10 Reasons You Should Never Quit Your Job

10 Reasons You Should Never Quit Your Job

Quitting your job and living a life of “total freedom” gets glamorized and glorified (I’m guilty of this).

But it’s not always what it’s cracked up to be.

There are a lot of things I wish someone would have told me before I quit my job. I would have been able to better prepare myself for the challenges ahead.

If you’re really passionate about being a rogue creator, by all means, go for it. It is most definitely worth it. But the path is not without trials and some things that absolutely suck.

So, these are 10 reasons you should not quit your job:

1. No one cares if you don’t show up, or don’t do your work.

When you’re in a cubicle, or on someone else’s time, there’s social pressure and accountability that comes along with it. We take this for granted when we’re an employee.

As soon as we start working for ourselves, we have to become self-motivated and personally accountable. Some days, it’s easy. Other days, anything seems more interesting than diving into your projects. You might be scared, it might be really difficult work, or you just might not want to do your bookkeeping. Whatever it is, it’s just a part of the package of not answering to anyone but yourself.

2. Working from home actually sucks.

First of all, no one thinks you actually work. Friends, family members and even your landlord think that you can just take time out of your day whenever you want and it’s no big deal. Actually, it is.

Not to mention, there’s a lot of distractions you have to constantly battle with. There are many times for me when cleaning the kitchen seems more interesting than editing a blog post (probably because I don’t want to deal with it being imperfect). The kitchen feels like something I can really control. And it has to be done, right?

Distractions can be the death of you working from home.

3. You never really clock out.

Your laptop is always there. And your smart phone. Just a few taps or clicks and you’re back in the social web, or back in your inbox. While this is becoming more true for some employees as well, it’s even worse when you’re working for yourself.

As an entrepreneur, you have to become ruthless about creating strong boundaries. No one is going to set them for you.

4. Too much freedom.

You can work on anything you want! What an amazing gift. Yes, I agree it is. But it’s a double-edged sword.

Sometimes you get paralyzed by the eternal number of choices you could make. Prioritization, planning and coworking must become your friends, lest you fall victim to paralysis by analysis and decision fatigue.

5. It’s really fucking lonely.

There are no water cooler breaks when you’re sitting alone on your couch trying to get your autoresponder sequence to work. No company picnics or holiday parties.

Of course, when you hire people, you can create these things. Or you can find other creative ways to get involved in your community. But still, it’s up to you. It’s not automatically included.

6. You have to pay yourself.

When you work for someone else, the money just magically appears in your account every two weeks. There is no magic being self-employed.

The first year after quitting my job, my income was up-and-down every month. There were some months I didn’t know if I was going to make my rent (luckily everything worked out). It was a roller-coaster of stress and anxiety.

While you do have more control over how much you make as an entrepreneur, you also have control over how much you make. If you don’t close deals, get new leads and clients, you’re S.O.L.

7. No one cares as much as you do.

You’re the boss. You’re the founder, CEO and owner. It’s your vision, your company, your mission. While you can hire amazing people that will make your life easier, they still will never care as much as you do.

Working for someone else, you have the luxury of not caring. You don’t get to just “check out” as a rogue. Caring, monitoring and nurturing is a 24/7 job.

8. No one tells you what to do.

There are many days I wish I could just show up and follow orders like a good little robot. It’s tiring making up everything all the time.

While I wouldn’t trade the freedom for the world, it does carry a lot of responsibility with it. I wish someone would have told me about this before I quit my job.

9. Taxes.

Taxes are really simply when you work for someone else. Just a W2 and TurboTax and you’re pretty much done in 30 minutes or less. Ah, those were the days!

Not as simple when you work for yourself. You either need to do your books, or hire someone else to do them for you. You have to keep track of receipts, expenses and 1099s. While there are a lot of things you can do to help make the process easier, let’s be honest: everyone hates doing taxes. And it’s much more complex working for yourself.

10. Doing everything yourself.

Freedom does not come cheaply. In the start up stages, you will wear pretty much every hat. If you don’t learn to become a master juggler, you probably won’t make it past the first year.

In time, you can hire other people to help you, and eventually you can even remove yourself from the operations of your business. But this is a slow process that requires years of effort. So if you just want to make art and not run a business, you might want to work for someone else.

Just be okay with them reaping all the rewards for your work. It’s the benefit of being responsible for making things profitable.

Anything I missed?

What’s one thing you think sucks about working for yourself?

Leave a comment below.

And pass this on if you think someone you know could benefit from it.

PS: A special thanks to everyone that answered my Facebook and Twitter posts on what they think sucks about working for yourself. You’re awesome!

Sharing is caring!

