Chapter 2: Dreamers vs Realists

The dreamer in me has come up with a million business ideas over the past year and the realist in me has shot them all down.

It’s easy to feel like these are opposing forces but I actually think they’re conspiring together to ensure I never accomplish anything. Think about it: both of these attitudes have the same effect. The realist is most comfortable if I never take a risk and the dreamer is constantly jumping from one idea to the next, never willing to commit to anything.

The root of the problem isn’t realism vs dreaming, but fear of failure.

You miss 100% of the shots you don’t take.

— Wayne Gretzky

Despite hearing this line so many times in my life, I've realized there's a lot to unpack here. When you take a shot, not only do have a chance of scoring, you also:

• Develop the skill of taking shots

• Exercise the mental muscle of failing and moving on

I recently heard Daniel Priestly say something to the effect that the early stages of entrepreneurship should consist of 90 day experiments where you commit to an idea for 90 days before moving on to the next. I like this model because its the practical application of Wayne Gretzky’s quote.

Its so easy to want to wait around for the perfect idea, but if I never act, I’ll:

• Never have the chance to score

• Never develop my skills at starting and finishing a project

• Never overcome my fear of failure

Notice that this isn’t a dreamer mentality. It’s easy to lump the Wayne Gretzky quote in with other cheesy lines like ‘follow your dreams’, but this one is extremely practical. Taking a shot in hockey is relatively low risk, and if a team has a lot of shots on net, it's typically a sign that the team is playing well.

So if I can set up my 90 day experiments to be low risk (time and money wise) then the practical next step is to start taking as many shots on net as possible. This is the dreamer and realist working for me instead of against me. The dreamer will find new experiments to try and the realist will ensure that I stop after 90 days. This way I can recover quickly, learn from my failures, and hopefully avoid making terrible financial decisions.

 In each chapter I give one concrete step that I’ve taken so you can follow along.

Concrete step #2: Try your easiest and cheapest business idea for 90 days

Make a list of all your business ideas, choose the easiest one, and commit to it for 90 days. If you succeed, you learn a ton and have a bit more money. If you fail, you will learn even more, and pay very little for your education.

For example, on February 18th I made a list of all the app ideas I’ve had in the past year, chose the easiest one, and now I’m working on a simple budgeting app until the end of May.

Why a budgeting app?

My reasoning:

1. I’m super passionate about personal finance → I’ll have fun making it

2. The app is based on the method my wife and I use to manage our finances → it will be useful to at least 2 people

3. As a full time app developer, it will be easy enough for me to complete → I’ll gain a ton of confidence from simply knowing that I can build and release something to the world

DISCLAIMER:

I've never done this before and I'm learning as I go. Be cautious because I will make mistakes, but also be inspired because if I can start a business, so can you.