How I Made My First Dollar Freelance Writing

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Updated May 2, 2017

OK, I’m an average gal.

Until the end of 2013, I believed the only way to earn money was through a 9 to 5 job.

At the time, I had already tried a few solopreneur ventures, but nothing seemed to stick or bring in any cash.

To be blatantly honest, each idea failed.

Sadly, I became convinced the only real way to make money was to fill out a job application, attend an interview, turn in a W-2, and punch the clock.

Sure, I saw other entrepreneurs making dough, but it felt like it wasn’t in the cards for me. I started to believe I didn’t have that “it” factor.

Then I made my first $25 freelance writing. I got a taste of the possibilities. And it tasted like fine wine.

freelance-blogging freelance-blogging-2 freelance-client-3 earn-money-freelance-blogger

Why is Any of This Important?

Not because I think freelance writing is the answer to quitting your job and riding off into the sunset.

I want to preface with that.

I think too often in the online space we share what’s worked for us without the disclaimer that everyone’s talents and dreams are different.

Doing something just because it’s working for someone else can take you away from your real calling.

Instead, I want to let you know that making money from whatever you’re good at is possible.

Now, for the story:

I met someone new randomly a while ago.

We got on the topic of my job and career history which sparked me to take a trip down memory lane.

The stranger (that I’ll likely never see again) is a recent immigrant working his butt off in three jobs to pay for college.

He still has about four more years before he’ll even graduate and he looked to be in his mid-20’s.

When I explained that I freelance/own my own business and I’m not in a career related to my major, he was flabbergasted.

He didn’t outright say it, but I got the impression he felt I was ungrateful for the degree.

He couldn’t believe I left regular jobs when other people kill for the credentials that can lead to a stable career. I felt the need to open his eyes to the fact there is money to be made outside of working for someone.

Because for one, I felt defensive.

Working solo is my choice – judgmental, much?

For two, making money on his own might save him a lot of energy. I mean three jobs? His story still has me feeling pretty, pretty, pretty guilty. (Shout out to Larry David.)

He saw the possibilities, but he had no idea where to begin and I was reminded how starting from square one feels like an uphill battle.

But it’s the same uphill battle for everyone. Remember that.

I made my first $20 outside of the 9 to 5 contributing two blog posts for a client or $10 per post.

Now, I’ve closed deals that pay over $400 per blog post.

Regardless, that $20 made me feel like a million bucks. And for a newbie, it made me realize anything is possible.

It proved I have what it takes to make money on my own. People want the skill that I possess. 

I do want to make one thing clear. Self-employment isn’t for everyone.

Heck, I’m not against accepting an offer down the road if it’s a great job.

There’s nothing wrong with climbing the corporate ladder as long as you feel happy doing what you’re doing.

But, just like my new acquaintance grinding to pay tuition, multiple streams of income (i.e. side hustles) puts more money in your pocket.

If for any reason your job stops providing you good money or satisfaction it’s always nice to have cash from other sources to fall back on.

My Journey From Peanuts to Lox

I love smoked salmon aka lox, but it’s expensive.

Scraping for assignments that pay peanuts to gigs that pay smoke salmon didn’t happen overnight.

I started a blog first which was invaluable.

I consistently made efforts to build my platform and then pitched for guests posts on major sites until I had enough experience to command a higher rate.

The First Writing Assignment

For the sake of showing where I came from (and so I can laugh at myself), I dug up my first ever pitch that turned into a writing job.

If you can even call it that. The job was a paid gig as a gossip writer.

I’m a recovering celebrity gossip blog addict, so I figured writing for them would be the perfect use of my skills.


I found writing about people I don’t know feels icky inside even if it’s just for entertainment.

Here’s the first pitch I sent out…



Yes, I promise. This email is real life. Medine is my maiden name (hey dad 🙂 and Gran <3 ). My negotiating skills have improved greatly…


My original quote was $25 per post, but I bartered far lower just to get paid.

I got paid $20 for two 250 posts or essentially $20 per hour.

How Did I Get to the Next Income Level?

First, I focused on a higher paying niche and ditched dead weight clients.

Gossip reporting doesn’t pay very well – at all – unless you’re one of the big names or writing for a seriously big publication.

Plus, it wasn’t my cup of tea anyway and to really earn the big bucks it’s best to be passionate about what you do. I moved to focus where there are businesses offering legit products to customers.

These companies need content to sell their product. And companies with tangible products have a bigger marketing budget. Gossip sites typically rely on ad sales.

Bottom line: If I pitched a gossip blog a $400 idea they’d probably laugh in my face.

Since getting hip to the freelancing game and understanding how it works, I’ve been able to increase my rates and transition into writing full-time.

The moral to this story is, just start.

All you need to do is start somewhere.

