10 Lessons Learned from My First Freelancing Client (who was both My Worst and Best Client)

Last Updated on: June 24th, 2021

 10 Freelancing Lessons I Learned from My First Client

I wrote this post when I was asked to contribute to a round-up post by a fellow freelancer. I was asked about my first freelancing client, and how I got the gig.

As I wrote my response to her, I realized that I had A TON of things I could share!

So, I shortened my response to her and wrote this post!

About Me and My First Freelancing Client

I’m a freelance writer and editor (for hire), and I’ll never forget my first freelancing client.

It was Greg Narayan from Dear Blogger.

He was both my best and my worst client. In this post I will explain why.

I will also explain what lessons I learned from him.

These lessons will benefit any content writer who is a freelance blogger!

Do not make the same mistakes I did. Instead, read about and learn from my experiences.

How I Met My First Freelancing Client

Back in 2013, I was a newbie blogger.

I followed many blogging blogs to learn more about blogging.

I read SEO blogs to learn about SEO.

I made sure to leave insightful comments on each post I read.

Dear Blogger was one of the blogs I read faithfully. I subscribed to his site. Back then, Greg posted really awesome, helpful content.

But… the one thing I noticed was that Greg had no posting schedule.

I recall that I couldn’t wait to get an email from him, notifying me that a new post was published, because his posts contained a lot of useful information. I learned a lot from Greg.

Dear Blogger's logo

When I left comments, I tried to really connect with Greg. But I also used many emoticons in them. As a result, most of my comments ended up in his Spam folder.

this is a screenshot of Greg indicating how WordPress kept us apart

Somehow, I caught his attention.

Maybe it was all the emoticons I used!

We began talking.

He ended up offering me a job.

The Different Freelancing Jobs I Did For My First Client

Greg created a hired position for me as a Social Media Manager. We signed a contract that he prepared. Together, we revised it, came to an agreement, and then we signed it.

Initially, all he wanted me to do was send out Tweets to my own Twitter followers 5 times a day. Tweets to his posts on Dear Blogger. I was happy to do this, as I loved his content. I was paid $5 a day.

In a sense, I was doing virtual assistant work for Greg. (Learn how you can become a high-paid virtual assistant!)

Around the same time that all this was going on, I was trying to land some guest posts on popular blogs. My goal was to eventually write for Make A Living Writing (which I did) and also Problogger (which I did). I was even paid for one of those posts! (Can you guess which one?)

I also tried to get published on one of Jon Morrow’s blogs, Boost Blog Traffic, which has recently been re-branded as Smart Blogger. (Jon is also the editor of Copyblogger… and an amazing man who has a terrible disease. His Spinal Muscular Atrophy, however did not prevent him from fighting and becoming one of the top bloggers and one of the best blogging teachers in the world!)

I created a post that was rejected by Jon Morrow’s (then) assistant, Marsha Stoppa. I was told it was not good enough. Yet, in reality, it was great! It was one of the best posts I had ever written… as a newbie blogger.

I talked to Greg about this experience. He read the post and suggested I turn it into an e-book. He said we could sell it right from his site.

I was thrilled! At least someone believed in me… even it wasn’t Mr. Morrow!

He granted me access to one of his accounts where I could create an e-book cover. He trusted me that much.

20 Blog Post Must-Haves ebook cover

We tried selling it on his blog. It sold a few copies, but not as many as I’d hoped.

I was disappointed.

In the end, I decided to use this ebook as a freebie on my own site, to give away to my blog subscribers. I still use it, and have updated it a few times over the last two years.

(NOTE that you can STILL get this book for FREE.)

Eventually, through our communications, Greg noticed my talent for both writing and editing. (I am an English teacher, after all.)

I asked him if I could guest post on his blog.

He had not allowed anyone to do this before, and so I was ecstatic when he gave me the chance. I was the first person he ever let guest post on his site! (I was also the first person to guest post on MadLemmings!)

Greg liked my style of writing so much that he asked me to write a post each month for Dear Blogger.

Back then, I was paid $50 per post. I did not have a word limit assigned to me. I could write to my heart’s content. I had complete freedom. I loved it.

Greg also hired me to edit his writing. I was paid more handsomely for that, but, since I was new to freelancing, I had to figure out what to charge. I created a page on my (then free) website and listed my rates.

I’ve since raised my rates a couple of times. Being a certified English teacher carries some merit, after all. 😉

10 lessons learned from my first freelancing client

The Pros and The Cons of Having JUST One Client

Eventually, I was doing three jobs for Greg. He was my only client back then.

After a while, he became very needy. He expected me to be there at his beck and call 24/7.

I felt like I was being taken advantage of.

I also thought I deserved a raise for all the great work I was doing, so I asked for one.

I got it.

A part of me wished I would’ve asked sooner!

In the end, I resigned from the Tweeting job. I was tired of sending out the same Tweets to my followers all of the time, and I wasn’t growing my social media presence as fast as I wanted to.

I also learned that my time was much more valuable than that!

Greg sort of got mad. But he saw things from my point of view. He also saw my growth as a blogger, and complimented me on it.

I worked for Greg for about eight months.

Overall, Greg taught me a lot.

Not only did I learn about blogging, I learned a bit of code, too. Plus, I learned some very valuable lessons as a freelancer!

What I Learned About Blogging and Coding

I learned coding skills.

I learned how to create boxes to put around text, or to put text inside of. I also learned how to make solid borders as well as dashed/dotted ones.

I learned how to highlight text in my blog posts.

I learned how to change the colors of both the highlighted text and also the colors of the boxes, using hex code, and can combine them, too!

I learned how to create page jumps (and you can learn, too, if you follow the instructions in this tutorial post). I used these page jumps in  my web hosting guide. It took me FOREVER to do this!!! (Btw, I hate code…)

BUT… for a non-techie like me, learning all of these things was a huge accomplishment!

I also learned how to cope with massive amounts of email notifications.

However, towards the end, I was no longer happy working for Greg. Things had changed. He was not reliable. In a sense, Greg became “the client from hell.”

He was needy. He didn’t treat me with the respect I deserved. He was also very hard to get ahold of sometimes. He ended up ignoring me. I felt like I was wasting my time working for him.

I struggled with my mixed feelings about Greg for a long time before I decided to resign.

When I did, I felt as though a huge weight was lifted from my shoulders.

And I have NO REGRETS.

I learned a lot from the whole experience of working for him.

10 Freelancing Lessons Learned from this Client

1: Ask for a raise when you know you deserve it.

(Here’s how to ask for a raise from a client and get one.)

2: Taking a break from blogging and freelancing is necessary.

(Here’s how to take a blogging break.)

3: Communication and setting boundaries is extremely important.

If you don’t, your client will walk all over you.

4: Being available to your client 24/7 is NEVER a good thing.

However, being prompt with your email replies IS.

That’s how Elna Cain managed to land one particular client of hers, which she revealed in How One Simple Thing Turned Into $1k of Freelance Writing Business.

NOTE: Elna teaches you how to Write Your Way to Your First #1K.

5: Setting deadlines and meeting them is essential to success.

If you don’t give yourself self-imposed deadlines (which I HAD to do with Greg, because he was so flexible and didn’t tell me what he needed or when), you will never get ahead.

Greg didn’t care when I gave him my monthly post. I could have given it to him on the 5th, or the 25th. It didn’t matter to him. BUT it mattered to me!

6: Your clients will wear on your patience.

You need to learn to let things go. You also need to learn to separate yourself from the job and not let it consume you. It’s just a job, and you need to make time for leisure in your life, too!

7: Sometimes you will care more about the job than your client does.

Your gig means everything to you, but not to your client! You need to stop caring so much, and treat it like the task that it is.

8: Clients will not always see things from your point of view.

It’s up to you to convince them what is best for them, especially if they don’t know. Not everyone has your knowledge. They have their own. Often there is a big difference in the skill set you each possess.

Even though I was a new blogger, I learned a lot from all the blogging blogs I followed. Greg didn’t practice what these pro bloggers preached. It was up to ME to educate HIM. (Yes, the roles ended up being reversed!)

9: Clients will try to control you by withholding your pay.

While Greg was generally pretty good about paying me promptly for work done, I sometimes had to remind him to do so. I now require payment up-front in most cases. I also encourage potential clients to order directly from my website.

I like being surprised with emails from people who have pre-paid for my services!

Email from a client who ordered my editing services

10: When you are unhappy with a client, it’s best to simply drop them.

No amount of money is worth the stress “a client from hell” can cause you.

My mother always told me to choose a job that I like doing, that way I would never have to work a day in my life.

She was right.

I love writing and editing. I love words. I love blogging. I love helping others.

But I don’t love all my clients.

Just most of them. 😉

Your Turn to Share a Freelance Client Story!

Tell me in the comments about YOUR first freelancing client. Did you learn anything from him or her?

Let’s share stories… and learn from one another!

And if you want to get started as a freelancer, or learn how to move your freelance writing career forward, you should definitely take Gina Horkey’s course: 30 Days to Freelance Writing Success!

Learn more about this course RIGHT HERE!

10 Freelancing Lessons I Learned from My First Client

Did You Know You Could Become a Freelance Editor?

Being a freelance editor, in my opinion, is even better than being a freelance writer. First of all, it pays more. Secondly, it is the best job I could ever ask for. I love editing, I love words, and I love helping others. Finally, I love reaping the many rewards (check out the many benefits of being a freelance editor).

If you are not currently working at your dream job and want to be a freelance editor, then sign up to get on the “interest list” for my upcoming course!

