Here’s Exactly How I Turned My Freelance Gig into a Full-Time Job

Stefanie O'Connell sitting inside a cafe
Photo by Caroline White

The first time I got paid to write, I made $25.

It was December 2013, and I was cobbling together a living waiting tables, babysitting and personal assisting, averaging around $15 per hour.

To me, $25 was almost 2 hours I didn’t have to work at a restaurant, change diapers or run around New York City picking up other people’s dry cleaning. So I emailed every personal finance blogger I could find to let them know my freelance writing services were available for hire.

It wasn’t long before I realized the total unsustainability of my approach. At $25 per post, I’d need to write 20 posts per week just to make $500, before taxes.

What I had initially thought of as freedom suddenly seemed impossible. I didn’t have it in me to write 50,000 words each month. That’s like writing a book every 30 days!

Struggling to Scale Up

I negotiated a 20% raise, but it wasn’t long before I realized that even $30 per post wasn’t going to be enough to become a full-time freelancer.

But what I wasn’t earning in cash, I was gaining in identity capital and network growth.

I was contributing to so many blogs in the personal finance niche that my name became practically synonymous with millennial money. I was getting calls from major news networks and media outlets, asking me to comment on stories I’d written.  

That fall, I decided to attend the annual financial media conference, connecting in person with my existing clients and expanding my network even further.

Coming home with a pile of business cards and conversations to follow up on, I realized the potential of my next move — a way to scale my freelancing in such a way that I could sustainably go full-time and leave the babysitting, waiting and personal assisting behind for good.

The Freelance Mistake I Didn’t Realize I Was Making

I had been stuck in an employee mindset, in which asking for a 20% raise seemed like a bold move. I had to start thinking more like an entrepreneur and reassess my market opportunity.

Writing for other bloggers was inherently limiting. I needed to start writing for companies with bigger budgets if I was going to reset my freelance rate in a meaningful way.

As I pitched these new kinds of clients, I started asking for double, triple and occasionally four times my initial rate of $25. The ease with which they agreed made me realize just how much I was undercharging.

I also started talking to other freelancers in my niche. Having spent a year interacting with them online and solidifying those relationships in person at the conference, I felt more confident asking candid questions, such as how much they charged, where they found the best opportunities and how they went about renegotiating their rates.

I started to let go of clients as my rates grew past the limitations of their budgets, all the while continuing to build my network, expertise and media presence to attract bigger and better opportunities.

My blog posts for clients started getting syndicated on major media sites, such as Yahoo!News and MSN, so I used the opportunity to pitch other media outlets, eventually landing a regular spot on the U.S. News & World Report blog, further building my credibility and capital.

The Day My Freelance Rate Hit 20x

I’ll never forget the day I got a call from a Fortune 500 company asking for my rates. I sheepishly told them $150, trying to push the envelope.

They got back to me with a contract offering $1 per word. That’s around $500 for one post — 20 times what I had earned when I was just starting out!

By the end of the year, I had built a roster of similarly well-paying clients. Not by steadily continuing along my current path and asking for 10 or 20% raises here and there, but by intentionally disrupting my status quo. I let go of work that was no longer in alignment with my rate. I also kept my eye out for opportunities to raise my value and encourage more well-paying clients reach out to me — things like becoming a published author and appearing regularly on national television as an expert in my field.

My Top Negotiation Strategies for Fellow Freelancers

On this journey of exponential income growth, I’ve learned a number of valuable lessons:

  • Remember, context plays a major role in determining price point. If you’ve maxed out your income potential in a particular market, consider pivoting to maximize your opportunities elsewhere.

Where I used to earn $25 per post writing for small and mid-sized bloggers, I can now get $500 doing the same work for print magazines and corporations.

  • Never stop building your identity capital. The skills, value and experience you bring to the table are what put you in a position to charge a premium, so spend time cultivating them every day.

    Take classes, develop in-demand skills (public speaking, video, social-media marketing, etc.), stay up to date on the latest stories and trends in your niche, and create content around those topics to showcase what you can bring to the table.

  • Leverage your network. Your network of fellow freelancers is one of your top resources. The more transparent you are about your own rates and client interactions, the more your colleagues are likely to share their strategies and contacts with you.

When and where you can, connect with people in person. Go to conferences, meetups and industry events — wherever you can put in face time and connect with people on a human level. Email inboxes are chaos for freelancers and more so for editors and producers. If you want to stand out and make a real connection, you need to get in front of people.

  • Always ask for a budget range when negotiating. I got lucky when making my “big” $150 ask and my client came back with their standard $1-per-word rate.

The lesson learned? Always ask for your client’s budget range, rather than leading with your rate. This can save you from seriously underpricing yourself.

  • Know when you’re willing to walk away. I know letting go of guaranteed income is scary, especially as a freelancer. But if you want to seek out or attract new opportunities, you need to give yourself the time and space to do it. That means being willing to let go of clients who aren’t ready to level up with you!

Stefanie O’Connell is the author of “The Broke and Beautiful Life” and founder of, a destination for millennial women who want to feel as confident with their money as they do in their lives.