I think it is no secret that I desire to be an entrepreneur. For all I know I may already be one, but I'll save that question for another time. The difficulty I have run into, as countless other would be entrepreneurs have, is what should I do?

I am at an impasse that requires a decision to be made. To go out on my own I need to generate income. To generate income I need to create something of value to other people. I need to create something. What should I create?

This question reminded me of something I wrote In a previous post, Red to Green. The article speaks to the necessity of action in obtaining desires. However, near the end of it I wrote this:

Instead of worrying about failure and what type of action to take, just pick something in the general direction and go with it.

This begs the questions, how do stop worrying about failure and just pick something? These important questions need to be addressed.

Where Do You Want to Eat?

Making decisions is hard. There is a paralyzing amount of fear and anxiety that comes with it that is difficult to overcome. The fear of being wrong is so powerful that we often avoid making a decision at any cost.

This reality plays out every time my wife and I are faced with the question of where we want to go to eat. If I was alone then I may weigh a few options and ultimately pick something that sounds the most appealing. Alone this is trivial, but add another person to the equation and it becomes terribly difficult. They may say they'll be fine with whatever you pick, but what if the experience ends up being terrible for them? What if your selection is wrong and the whole dining experience is terrible? This fear adds considerable weight to an otherwise simple decision and makes it hard.

A strategy my wife and I use in this situation is to share in the decision. I request that she provides me with 2 or 3 restaurants she would be fine with, and then I make the ultimate decision from the list. This provides me with an out because I can always rationalize a poor experience away knowing it was one of the restaurants she suggested. The fear of failing her on my restaurant choice is mitigated and the decision becomes trivial once again.

Decision Making Systems

The key takeaway from this story is that decision-making requires a system. The strategy we use to help select a restaurant is a system that works pretty well.

Other decisions I make day-to-day rely on systems as well. Despite being sick with a sore throat as I write this, the decision to write it was made simple because of the quota system I created that requires me to write 3 blog posts per week. Without this system I may have agonized for hours about filling my commitment to blogging 3 times a week or taking an off week because I just don't feel up to it.

Unfortunately, I have not devised a proper system for making the big one-time decisions that are preventing me from fulfilling my desire to be an entrepreneur, that is, until today.

My 5 Directions

To make money I need a product. Given my skill set and interest I devised a list of 5 directions I could take for product creation. These are things I have, at one time or another, started working on and never finished. My list is as follows:

  • Write books
  • Create apps
  • Create games
  • Create a SAAS product
  • Create training videos

These are fairly broad directions I may take, but I've started on and abandoned completing things on each one of these tracks. Coming up with this list was the easy part.

Each one of these directions has income potential. What makes choosing one difficult is the fear of being wrong. What if I write books and they fail? What if nobody downloads my apps or games? What if I invest time in a SAAS product nobody wants? What if I look like an idiot in my training videos? The problem is that no one of these ideas stands out as the clear path to take. There are equally potential risk and reward with each of them. How do I decide? What should I do?

The Chesire Cat

I don't care if it is apps, books, games, training videos, or SAAS products that results in income generation. I just want to get somewhere other than where I am currently (which is nowhere). This reminds me of this passage from Alice and Wonderland:

“Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” said the Cat.
“I don’t much care where–” said Alice.
“Then it doesn’t matter which way you go,” said the Cat.
“–so long as I get SOMEWHERE,” Alice added as an explanation.
“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”

I have before me 5 directions, with no particular desire other than to create something of value. The answer to my dilemma starts with the realization that it absolutely doesn't matter which direction I go... I only need to commit to a direction and "walk long enough."

With the knowledge that direction does not matter, any direction I choose will take me somewhere, the decision seems much more trivial. However, lest I starve like Buridan's ass a decision must still be made.

Embracing Randomness

The I recently started listening to the book Antifragile by Nassim Nicholas Taleb. I find this book fascinating, particularly when he discusses the beauty of randomness. What is quite peculiar about life is that this book came into my life at the exact moment I needed an answer on how to decide between a number of equally compelling and risky directions. The answer I found, the system, is to embrace randomness and use it to pick my direction.

So that is what I did. Today I wrote these 5 directions on sticky notes. I folded them into squares and dropped them in a hat. I had my daughter pick one out of the hat. I threw out the remaining pieces of paper and revealed my fate.

I will Create Apps.

This is the direction I am going to take. I will strike from my mind that books, games, SAAS products, and training videos are paths I might otherwise take. That is not to say I must be blind if opportunity arises, but to get started this is the direction I must take.

The System

Distilling everything down into a simple set of steps to follow, this system can be summarized as follows:

  1. Create a list of all the directions you could go to obtain some desire.
  2. Remove items that are clearly inferior until the decision as to what to remove become difficult.
  3. Assuming more than one direction remains, use randomness to make the decision for you.

Realize that if you want to get somewhere, anywhere, but the direction to go is not obvious then it doesn't matter which direction you go, but choosing, even if by random, is the only way to ensure you'll get somewhere.