“I wish I got a real job when I was young instead of following these delusional plans to work for myself.”

This is what an older dude said to me. This gentleman is likely in his 50s and he hates his job/likely his life. He’s not the happiest person. Actually, he’s pretty miserable most of the time. I just don’t entertain the negative conversations because we all know that misery loves company.

However, this time around, he got me thinking. He said something that made sense. We all like to glorify those that followed their passions. We all put entrepreneurs on this pedestal. We cheer them on for being so bold and so courageous. We write books about them. This all happens… when they succeed!

What about the dark side of trying to work for yourself when you’re young?

There are many negatives to following your passions. It’s not all glamorous. You don’t go for drinks every night and tip with hundreds. You don’t make thousands of dollars while you lounge around the beach. You likely work harder than those that have a job. You can’t leave your work at work. You can’t forget about things. You’re responsible for everything.

I was trying to explain this to a student of my newest course of dominating life in your 20s. You don’t have to start a business. It’s okay to move up the corporate ladder or to work a part-time gig while you try your hand at other ideas. It’s okay to do whatever you want. You don’t have to listen to your family and those around you.

What if I really don’t want a steady job?

Maybe, you’re just in the wrong field or the wrong company. That could be causing trouble. Not the actual idea of going to work everyday.

You also may think that you want to work from home, but what happens when your family thinks that being self-employed means that you’re there to do things for them all day? What happens when you discover that you can’t focus at home or without a boss breathing down your neck? These are all harsh realities.

I’ve seen friends first-hand claim that they’re going to be self-employed and then nothing happens. They just can’t launch. They do nothing. Time passes them by and they keep on delaying that launch. This happens to the best of us.

This is a guaranteed ticket to permanent misery. Not being able to do what you want just because you can’t put it all together.

This then begs an important question…

Do you want to get rich or build an ideal lifestyle?

I personally am a huge proponent of lifestyle. I enjoy going out. I also like having money in the bank. I want to travel. I also don’t want to go broke.

For me, the goal is to build the ideal lifestyle today without comprising tomorrow.

There will always be the negative aspect to trying to get rich as well. The problem with focusing all of your energy on profits is that you might end up doing something you don’t like, be miserable, miss out on amazing connections, and never really get there.

Then there’s the other side to working for yourself. There’s also that something that keeps me up at night.

What is this? The thought of regret for what you didn’t do.

I don’t want to have any regrets. I really feel that I would rather be able to say that I tried than to wonder about what could’ve been. The aforementioned gentleman isn’t too happy with how things turned out.

Maybe he didn’t try hard enough? Maybe he was close to achieving his goals when he quit? Maybe, just maybe, he might be right?

The truth is that you can load up on motivational quotes and buy every eBook on the Internet, but none of it matters until you execute something. Execution is also pointless until you see some results and make some moves on those results.

How do you become miserable forever?

It might happen when you spend your youth chasing dreams. It might also happen when you do NOT spend your youth trying to work for yourself.

This post was intentionally all over the place. I just wanted to throw all of my thoughts out into one post. I don’t want anyone reading this to be miserable today or 20 years from now. I would love to hear from you guys.

Are you afraid of quitting your current job? Are you tempted to become self-employed, but just don’t know if you have what it takes?

"Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose." — Steve Jobs