My Worst Freelance Gig Taught Me Some Shit

I was thrilled and excited… then I was verging on an emotional collapse.


Georgina Pinou

3 years ago | 10 min read

Fresh out of a 3-year job that wore me out emotionally, I felt a new sense of relaxation wash over me.

I was excited and enthusiastic about the clear open path ahead. This path, although unsettling, would now be the one that I hoped would define the direction of my career.

By the time I left my job, I already had a promising freelance job secured. I had obtained this role through a direct relationship, with the lead designer and president of an independent-fashion company.

*For the purposes of this story, I will call the Designer and President, Tonya.

I was ecstatic. The role remained in the same industry as my previous employer, and this was something that I was truly grateful for.

It wasn’t for my lack of love for the industry that led me to move on from my previous job, but rather a lack of new opportunities and growth.

I actually had hoped to start my own business within the fashion industry. I saw this freelance position as my golden ticket to jumpstart the process of gaining contacts and ultimately, building my own agency.

During my first meeting with Tonya*, we mostly gossiped about mutual colleagues. At the time, I thought it was a bit odd since I was supposed to be there to pitch myself for a social media gig, but I just let it slide.

After a few more jabs at colleagues, actually… friends of mine (unbeknownst to her), we got to business and discussed how we would move forward.

She gave me a run-down of her company and previous roles in the industry, and I responded with examples of work I had done in my career. We both agreed that I could play a pretty large marketing role, helping her to grow and develop her brand.

Everything she said seemed to tick off a box on the imaginary lists of, “Components of an Ideal Freelance Role” and “Things Georgina can Professionally Offer”.

She worked out of her apartment so my role would be remote. Check.

She needed someone to handle her email marketing, social media, and branding plans. Check.

She needed someone in the industry with press contacts. Check.

She needed someone to assist with photoshoots and uploading new products and copy to the website. Check.

She could pay me $40/hour for a max of 20 hours a week. Double Check.

Lastly, she stated that she was not the type of person to micro-manage. She expected me to take control of my tasks and really bring a fresh perspective. Triple Check. Golden Star… whatever. You get the point.

I was so ready to get started working with her, I went out to Staples to get some new color-coded pens and notebooks for my at-home office.

This was it, I was doing it, I was now officially a full-time freelancer.

By the title, you are probably waiting for when shit started to go downhill. Well, it didn’t take long. My experience working for Tonya, led me down the most emotional and professional self-journey,

I had yet to experience in my life. During this time, I was taught some truly valuable lessons that I hope by sharing, can benefit anyone who experiences a toxic work relationship.

Do not ignore red flags.

As you just read, even during my first encounter with Tonya, I felt uneasy. It felt odd to talk negatively about people I knew, especially when I was supposed to be there for a business consultation.

At the time, I took it as her trying to gauge my knowledge of the industry and its key players. But, now looking back, it truly was Tonya just bitching about people, asserting her stature in the industry with an arrogant manner, and ultimately, downplaying others’ success.

The second set of red flags came within my first 2 weeks of working with her. On my initial start date, she had sent my consult brief back to me with a few areas highlighted that were to be the priorities for the first 2 weeks. She sent over a few logins and passwords and that was it… for a few days.

Her comments detailed that she would provide further materials to get started. So I waited on these assets after following up with her to inquire when I would receive them.

I had no guidance on brand imaging, product collaterals, brand messaging… other than what I could uncover, feverishly scrolling through her website and social media trying to find some insight to guide my work. (Keep in mind… I was doing marketing work for her. All of this is essential to aligning work with a brand.)

It all seemed a bit odd when she went radio silent, but I assumed she was busy. She traveled a bunch for work and I remembered that she said she did not want to micro-manage, so I took the reigns and drove forward with some tasks on my priority list.

Do not let anyone tell you are lazy (assuming you are not).

During my first session, working directly in-person with Tonya, I was excited to hear feedback on several things I had completed for her.

I walked into her apartment and was greeted with a big smile. This was interesting to me… Since, only 12 hours earlier, in response to asking for clarification on something, she had responded in a passive-aggressive tone, that she had too much work to “look after me”.

No matter, I was happy to see that her downgrading attitude seemed to not be present for the moment.

I opened my computer to several files of analyses on her social media and ideas to improve, a 2-week content plan, 3 email flows, and an outline for a brand guide. She pulled up a chair next to me as I began to take her through everything.

First, she was upset because I had “basically said, her social media was garbage.” Which, to clarify, I most definitely did not say in any way. My report showed her low engagement rates across the last year.

With my report, I also had built a new strategy to improve her dismal growth and reach. She wasn’t impressed.

Then, she was upset that I could not sync in all her contacts from her website to the emailing software… although this was set up prior to my time working with her and I truly lack IT skills. As I called the software company to troubleshoot, she rolled her eyes and said: “Can you do something productive while you are here?”

She hated the social media content I selected. The emails were — OK, but something was off she wasn’t sure what. She asked my opinion on the homepage image, then went with the opposite of my response.

