Most people have at least one of the following dreams:

1. Travel the world

2. Become their own boss

3. Threesome with two attractive chicks

Unfortunately, even though I may seem like a ladies man, I cannot help you with number 3. You’re on your own with that one. I will suggest alcohol, and lots of it.

Instead, we’re going to talk about becoming an entrepreneur. But, like I usually do, I’m going to put a little twist on it. That’ll come in a little bit. Oh, I’m such a tease.

(Looks back up at the title) Oh, you already know?

Who hasn’t had the dream? You’re at work, minding your own business, just doing your job, when your boss bursts in. Somebody has pissed in his Corn Flakes this morning, so he’s mad. You’ve been working hard on the ninja report, but it just isn’t done yet. He wants it, so you give him the bad news. Since he’s so angry, he tears a strip off you, leaving you practically in tears because you’re sensitive, dammit.

Screw this you say to yourself. I don’t need this. If I went out on my own, I could charge more, and not have to put up with the whims of my boss. This would be the greatest thing ever. So, right after you finish the ninja report, you allow yourself a few minutes to dream. Just don’t go acting on this dream just yet, because it might just turn into a NIGHTMARE.

Ooh, scary. You almost wet your pants there, didn’t you?

Regular readers will know I spent some time as a mortgage broker. Even though I worked under a brokerage, I was responsible for getting all my own business. As in, if I didn’t do some mortgages, I didn’t get paid. There were various things I did in an attempt to drum up business- an ad in the local paper, mailing out flyers, among others- but they weren’t ultimately very successful. The reason? They were too passive.

In any sales related field, the business goes to whoever is the most aggressive in asking for it. And there I was, in a sales position, as a guy who didn’t want to be that aggressive. I hate that proverbial used car salesman stereotype, and didn’t want myself coming anywhere close to it. So I intentionally became less aggressive. In that industry, you can imagine how badly I was shooting myself in the foot. After a couple very mediocre years, I was ready to throw up my hands and get a real job again.

The point of my story is simple. There are certain businesses that require a great deal of sales skills in order to get ahead. In the mortgage business, you’re always looking for the next deal. Even repeat customers will only darken your door every couple of years, since you can only buy houses so fast. Your knowledge of the business becomes almost secondary to your ability to generate leads. If you suck at doing that kind of work, maybe entrepreneurship isn’t for you.

And then there’s time management.

How often do you sit down with the intent of accomplishing something, and then realize an hour later you’ve pissed away the last 45 minutes watching cute kitty videos on Youtube? If you’ve never done this at least a few times you’re either not human or a liar. I’m just as guilty of it as the rest of you, except I watch stuff that doesn’t suck.

It’s human nature to avoid tasks we find unpleasant. Personally, I do the stuff I want to do the least first, getting it over with. Sometimes though, I’ll procrastinate because the job is just so unpleasant, like I do every year with my taxes. How many of you have stayed in a relationship you knew wasn’t going to work because the thought of breaking up with just so horrible?

As an entrepreneur, the buck doesn’t just stop with you, it also begins with you. That very freedom that you craved can be your worst enemy if you can’t just buckle down and get to work. Procrastination will kill any entrepreneur, including me. I would spend hours avoiding tasks I didn’t want to do, instead doing the most pointless of crap to avoid what was important.

You will have to work harder as an entrepreneur than you ever did as an employee. Sure, you have the freedom to do that work at 2am, or on a beach somewhere (depending on the nature of your business) but you still need to get off your ass and do it. If, like a lot of employees, your primary motivation is fear of your employer, I’m not liking your chances of going without a boss. Motivating yourself isn’t nearly as easy as you think it is.

This post isn’t to discourage any dreams you have of going out on your own. I’d still encourage anyone to start a side hustle. And even though fear can be a great motivator, I’d recommend against just up and quitting your job. Instead, wade into the ocean of entrepreneurship. Start freelancing. Spend a couple nights a week on some sort of sideline business. Instead of drinking too much on Friday night, spend it working on something that can grow into something bigger.

You’ll accomplish two things by approaching entrepreneurship this way. Firstly, as you gain traction and get busier, you’ll be forced to learn time management, because your time is limited by your day job. Secondly, you have a safety net just in case your new business isn’t the road to riches you first thought. You can pick yourself up and try something new without having to risk starving.

You might have the means to make it self employed. Or, more likely, you won’t. Instead of taking a huge risk to find this out, why not be cautious about it? Calculated risks are the best risks of all.

Tell everyone, yo!