Why Courage?

When I moved my blog to this URL, I went through each post and sorted them all into my current categories. And as I did so, I noticed that a lot of my pages are filed under Personal Development, and most of those are filed under Courage. What gives? Why is personal development even on a website about money anyway?

The short answer is that the test market wanted it. I started this blog because I had met actual people who had questions about monetizing their skills and talents and experience, and so my posts have been answering their questions, or explaining things they didn’t understand. And a lot of that was not about the differences between LLCs and S-corps, or the selection of a logo, but about more fundamental, fuzzy things. Like organization, frugality… and courage.

In my personal, limited experience, very few people fail in business because they don’t have the technical skill or the ability to research business entities. They fail because they ask the wrong questions. They fail because they don’t bother to look up the answers. They fail because they let their brother-in-law talk them out of it.

Most people end up in an uninspiring dead-end job that they hate because they don’t have the courage to change it.

Courage in Self-Monetization

Courage to Be Different

The fact is, most of our world, and all of Western society, is oriented on employment. If you ask someone how to get more money, they will tell you to get a higher-paying job. If you ask someone what you should do out of college, they’ll tell you to get a job. If you don’t ask what you should do out of college, they’ll still tell you to get a job (I’ve been going through this a lot).

And to buck that trend takes courage. To tell your mom that you’re not going to get a job. To tell new acquaintances that you don’t have a job. To have to explain, for the 200th time, that it’s OK, you don’t need condolences, you like being unemployed. You have to have the courage to be different.

The Courage To Try Something New

There are lots of things that are comfortable and familiar to you: writing 2-page essays with 12-point font and 1/2″ margins, tuning into your favorite TV show, going shopping, cleaning the house. And given the option, you’d rather do something that’s comfortable and familiar than something that’s new and scary. But all of the non-job monetization options are new and scary, by definition (anything new is automatically scary).

It’s easier to fall back into your routines. But if you’re going to monetize yourself without working 40 hours a week, you have to have the courage to try something new.

The Courage To Take A Risk

Employment is a world of known outcomes: you go to work in the morning, you get to leave at night and take home a paycheck each Friday. That’s the deal, and it’s your employer’s job to make it happen. OK, from time to time there may be BIG moments of uncertainty, where you get downsized or you change departments or whatever, but basically your day-to-day routine involves no risks at all.

Everything else, not so much. When you wake up on January 1st, you don’t know how much money you’ll make this year. When you start a month, you don’t know where your rent money will come from. Depending on the business you’re in, you may wake up in the morning not knowing if you’ll have any work today.

And you have to try things without knowing what will happen. An ad writer who’s an employee knows that they’ll get paid their daily salary regardless of how successful the ad is. A small businessperson has to launch an ad into the world with no idea whether it will be successful or not. A restaurant owner has to start the business without knowing — for sure — whether they’ll get enough customers to stay open. An investor has to buy the apartment building without knowing whether the economy will take off or tank.

There are no certainties in an entrepreneurial lifestyle, whether you’re an occasional freelancer or a multi-million-dollar stock trader. Your day-to-day life is full of unknown outcomes. You have to have the courage to take a risk.

The Courage To Take Responsibility

An employee can always blame someone else.

    “I’m sorry; it’s company policy”
    “My boss told me I had to do it this way”
    “The board made that decision; I have to carry it out.”

An entrepreneur can’t. It’s all you. You made the decision to run that ad. You made the decision to carry that product. You made the decision to deny that refund. It means you get credit for the good stuff… but you have to have the courage to take responsibility, however it turns out.

The Courage To Fail

I don’t like failing. You don’t like failing. No one says to themselves, “Gee, I’ve got a whole day off! I think I’ll go seriously suck at something.” It’s not fun. And that’s a good thing: hating to fail is what makes you try to succeed.

But, I’m sorry, you are going to “fail” at least some of the time. Learning to be an entrepreneur is just like learning any other skill: you missed the goal a bunch when you were learning to play soccer, you wrote a lot of illegible stuff before you figured out how to write, and you’ll have trouble selecting products, naming the company, developing a brand, and writing a business plan, as you learn how to monetize yourself. It’s just the way it goes. If you’re so afraid of failure that you won’t give it a try, you won’t get anywhere in this project. You have to have the courage to fail.

You Have to Have Courage

If you have all of the above characteristics, you don’t need me to teach you how to do business taxes; you’ll do the research and figure it out for yourself. If you don’t have the above characteristics, there’s no amount of education I can give you that will let you succeed.

In the end, it comes down to you.

Resources For Further Reading
The Invisible Mallet
This Ain’t Middle School
Risk Analysis