I Went Freelance Full-Time Before I Was Ready, Here’s What Happened (Part I)

This is a long one folks, but it is a crucial read. Enjoy laughing at my mistakes, especially before making them on your own.

As per the title, I entered the Wonderful World of Freelancing. It was February 2016, less than two years since I graduated college. I was ready. I had non-profit, start up, and corporate experience under my belt. I was over working under a manager, having to go into an office and clock in every day, and feeling like I was a child still in grade school having to track each task I did online of every waking minute of my work day (yeah, I actually had to do that). I had a number of clients lined up and was ready to do my own thing in the design world and take on whatever obstacles it threw at me!

Or so I thought.

Truth is, I got my ass handed to in this new world of freelancing. My fundamental skills were there along with the talent, but I was not prepared in many other ways. Here are the following speed bumps and road blocks I hit during my first six months of freelancing full-time:

1. I didn’t possess the business background that I needed to thrive in this work environment. While I wasn’t completely in the dark about contracts, and did put them together, I missed out on some key points to include within them, such as kill fees, rush jobs, and revision limits. I was also not strict on enforcing the contracts in general, which allowed for clients to take advantage of me and my time.

2. This brings me to my next point, I had a weak backbone. Naturally a people-pleaser and pretty easy going in general, I was also easy to take advantage of. I was young and still fresh out of college, so I was willing to bend my rules for clients. I had this false idea in my mind that I was lucky enough to get the experience.

NOT TRUE and not a great mindset to start out with.

Let me include a personal experience to drive this point home.

A start-up I was working for at the time referred me to a client who needed a logo created for her business. We met for the first time over a Skype meeting on a Friday to discuss the project and her goals. Somehow during that meeting, I was convinced to essentially sacrifice my weekend to whip up a final logo for her by that following Monday, all for a fee no more than $100. I had warned her that with that limited amount of time, I could only provide so much since research had to be done, sketches, and variations to be explored, none of which allowed for time for feedback in between. Needless to say, she wasn’t happy with the results, and chewed me out over the phone for not having the logo done to her liking.

But the horror didn’t end there. I was then persuaded to work on her original god-awful logo that was created in Word, and the only version of it that she had to give me was an uneditable JPEG of course, because what else would it be after all the previous luck I was having with this client from hell. And I was to do it free of charge, mind you. Do not give your time to clients you do not vibe well with. In other words, if clients set parameters that are tight and demanding, with inflexibility and an inability to understand the design process or respect your time, do not work with them. Do not work with clients from hell!

3. I didn’t set boundaries with my time. It is sad for me to admit, but I put up with far too many clients who talked down on me, expected things right away or with a rush deadline, and was never compensated appropriately for it. However, this is not their fault, it is mine. I was not clear on my work hours and when I would and would not pick up the phone. I responded to emails promptly, which was great, until they realized that they could get me to do a task during dinner hours. People will not respect your time if you don’t respect it yourself.

4. Clients ghosted me. You know, that new age term for leaving you in the dust without a word or warning. I had a couple clients do this to me during those six months, one of which I never expected it from since we were previous colleagues and friends, and the project seemed to have been going well. I’m still not quite sure on the specific reasons for why they decided to go cold, if it was because of me or due to internal reasons within their company, but it didn’t feel good. The best way to combat this behavior is to always be in constant communication with your clients and follow up on a regular basis. But first and foremost, always have a contract signed and set in place!!

5. I was not strict on my rates. I was scared of not getting enough clients so that I could keep a constant income, so I became incredibly anxious when the topic of rates came up. I would dodge the topic, put off answering when the client asked over the phone (which you should still actually do, by the way. More on that topic in a future blog post), and stutter or just plain not sound confident when I told them my rates. Of course, looking back, I was way undervaluing myself and lowering my rates in order to win over a client. Today, I have learned to price my work appropriately and stay firm on it, and you should do so too.

6. I struggled, struggled, and struggled HARD to say “No.” I dealt with guilt if I said no to a potential client, but then resentment later for that client because of my false yes. There is no winning this situation if your heart is not in it. Your work will suffer, and your client will not be happy. Do not take on work just for the job. If you are not passionate about it, do not have a good feeling about the client relationship initially, or are not satisfied with the compensation, it is okay to walk away. Say NO.

7. Let’s face it, I became lazy. Waking up, putting on my robe, and sitting on my couch wasn’t the best office setup for a motivational workday. Sure, I went to coffee shops and the library from time to time to spice things up, but I definitely had my days of lounging around. No one is there to tell you what to do, you are your own motivation and disciplinary, and that can be really challenging at times. It is actually one of the main contributing factors as to why I decided to work in-house again. You just have to make sure that when you do decide to freelance full-time, that you have the space to do so and will stay in work mode because of that environment.

I didn’t mean for this post to come off entirely negative, but I must admit that I did have fun writing it and reliving those painful yet educational experiences. Next week, I will write a part II to this post recounting all the great lessons I learned from freelancing and all the positive aspects of it, because there really are many amazing aspects to working as your own boss. If you made it to the end, I applaud you and would also love to hear any freelance horror stories of your own if you have them to share in the comments below.

Until next week, happy designing and freelancing!


Cover photo credit to Gratisography. (Love his work, and you will too.)

Nicolette Shasky

About the Author | LinkedIn
Nicolette Shasky is a creative soul with a specialty in visual storytelling and UI/UX Design. She currently works as a Visual + Analytics Designer at Interactions Marketing in San Diego, California.


  1. YaksterX says:

    Same here. Working freelance or having your own business is rough specially when you get comfortable. The part where others walk all over you is also a step somewhere in there, and not knowing what to charge or when to put your foot down doesn’t make things easier.

    But the funniest part is the feeling of “Yo look I am my own boss” for the first few weeks-months.

    Hope more people read this so they don’t think it’s easy stuff and actually prepare themselves better.

    /thumbs up

    • nicoletteshasky says:

      Hey YaksterX,

      Definitely, freelancing is no joke. I had a good run for 6 months before I got picked up on contract work, but I learned a ton. I’d go back to the lifestyle in the future, but now I know how to move forward from my past mistakes🤓 Thanks for reading and glad to hear you can relate! Have an awesome day!

  2. Orysya says:

    Really great post! I appreciate your honesty and willingness to learn from all those experiences, I am sure you have become a better designer because of it!

Leave a Reply

%d bloggers like this: