8 Lessons I Learned in My First Year of Freelancing

Jyssica Schwartz
Write Out Loud
Published in
6 min readSep 16, 2019

I got my first freelancing clients almost on a whim, on October 31st, 2016. I began working with clients in the evenings and weekends for November, December, and January.

Once I realized that being a writer was a viable career for me and people were willing to pay me, I made plans to quit my day job as a Business Development Manager at a recruiting firm.

January 27, 2017 was my last full-time day at my day job.

I was a freelancer.

Though I did a lot of research and asked many questions, I had a lot to learn.

Here it is years later, I want to look back and see some things I learned in that critical first year. I’ve been building on these lessons and learning more ever since.

Use this to learn from my mistakes so that you can not repeat them and instead make new mistakes and learn new lessons. Every failure or misstep is an opportunity for growth.

1. If someone is willing to pay you, then you are skilled enough.

When it comes to freelancing, especially something as subjective as writing, many potential freelancers question their abilities and whether or not their writing is “good enough” for them to be a writer as a full-time career.

Instead of trying to find new ways to judge your writing, use your clients as a barometer. If people look at your writing samples and are willing to pay you, then you are definitely good enough.

Pack away the insecurity and focus on improving and on the work for your clients. There is no point in questioning yourself so much, and that insecurity can lead you to not marketing yourself or not having the confidence to attract new clients.

2. You are definitely not charging enough.

Pricing yourself is an exercise in frustration sometimes. You do tons of research on what other people are charging, you try…

Jyssica Schwartz
Write Out Loud

Entrepreneur, writer, editor, book coach, cat lover, weirdo, optimist. Author of “Write. Get Paid. Repeat.” & “Concept to Conclusion.” jyssicaschwartz.com