The American Dream Is An Entrepreneurs Nightmare: When More Creates Less

The American Dream can actually rob you of the things that matter in the end.

The American Dream can actually rob you of the things that matter in the end.


I talk often about “winning”. In fact, I have a whole concept called Win Then Play. And when I say win or winning, it isn’t the typical definition of success as defined by society. It’s about you being the author of your own story, life and goals that lead to lasting happiness rather than temporary acknowledgement at all expense.

Entrepreneurs are great at achieving goals, completing objectives, but not as great at appreciating the journey, celebrating and acknowledging the wins or creating a life outside of their business. All of the awards, recognition and profit can be ambiguous definition of success.  Society isn’t great at promoting the value of hobbies, time away from the office, recreation, relaxation or even rejuvenation isn’t part of the equation I was ever taught.

This means it is critical for you to define exactly what your win is. What does success look like and mean to you? The American Dream and everything we’ve been trained, taught and educated may not be what brings you lasting happiness, and can actually rob you of experiences, memories, and the things that matter in the end.

Everyone has a different vision, and in turn the spirit of their goals differ also. When you define exactly what you would do if money were of no concern, as if you had an unlimited checking account, you can gain new insight on building the life you love. Most people reserve the items on this list for one day, someday in the future, and call this retirement.

Defining your win requires that you let go of some myths and beliefs that are rampant in the entrepreneurial community. If any of these apply to you, and you don’t let these go, that vision of yours is unlikely to be clear and therefore will be impossible to bring to fruition.

The “Do It Yourself” Myth

There is a popular myth that if you want something done right, you have to do it yourself. The problem with this way of thinking is you can’t be two places at once. As your business grows there will be not only more product and service labor required, but the managerial duties will scale alongside your company’s growth. Do you always have to be the one that has the final say, last look, or to check on something so you can make sure it was done the way you would have done it? If so, that will never allow you to truly grow and freedom will be elusive.

Often when dreamers become entrepreneurs, it begins with hustle and requires being in the trenches with their work. This is where they lose the dreamer part of what made them start in the first place. Time goes by and all they end up with is the work, while the “win” they dreamed of long ago is just as far off- sometimes farther.

I want to cover a few principles to create the space to achieve your win…

The 5 Things You Love In Business

You want to free yourself up from the things that are NOT what you have defined as your “win”. I suggest looking at 5 things that you want to do- that only you can do– and that you get energy from. For me, that’s speaking, writing, creating programs, filming videos, and working on my vision. Those are my 5 things.

What I don’t want to do is operations, sales, management, and coaching one-on-one. None of those things are winning for me. There are other people who can do those things just as competently and effectively as I can.

Determine what you’re doing right now that you’re going to stop doing, so you can start doing more of the things that embody who you are when you’re at your very best.

Roles Vs. Tasks

Once you define the 5 things you love doing that align with your vision, it is time to delegate.

To properly delegate it requires hiring the best, often more expensive employees. If you hire cheap, you will end up worrying if things are getting done, having to redo things that weren’t done right, and spending more time in management rather than your top 5.

The key is to permanently delegate. If you delegate something to an employee and when it is complete they come back and say “What’s next?”- that’s not delegation. It’s task management. It’s micromanagement. True delegation is when you pass off a job that has to be done, and then effectively say to that person, “You are going to own this. This is your project. I’m counting on you. And if you require anything, let me know so I can support you, rather than manage you.”

Have them own the role and choose what tasks fulfill that role.

Win And Profit Through Purpose

Let’s use the counsel any financial advisor or CFO will give you with your numbers. You are taught to look at P&L regularly, check your pricing or margins, and pay attention to your savings and investments.

Forget your budget.

Simply pay yourself first and spend the time to create clarity and laser focus on your purpose. Course correct, expand and update your win when necessary.

If you’re going to grow your happiness and wealth, it will be in the focus on your purpose first and this will in turn increase your profit. If you put profit in proper context, as something that follows your purpose, you’ll be in charge of your win.

Big Vision Equals Big Results

The rarest commodity in the world is vision. A vision is something that inspires you and may even elicit some fear. The fear of not knowing how to achieve it is where the vision has value. It allows you to collaborate and hire. Think beyond your current financial capability or ability because the vision that matters to you is where you’ll find your greatest win- something worthy of your time and life.

The game worth winning comes from constantly looking at how to grow your purpose, and then how to monetize it. If you think about your money first, and your purpose second, you’ll consistently be limiting your abilities. If you look at what you have the ability to achieve today, you will limit the context of what you are capable of over your lifetime. If you worry about what others will think, you are giving people too much credit. They typically are busy thinking of themselves.

When you create a vision bigger than any of your problems, you’ll always find a way to solve it. You’ll inspire others to rally and support what you are up to. A vision worthy of your life, defined by you, is a win.


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