Sam Gimbel

Tech, Beer, and Strange Thoughts.


I stared out at 50 sets of bored eyeballs, the eyeball owners still confused about leaving their routines to listen to me. I'd done my research, set up sample projects, and now it was my job to train 50 DigitalOcean staff–mostly engineers–on how to use JIRA. I don't hate public speaking, but it's not my favorite. I take a deep breath, introduce the topic, and look up for a second. Ben, the CEO, sits down in the crowd with a pained look on his face. His shoulders are tense. My heart goes out to him: he looks like this a lot, especially during this major re-org we're undergoing, not to mention the ongoing struggle of building a functional product team. I was hire #1, and six months later there was no hire #2. There were plenty of reasons for him to look pained.

I'm not sure what happened. Maybe I over-thought it. Maybe I got spooked. But it's at that moment that I lose my confidence. I couldn't speak clearly, the demo fell apart, and the leader of the company saw the whole thing. He looked down at the table he was sitting at and I saw him visibly deflate. I had spent the last few months building consensus on the importance of good product process and this flubbed moment was a setback for both of us. I was embarrassed at my fuck up, but moments like this are thankfully rare. I finished up the demo, walked out, and made a comment to a co-worker about how poorly I'd performed. He laughed it off and we went to lunch.

This was a minor failure. It didn't have many consequences for the organization or the product. It certainly wasn't critical. Nonetheless, screwing up this JIRA demo marked the beginning of a year-long search for my confidence, a personality trait I'd never thought I could lose.


It wasn't until much later that I realized what I'd lost. Anxious people tend to second-guess themselves often, and I'm used to listening to the self-doubt narrative and letting it roll in the background while I continue on the best path anyway. Plus, my time at DigitalOcean was extremely taxing. The breakneck speed of growth at the company had us consistently under-staffed and over-stressed in the face of challenging goals. I had reason to question my decisions: there was a lot on the line, and no one person or group had the knowledge necessary to make fully informed decisions.

My lack of confidence showed itself in corners, peering out from the piles of junk I couldn't part with, whispering in my ear as I'd prepare to give my order to the waiter, leaving me tongue-tied and indecisive. I went on a trip to the Bahamas with my girlfriend last April and found myself having trouble picking a book to read on my Kindle. The desire to read was there. So was the familiar neural locking of preferences with descriptive blurbs, urging me to read The Martian before Born To Run. But when I'd go to click on the icon of the book I'd freeze, paralyzed with the fear that maybe I should be reading something else.

I remember thinking, "That's not like me," and choosing a book at random.

Difficult book choices grew into a fear of public speaking during my time in the Blue Ridge Labs fellowship, indecisiveness regarding the path we should charge down, and a complete lack of motivation to speak with others in the industry about what we were working on. Time and time again my fear was invalidated and I pushed forward, first by rehearsing pitches, then by asking (too many times) for validation from loved ones, then by forcing myself to listen to my instincts and push back even though I didn't always emotionally agree with myself. I was scared.

My whole life I've been able to sit down, do a thing, and know it reflected who I am.


It was around this time that I started digging into the intersection of introversion, anxiety, and childhood trauma. I suffer from the first two directly, and the third was dispersed among my family members when I was 9 by my aunt's murder by her ex husband after an extended period of domestic abuse. I was uncovering just how fragile I was as a result of living in a world that expects me to be social and outgoing without heeding the anxiety generated by so many [illogical, unwarranted] daily sources.

Anxiety is a prominent driver of indecision in those who suffer from it, resulting in localized inability to differentiate bad decisions from bad feelings about decisions. It leads me to equivocate and stall and to accept the decisions of others whose opinions I perceive as stronger than my own. Add in a natural sensitivity resulting from introversion and being touched by violence and the stage is set for me to cognitively run away from my own decisions.

When we talk about making decisions, we're referring to the result of confidence, not confidence itself.

The logical pre-frontal lobe driven decision-making apparatus was consistently competing for bandwidth with the fear-driven amygdalic and limbic response. The signal was frequently getting stuck, exacerbated by anxiety and resulting in high cognitive load even when deciding on simple things. For instance, today I was deciding between writing this and playing video games. It took me 20 minutes to realize I could do both. Just not at the same time. At the time, I was concerned that I was suffering from Aboulia as a result of the early stages of Parkinson's Disease. While not thought to be genetic, Parkinson's has affected several people in my family, most notably my mother. It's unlikely given the isolation of the symptoms, but the fear was there, driving even more confusion.


The struggle came full-circle: I was paralyzed in my own home wondering whether this lack of confidence was self-imposed and thus curable or simply genetic and only going to get worse.

When you're paralyzed, start looking for quick wins.

I'd been fundraising for Populace and striking out left and right. The lack of external validation had me leaning towards the "genetic and getting worse" explanation, but I wasn't satisfied with that. So I started pushing myself out of my comfort zone and looking for simple victories. Let me tell you. Forcing yourself to move when you're paralyzed by anxiety uses up a lot of spoons. You can't do it a lot. But once you do, the results are positive, widespread, and validating. For me, it was asking for introductions to people I should be talking to, reconciling with friends I'd put on the back-burner due to my fragile mental state, and finding ways to heal my relationship with my partner which had frayed due to my constant second-guessing. Once you push yourself to look past the trap of making the "perfect" decision and trust your own instinct, things start falling into place.

Which self will you listen to?

My mind was opened to a new reality, a new theory of the system I live in. I'm not living in a world where objective reality is unattainable by instinct. I'm not so inept that I must continually appear competent to survive. And I'm not intrinsically broken. I'm a complex being, strong-willed and well-suited to make decisions, but also anxious and sensitive. It's stressful to make important decisions. It's hard to be confident with the people around me. And it takes courage to build the meaningful relationship I want and my partner deserves. But similar to running your first mile, it takes time to train yourself to balance the flailing of the different aspects of yourself.

The part of me that is excitable is also extremely sensitive to setbacks. The part of me that executes effectively is also not great at advocating for the ability to do so. And the part of me that ties all this together tends to defer to the loudest actor. As humans, we forget how loosely integrated our different functions can be at times (it's scary to think about), but by recognizing this you can start to dig into the needs and interfaces provided by those different functions. For me, being confident means amplifying the part of me that loves people, ideas, and success. It means building emotional momentum to overcome the sensitivity and fear of potential failure. And it means counting the victories, being mindful of their existence and the patterns they represent, and being OK with the fact that this is you, this is how you thrive, and this is OK.

Confidence is recognizing past success and identifying similar opportunities.

It's not easy being a human on earth. It's even harder when we expect ourselves to behave in certain ways without recognizing the underlying realities of our existence. Doing so may scare you, and will certainly have you seeing yourself in a new light. For me, it's been a path to new growth and a better understanding of how I can do the things I want in a world that doesn't always expect me to be here. Set your own expectations. The world will come around.