Why I’ll Never F****** Freelance Ever Again

“A woman working on a laptop outside a coffee store” by Christin Hume on Unsplash

To set the record straight — I owe a lot to freelancing.

It gave me the initial freedom to travel the United States on a 5-month road trip.

It helped me find work after college (I couldn’t find a job to save my life).

Most of all, it helped me hone my writing skills WHILE getting paid for it.

But I’m never going to fucking freelance ever again.
That would be like Lebron James quitting basketball and going back to work at McDonald’s (I’m assuming he worked fast food at some point before the NBA).

Here’s why I hate freelancing and decided to make the jump to blogging full-time 7 months ago despite having no idea how to make money as a blogger..


You’re Free, But You’re Not Really Free

What I loved about freelancing at the beginning was the work-life balance. I could wake up whenever I wanted, work wherever I wanted, and wear whatever I wanted.

I felt really, really free and in control of my own life.

I’d Facetime my Mom and tell her I was working in my pajamas. It was great. I did all that “This Is My Office” Instagram shit, too, where I’d take a picture of my laptop at a Starbucks or something and post it.

But I wasn’t free.

I ended up writing blog posts for local breweries in Montana and writing billboard copy for apartment complexes in New Jersey.

It was straight up weird.

What did I know about local breweries in Montana? Heck, what did I know about beer?

Yes I could sort of pick-and-choose which clients to work for, but during famine weeks I kinda had to take whatever I could get on Upwork and Indeed.

Freelancing is a work-life purgatory. It’s like this oasis between cubicle life and straight-up entrepreneurial freedom.

“I mean, who needs entrepreneurial freedom right? How many of us really have the skills to do that? I’m good right here in this freelance oasis,” I used to tell myself.

But when you get down to it, there’s not much room to grow as a freelancer. It is a purgatory.

You can charge higher rates, work less hours, and eventually collaborate with some awesome clients, but the problem is at the core of freelancing itself, not in the money you’re making or the hours you’re working.

The problem is that you’ll never REALLY be in control as a freelancer — you’ll be stuck in this perpetual cycle of winning clients, losing clients, and searching for clients again until the day you die.

Honestly that’s just not fun.

I don’t know how else to slice it.


You’re Creating, But You’re Not Creating Stuff You Want To Create

I used to enjoy writing up freelance articles about coffee clubs around the country.

I used to think it was cool that I could learn something brand new every day and THEN write about it.

But it got old really quick.

After a while I felt like I was whoring out my writing talents too much.

I started wanting to write words for the sake of writing my own words, too, so I started blogging as a side-project.

Most nights I felt like writing a 500-word blog post at night AFTER writing 2,000–3,000 words was actually therapy.

Most people who message me/email me wonder how I find the motivation to write 3 new posts per week.

Oh brothers and sisters, I used to write new blog posts EVERY NIGHT after writing ALL DAY.

You either want to write or you don’t. I don’t know what else to say.

The problem with freelancing is that you’re creating shit, but it’s nothing that you actually want to create — and I promise you this will get old really quick as well.


You’re Not Really Achieving Your Main Goal..

Chances are you took up freelancing for a variety of reasons…

  • Maybe you wanted to not work a 9–5 job again.
  • Maybe you freelance as a side-hustle.
  • Maybe you can’t find work at all and decided to freelance for the hell of it.

At any rate, you won’t take up freelancing if the regular 9–5 is working for you. You just won’t. Why would you?

Chances are if you’re a freelancer, you aspire to doing stuff completely on your own.

And I applaud you for that.

But freelancing is a hamster wheel. You’re spinning the wheel a ton, handing in freelance project after freelance project, but it’s not doing anything to get you closer to what you REALLY want..

Complete freedom from other people telling you what to work on.

That’s because you have no time to build a business — you’re too busy building it for other people.

Let’s face it — you’re a slave as a freelancer. It’s nice, but it’s almost worse than a 9–5 because you’re almoossssttt there but have zero benefits and have to take out 25 percent of all your meager earnings for taxes.

Freedom is amazing, but you pay a high cost for it as a freelancer.


If You’re A Freelancer, Don’t Click Away Yet — Read This

Okay, I’ve bashed freelancing well enough, it’s time for me to redeem it. I always save the last part of my articles for a little redemption.

Freelancing is hard — therefore it teaches you a lot of lessons.

It immediately makes you the face of your own business. You’re the one who has to sell yourself to clients.

✅ Selling Skills

You’re the one who has to deliver projects on time.

✅ Time Management Skills

You’re the one who has to communicate with clients to make sure you create great work.

✅ Communication Skills

You develop a fuck ton of skills as a freelancer, that’s the best part.

What you don’t know in the moment, though, are that these skills are directly transferable to the lifestyle of an entrepreneur.

Like I said before, as a freelancer you’re basically stuck between cubicle life and flat-out entrepreneur world. This means you’re closer to being an entrepreneur than you would be if you still worked a 9–5 job.

Freelancing is actually the best first step you can take towards being an entrepreneur in my opinion.

It’s sort of like college for entrepreneurs.

You deal directly with clients, sell yourself, and hopefully create some great work.

What’s stopping you from starting your own agency? What’s stopping you from REALLY taking that next step and traveling to entrepeneur-land?

I wouldn’t be who I am without freelancing, but us humans need to keep evolving. Freelancing was just a stepping stone for me to something bigger.

And that’s why I’m never going to be a freelancer ever again.

Want to get started blogging online? I actually have a free 5-day email course called “Your First 1,000 Medium Followers” that will teach you how to build an audience here on Medium! Sign up for it right here. I’d love to teach you a couple things.

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