The Ups and Downs of My Freelance Life (And Why You Won’t Get Rich Quick So Stop Googling It)


Wake up. Watch TV. Paint my nails. Make some food. Eat food. Look for jobs. Apply to unqualified jobs. Repeat.

This was my sad life after hiking the Appalachian Trail. I found myself with a college degree and a certificate saying that I completed the AT. That should be enough to land me a job, right? Yeah, right.

“But why don’t you get a job associated with your degree?” – Everyone.

Just like nearly every college graduate, I had apprenticeships and internships under my belt. I didn’t get a great paying job after college, so I traveled. After traveling, I then once again attempted to get a good paying job but that didn’t change a thing. I never seemed to be qualified for entry-level gigs associated with my degree. So I gave up on applying altogether. I decided to sell some shit on eBay and paint my nails instead. I tried to do those stupid surveys for money too (don’t do that). Oh yeah, and I blogged too. That happened.

“I’m going to hike the Appalachian Trail.” – Me. “Why?” – Mom.

I blogged my entire journey while hiking the Appalachian Trail. Friends from home, family, and people I met along the trail consisted of the readers on my AT blog. My mom thought I was pretty good at writing though. Oh and so did my aunt. My sister thought it was pretty neat too. Obviously, my family likes me or something.


“Write for free! You’ll get exposure!” – Cheap-ass editors.

I never considered writing for money until my mom asked why I stopped blogging after life on the AT was over. I didn’t really know why I had stopped. I loved writing. So I started looking into creating my own blog, this blog actually. But I also started looking into writing for free for other blogs. I had no experience, no degree in writing or journalism, and no published clips besides from my own blog. So writing for free seemed to be my only shot at making a name for myself in this industry.

Don’t get me wrong, free writing has a purpose. For writers just starting out in the industry, it is a great way, and possibly the only way, to get published on a blog that isn’t your own. And just like any other industry, you won’t get high-paying gigs without experience. By writing for free, I learned more about WordPress and code. I perfected writing in AP Style. Writing for free got my foot in the door. However I do wish I didn’t spend as much time on some of the articles I wrote for free. Hours of free work. Ugh. Can you tell I’m still bitter?

“Wait, I’m not making rent though!” – Me.

After gaining a few small (paying!) gigs within my writing niche of travel and yoga, I was finally making some money. Okay, let’s be honest. I was barely making any money. But I was making money, but just not a lot (let me remind you – like barely any).

I quickly found that only truly experienced writers with years of experience make money. With only six months within the writing industry, I got paying gigs. But those gigs only paid pennies, like $5 for a 500-word article. Bitch please! But did I do it? Yes, I did. But I wasn’t able to pay for anything. I needed a side hustle. I needed something besides writing to sustain me.

“I’m gonna create a business without having any background in business! It’s gonna work!” – Me.

So since I didn’t have a 9-to-5 job (queue Dolly Parton!), I did have some free time. I can’t lie to you. My hustle wasn’t as strong back then as it is now. So I spent my days writing in the mornings, doing yoga in the afternoon, and maybe even hitting up the local thrift store for half-price finds.

My obsession with thrifting for clothes came about while in college in Austin, Texas. Austin has some great thrifting opportunities, from Goodwill shopping to local markets. I loved finding vintage clothing. The thrill of the hunt was real, and real addicting. Being a babe on a budget (story of my life), my options were always to thrift. Vintage clothing that transcended decades would always catch my eye – not the ugly-ass 80’s woman’s two-piece suit. No. I mean vintage finds that have a place in modern fashion.

My obsession with cheap vintage grew into a business idea. Since I had already sold some of my old hiking gear on eBay, I was quite familiar with the online selling platform. Therefore, I tried to sell some of my thrifting finds on eBay as well.

“Buy my shit!” – Me when nobody bought my shit.