Although this was never set as an expectation, she asked with accusatory nature, “Where is my brand guide?” A bit confused, I instead showed her the outline I had created, which had been on the priority list… that she had provided me. We reviewed my branding brief and she changed this to a top priority. She claimed my outline had been “lazy” and she needed to see it in a designed template.

5PM couldn’t come fast enough. I had to get the fuck out of there.

I gathered up my laptop, not a second past 5, and headed out. As I left, she waved and smiled, completely unaware of the fact that I was now on the verge of tears and feeling extremely incompetent.

Do not allow anyone to silence you.

I really thought that after aligning with her in-person, our working relationship would improve. To my ignorance, it was quite the contrary, our relationship was about to enter a rapid decline.

The following day, I got to work on her brand guide. I had finally received what she had created in the past, a simple PowerPoint with brand messaging. Based on this, I paid for and downloaded a beautiful InDesign template on the web (one that I thought matched the empowering-feminine vibe she was going for) and created 3 different layouts.

I sent them over to her and she immediately texted me asking for a call. The speed at which she responded, gives me the inclination she didn’t even bother to read the content I had sent over.

As I picked up the call, I braced for feedback and prayed that it was constructive. I truly wish I remember the depths of the conversation, but when I think back… only a few of her sentences stand out.

“You told me you’re not a graphic designer so why would you think that you would spend your time creating this? This is not good at all.”

What I should have said — “Based on my notes, we had aligned that I would download a template and design you a brand guide based on the assets you sent over.” What I said — Nothing.

“Why would you pick these colors/pictures?”

What I should have said — “Because I am still waiting for the HEX codes of your brand colors, so I based the tones off of your newest collection. The pictures were the only ones that you had sent to me, I am happy to update these when I receive the new files.” What I said — Nothing. (Keep in mind, at this point my eyes are welled with tears)

“How much time did you spend working on this? I do not want to be paying you for work that I can not use.”

What I should have said — “I actually spent 4 hours re-working your past brand guide, re-wording and creating a brand story, creating 3 separate designs with different layouts and colors so, that you could tell me which one you liked.” What I said — “It’s fine, I won’t invoice these hours.”

“If this is the work you are going to provide me, then I can just do it myself.”

What I should have said — “I am sorry you feel this way. Please let me know how we can better align. From the notes I took during our meeting, my work seems to align with our discussion. I am happy to send over a recap of these notes to see where I misaligned.” What I said — Nothing.

When I hung up, I was in full-blown tears. I had not received an ounce of constructive feedback.

Instead, I felt like my work had just been verbally assaulted and my professionalism skills were non-existent in her eyes.

At the time, I thought… clearly, I had been the one that fucked up? I mean… right? To receive a phone call like that, it had to have been the case. I’m someone who never shuts up, but after that call, I was speechless.

Do not let anyone make you question your abilities.

I hit my breaking point, at just shy of a month working with Tonya. After several phone calls that scripted very similarly to the one above, I began to wake up each morning feeling down.

I had just left my job a month prior, and I felt that if I quit my new freelance job after just a month, people would look at me as a failure. I reluctantly trudged forward and continued my strained professional relationship with Tonya.

All the turmoil would now finally pay off at least, I thought, as I submitted my invoice for the previous month’s work. The very typical text came in from Tonya, “Can we hop on the phone real quick?” Reluctantly, I dialed her cell and prayed that suddenly now was not a good time for a call. Unfortunately, she picked up.

On this call, I cracked. Tonya got on the phone and proceeded to ask me…

“What are you even good at? I see that you completed a lot of things at your previous job, but I have had no benefit from working with you.”

“You are cheating me, by sending this invoice. Please review it and subtract some hours… because I am not paying it.” (I had stayed within and slightly below the work hour limit. I am an extremely quick and efficient worker. I was stunned.)

I said… “Fine.” Then I hung up.

A few minutes later, I called back — I gave my notice and that was that.

My only regret in this experience is that I never fully expressed to her, how hurtful and unproductive our time together was. How she had emotionally taken a toll on me. How she made me doubt my abilities and the quality of my work.

I wrote an email expressing all this, but I decided not to send it since at the time, I did not want to create waves for myself in an industry I hoped to still work in.

Although this time was rough, I would not take it back. Her criticism, although hurtful, did provide me some insights into where my skills were lacking.

While I would say that I did give her my best quality work, we did not align on where the brand was going. Through this discrepancy, our partnership was doomed from the start.

Whenever a client or someone at my current job is scheduled to provide me feedback on my work, my heart still jumps a bit in my chest as my nerves build up.

I am happy to say that at my current job, I now thrive on constructive criticism. It is through positive feedback and adjustments that my best work gets completed.

Noone in your life, especially someone you are working together with towards a united goal, should ever make you feel bad about yourself.

Through these experiences, we must learn to effectively communicate when how someone is speaking to us is unacceptable.


Created by

Georgina Pinou







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