The Art of Making You Feel Small

Confidence doesn’t have to be a zero sum game. Some lessons from both sides of the table.

Work in Silicon Valley long enough and you’re sure to have experienced this: you sit down to talk with someone… and get up feeling small. Something about this person convinces you that you simply haven’t worked hard enough, you don’t know that much, you aren’t advancing. You were OK before you sat down with him or her. But not now.

This person lets you know about the important people they spend time with. And the events they go to. The money they’re making, the trips they’re taking. Even the super special coffee beans they’re drinking. It’s not quite envy, though that can figure in. You just don’t feel that good about yourself anymore when you hear all this. You’re behind, outside, a little irrelevant, small.

We’ve all sat in both chairs. Wittingly or not, you’ve probably made others feel small too. I’ll be first to admit, ashamedly, that I have caught myself talking way too enthusiastically about that great, big superior ME — dispensing names, titles, experiences and yes, coffee-bean-dropping with the worst of them, thinking not-a-bit about the feelings of the poor person in the small chair.

The last person who made me feel small was an investor for a group I hadn’t heard of. I don’t think he was trying to be unkind, but his narrative was so exclusive — stories full of important-sounding people I didn’t know. Only founders, he said, could do early stage investing the right way. Was he trying to say I wasn’t qualified? I walked away wondering, ‘Why do I feel so puny after meeting with this dude?’ I know where I’ve been. I’m happy with where I’m going. How in the world did he make me feel so out of the loop?

And — then when I think about the most accomplished people I’ve worked with, none of them ever made me feel small! They were humble. They encouraged me to work to a potential higher than I thought I had. They collaborated. Opened doors for and took chances on me and others like me. Yes, these people were very self-confident. But when I sat with them I felt their confidence in me, too.

Confidence doesn’t have to be a zero sum game. When you know, love, and are at peace with who you are you can work smarter, better, and harder simply because your ego is out of the way. When you remove ego-stoking as your top priority, you’re freed up to actually work! So go, do great work! Don’t just live to feed an ego that will never be satisfied! And even more, unencumbered, you can form more meaningful, positive relationships.

I’m working on more deeply cultivating that solid confidence. It’s a process of recognizing when my ego feels threatened. I’ve found that when I feel my hackles rise, perhaps in self-defense, perhaps in the flush of pride, at that moment my concern for others departs.

I can hear my ego bark and snort, “I am important! You should know!” What to do with the guard dog of my ego? A pat on the head and a little treat- just some reassurance: “You know what self? You are important — but trying to prove it here is a waste of time and not very nice. And I know you’re a good pup, thanks for trying to take care of me.”

Photo by Alvan Nee on Unsplash

Here’s how I’m trying to make myself better. I hope these applications might also help you.

Let’s do this thing:

  1. Try approaching others with curiosity and the desire to understand them as a human being. Regardless of “power, ” approach others with the desire to build up and support the good in their identity and purposes. There are some caveats to this point, but I find it generally applies.
  2. Start listening to yourself — how often do you use numbers, names and exclusive jargon? Feel out the person you’re talking with — are they comfortable with getting into specifics, or are you making them squirm? Think about how you can serve them and not yourself. If sharing names and numbers is helping, then go ahead, but if you see it’s cultivating FOMO and self doubt, then quit it.
  3. Check your gut in conversation. This is a less others-oriented, more you-oriented approach to point (2). It’s simple: are you sharing from a kind and genuine place? Or are you trying to big yourself up from a place of pride? Course correct accordingly.
  4. Finally, when you inevitably sit with somebody who makes you feel small, judge for yourself where the toxin comes from. Self defense, or just a full blown jerk? Either way, shake it off and move on. There are better ways to spend your time. You can love you. Others don’t define you. Want to go above and beyond? Be extra humble — and quiet. Hold back your reactive, self-protecting measures. This person’s behavior doesn’t merit opening up. You can be disarming, self assured and you’ll actually walk away bigger.

I know this may seem like Being Human 101, but in my last job (investing) I met with dozens of new people a week. It makes a huge difference when you connect with someone who isn’t trying to puff out their proverbial chest and dazzle you with their achievements. So, let’s try to make ourselves a little better. Let our lives speak for themselves, and truly get to know the people we interact with as humans, not as mirrors in which to admire ourselves.


I know there are lots of caveats and nuances on this topic. Feel free to discuss in the comments.

Of note — on the investing front, I actually have started angel investing! If you are a founder and want to chat, I’d love to discuss further —@cecistalls. Looking at all things b2b, platform oriented, built on Slack and…somewhat randomly, but as a passion side project, consumer video-related.

P.S. Thanks to Mari Ju for editing help!