How to Get to the Bottom of Why

It’s good to have goals. It’s even better to have the drive and ambition (and perseverance) to follow through on pursuing those goals. Goals can empower you with a sense of purpose, a sense of direction. You know where you want to go and it’s just the “simple” matter of figuring out how to get there.

“I want to move to California,” you might tell yourself. “I want to own a million dollar mansion,” you might say. (For context, a million dollars won’t get you very far in many parts of California.) “I want to quit my job and live the dot com lifestyle,” you might exclaim. These are all valid and they are perfectly reasonable goals that you can set for yourself… but they’re ultimately empty until you can answer the question of why.

Why do you want to move to California? Why do you want to own a mansion? Why do you want to quit your job and live the dot com lifestyle?

What is critically important here is that you need to dig a lot deeper than just a superficial response. What is it about the $2 million mansion in California that appeals to you? Is it the perceived lavish lifestyle that this would presumably entail? Why do you want to have that instead of a centrally-located penthouse in the heart of Manhattan? Why do you want that instead of a quaint cottage in the country? And why do you want to quit your job? If that’s the case, why are you working this job in the first place at all?

It is perfectly understandable that a lot of people, myself included, dream of the day that we can enjoy untold riches beyond our wildest dreams. But why? It may or may not surprise you to hear that the greatest power that money can wield is that, at some level, it can free you from worry about money at all. This is almost ironic, because it is the people who meticulously track their money — both income and expenses — who have the best shot at making more money.

If you want to make it in the world of business, online or offline, you need to have a firm grasp of your numbers. I think we can all agree on that. Passion alone is not enough.

Now, everyone’s situation and preferences are going to be different. Of course they are. That being said, when we drill all the way down the question of why, a few common themes typically emerge.

1. I don’t want to worry about money.

This is a nice hope to have, but the truth is that unless you become someone like Amazon CEO Jeff Bezos overnight, there will always be someone who is wealthier than you are. Until you can get past the point of envy and be happy with what you have, you will always worry about money, at least a little bit, because there is always something better, something more than you desire.

At the same time, it’s awfully freeing when you can sit down at a restaurant and actually order what you want without going through the mental math of how much the check is going to be at the end of the night. It’s awfully freeing when you can walk into the Apple store and walk out with the computer you actually want and not the one you can simply afford by maxing out your credit card. That’s freedom.

2. I want to be in control of my own career.

Even if you love your current supervisor or manager at your day job, you are still at the mercy of someone else. You are not the true captain of your ship. When you strike it out on your own, there are risks involved, but it means that you control your own destiny.

You choose what projects and opportunities you want to explore. You choose who you want to work with. You choose when and where you want to work. You’re the captain now. One of the single greatest components of happiness is the sense of perceived autonomy. That’s the ability to do what you want, when you want. That’s freedom.

3. I want to be free from obligation.

Perhaps this is the biggest and most profound answer to the question of why. The reason why most people work from 9 a.m. to 5 p.m., Monday to Friday, is because that is what is expected of them. What if you wake up Wednesday morning and you don’t want to go to work? What if you would rather work on Saturday? You can’t. Because business hours are what they are.

And you want to have that paycheck at the end of the week.

This is where our discussion comes full circle. When you get to the point where you are no longer doing something because you have to, but only because you want to, you are truly free. Anything that is done out of obligation, no matter how pleasurable at first, eventually becomes a chore when it’s something you have to do.

So why choose the dot com lifestyle? Because it’s a choice that is wholly your own and you can shift and pivot and adjust to keep things fresh and interesting (and profitable) for years to come.

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