two-part documentary Leaving Neverland, in which two men recount experiences of being sexually abused by Michael Jackson. Then I saw The Inventor: Out for Blood in Silicon Valley, which unravels the story of the former company Theranos and its founder and CEO, Elizabeth Holmes.

Then, coincidentally, I listened to the podcast series Dirty John, which tells the story of successful businesswoman Debra Newell’s relationship with violent conman John Meehan.

After the third story in as many weeks, I woke up feeling overwhelmed by the sense that we live in an age of deception and it is all around us. 

How could so many people have been duped? Is there anything we can take and apply to our lives?

Appraisal is one of the powerful elements of a coaching relationship. It’s a lens through which you can examine your life and opportunities.

Appraisal requires that you take a step back and look at a circumstance from a slight distance. The questions of appraisal sound like, “what do you make of it all? What do you think is best? How do you feel about it? How does it look to you?”

Or this question, which I like a lot: What is the story in your head? 

Out for Blood sets up the surprising lack of critical appraisal demonstrated by the businessmen who invested in Holmes and Theranos. They told themselves a story about her genius. She was described as “ethereal” and a “revolutionary in the truest sense.” She was considered “the most important inventor of our time.”


Similarly, what was the story in the heads of the parents whose young boys were singled out by Michael Jackson, the King of Pop? Their kids also had ambitions to dance and entertain; this was a lucky break! What was the story in the head of Debra, who wanted to be loved? Here was a handsome doctor who doted on her.

Everyone wants to be special, to be chosen, to be adored. We want to believe that intuition, or vision, is enough to transcend reality. We want to think that dedication to an idea is enough to make it come true. It’s a great dream, right? It’s beautiful. It’s magic. 

And yet we need the crazy dreamers, the outlier inventors, the entrepreneurs. They’re the ones with a singular vision and a strength of character to pursue the impossible. And surprises happen, like being a kid and turning $2 into $100. That’s a story my nieces and nephew will remember forever, and I hope it helps shape their sense of what’s possible.

Behavior economist Dan Ariely gives some context to this dilemma. He says over-confidence is essential to make the extraordinary happen, but it needs a foil:

“I don’t want to create a society where people are not over-confident in what they could achieve. Who would open a restaurant if that was the case? Or launch a start-up? But I think this is really the issue: How do you become a person of vision, on one hand, and how do you sell that vision on the other hand? [Yet] you also want to stay realistic, or closer to realistic, when the task needs it.”

I am picturing a teeter-totter with the two bodies of vision and reality on each end. And the thing about a teeter-totter is that isn’t not fun when it’s static and perfectly in balance. It is designed to be in motion, bobbing up and down: Reality springs up, vision sinks down. Vision springs up, reality sinks down. But they always need the weight of the other to stay in motion.

Switching gears, I want to distance us from people like Holmes, who are not simply suffering from an imbalance of vision and reality. She has far more complex stuff going on that I cannot begin to understand. Most of us are not capable of — or inclined to — commit massive fraud. And yet what grips us about her story is our vulnerability to trusting the wrong people. She gives ambition a bad name.

But lots of people come to coaching because they have ambition – to write, to start a business, to build a movement. And they are suffering from the burden of the unrealized dream. The story in their head sounds like this: I am not ________ enough. It’s doomed to fall apart anyway. I don’t have enough ________ to try.

You know the adjectives that fill in the blanks. I’m not smart enough. I’m not talented enough. I don’t have the time. I don’t have the money. I’m too old. Well, guess what? That is also an inaccurate appraisal. It is invested too heavily in fear.

It’s like these ideas are always in tension.

You must be able to see the world as it is. But you must do something else, too: You must see the world as it could be. 

Appraisal is a work in progress. We need people who encourage us and remind us of how great we can be – and lots of times that’s the role of a coach. And we need practices and individuals who keep us grounded, too. For me, reality checks come as a spiritual practice that involves reading, meditation, and prayer. It takes me back down to right size. 

You get to decide what’s missing in your life and where you need to lean in. Do you have a champion? Do you need more grounding? Whatever it is, do the work of being able to take more accurate appraisals. You’re worth it, and the world needs it.

About Me

I’m Stephanie. I’m a writer, coach, and facilitator. I work with individuals, teams and leaders in creative, entrepreneurial, and nonprofit fields to improve communication, find a true purpose, and deepen connection and meaning. If you enjoyed this post, share it with a friend! And I’d love it if you would subscribe to my email list, below.