Your start probably wont be as sexy as the “starts” you see on social media because that’s just for show anyway.

What you do behind the scenes (like sending gossip pitches to random sites) and then building on your experience will get you to where you want to be.

Not sure where to start?

Or just looking to get a little productive right this second? I have a mega list of 107 Productive Things to Do Instead of Spending Money to share! It includes ways to get your finances together and ways to bring in more income. Grab the PDF version of this list below!


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Taylor K. Gordon is a writer and money blogger. She writes on how to live your best life without going broke.

  1. Reply Chonce September 29, 2015 at 7:55 pm

    Love this post! And thanks for opening up about your humble beginnings as a freelancer. My first real freelance gig actually came to me when a current client of mine emailed me inquiring about my writing services after taking a look at my Hire Me page. I was lucky, but I’ve definitely had to work hard sending pitches out to prospects since then. The major issue I’m running into now is having the courage to scale up. I would love to earn $300 per post (who wouldn’t) or even $100 per post since I haven’t even gotten to that point yet :(, but I just need to find the confidence and courage to trust in my skills and ask while looking for the right clients.

    • Reply Taylor September 29, 2015 at 8:26 pm

      Don’t worry!! You will. It all takes time. And I’m getting less inbound leads than I used to get, so I applaud you for getting bites on your page. I may actually have a lead for you. Heading over to your site for your email!

  2. Reply NZ Muse October 17, 2015 at 11:28 pm

    Woop woop!

    It makes a huge difference also moving from writing for traditional publishers, to brands/businesses that are starting to invest in content. Their budgets are a LOT bigger.

    • Reply Taylor October 28, 2015 at 12:05 pm

      Yes, plus I have better writing samples. In the beginning, I was doing a bunch of work and then realized I had no writing samples on sites I could be PROUD of.

  3. Reply Latoya S November 8, 2015 at 9:43 pm

    Hi Taylor,

    I found your site a few weeks ago and can you say, inspired?!!

    Thanks so much for sharing your beginnings as a freelancer. I’ve been scouring the web for honesty because I like to know how each aspect works and I’m not anticipating this to be an easy journey, but I still want to know where I’m headed.

    My major hangup is a lack of writing samples. Right now I’ve been focusing on guest posting, but I’m slightly (okay, a lot) intimidated to approach some of these bloggers I’m inspired by.

    I need to get over it with a quickness and simply ask. Once I do, I will have that nice portfolio that I’ll be proud to call my own.

    Did you guest post to build up your portfolio?

    • Reply Taylor November 9, 2015 at 11:37 am

      Hi Latoya!! I’m so excited you found my blog and find it helpful. I’m all about the honesty! You’re right it’s a lot of work, but you’ll have fun along the way. I did guest post in the beginning of my career and I still do. It’s a great way to connect with new audiences, get your name out there and build your portfolio.

      I completely understand where you’re coming from being intimidated. I’m not sure that’ll ever go away – I still feel it! But, remember the people you’re writing to started out where you are, so they’re usually happy to help. Once you get your feet wet the first few times it’ll get easier. Let me know if you have any other questions!

      P.S. Love your site!

  4. Reply Shirria @ GDTH January 13, 2016 at 2:55 pm

    It’s encouraging that you post an honest starting point. I just recently posted my second online income report to 1) encourage other bloggers starting out and feel discouraged and 2) to track my progres. My biggest struggle, like Latoya, is pitching especially to bigger blogs. I have a limited portfolio because most of my paid work isn’t live anywhere. I’ve also pitched for guest blogging but NEVER hear anything back even after follow up emails. What would you suggest?

    • Reply Taylor January 13, 2016 at 3:42 pm

      Hi Shirria! Thanks for the comment! Pitching guest posts to large blogs is often a numbers game. Don’t feel discouraged if you don’t hear back, I’ve gotten many non-replies. To build your portfolio, I would do guest posts on sister sites until your other work goes live, so you have something published. One of my mistakes early on was thinking “big” blog or bust. But there’s definitely something to be said about writing several knock it out of the park guest posts on smaller site within your niche. And then using them to show off when applying for gigs.

  5. Reply ashe June 15, 2016 at 7:03 pm

    wow! i am so late and behind on it all but i feel so enlightened right now by this post… your entire blog actually! I’m on a different path ( I major in fine arts & graphics ) but i can finally put all the pieces together! thank you for sharing, I’m having a hard time “putting myself out there” in the blog world, but i find it all comes with time and patience.

    • Reply Taylor June 16, 2016 at 9:02 am

      Never too late! Thanks for reading 🙂 If I could choose a talent it would be design, so go you! You’re right about time and practice. It builds your confidence. I’m not sure that initial fear of new things in business/blogging ever totally goes away, but once you have some positive experiences under your belt it becomes easier to at least manage it.

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