5 Things I Learned After 5 Years of Freelancing

Jaime L. Brockway
5 min readFeb 1, 2023

Conclusions I’ve come to

Photo by Ryan Graybill on Unsplash

January 8, 2023, marked my fifth anniversary as full-time freelancer.

In January 2018, I left my role as national copy chief of Time Out North America in NYC. I had been freelancing on the side for a few months but decided to retry it full-time; freelance editing was one of my jobs when I first moved to NYC, but I knew next to nothing about the magazine publishing world at the time, which made navigating freelance quite difficult. (What pay rates are good pay rates? When is a client’s expectation standard or unreasonable? What does an edit for this type of project usually involve?)

Five years in, I’m still learning a whole lot, but I’ve amassed a humble collection of lessons.

Giving 100% to every project is the best way to get new clients.

The past two years, I’ve experimented with many methods of lead generation and client acquisition. I launched social media, my website, and my newsletter. I applied to jobs on Upwork, LinkedIn, and Indeed. I cold-pitched. Far and away, the best method is referrals.

Of the 12 clients who paid me in 2022, 50% were from referrals. Whereas I worked hard to get the other 50%, all I had to do to get these referral jobs was to do my best on paid projects. In 2021, I landed a big client who hired me because a staffer there had gotten a referral from someone I worked with three years’ prior on a one-time project. Never underestimate the power of providing quality work.

Clients love knowing a reliable person who delivers quality work because it makes them look good to recommend me to their connections who need editing or writing services.

Being a freelancer has made me a more valuable hire.

Working in a more traditional, one-company role, I did my part but never learned how the departments outside of my immediate orbit operated. I was more concerned with my own tasks and responsibilities and didn’t understand the full picture.

As a freelancer, I do invoicing and budgeting, project management, marketing, copywriting, contracts and client acquisitions…in addition to my core services of editing and writing. I have grown so much, and my knowledge of business operations has vastly increased, as has my respect for how businesses of more than one person function 😂

Freelance is a constant experiment, and you have to be comfortable with that to do it.

You might reach a plateau in a full-time, one-company role, but that will never happen in a freelance role.

For me, every year of freelance has looked different than the one before it based on my attitude, my finances, my clients, my accompanying lifestyle.

That’s what most freelancers love about their work. It evolves along with them. It is never finished. I have a long list of things I would love to be doing in my business, each of which will bring a new facet or layer to my work.

The fluidity of freelance can be frustrating and nerve-racking, but it’s exhilarating too. Time never drags; my days fly by.

You can travel while working remotely, but to grow, staying in place is best.

I freelanced full-time for eight months in NYC before I took it abroad. From September 2018 to August 2020, I traveled to Mexico, Cuba, Guatemala, El Salvador, Honduras, Nicaragua, Costa Rica, Panama, Colombia, Peru, and Chile. I moved every two days to three weeks, expect for the last 4.5 months, which I spent in Coyhaique, Chile, and I worked on my laptop the whole time.

I maintained my existing clients but never attempted to get new ones. It wasn’t until I came back to the States to live in my parents’ house during the pandemic that I had endless time to take online courses, create an online presence, and build my client roster.

I never would have had the time (or the desire) to do that as a backpacker. Staying on one place was the only way to focus on it. (And my income doubled from 2020 to 2021 as a result.)

Contracts come in handy before you even use them to take legal action.

  1. They filter out questionable clients.

Once a person contacted me out of the blue to hire me for a project I had never done before. We talked on the phone and she was pleasant, although she seemed slightly unsure of what she wanted. We sent several emails back and forth before agreeing to collaborate.

I sent her the contract and never heard from her again. I consider it a blessing!

2. They help you nail down specifics with clients.

It’s impossible to complete a project well if you don’t know exactly what you’re supposed to be doing. Adding all the project details and expectations to the signed contract encourages each party to be clear.

If you’re writing blog posts for someone, talk about word count, deadlines and frequency, time/pay limits, pay rate (flat fee or hourly?), the onboarding process (will you do a trial period with the option to go your separate ways if it doesn’t work out?), style and voice…everything.


Your relationship with the people you work for will fundamentally change for the better.

I may not have coworkers anymore, but some relationships with my clients border on friendship. Two clients have been with me for nearly six years, and a few more are approaching two years.

By freelancing, I knew I would never have to be pigeon-holed into one role. But I never realized how my professional life would improve by collaborating directly with clients.

As a freelancer, I see the impact of my work. When clients appreciate my contribution, they tell me so. Sometimes when I’m experiencing some imposter syndrome, I read testimonials from clients and am reminded that I’m very good at what I do.

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Jaime L. Brockway

Copy editor with 10 years’ experience. Former National Copy Chief of Time Out North America. Semicolon lover, despite what Kurt Vonnegut said.