7 Reasons It Sucks To Work For Yourself

Scott Kalwei
8 min readApr 26, 2017

Listen, I love working for myself. I really wouldn’t change it for the world. But it’s not all rainbows and unicorns all the time. Allot of the time it can really suck. I get tired of reading all of these articles about how awesome it is to be an entrepreneur working for yourself. Yeah everybody has an asshole boss at some point in their life. Nobody likes to get bossed around all the time. Well I’m here to bust your bubble, sometimes the grass isn’t as green as it looks on the other side. Here’s some good examples why:

Accountability

You know you get pissed off when you have a boss breathing down your neck to get something done on time. It’ll be some stupid report that no one is going to read, yet your boss will email you 15 times to make sure your doing it. Seriously dude? It’s like bosses have too much time on their hands so they just fill the void with annoying the living shit out of people.

Well I’m sorry to bring you down, but you’re probably a really lazy person. No I don’t actually know you, but in general people are really lazy. I’m not saying that that’s necessarily a bad thing so don’t go getting all offended about it. I still remember my engineering professor telling us in his old timely voice, “Laziness is the mother of invention.” Everyone knew that the real quote was about necessity but as engineers we agreed with the slight modification to fit our context, aka laziness.

The only reason I bring up the laziness is because you have to be highly motivated to work for yourself. Having that annoying boss might bug the hell out of you but they are making you get your work done in time. There’s something to say about that! What do you do when you have free time? Watch television? Kiss your free time away if you work for yourself. You better be working or networking and you better be doing it without anyone there telling you to do it.

Time Management

I wake up at 5am every single day. Why? Because after trying all kinds of different “life hacks” and waking up at different times, I’ve come to the conclusion that I’m the most efficient when I wake up at exactly 5am. I don’t wake up that early just because I want to. I don’t wake up that early because I need to be to work. I wake up that early because I’ve told myself that it’s important, so that I can better myself.

Have you ever woke up early just so you can make oatmeal and go for a jog before reading a book at the coffee shop before going into work? Have you ever went into work when you didn’t have to? I wake up every day with nothing on my schedule that I absolutely have to do. Yeah, there’s usually stuff that I SHOULD do but never anything that I have to.

That means I have to fill out my entire day, everyday! That probably sounds like it would be awesome, but if you’re trying to improve yourself and your business every single day for years on end, then you can see how at times it can be difficult. That’s a whole lot of time to fill! If you don’t stay on task you can quickly fall into the quicksand of stupid cat videos and meme hunting. You don’t have reports, bosses, deadlines, or any of that to keep you focused. Staying disciplined when managing your time is a never ending battle!

Being Lost

Ever go to your boss with a question about how to do something? Maybe you’re just feeling a little lost and need some direction, what do you do? You go to your boss. This is such an overlooked responsibility of the boss that people tend to overlook it. People can explain in great detail everything their boss has done wrong over the years. But to be fair there were probably allot of things that they did for you that you never took notice of!

Having a superior above you that can help to guide you in the right direction can be a godsend at times. But if you’re lost and you don’t have a boss you can be in real trouble. I think this is probably the reason that entrepreneurs work so much more than those with normal careers. Because we don’t have anyone that we report to that can help to guide us, we have to work twice as hard to figure it out.

Just about every entrepreneur I know has a rolodex of contacts that they would consider to be mentors to them. If you work for yourself and you run into a problem you start with Google and then you go to your rolodex of contacts. But allot of times what you have questions about is so specific to your particular situation that no one really knows how to help you. So you’ll be out on your own with no guidance. Figure it out!

Noone to blame

At my last corporate gig they had turned passing blame into a freaking art form. I’d never seen anything like it. Grown men out on the manufacturing floor acting like a bunch of children in front of their angry parents. Everyone had an excuse and a scapegoat. Anything to keep them out of trouble. Allot of times they even believed the crap that they were selling to upper management.