You may have guessed it, but eBay is not the best platform to sell vintage clothing on. I tried though. I sold some things. But I knew I needed to either quit eBay selling or get serious about selling vintage online. That is how Dizzy Dreamer Vintage was born. I opened up an Etsy store. This damn vintage clothing shop was my baby and still is my baby. And Etsy was the platform that truly created my empire. Okay, empire is a strong word. But not to toot my horn or anything (TOOT! TOOT!), Dizzy Dreamer has grown into something way bigger than I ever imagined – MONEY, I mean damn dollar signs.


“Follow me on Instagram! Both of my Instagrams! Yes I have two!” – Me, then and now.

So even while posting new vintage clothing in my Etsy shop every week, I was also still writing. A way to promote both my Etsy shop and my writing was through Instagram. So I started posting on my personal account a lot (Follow me @madidragna), which focuses on travel and yoga. Like I was on Instagram all the time.  Hashtags were my life. “Liking” became a job. And before I knew it, I gained a small following. Through Instagram, I’ve met friends, gained clients, and found inspiration. I did the same thing for my shop’s Instagram @dizzydreamervintage, where I’ve met customers, like-minded individuals, and other shops in my area. I’m a millennial woohoo!

“WTF? I have deadlines now.” – Me when I got what I asked for.

Let’s fast forward to right now. I probably shouldn’t be writing this right now. I literally have seven articles to write by Friday and still need to prep, model, measure, and list 10 articles of clothing in the shop by Sunday. Bitch got deadlines!

My article deadlines are put in place by my clients. My shop deadlines are put in place by me. When it comes to my vintage clothing customers, I know they love my shop because I post new vintage in the shop every single week. It’s what makes my shop successful – consistency.


“But my business I just opened yesterday is gonna make me a shit-ton of money by the end of year right?” – People who think they can get rich overnight.

So this entire story happened in the span of THREE years. Yes, it takes time to make money. It takes time to make money as a freelancer and small business owner. I now can pay my rent though. I’m still broke sometimes, sure. But every day I hustle. At the end of every day I ask myself, how much money did you make today? Sure life isn’t about money and blah blah blah. But as a freelancer, you have to always consider the bottom line. As long as you stay consistent, focused, and dedicated, you will eventually make some cash. It just might not happen as quickly as you are hoping it will.

“Don’t call me an entrepreneur AND don’t say that my job isn’t real.” – Me, always and forever.

Let me address the people that want to call me an “entrepreneur” first. I hate that word. It reminds me of somebody that really doesn’t do anything and “waits” for opportunities to come. If you’ve made it this far, you know I create my own opportunities, not wait for them. And I don’t care about business opportunities you have for me. I don’t want to invest in your Lularoe business. I don’t want to throw a party for the make-up you are selling. I don’t want to work underneath you to become a pawn in your pyramid scheme. All I am is a writer and business owner. I could care less about your shakes and your body wraps.

Next, my jobs are real. I make real money from them. Stop telling me that I should “be a teacher” or “go to grad school” or that “your restaurant is hiring.” It’s demeaning to say those things to me. You’re demeaning my hustle. Bye.

On that sassy note, I just want to be clear that I love what I do. However it is not easy to be your own boss. There are ups and downs. I’m unsure if this will be my life forever, but it’s my life right now and I’m enjoying the journey.

Do you work as a freelancer? Tell me about your hustle in the comments below!

5 thoughts on “The Ups and Downs of My Freelance Life (And Why You Won’t Get Rich Quick So Stop Googling It)”

  1. Lovely post! I love writing…very inspiring! I’m looking forward to see if I can figure out my life as Freelancer something!

  2. Fire in the belly! I love your strength. Freelance life is hard, really hard. For me, it matches the way I think. Sure, it would be nice to have a fat paycheck magically appear in my bank every two weeks, but that is not my path. Been there and quit, laid off, laid off again, quit again and then after waking up to another employment reset I finally realized I need to get out of the cycle and take control.

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