I Quit the Best Job I’ve Ever Had, and Here’s Why

Freelancing wasn’t exactly as freeing as I had expected


I quit my job - tiff and coco - tiffandcoco.com

In 2017 I took what was honestly the best job I have ever had. The pay was fair, our benefits were good, and the work perks were amazing. My bosses were understanding, honest, and candid about the company and my position in it. They allowed me to work at my own pace and if ever I needed to I could work from home. Sick days weren’t questioned and mental health days were understood.

Not only did they care about us personally, but they truly cared about our professional welfare as well. They provided me with ample training to do my jobs well and stay abreast of industry trends. They also allowed me space to spread our wings and pursue the things that I was passionate about.

On the surface, it truly was the best work situation a person could ask for, but I wasn’t happy. The more I stayed there the more unhappy I became. It wasn’t anything that my boss or coworkers were doing, but after a while, it was like my body began physically telling me “you’ve gotta go.”

This feeling drove me to begin questioning everyone I knew about how they felt at work and what their true aspirations were. I would literally just pull up on people and ask: “Do you like your job?” “Was this what you always wanted to do?” “Are you happy?” And, more often than not the answers would be no.

It was disheartening and scary to know so many people were living life the way they HAD to because they never took the time to seriously pursue the things they WANTED to do.  They were just going through life instead of actually living it. As I sat at my desk watching my bosses manifest their dreams before my very eyes I couldn’t help but wonder why I wasn’t working on my own. Every day working for someone else felt like my dreams were slipping away until I finally decided now or never.

The timeline

  • Quit my job to full-time freelance in 2017
  • 2018 got offered a full-time position in a completely different field, which like an idiot I took, and freelanced part-time
  • October 2018 went back to full-time freelance
  •  Feb 2019 became 9-5 shawty again creating a few dope things around the city

What I did

When I quit my full-time marketing job I started freelance digital marketing, social media management, and brand management. For the most part, my clients were entrepreneurs and small business owners. I started out working with people that I knew from previous events and partnerships, and from there got more connections and was able to grow my client list.

What I loved

Becoming a freelancer allowed me so much freedom. Through freelancing, I was able to find my voice. I got to work with a variety of clients who trusted me as a professional and respected my suggestions. For sure not all of them were perfect, but even the tough ones challenged me to stand up for myself and demand a certain level of respect.

Another major perk of freelancing was setting my own schedule. I tend to catch my tempo around 10 p.m. as a freelancer as long as I was good about communicating and setting proper deadline expectations I could work whenever I wanted from basically wherever I wanted.

I also got to experience a lot of first as a freelancer. In 2017 I took my first flight and left Nashville for Puerto Rico. It was absolutely terrifying and amazing all at the same time. I also got to go to New Orleans for the first time and vibe out on a few rooftops, coordinate my first fashion show, create promotional material for some amazing brands, and a couple things I won’t mention here lol.

So many of the things I got to experience as a freelancer seemed out of my reach once upon a time, and crossing them off of the bucket list was truly life-changing.

What I hated

Whew chile’ if I went down this whole list it would take way longer than I truly want to spend on negative things. The two main things I hated about being a full-time freelancer were lack of respect and money.

Unless you have a banging portfolio and a certain level of access finding clients willing to pay freelancers top dollar is HARD! Basically you’re in competition with companies who have teams of people and proved case studies that make it easy for potential clients to see their value.

In addition to finding and securing new clients, getting my current clients to pay me and ON TIME was an additional pain in the ass. As I mentioned many of my clients were small business owners and entrepreneurs. As a fellow entrepreneur I completely understand the ebbs and flows of income, however, there’s not a person I know who does high quality work for free. Collecting payment became hard because not all of my clients had me in the same rotation as their regular bills. To them I could always wait. I could always be paid last.

In addition to the lack of respect when it came to payment my time wasn’t always respected either. I’m not always great about setting boundaries, but my time is something I try hard not to waste. I made it clear to all my clients how I expected them to submit work requests, what a proper request time frame would be, and that unless there was an emergency all requests would be completed in the order they were submitted.

Most of my clients were fine with this because it made it easy for them to set schedules and complete projects, but there were a few who didn’t take anything I said seriously. Requests would come in via broken text messaged or 10 pm phone calls requesting a 24 hour turn around. The lack of preparation on some clients part was placed on me with urgency and they would be upset when I couldn’t complete their last minute tasks.

What I learned

  • When things aren’t serving you and your best interest get up from the table. No matter what.
  • Set boundaries early and don’t waver on them.
  • Be understand, but don’t be a fool. Business is always business.
  • Don’t let anyone make you feel bad about the work that supports your side hustle.
  • Map out your business plans as far as your mind can comprehend and them go a little further.
  • Don’t forget about your dreams trying to help someone else actualize theirs
  • Know your worth and add the tax.

Why I went back to 9-5

I’ve gone back to working for someone else full time for a few reasons. Number one, my priorities have changed. What I thought I wanted in 2017 is far from what I want in 2019. I love digital marketing and brand management but not the way I thought I did. I still want to work for myself and have set the foundation to do that, but what I’m doing now is much different that what I was doing them. I’m more focused now and I’ve grown a lot which meant doing what I have to do in order to do what I want to do. Second, freelancing wasn’t funding my dreams the way I needed it to. I found myself spending way more time working on other people’s visions and not enough working on my own. The worst part was that I HAD TO in order to pay my bills. I was maddening. Third my bosses are amazing. I am now back to the job I left two years ago and happy. My bosses know my true passions and support me in them 100%. They two are entrepreneurs and know the side hustle struggle all too well. So, here I’m able to have stability and dream chase all at the same time.

Share your entrepreneurial stories with me in the comments. I’d love to here your thoughts!

Lifestyle blog- Nashville TN- TiffandCoco

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