When I was younger I had a goal to make $1 million dollars by the age of 25. I’m sorry younger self, but today that dream was not realized. This type of thinking is all too typical of the Entrepreneur’s dilemma. You think big, dream big, but eventually fail. Why? There are too many reasons to discuss in this post, but I can reflect on a few lessons I have learned along the way.

Even though I did not meet my financial goal, striving towards it proved to be much more fruitful:

1. It enabled me to discover what I love to do
2. I learned to Dream Big, but Plan Bigger
3. I realized Money is not the Goal

What I love to do

For a long time I thought I was going to be on Wall Street. I’m a numbers guy, and the allure of making it big as a trader was very tangible for a long time. When I was in school, I took an elective course for my Finance major that completely changed my outlook on business, Internet Business Applications.

I had always been fascinated by code, but like many others did not know where to start. Thankfully within the construct of a classroom, I had projects that exposed me to a variety of platforms such as Joomla, WordPress, Adwords/Adsense, Filezilla, and many others. After that class forced me to start thinking digitally, I began to build and tinker websites for my own personal projects. Many of them were terrible, but I learned by trying and after a short time I later founded my first business, a web development company. Learning to code became a passion of mine and has enabled me on a career path that I love.

The takeaway for me was even though I dreamed initially of hitting my $1 million goal on Wall Street, I realized my passion along the way and took the opportunity when it arose.

Dream Big but Plan Bigger

A lot of Entrepreneurs focus on the big exit, either through an Acquisition or IPO. There is nothing wrong with being an optimist – I’m definitely one of them – but many fail in the pursuit of this dream. Roughly only 18% of 1st time Entrepreneurs are successful. That is an incredibly low number. I personally believe its because in the pursuit of that dream, we are blinded by our optimism and fail to look objectively at ourselves and our businesses.

My colleague Mathew Sweezey has a great exercise/metaphor for this problem. Draw two dots equal distant (about 3 inches) from each other on a blank sheet of paper, Dot A and Dot B. Dot A is representative of where you are today, Dot B is where you want to be. Put your pen/pencil on dot A, close your eyes, and try to draw a line to Dot B. If you were able to hit dot B, congratulations you were one of a select few. I was not one of them.

Now instead of closing your eyes the entire time, open them four times while trying to draw from Dot A to B.

This is much easier isn’t it?

The purpose of the exercise is to demonstrate that planning and iterating on ideas will give you a much higher chance of success in striving toward your goals. The problem I had with my $1 million goal is that I failed to set milestones or plan on how I would actually go about achieving it. I simply relied on the belief in my self drive and eagerness for success, and that it would naturally come.

Self belief is definitely important, but this type of thinking is flawed. Plan as much as you can, and adapt when necessary. Sometimes that means killing an idea to give rise to the next.

Money is Not the Goal

My outlook on business is to always try to find the Win-Win situation. One of the most rewarding things about having a service business, is that I can help others achieve their business goals. This blog exists mainly for that purpose.

One individual that helped me define this mentality was Tim Ferriss. If you have never read Tim Ferriss’s books or blog buckle up, because he is a writer who gives great actionable advice. His book the The 4-Hour Workweek, is a great resource to learn about productivity and bettering yourself rather then just making money.

In it he has a concept known as the New Rich:

The New Rich (NR) are those who abandon the deferred-life plan and create luxury lifestyles in the present using the currency of the New Rich: time and mobility.

Instead of focusing on a fixed $ amount as my goal, I should have focused on my desired outcomes: Owning my Own Business, the Ability to Travel, More Time with Family/Friends/Dog. Then planned backwards on how to achieve those goals. Having a lot of money in the bank is no guarantee these will become true, but thinking objectively and taking action will.

With most aspects of life hindsight is 20/20. You think back and realize how silly, great, or poor your decision making was at that time. My thinking of achieving $1 million dollars by 25 is laughable to me now, but made me realize what truly matters to me in my career.