How to Stop Measuring Yourself Against Other Founders

Years ago, a lot of my friends were far more successful financially than me.

I felt a lot of scarcity, like I was less than them.

There was a time when I believed that if I had a certain amount of money, that would be it. I would feel free and peaceful, and I would never worry about anything again.

But then I went to New York and visited three friends.

The first had a modest apartment in Hoboken. He was a mid-level executive at a media company.

The second was a banker, with a much nicer apartment in Midtown.

The third had started his own private equity fund. He'd bought four apartments on the Upper East Side and combined them all into one huge place.

Seeing them all and talking with them all, I had a realization that really freed me up. And once you see it too, comparison may start to loosen its grip on you.

What Your Mind Leaves Out When It Compares

They were all married. They all had kids. And I realized they were living basically the same life.

The money showed up in the details: a bigger apartment, a nicer apartment, nicer hotels when they traveled. Those were just slightly different accoutrements.

My mind had been doing what the human mind tends to do when it compares. It leaves out most of the picture, in two ways.

First, it picks who to compare us to. It usually doesn't compare us to the billions of people who are worse off than us. It just compares us to the few people we can find who seem to be better off.

Think about the people in the world who don't have running water, let alone a hot shower. If we compared ourselves to them, we'd just be full of gratitude. But that's not where our minds tend to go.

Second, it judges those few by the one slice of their life we can see. With my three friends, the slice was money and the lifestyle it buys.

Each person's life is like a robot. You see your own from the back, where it's all duct tape and bubble gum holding it together. You see everyone else's from the front, where it looks all polished, so you assume theirs are perfectly polished inside and out.

We get the glossed view of everyone else, while we have the full picture of ourselves. So the people who seem better off may not be.

And because the mind keeps finding someone who seems to have more, catching up doesn't end the comparing. When we first moved, we bought a small condo, and all my friends had these big houses. I told myself, when we can just get our big house, that's it. That's everything I want.

Then we bought it. It's nice. I love it.

But it didn't keep my mind from saying: I expect more. I want more. There's something missing.

I like to call this voice Comparison Charlie, the scorekeeper measuring worth against others. His core story is "They're ahead, I'm behind."

Comparison Charlie is one of my most consistent patterns, and he shows up sometimes when I'm working with clients. With one longtime client, whenever he brings up a challenging situation, my mind immediately says: He'd be so much better off with another coach. They'd know just what to say.

In that instant, I'm no longer fully present with him.

Because I know this pattern so well, I can recognize it for what it is: Oh, there's Comparison Charlie doing his comparison schtick. This enables me to let go of the unhelpful thoughts and return to being fully present with my client.

You can do this with your own patterns, too. The fact that you can see a pattern tells you that you're not it. If it's an object of your awareness, it can't be you.

That gives you some space, and some choice around whether you want to keep playing it or let it go.

There are lots of different experiments you can run with it, as long as they're something other than listening to it, believing it as true and engaging with it.

Five Experiments for When Comparison Charlie Shows Up

1. Keep a thought journal.

For a week or two, literally keep a journal. Write down every thought you notice and look for the patterns. You might find: Oh, comparing, that's one thing my mind does.

Once you know that, catching your mind in the act is already a way of seeing through it. Oh, that's just my mind doing what it does.

2. Ham it all the way up.

For the next week, see if you'd be willing to exaggerate Comparison Charlie on purpose, almost like an actor playing a role. Compare like crazy. Compare to everyone, to everything, and just see what happens. It will probably feel uncomfortable and a bit embarrassing. Do it anyway. Exaggerating a persona makes it easier to see the pattern clearly, and to take it less seriously.

3. Take the whole trade.

Next time you feel envious of someone: imagine you'd have to trade your entire life for theirs. All of it, including the parts they don't like to share publicly. Would you still make the trade?

4. Welcome the envy.

Emotions can mature when we meet them with loving awareness. So when envy shows up, imagine enveloping it in love like you would an upset child, and see what happens.

As envy matures, it can turn into inspiration. "I wish I had what they have" leaves you feeling less than. "I can't wait to have what they have!" leaves you feeling inspired.

So you can still want what they have. Nothing against money or material possessions, to be clear. I want you to be as effective and powerful as possible in creating wealth and results.

5. Find the feeling underneath.

Often what keeps a thought pattern in place is some feeling we haven't been willing to feel.

So when Comparison Charlie starts talking, ask yourself: What would I have to feel if I couldn't think this thought?

Building From What You Want

Seeing my three friends in New York living the same life freed me from the idea that a certain amount of money would finally make me peaceful.

From my experience, if you can't be peaceful now, you won't be peaceful then. But you can be peaceful now.

The comparing mind shows up in nearly every area of our life, especially in how we lead. Many founders try to figure out what to do by asking themselves, "What would Elon Musk or Sam Altman or Brian Chesky do?"

But what if their secret of success was being unapologetically themselves?

If you're the CEO of your company, your authentic and intuitive wants will be a better guide than someone else's idea about the "right" answer.

So the next time your mind says someone is ahead of you, ask what it's leaving out. The full picture can free you up to build from what you actually want.

With love,

Dave Kashen