How to avoid the envy trap

Jan 19, 2023 8:01 PM

I’ve got some baller-ass friends.

There’s an entrepreneur who sold a company after 2 years, personally pocketing $50 mm. (After taxes.)

There’s a law firm partner who owns not one… not two… but three homes.

There’s an early buyer of Bitcoin at $30, who after crypto winter is still worth 8 figures.

And there’s the hedge fund manager who regularly collects a $10 mm paycheck. Every. Single. Year.

Meanwhile, over at RadReads, we celebrate – wait for it – a $5,000 invoice.


Now I feel blessed. Our business is kicking butt. Our family is healthy.

Heck, I’ve surfed 1,200 days in the past 4 years.

But I gotta be honest.

Hearing my friends’ success stories still makes me jealous.

What’s happening here?

The comparison trap

A former coach once gave me the mantra:

Compare, despair.

Unfortunately, when I curse under my breath at my friends’ success (lovingly, of course) – that mantra doesn’t help.

Here are 5 things I try to do when my envy flares up.

1. Practice Gratitude

Whether you missed a promotion, a raise or a funding round, it’s important to remember that you’re still doing damn well.

Despite the setback, you’ve still got a roof over your head, your bills are easily paid for and friends and family who love you unconditionally.

Taking it a step further, there are probably a billion people on this planet who would dream to trade spots with you.

Greg McKeown, author of Essentialism puts some powerful perspective around this gratitude:

When you focus on what you lack you lose what you have. When you focus on what you have you get what you lack.

2. Apply some perspective

Envy can trigger our recency bias. When we look at other people’s accomplishments, we tend to only see what we’ve done in the recent past.

Bill Gates shared a famous quote about this distortion of time and reality:

Most people overestimate what they can do in one year and underestimate what they can do in ten years.

So when you find yourself making unnecessary comparisons to peers, ask yourself:

“What would 13-year old Khe think of 43 year old Khe?

Answer: “Damn kid, you killed it!”

Even over a shorter look-back window, the same reasoning holds:

What would 5 years ago Khe think of Khe today?

Same answer.

Go ahead, you try it

3. You gotta take the whole enchilada

When I see my hedge fund manager friends swimming in cash, I’m struck by one thing: they are always checking something.

Stock prices during market hours.

News during the evening.

Asian markets at night.

Futures markets during breakfast.

There’s a price to pay for that cheddar. Your freedom of attention.

My friend, Thomas Frank uses the following mental hack: Do you want this person’s average day?

After all, you can’t cherry pick the best attributes (ahem, hedge fund manager compensation) and drop the worst parts (being tethered to markets).

We can extend Thomas’ line of thinking even further.

If you want that cheddar, you have to take everything that’s going on inside that person’s mind. Their relationships (good and bad), their fears, their insecurities, their anxieties and all the childhood trauma.

Still want to trade?

4. Apply curiosity

What if you turned envy into a teachable moment? If you see someone who has something you desire, or achieved a goal of yours – there are lessons to be learned.

How did they do it? What path did they take? What obstacles did they face?

There’s a tremendous opportunity to open-source a playbook for something you truly want.

Lean into it.

5. Look inward

Behind all emotions and desires lie an unmet need.

Some crave fame because they fear being unlovable.

Others crave status because they fear irrelevance.

And people crave money because they want to feel seen.

Your envy is giving you a clue. Don’t dismiss it.

Investigate this craving more deeply – with compassion and curiosity.

Another friend, Cady Macon suggests taking envy and telling yourself: “Oh! This must matter to you.”

So success matters. But why?

6. Celebrate

“When my team wins, we all win,” said the late Virgil Abloh.

Wins are wins. Especially when it’s your friends’ wins.

They should be celebrated. Loud. And visibly.

Shouting from the roof tops.

It feels awesome. Trust me.

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