What’s in your Jar of Awesome

In my old world of hedge funds, there was a type of investment that was always accompanied by a buyer beware sign.

It wasn’t a tiny pink sheet microcap. Nor was it a hair-brained ICO that promised the Lambo Life of the crypto bros.

In fact, its dangers were masked by its nerdy name: Negative Convexity.

Bloomberg.com refers to these types of investments as “a beast in the market” and here’s why:

When you win, you win a little. But when you lose, you lose a lot.

You know what else displays “negative convexity?”

You. Me. Your co-worker. Our fellow Sapiens.

Let’s look at Exhibit A: You mess up a sales pitch.

And as you walk out of that meeting, the “what-ifs” start racing through your mind.

My boss is gonna berate me…
I bet I just halved my bonus
What if I get fired?

I’m destined for the poorhouse
How will I explain this to my spouse?

Mr. SaltyPoop (i.e. the inner critic) is fired up. Scarcity thinking pulses through your veins, and – on the spot – you grow a few gray hairs.

Now for Exhibit B, the opposite happens: You NAIL the sales pitch.

A few smiles, some high fives. Then on to the next win.

A perfect example of negative convexity (the when-then trap at its finest).

So to recap:


  • The loss = PERSONAL DOOMSDAY!!!!!!
  • The win = Yeah, whatever


I see this with my coaching clients all the time. They come to me with impressive bodies of work. Heck, they’re all crushing it – yet in their own eyes, they’re not enough.

And this negative convexity is a happiness killer, according to UPenn professor (and RadReader) Adam Grant:

“These moments of joy are really important and part of what makes life worth living and what we have to look forward to. Being human is being able to enjoy life.”

A two-step process to squash the Negative Convexity

You’re still employed. You’ve still got insurance. And a roof above your head. So that sales meeting hiccup? It didn’t even register as a blip.

Here’s a simple trick to squash this mindset. I have my clients come up with two lists:


  • Jar of Awesome (inspired by Tim Ferriss)
  • Jar of Poop

Every time you get find your foot in poop or are blessed with a win, log it. On the poop side, it de-fangs your losses. In fact, with a little distance you’ll laugh at how worried you were. Here were two of mine:


  • 3 single guys move in next door to us in Brooklyn
  • I entered the wrong SSN for my COBRA


Let’s just say that the single guys didn’t throw a single party. And, regarding COBRA… well, we still get to see our doctors.

But it gets better

Re-reading the Jar of Awesome will become one of the most joyful parts of your week. You see the full picture of accomplishments. You get transported back to your first paying customer. You re-live that promotion.

A RadReader’s actual Jar

And if you believe Daniel Kahneman’s happiness definition (of how you feel over 3 second intervals), you’ll unlock happiness on tap. And as Grant writes, you’ve demonstrated both “what makes life worth living” and “what you have to look forward to.”

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