Founder Insecurities and Practical Tips For Feeling Insecure

**I found this post sitting in my draft folder from 5 years ago. Decided to published all of my draft posts today without editing.***

If I would’ve wrote a blog post last week, (like I planned), I’ve would’ve entitled it “Having a Kick Arse Week”, (but I’m was too busy having a great week to sit down and write it). But I’m writing a post today, and its called “Founder Insecurities.” Or it could also be called the ‘The bipolar entrepreneur.’

I attended a networking function yesterday, and as expected at networking events, I’m often asked, “What do you do”; or “What are you working on.” Describing what I do can sometimes cause anxiety depending on the day. On the days, where doubts and fears are high, I may quietly reply “I’m a software developer.” On great days, especially following a great week, I may excitedly reply, “I run a software consultancy company, where we help startups build better products using data.” And this is how I replied yesterday.

Queue next question: “So how large is your company? How many people do you have working for you?” And then the following:

Me: “We’re two people”
Them: “Oh.”
Me (in my head): “Oh? Wtf does that mean?”

This is not the first time that I’ve been asked this or similar questions. And its normal for me to feel less confident when asked these questions. But today is the first time I’ve dissected why it makes me feel less confident.

When I hear questions like the above, I believe I’m being judged on my level of success, and subsequently my ‘worthiness.’ The questioner may or may not have been trying to determine my ‘important’ factor. Or maybe I thought they were because maybe I secretly give people ‘important’ ratings based on the information they tell me. But it really doesn’t matter. The point is my confidence hit a low and now its affecting my mood and productivity.

Here’s my way of handling founder slumps: (well, at least what worked for me today)

1) Is there a really a good reason to feel insecure?
In this case, there was absolutely no reason for me to be insecure. There were a few times when we thought about expanding beyond the two of us due to a surplus of work. However, we made a conscious decision to remain a small consultancy and use the company as a tool to aid in our goal of becoming a product company. There have been other times where my insecurity was somewhat warranted due to failure or lack of progress. When I get to those places, I need to remember that failures are only lessons learned, and reevaluate my plan to completion for lack of progress.

2) Look and reevaluate my goals
I am a goal freak. I have goals for all areas of my life. And they are all written down. I would like to believe that I am always striving for improvement. It’s very easy for me to become distracted. Often I may read a Facebook status or an article and think, “I should be doing that”. Rereading my goals helps me to focus on what

3) Celebrate my accomplishments

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About Hadiyah

Software Engineer, Entrepreneur, and Startup Aficionado. I co-founded a student venture firm for students at historically black colleges, HBCUvc, software development agency, Playpen Labs, and Black Founders nonprofit.