Well guess what, that shit don’t fly with entrepreneurs. You can pass the blame to someone else if you like but at the end of the day it’ll only affect your pocket book. So you can live your life in denial, always blaming other people for your problems, but you’ll end up broke while bragging about how awesome you are. Nobody wants to be that person, bragging incessantly when it’s abundantly obvious that they’ve screwed up just as much if not more so than you have. Don’t be that person!

It’s easy to look at braggadocious idiots and laugh about how out of touch they are. But think about it, have you ever bitched about a co-worker not doing their job? Someone else screwing something up and making your life more difficult? I always hear this from people working 9–5’s. That’s the same thing! You’re blaming other people any time you sit and bitch about what they do at work. Working for yourself, people don’t care who screwed up your product/service, it’s ultimately your fault and you have to fix it. No one is going to do it for you and blaming others won’t help the situation.

Inspiration

I can’t convey in words how important I think inspiration is. I attribute everything I have in my life to different inspirational moments I’ve had along the way. I thrive off of having big goals, I live with my head in the clouds, and I find most of the joy in my life comes from figuring out how to achieve those goals. I’ll have a spark of an idea from the most obscure situations, leading me to want to change some major part of my life.

For me, working for myself actually helps me find those inspirational moments. I’m a wanderer and explorer though. I crave new experiences and constantly go out of my way to find them. I can’t say that that’s true for most people. From my experiences, most people don’t want to go outside of their bubbles to really explore foreign ideas.

If you’re an entrepreneur you make a living by seeing the world in a different light. You’ll constantly be looking for inspiration. This honestly takes away some of the fun of those wandering moments. You aren’t living in the moment and letting life come to you. Your actively seeking inspiration instead of letting it come to you which adds an element to the equation that can really screw it up. So as you search for more inspiration it becomes harder and harder to find. Can be a blessing or it can become a curse depending on your personality.

Lonely

Working for a big company gives you a built in social structure from which you can build relationships. Working for yourself isn’t like that at all. Making friends and being around people is no longer a passive activity. You have to actively go out and seek new friends and relationships in the form of “networking”.

Networking can be extremely fun but allot of times it becomes a part of the job that you have to force yourself to do. So making friends and building relationships isn’t something that you just have built into your job. The fact that it goes from something that is passive and fun to something that is active and a chore, makes it hard to keep your networking game strong.

While your hammering away on your computer for hours away in a lonely frenzy you can sit back and be assured that your friends our out there having a great time without you. Then when you have free time you’ll have to go to a networking event where you rub shoulders with a bunch of old men in stuffy suits. So although it’s possible to have a great social life, you will definitely have to work allot harder to maintain it.

More Bosses

Everybody I talk to thinks it so awesome that I don’t have a boss. They’d just love to not have a boss breathing down their neck all the time! Technically they’re right, as an entrepreneur you don’t have a boss. But, every single customer that you want to have becomes your boss and they will be way less understanding than your boss.

Not only will they be less understanding, but they can destroy your livelihood. So you better treat them right! You’ll have to deal with all types of people too. So don’t expect to always be dealing with smart reasonable people. You will get the worst of the worst wanting to just tear you apart.

These people will write bad reviews, demand their money back, call BBB, file lawsuits, and steal from you to try and make their point. I just recently had an employee that I had to let go for poor performance write atleast 10 bad reviews about my business on different websites. So ya you trade one boss, who probably worked their way into that position, for a bunch of random crazy people that would love to ruin your life.

FINALLY

Now that I got all of that off my chest, I gotta say that I still love working for myself. I just think it’s important to see the good with the bad. I wouldn’t change my lifestyle for anything in the world. But I don’t think it’s for everyone.

So if you’re considering going out on your own. Take a look at this list and ask yourself if you can handle all that. Because, although this is a fairly negative article, the real world can be a very harsh place and this list isn’t all inclusive. So you gotta be tough and you’ve got to be prepared for what you’re getting into! If you can jump those hurdles you’ll be that much better for it.

Originally published at ScottKalwei.

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