8 Reasons Why Self Employment Sucks

I have been completely unemployed since sophomore year of college in 2012. The last “job” I worked was pushing shopping carts at Target and got my break after building affiliate websites between and after classes. This allowed me to go from wondering if I should go to Law School to pursuing my own projects after school.

After working for myself for several years I would like to share a few thoughts that have passed through my head of why self employment sucks (sometimes!).

Unrelenting Stress

The stress simply never stops.

For some, it may start out as a stress that starts building up that you need to be successful. You work on your projects, you stress about how they will work, and then some day, something FINALLY works. Your project becomes a reality and all of a sudden you finally have an internet business that allows you to work where you want, when you want.

Everything should be great…


Once you finally get your business growing, have plenty of customers, and everything is running like it should, stress actually increases. You now have new, higher targets. You are making more money, but you also have more problems (yes, the song was right!). You have more fires to put out each day, more headaches, and more people to deal with.

The stress never really ends, all you can do is learn to live with it.

“Must Be Nice”

Everyone has this idea that you live in a fantasy world and that whenever you want, you can make your own schedule and simply skip out on work.

Yes, while it is try you CAN make your own schedule, there are just so many things that are constantly weighing on your mind and that are piling up on the list of what you “should be doing”.

If you work for yourself, you will probably hear the lines “it must be nice…” over and over again. Little do they know it is NOT so nice at the time, and is actually a ton of stress and headache that you simple cannot get rid of.

Can’t Escape (always thinking about business)

It does not really matter what you are doing, but you are somehow, somewhere in the back of your brain, thinking about your business.

Not too long ago I was at a ski resort with my girlfriends parents, learning how to ski for the first time, having a blast.

I should not have had a care in the world. However, at the back of my mind I was wondering about that new update we just pushed to the software. Is that what customers really want? What if we would have shipped the update in a different fashion? Maybe I could have done more before we left for the mountains in order to promote the new update?

These thoughts will not leave your mind, you cannot escape them.

Even when I was mainly doing affiliate marketing, these were just constant thoughts I had. You will always want to do more and feel guilty you are not working on that goal.

Lack Of Social Interaction

How was your weekend? How many times inthe last year has someone asked you this one? I can tell you how many people have asked me, zero. A big fat zero.

This is not because I haven’t done some fun things on the weekend, but simply because there is just not anyone around to ask me how the weekend was.

During the few years I worked part time in College, I worked retail so I was constantly surrounded by people. In school people would invite you out to do things. Now, the only people I really communicate with outside of when my girlfriend gets home for work, is over Skype/Facebook and rarely over the phone.

I leave the house each day for a few hours to hit the gym, which has certainly helped my entrepreneurial endeavors, but you really do not get much social interaction if any as you are there to work on yourself.

This is partially my fault as the goal is to constantly build your business by 50-100% per year. This is a massive goal, and requires an absurd amount of attention. When you feel your back is constantly against the wall, there is no much else you can do but keep your head down and focus.

Get A Real Job/Not Understanding

When you first start your journey into online business and entrepreneurship, MOST people will probably not have a single clue of what you do for a living. They will see you at home, or in a coworking space and not have the slightest understanding of what you are trying to accomplish.

I got this for the first few years of my journey. I was building affiliate sites, and even when I was making a full time income, my close family still did not understand it.

It was not until one of my sites using blog network links got penalized (in 2012), that I told them I got an unnatural link penalty, that I started to really get some fun poked at me.

Even though my family never really understood what building affiliate sites meant, they remember that unnatural links. Even all these years later, I still hear about it!

No one will understand what you are trying to accomplish, and many people will ask you why you do what you do. Why do you not get a real job? It certainly pays better! (to start with).

Hearing this over and over again certainly gets old.


You are not going to be motivated to work half the time. Half the time, your tasks for the day are going to be boring and mundane and you just will NOT want to do them!

Being self employed sucks because you will run out of motivation incredible quickly. What you have to do is find dedication.

You must find some sort of routine, even if it is a bit chaotic. Find something that works for you and stick to it until it becomes habit.

For me, I get up around 5:00 – 5:30am and work till around 10-11. I will then go to the gym for a few hours, then come home and work until the significant other gets home for dinner.

If you do not have a routine, you will find yourself drifting off and NOT working on what you need to be doing. You may feel like you are working 100 hours a week, but without a routine, you are working a lot less than you think you are.

Self Employment Tax

If you are reading this and have ever been self employed, you know how much this one bites. I hate the self employment tax!

When you get a check in the mail, or someone pays you out, of a customer deposits money into your account, I get that feeling in my stomach knowing that I owe at least one third to the U.S. Government.

When you work for someone else, your taxes are taken from your paycheck and what you get in your account is what you get. When you work for yourself though, you quickly realize that you owe all of this tax AFTER the fact that you get paid.

You have to pay taxes on the money you get, and when you finally sit down to calculate what that may be, you are probably about to be shocked.

Everyone pays 6.2 percent towards Social Security, and 1.45 percent for medicate. When you work for yourself though, you owe DOUBLE that, because when you are an employee, you employer matches your half.

You owe more taxes simply because you decided to try and live life on your own terms. It is a hard pill to swallow, but it is reality.

No Set hours

When you have no set hours, things can get a bit jumbled up. When you have a 9-5, you know exactly when you are going to work.

When you are an entrepreneur, you will have to set yourself a schedule and make sure you stick with it.

Even though I will very often work 14-16 hours a day, there are some days where I will literally sit on my computer and do NOTHING but browse the web simply because I do not feel like working.

Even though these days happen, you will need to be well aware of them and make sure you snap out of it and get back to work!

Self Employment is ALL Worth It!

Even with all of these different draw backs, there is no other way I would have it. I love working for myself and simply cannot imagine getting up at a set time each day, driving in traffic to a job that that I did not want to go to, to work for a boss to build his dream and not mine.

All of the stress and issues that come with entrepreneurship also bring the freedom to pick and choose what I work on, and exactly how everything gets done.

Even though this is a hard way to make a living, I am a massive fan of building online businesses. It allows you to make money anywhere in the world, and on your own time.

YES you will need to spend a lot of it, and YES you will need to be dedicated, but it is 100% better than the alternative of working for someone else and building out someone else’s project.

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