Eating Worms.

Dealing with Self Doubt.

Nobody likes me! Everybody hates me! I think I’ll go and eat worms!

These are the first lines of a children’s song that popped into my head.

A few months ago my wife and daughter were away for a few weeks checking out a college and I ended up having a lot of free time without much to do. When I don’t have much to do, I often get deep into thought and start pondering those existential questions of where I am going, and what I am doing with my life.

I must have shark blood in me as I always feel that if I stop moving I will die. I don’t know why this happens, but my assumption is that something rooted deep in my biology has me compelled to run away from the hyenas that are stalking me. I have experienced this strange sensation before so it is not unfamiliar, and it manifests itself in such a way that it can be represented mathematically.

As the amount of free time approaches infinity the value of that time approaches zero. It has been a constant battle for me to remind myself that the value that I bring is large — but the ‘demon’ of doubt keeps creeping in and I get down on myself and question my self worth.

If I am not producing, and in my case, not producing at some multiple of what others can do, I am failing.

I feel like I am not worth anything, and I extend that to think that others think I am not worth anything. This is my ‘demon of doubt’.

I unfortunately spend probably too much time looking at the 10% of things I have not yet done and too little looking at the 90% I have accomplished. I am a victim of not living up to expectations I have put on myself.

When I moved to Oregon, I had no expectations that I would ever be ‘successful’ — my goal was to just get a job doing something creative. I was able to achieve this goal before I graduated from college, as my internship at a local game company lead to a full time job, which began the crazy series of events that led to two startups, running an accelerator, and a small venture fund.

Now that I am at where I am in my life, it is hard to not look ‘up’ to the bigger and better next thing — and the expectations I have of myself have grown to reflect how others see me. My daughter told me the other day that I am the most successful person she knows.

I was reminded of an interaction years earlier, which still makes me chuckle. It happened at the first face to face meeting with someone I had met online and with whom I had a few years of online interactions. I am not the tallest person (5'7") — and the individual (who was quite tall) was surprised by my not so large stature, saying while looking down at me with a bit of surprise, “your reputation exceeds you!”

These external perceptions of me create a dissonance between my own self image and how others view me. In my own mind I am not even close to the level of ‘guru’ that others perceive I have obtained.

I worked hard, and also got very lucky. I am smart, but do not feel that I have obtained the level of ‘master’ that some seem to have bestowed upon me. I feel like I am just getting started.

I strive to live up to the expectations of those I have worked with, and my wife and children. I need to become the person that everyone thinks I am by pushing harder, going faster, and going bigger.

Here I am.. feeling like I need to be doing something BIG — that I need to hit the next level, tackle bigger game, and prove that I have what it takes. The perceived external pressure has become an internal struggle. I need to measure up, to prove it to myself.

When I get in this mode, where I feel like I am not measuring up to the expectations others may have of me, and the expectations I have then placed on myself, I need to breathe and do a little reset.

The reframe that I am working through is really to remind myself of what I remind others of all the time.

I have a first world problem.

Right now I am struggling with issues that are really great problems to have. I have moved so far up Maslow’s hierarchy of needs that I am attempting to fine tune the process of self actualization and find where I fit in the world that allows me to be the best expression of myself.

For the last three decades, I have been doing pretty much what I want, when I want, and bending the world to fit the circumstances to be ideal for the life I want to live. I have never had a ‘job’ in my entire adult life, having started or fallen into the next thing in an endless string of discovering what I wanted to do next in real time.

I have been able to provide for my family in a way that has given us an upper middle class lifestyle — which to me is a crazy notion given that I was comfortable living out of a van.

My goal had always been to live an interesting and full life. I have definitely succeeded there. My life has been very interesting (to me at least), and is more full then I could have ever imagined it would be.

This demon of doubt, that I ‘should’ be doing more, be richer than I am, that I don’t measure up, that I am not good enough.. are all negative self talk that I think we all indulge in far too often.

How lucky I am to be in the position that I am in, to be worrying about how I can bring the most value to the most people, and to grow both my wealth and to do things that interest me and help me to grow.

I will continue to fight this battle. I believe that to some extent we are all fighting it. I will probably never be able to overcome the internal relentless drive that keeps pushing me forward, to continue running from the imaginary hyenas that are stalking me, ready to move in for the kill as soon as I stop running from them.

I will not to let this demon of self doubt win. I KNOW that the feeling of needing to keep moving is irrational. I also know that I feel it constantly and that I need to constantly center myself as to not let it rule me — and not let my own expectations of what I have NOT (yet) achieved take away from what I have done.

And with this affirmation, I will push off eating worms, at least for today.