6 Things I Wish I'd Known Before Quitting My Job To Freelance


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Jessica Kay10
July 20, 2024 at 3:26PM UTC
I started my professional career in corporate American, and have always thought that that’s where it would end or at least last for a few decades. Earlier this year, after 7 years in marketing, I decided to take the plunge and turn my 3-year blogging hobby into a full-time business.
This wasn’t a decision I came to overnight. Many information interview and case studies, much mental preparation and financial preparation led to this weighty decision that affects me, my career, my family, and my husband’s world. So, in many ways, I was prepared for the irregular income, lifestyle adjustment (no more shopping budget!), the test on my time management and self-motivation skills, and lastly, the lack of every day coworker chats. Before I quit my 9-5 job, I spent a lot of time crafting what my eventual everyday work schedule would be like and define weekly and monthly goals that I’d like to achieve. I thought in every way I was prepared. And in some ways, I was as prepared as I possibly could have. There are things in life that without experiencing it firsthand, you will never thoroughly understand.
After almost 4 months of the freelancing, full-time-blogging life, I have definitely noticed a few things about the freelancing life that I wasn’t anticipating. Here is a list of things, despite my preparation and research, I wish I had known before I quit my job to freelance:
1. Nothing happens if you do nothing all day and just watch TV. 
Really. You should try it. I certainly did. And at the end of a day with 5-8 hours of TV watching, no one yelled at me or checked in on me with a “what the hell did you do” look on their face… and I wish that was the end of it. My conscience and guilt would not shut up and they basically personified and yelled at me for the lack of productivity. It scared me.
2. It becomes just a bit harder to explain what you do. 
When you order coffee at a hip café on a Tuesday morning at 10:30 AM, dressed in yoga pants and a t-shirt, and people ask you “so are you in school?”. The first time it happened, there was a moment of awkward silence because my thoughts went from “aww, they think I’m still in school” to “wait, but how do I explain what I actually do”. And when I explain that I work from home and work on my blog, then these questions inevitably follow: “oh, what is your blog called” and “do you have a lot of followers?” with the first being much easier to answer than the second. I was not prepared.
3. Work-related stress and anxiety take on entirely new meanings. 
The stress and anxiety I feel these days are caused by abstract and intangible things like my self-imposed goals and lack of productivity. I can’t say that I will choose the corporate company kind of deadline over this yet (although it could change) but it’s surely a different kind of stress that I haven’t experienced before.
4. Personal to-do’s and work-related to-do’s start to merge. 
Because I now work from home, many things that I “have to complete” for the day start to blend together. “Complete 2 blog posts” and “finish laundry” are side by side on my to-do list. It was a big problem for me initially. The system I developed to combat this issue is to divide my to-do lists into a “home life category” and a “work-life category”. This way, I know how much progress I am making in each perspective areas.
5. You’re the only person that is responsible for progress and meeting goals. 
This sounds pretty self-evident and like something you would naturally expect. But when you have no performance review, weekly 1:1’s, 3 layers of management on top of you and all of their expectations for your greatest performance, things are a little different. In psychological terms, instead of extrinsically motivated, you have to be intrinsically motivated. As it turned out, switching gears in the way I find motivation has been harder than I anticipated.
6. Is “Water cooler conversation” important to you? 
As I alluded to at the beginning of this post, I was expecting this to be a big change in the social aspect of my work life. I understood how things would change. What I hadn’t realized was how seriously it was going to affect me. I am an inherently social person. I have found social influence to be stronger than financial influence in terms of what motivates me. Let’s put it this way, if you paid me $100 to go to an event, I will go. But if you told me that 3 of my friends are going to the event, I’d go for free. I thought when I transitioned to freelance on my own, my clients, other entrepreneur friends, and friends that worked from home could all be my social network through the internet. But the internet is still the internet, and social interactions IRL person has proven to be irreplaceable.
Ultimately, your lifestyle, personality/maturity, and financial status have to all align in order for this transition to be meaningful and productive. And don’t be surprised if you find yourself missing your old work structure, co-workers, deadlines, even meetings.
Jessica is a writer, a digital marketer, social media aficionado and a lifestyle blogger at Cubicle Chic. Through her writing, Jessica aims to connect with fellow corporate 9-5ers who may be bound by an office physically but crave for much more in life. She writes blog posts about inter-office politics, how to climb the corporate ladder, resolve interpersonal conflicts, and how to do it all in the best outfits possible. Jessica lives in sunny San Diego with her husband and two cats, Lulu and Miles.

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