8 Reasons Why Being Your Own Boss Isn’t the Greatest Job in the World

I’ve been working for myself for about five years now. And while being my own boss certainly has its privileges, it also has some serious downsides. I know a lot of freelance writers who’d easily agree, especially when it comes to the whole “feast or faminine” part of the job. Some months you’re just rolling in the dough, and others, not so much.

Anyways, besides the straight-up obvious salary part of working for someone else, there are certainly a lot of issues with being self-employed. I figured I’d rattle off a big ol’ list for you, just in case you thought my days were always filled with double rainbows, chocolate walls, and monkey chauffeurs.

1. If I don’t work, I don’t get paid!
Pretty straight forward, right? But it’s more than that. I have to actually FIND work, it’s not like I can just go in and work. As a freelancer, I need to constantly be digging up new clients, following up with old ones, etc. Half my job is finding new jobs!

2. I never stop working.
At a previous hell job, I used to have a Blackberry pager on me. I was working for an evil startup and was on the product management team, which meant that if anything bad happened to one of the sections of the site I was responsible for, site monitors would alert me via my pager, and I’d have to follow up with the programmers to fix it. No matter what time of night it was! Nowadays, I don’t have a pager. But I have a computer and a smartphone and I am ALWAYS checking my email for work-related notes. Whether I’m on the treadmill during lunch, or watching a Yankees game on the couch at night, I am always plugged in. That goes for 24/7. It’s my own gig, so if I don’t stay on top of myself, no one will.

3. What’s a vacation day?
Sure I can take off as many days as I’d like, but remember, if I don’t work, I don’t get paid. And there’s always work to be done, especially when you’re struggling to pull in new clients or finish off big projects. Everyone needs to take time off though, so I do my best. But honestly, I can’t recall the last time I took a legitimate vacation with my family for more than an extended weekend.

4.  Insurance, Insurance, Insurance
Next to “no salary,” the next worst thing would probably have to be health insurance. After leaving my last employment, I was able to have short term insurance thanks to COBRA. (No, not G.I. Joe’s enemy. I wouldn’t trust their insurance.) But after that, I was on my own. My wife and I did loads of research to find the best (not necessarily the cheapest) plan we could find. We investigated insurance in any state and finally found a few plans in NY that had some great coverage. But it’s amazing how expensive things can be overall if you end up paying for it completely yourself. Just one major reason so many people look for a full-time job with benefits.

5. I make my own coffee
Okay, in the morning, I get to use my Keurig. And my lovely wife even turns the machine on for me before I come down. But once I hit the office, it’s all me or else it’s all Dunkin Donuts down the street. I miss having free, unlimited access to coffee at the office.

6. Firing people sucks
Whether you own your own company or you work solely by yourself, chances are one day you will have to fire someone. Even if it’s just someone you work with remotely. And trust me, it’s never easy. Even if you 1000% despise the person and cannot wait to see the door slam them in the ass, the physical act of letting someone go is probably the hardest thing you’ll ever have to do in your career.

7. Paperwork Mountain
It’s bad enough I don’t get paid if I don’t work. But it’s even worse than that. For most jobs, even if I work, I don’t get paid… at least not until I get off my duff and whip up a handy invoice for the jobs I’ve done. Filing paperwork is just so boring and time consuming, especially when you’d rather be spending your time landing new projects.

8. Quarter for your thoughts
Nobody likes the Taxman (save for Uncle Same). As a freelancer, it’s even more fun because you get to file “estimated” taxes quarterly. That means you need to keep solid records of everything and file paperwork (and send funds) four times a year to the feds and the state governments. There’s something to be said for just having taxes deducted automatically from your pay stubs.

Don’t get me wrong, running your own start-up certainly has its advantages too. But unless you’re some kind of florist, it’s certainly not all coming up roses.

What’s the worst part of your freelance career?

This post was supported by Short Term Health Insurance.

2 thoughts on “8 Reasons Why Being Your Own Boss Isn’t the Greatest Job in the World”

  1. Loved your GI Joe reference 😉 Since I am just starting out I guess the worst thing has to be staying motivated – even when my husband is off work. Also not getting discourged by the very slow start up – it can be so discouraging when you write an article you think is great and it gets 0 comments – makes me wonder if anyone is reading. Or when a slow day rolls along and I have 30 page views….*SIGH*….but it gets better…right?….RIGHT??? LOL!

    I am lucky my husband is in retail management because the insurance thing is covered. As far as firing people – unless I fire my son (NEVER) or my husband (NEVER…well unless he leaves the toilet seat up then maybe) I only have myself to worry about. But I a manager of a retail store for 6 years so I had my fair amount of firings…yes very fair amount. It wasn’t the firing part that bothered me – if you can’t do your job you need to GO- it was what their reaction would be – I had people cuss me out – start throwing things – make a scene trough the store as they left – start crying uncontrollably – and once thank me because they hated this F****** job anyways (that was the oddest)

    • Gotta have a GI Joe reference whenever I can, right? And yeah, it’s not that I feel bad about firing people (though in some cases, when it comes to budget cuts, then yeah I feel bad), it’s just the entire process is sickening and not knowing someone’s reaction is the worst.

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