I am in the process of designing a course that will teach you EVERYTHING about being a work-from-home editor and entrepreneur.

This includes:

– how to get paid up-front… ALWAYS! (before you do any work)

– how to get testimonials

– how to market yourself

– where to find work

– how to leverage social media for your business (because, YES, you will be actually running a business if you are successful!)

– how to keep accurate records

– how to easily calculate your costs

– how to communicate with potential clients so they turn into ACTUAL clients

– how to organize your time (so you can complete all of the tasks involved in running your biz)

– how to deal with difficult clients

– which projects to accept

– when to raise your rates


Plus, I want to get to know you so that I can give you EXACTLY what you need to succeed!

So, DO you want to know more about how to become a freelance editor?



14 thoughts on “10 Lessons Learned from My First Freelancing Client (who was both My Worst and Best Client)

  1. says

    Hi Lorraine,

    It’s my first time visiting you – and I just loved this post 🙂

    I worked with a client a few years back. She hired me on Elance (now Upwork). She mentioned her budget was below what I was asking (by half), but said that if I was willing to try it out, the rates would go up soon – as her blog took off. Being that I liked what her blog was going to be about and the work wasn’t too challenging, I accepted.

    Unfortunately, she not only didn’t pay me, she also skipped out on a couple of the other writers. I hadn’t installed the tracker, so there was nothing Elance could do other than shut her account down (which they did).

    It’s too bad when it works out that way, but these people are out there.

    I enjoyed reading this. Filled with valuable info. I pinned it for reference and I plan on revisiting.

    Great to meet you, Lorraine.

    • says

      Hi, Dana. It is great to meet you, too! (Thank goodness for our mutual Facebook friends!)

      I enjoy connecting with other freelancers. You never know when a writing assignment mught come your way that you don’t want… and it’s good to be able to pass it off to another writer! 😉

      Plus, you get to share stories about your experiences, like you did here.

      It’s too bad you had such a horrible time with that client! Geez. Some people have no scruples. Such a shame.

      I look forward to getting to know you better, Dana. 🙂

      Thanks for stopping by!

  2. Hi Lorraine,

    Thanks for sharing your experience with us. This goes to show we can always take a bad experience and learn from it – it’s how we grow.

    My first eBook didn’t do as well and I ended up giving it as a free gift too. I’m actually working on my second one in hopes this one will do better.

    I didn’t know using emoticons could drive our comment to spam…I love using them. 🙂

    You’ve shared valuable information new freelance writers should know – especially the lessons you learned.

    I’m passing this along!

    Hope you’re having a great week so far.


    • says

      Cori, we all go through phases of learning, especially when we are new to something!

      I am glad your comment came through. 😉 However, you only used ONE emoticon. LOL So WordPress and Anti-Spam must know that we are good friends. 🙂

      Thanks for sharing this, too! I appreciate it!

      Good luck on your second book. 🙂 If you want help self-publishing it or making it available as a print book, let me know.

  3. My first comment would have been brilliant but your blog was down and then my power went off; comment gone. lol

    What I think I remember saying is that I had to drop my association with one of my early clients because she only complained when I didn’t give her things the way she wanted them, but she never actually told me how she wanted them. I allowed it to go on for 7 months before I realized we weren’t going to work well together and sent her an email telling her I was done. She never responded, and that was that… until I ran into her at a convention 8 years later and she acted like none of it ever happened; people can be strange lol

    I’ve dropped other clients also; that’s the beauty of being self employed but also the scary part because you have to find someone else to replace that lost income. Still, I’d rather do that & be happier than I would be making money from someone I either didn’t like or respect.
    Mitch Mitchell recently posted…How Are You? Life And Blogging

    • says

      Mitch, I would rather work with people I respect, too!

      However, it’s not always the case. Sometimes we are hired to do a job by people who have a ton of money to spend who also have little or no respect for US.

      Thanks for dropping by AGAIN and commenting. I had some issues with my site recently when my host moved servers. These issues were a one-time thing. All is well now, and should remain so from now on.

    • says

      Elna, the post I remember writing that I didn’t like (after I was freelancing for a while) was about insect farming, of all things! I had no idea what this even was before I began my research! So I totally know how you felt when you wrote about gas prices. LOL

      Oh, the things we do just for a few bucks!

      As for turning a semi-bad situation into something positive, I generally, as a rule, try to find the positive in ALL situations.

      Thanks for stopping by and commenting. I always love interacting with you. 🙂

      Hopefully we can meet for coffee again soon, too, before the end of the month!

  4. Dr. Johnny Velazquez says

    Great post, Lorraine. Much to learn, and also when to say enough, in order to maintain one’s sanity. I have also had clients from hell. There comes a time when one must decide his/her own future, instead of going with the flow. Good read. Blessings.

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