Leave a Reply

15 Comment threads
1 Thread replies
Most reacted comment
Hottest comment thread
14 Comment authors
David Briard5 Reasons You Should Quit Your JobVirgil ContosIan HoytMathias Recent comment authors
newest oldest most voted
Notify of
Kimberly Houston

When I read this post I had to smile, because I can tell you that as a freelance writer/copywriter, I have cycled through feeling all ten of these things intensely at one time or another. During some of the more challenging times, my mind wanders to how it would be so much easier to just show up at a job and do what you’re told, collect a paycheck at the end of the week, and have your free time at night and on weekends actually be “free time.” This is not something missing from the list here, but more like… Read more »

Cynthia Dagnal Myron

Wow. I’m sorry. I quit my job to write and…none of the above applies, I’m afraid. In fact, you could say that each of the things you listed turned out to be “plusses” for me. Even the fact that no one “cares” if I show up was empowering–I care. I care more than any of my bosses ever did, because I’m doing something I love. And because I love my work, the other nine things listed aren’t a problem for me, you see? I never get lonely, I love all the freedom…you get the gist. So, I have nothing to… Read more »

Charles Martel

That’s GREAT Cynthia!

Charles Martel

In my case, it’s not me who quit the job, but the job(s) that quit ME. :-) Mind you, I’ve always known that I’m not a job kind of person. Taking a job feels just like being sent to prison, except I don’t know for how long! :-) So I don’t really have a choice in the matter. I have to live with that as best as I can. :-)

John Chang

Hey Jonathan – I’ve been following your stuff for some time. It’s interesting timing that you wrote this now or I’m coming across this right now. At the moment I just got contacted by a recruiter for a $120k job. Who knows? Maybe nothing will come of it. On the one hand this is the income level I’ve been trying to achieve as a freelancer. On the other I feel like I’d be a sellout. It’s for project management work – which I really enjoy. Banking that kind of money now that I’ve become used to a lot less would… Read more »


I’m not yet self employed (very soon will be), but to be honest, if these are the worst things that will happen to me- I’m very happy to make that sacrifice!
Interesting post, though- thanks :)


Thank you so much for this post. Some people have a misconception of time and how it relates to freedom. My ultimate goal is to leave the corporate world one day but my priorities right now do not allow me to do that. I can’t wait till my time comes but I am working on stacking the deck in preparation for that day. If you are like me, it is troubling seeing those who work so hard for some company when they could be investing that time and effort in themselves. This is a great article and you can be… Read more »

Tracy Chapman
Tracy Chapman

I think you nailed it! All of these things are hard. I was going to comment that I think the thing that sucks the most is doing all of it alone. But all of these things are issues.


You nailed the cons of working for yourself, especial the taxes. I hate keeping track of everything for taxes. It’s all a trade off though. You can find something bad about anything. I love working for myself even though it is a struggle sometimes. No one cares about what I’m doing as much as I do, but boy do I care. I love finally caring about my work.


You absolutely are spot on with this list. I don’t work for myself full time yet, but I do work from home for a company based outside of the US and am also in the process of creating my own startup company. Almost all of these apply even working from home, especially the lonely part (I’m single and don’t have a roomate). One thing I would have really liked to see, and maybe you can post a followup article to this one, is your thoughts on overcoming each point. I’ve been working from home for 3 years and it’s taken… Read more »


Oh my god you’re so right, especially about people not thinking you actually work and all the distractions and cleaning the kitchen. It’s so hard. I’d definitely like help/a structure for this


Way to go pointing out some of our greatest fears! I do believe quite a lot of these depend on your personality though – most of them don’t matter if you’re a driven, confident person with a strong self-discipline.

To some, these reasons might seem like terrifying examples of why you must never quit your job, but to others they are just the opposite!

Ian Hoyt

You can easily let yourself go. Perhaps skip the shower in the morning or not workout. I find myself always wanting to get back to my computer so I end up eating less healthy food than I did when I was working the cube life.

But as shitty as it sounds, I wouldn’t trade it for the world.

Virgil Contos

I liked the attitude this post was written with. People who are looking to work from home often don’t realize how difficult it is to start. So if you are looking to start working from home please be aware that you will have to work until your fingers are sore. I’ve failed many times over the years and finally got motivated to get back at it. There’s no denying it, so many choices exist as a writer that it can be hard to narrow your focus down to just one thing. Good, basic stuff about the pluses and negatives of… Read more »


[…] will tell you that you should never, under any circumstances, quit your job. Just wait until you have your next gig lined up, put in your two weeks and be on your way—even […]

David Briard

No one cares as much as you do and a lack of regiment were the biggest issues I faced. Years ago I adopted waking up early and have structure to my day like I would a job. Before that, for the first few months I would not work until late afternoon. Wasting the entire morning because, well I you can when you don’t have a job (wasting time is never a good thing).

Previous post:

Next post: