Pros and Cons of the Freelance Lifestyle


I LOVE being a freelancer. It’s the only way to go as far as I’m concerned, BUT it’s not for everyone. Perhaps there are people who prefer to work in cubicles, or others who really enjoy clocking out at 5:00 on the dot, or even others who revel in office politics or living for the weekend. Ok – so no one with an actual soul or a pulse probably enjoys those scenarios, but the truth is that – like everything – there are pros and cons to the freelance lifestyle that you should be aware of before diving in.

Let’s start with the bad news first. The cons of freelance…

Lack of Benefits
Perhaps the most obvious of the cons is that freelancing doesn’t come with health insurance or a pension. While this fact alone may be enough to scare off a few of you… it’s not that big of a deal. And to be honest, if you can’t handle being responsible enough to look for your own health insurance and retirement plans outside the box… freelance/entrepreneurship is most definitely not for you! Before my husband got a real job with benefits I could attach to, I had health insurance through for $48/month. And I swear it covered way more than our current plan does. Granted, that was a long time ago. I also have a SIMPLE Retirement plan and a Roth IRA that I contribute to each year, which is more than a lot of people with corporate benefits choose to do!

Tax Crap
Nothing wants to make me fall asleep more than writing about taxeszz… zzzzzzzzzzzzzzzz. Whoops – I’m back! This is another responsibility that falls to the business owner (freelance you) instead of relying on someone else to take care of it. Paying in monthly or quarterly estimated tax payments to the government is something us freelancers simply have to do. Personally, I highly recommend finding a bookkeeper/accountant that you can trust to take care of all the tax mumbo jumbo for you. I’d rather pay them $100/month than spend hours pulling my hair out (and randomly falling asleep) while attempting to do it myself. Again – if this scares you off… freelance is not for you.

Lack of Structure
If you didn’t have to be at work from 8 until 5… what would you do with your time? Would you sleep until noon, play Zelda until dinner, and then binge-watch Netflix until you wake up in a pool of drool with empty pizza boxes as your pillow? While a flexible schedule can be a giant PRO of freelancing… it could be a con if you can’t handle it. Creating and sticking to a routine that works for you and your clients is an important part of the freelance lifestyle.

Lack of Coworkers
Alright so maybe you hate your coworkers and this is happy-dance worthy. But working for yourself by yourself can be a lonely place. Especially when you stay at home with kids and the vast majority of your conversations revolve around potty training and fruit snacks. Meeting up with other freelancers to work at coffee shops or joining a coworking space are great options for you extroverts.

Never Clocking Out
When you work from home it can be difficult to switch from work mode to personal-life mode. I’m definitely guilty of working on a fun website project at 9pm when I should be snuggling up with my hubs watching our latest Netflix show. Sorry babe.

Inconsistent Work
I almost didn’t add this one, but it is a common misconception of freelance work. And while it is certainly possible to have a roller coaster paycheck, if you setup your business right and dabble in that goldmine known as recurring revenue, inconsistent work should never be an issue.

Now for the good stuff! I tried to keep this list short, but there are bajillions of pros to freelancing. Let’s chat about why the freelance lifestyle lives at the corner of bomb diggity and awesomesauce…

Who read that while hearing Mel Gibson’s yelling voice? Just me? The ultimate pro to the freelance lifestyle is freedom. Freedom to work when you want, from where you want, with who you want, on what you want. Want to work from coffee shops while traveling the country with your band? Or from home while raising your babies? Or from a van down by the river? Well the wifi might be tricky, but as long as you have a hotspot and loads of data, go for it! The options are literally endless.

Unlimited Potential
Let’s call this an extension of freedom. Have you ever wanted a raise? Thought you deserved to earn more money and your boss laughed at you (well maybe not to your face). There is no cap on your earning potential as a freelancer. No set salary, no limitations… you can raise your prices when you want and work with as many paying clients as you like. Now obviously there are concerns surrounding those (you know – economics and cloning), but there is literally no limit to how much you can make.

Drama Free Work Zone
While freelancers may lack coworkers (see above), they also lack office politics and coworker drama. Can you see that beautiful and peaceful silver lining? Zero gossip, zilch rumors, no brown-nosers sucking up to your boss. Speaking of bosses…

Best Boss Ever
Yeah that’s right. YOU.  You are your best boss ever. For so many reasons. Not happy with your work? With productivity? With your income? Guess who’s to blame. Have an awesome freelance-y day? Or your highest profit month yet? Or love waking up on Monday mornings? Guess who’s to thank. The freelance lifestyle forces you to look in the mirror and praise your mug or make the changes needed to make it work.

No Traffic
This one may not be a big deal… or may be the biggest freaking deal ever. There are people with over an hour commute ONE WAY to work. Can you imagine getting that time back every single day? 10 hours a week? Do you know what kind of freelance magic you can make happen with an extra TEN HOURS a week?!

So there you have it. Sure – there are cons to freelancing, but if these pros don’t get you pumped out of your mind… then freelance may not be for you. Perhaps what gets you pumped is the idea of getting your ‘cheers to 30 years’ mug on your 30 year anniversary at your secure job in your safe cubicle with paid health insurance. Or just maybe… you are itching for an adventure to work outside the box and live a life full of freedom and pride. Hmmm… tough one…

Kelly Diekmann

Business Instructor

Kelly is owner of KDesign. She has an MBA with a Marketing emphasis from the University of Nebraska – Lincoln, and a BS in Information Systems with minors in Math, Spanish and Art from Nebraska Wesleyan University. Learn more about Kelly