8 Lessons I Learned in My First Year of Freelancing

Jyssica Schwartz
Sep 16 · 6 min read

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.

Now that I am at almost 3 years of freelancing, 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.

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.

Pricing yourself is an exercise in frustration sometimes. You do tons of research on what other people are charging, you try to undercut them, but then you may find that the lower price makes it not worth your time.

As a freelancer, time is your commodity.

Whatever you’re charging, it’s too low. I have seen it time and again from freelancers, including myself, where we are charging one price, but then the actual time the project takes is more than we thought, or there is more research involved or the project is longer, and suddenly your “decent prices” are getting you way less per hour than you want.

Charge more. The good clients will pay you for your skills.

And remember: Just because writing comes easily to you does not mean it should be cheap. If clients could do it themselves, they wouldn’t need to hire you. Your skill is valuable.

The clients who email you at 3 am expecting an immediate response, or who are constantly changing the specs of the project. The ones who are never happy.

The ones who harass you about your prices over and over until you offer a discount.

Just say no. It’s difficult to turn away clients, especially when you are new to freelancing, but the hassle and difficulty in dealing with them and the extra time it takes for you, on top of the lower rate, will bring you down. Not only that, but they take away from the clients who would be paying your regular rate and be great to work with and appreciate you.

Here is a piece I recently wrote about how to identify the bad or negative clients before you start any work.

When I first started freelancing, I was doing almost entirely one-off articles and blogs for clients and charging per-word prices.

A year later, I had evolved and changed the work I did as I learned more what I enjoyed and how it makes sense for me. I focused on monthly retainer clients and having long-term relationships with them instead of one-time projects, have developed a book coaching service, and have been able to try things I never thought I would — like writing a comic book!

Now, 3 years later, much of my work is editing books.

Be open to new experiences and allow yourself to evolve and grow and change as the work you enjoy evolves. Do not force yourself to stick to just one type of work. Try new things, get creative, stay interested.

One piece of advice I saw a lot of at the beginning of freelancing was to “just pick a niche and specialize!”

I prefer significant diversity in what I work on, so instead of focusing on one industry or type of client, I chose to be a generalist. This has allowed me to have a ton of experiences and learn new things.

I have blogged for law firms, cannabis companies, business consultants, life coaches, real estate investors, cryptocurrency and blockchain companies, professional speakers, authors, home remodeling companies, and more. I’ve edited fiction, nonfiction, and even children’s books.

As a self-described jack of all trades, I have gotten to explore opportunities I never would have if I’d just stuck to sales, marketing, and career coaching, which my 10 years of corporate experience prepared me for.

Don’t be afraid to try something new and to be a generalist! It’s so much fun having a diverse client base and getting to work on something different each day!

I like to get to know my clients. Who are they? Why do they love what they do? What are they hoping to get out of the writing services?

Creating a monthly retainer business model has allowed me to have longer relationships and really get to know my clients as people.

I have weekly calls with each of my clients to manage expectations, discuss the tasks and work for the week, and stay connected.

Having been in corporate business development for so long, I acknowledge and understand the strength and use of a great relationship with the people you’re selling to.

Really make a point to get to know your clients as people. Ask questions and be kind and genuine. That relationship is so important! Nurture it!

Portfolios are not a bad thing, you CAN have one. But you don’t NEED one to get started as a writer.

As long as you have writing samples, you are good to go. You can publish those samples on a blog or site, or you can just have them as PDFs you attach to emails.

Much of my work is ghostwritten, so even though I have tons of published blogs and articles, none of them would be able to go into a portfolio.

When I first started, I grabbed pieces from my personal blog and wrote a couple of samples, and that is all I had to show. These days I just direct people here to my Medium blog!

The most important thing I learned through my freelancing journey so far is that you don’t need to be super prepared or have a website and business cards and a fancy briefcase.

You can just go out and find ONE client. As soon as you have one, find another.

Figure out the rest as you go. You can research contracts and build a WordPress site later. For now, go out with your writing samples and find a client. The rest will come after.


Jyssica Schwartz

Written by

Entrepreneur, writer, editor, book coach, cat lover, weirdo, optimist. Author of “Write. Get Paid. Repeat.” and “You Are Not Alone.” jyssicaschwartz.com

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