What’s Hot with Lena

Episode 6:
The Realities of Working For Yourself

Freelance does not equal free time


Written by: Magdalena O’Neal

---

February 22, 2024

I could spend every week writing this and finding six ways to Sunday to explain that I am T-I-R-E-D. Alas, I try not to complain about a life I once prayed for.

This week I am going to bore you with the intricacies of what it takes to be a full time freelancer and not unalive yourself due to the invoicing, workload, (lack of) payoff, and recognition that comes along with the task. Then, I’m going to share some things that are H-O-T right now from a young legend to us all!



I started freelancing full-time about three years ago after quitting a job where I was being limited within the company due to race and gender. I wrote the best piece of writing I have ever produced (my resignation letter) and only questioned the decision to leave every day for six months before I felt solid in my decision.

When I first quit, it wasn’t with a plan to freelance forever. I knew the ripe age of 26 was encroaching and that I would soon need health insurance and was notoriously bad at invoicing on time so I thought I would get a new job quick and easy no problem. Obviously, that didn’t happen.



It didn’t not go as planned because I wasn’t capable of getting another full time job, but instead because I realized I wasn’t built for that kind of work. I have always been multifaceted and also suffer from undiagnosed ADHD, so working just one job never felt good enough.

I was a double part time job girl or a full time with a part time on the side kind of hustler. If you ask my dad why I am this way, he will tell you it’s because I have an incredibly expensive lifestyle that nobody else is going to pay for (and he’s not wrong). But if you ask me I will tell you that it is more fulfilling to do everything than to suffer from career FOMO later down the line (and I have a very expensive lifestyle).



Since going full time freelance I have worked doing everything under the sun. As a line cook, a food stylist, food writer, caterer, Jell-O maker, culinary producer, personal assistant, editor, dog walker, you name it—whatever means I can waltz into Whole Foods and buy whatever spices my hungry heart desires, I will do. Freelancing is not for the fainthearted or those with a limited skillset. It requires adaptability, fear of the unknown, a little bit of delusion, and a lot of personal overtime.

I say all of this to say, this past week I cut back my workload for the first time in a year and a half and I feel fucking uh-may-zing. I have been working as a freelance branded content editor five days a week for over a year at a distinguished media company, and after a few months of working while living abroad I realized I actually hate my daily tasks.



The work isn’t hard and my boss is the best boss I’ve ever had (outside of Chris who edits this column every week) but I have reached a point in life where I want to find comfort in saying “I don’t want to do this anymore.” Now, saying that doesn’t mean I just quit jobs with no back up plan, I decided about a month ago and spent the last four weeks securing new contracts, creative projects, and making sure the lights are going to stay on at home (I don’t actually have a home right now because I’ve been living nomadically for the last four months but you get the jist).

I find that a lot of my freelance friends are stuck in a cycle of not being able to leave their comfort gigs even though they can’t stand them. How do we find the freelance equivalent to having our dream job/s? Sometimes I get a gig that is my dream to do and then I do it and it’s done and I’m left like the boy with the soup bowl “Please sir can I have another gig?”

I ask this as a serious question and I want any and all freelancers out there who have found success and comfort in knowing all the gigs they work are answering their WHY to tell me how it happened and what boundaries they had to put in place. Occasionally, I have all of the answers, but once in a blue moon I have to ask the community for some much needed guidance. I want to know! So I can do it! Tell me your secrets, please?



Right now I am beyond blessed and working on two new projects that feed my creative consciousness in a way I could have only dreamed of. How did I get there? If I’m being honest, I asked for both of these opportunities. I sent texts to the people who hold the keys to the doors I wanted to open and said, basically, “Please sir can I do some work for you?” and they said yes, and now I have to show up and do the damn work. I mean, what would be worse than asking for work, getting it, and then dropping the ball on it? You’d never work in that city again!

My advice for this week: if you’re considering going full time freelance, do it. You’ll only hate yourself and think about ending it all once or twice a month when your bank account is crying and Apple keeps charging you for subscriptions you forgot you had and taking money you needed to survive until your next invoice is fulfilled.



Thrive in the delusion of it all and keep a close enough relationship with your parents that you can move home at any point with no notice if you truly go broke for a few months. That’s it, that’s my advice on how to support yourself. And please, email, DM, or text me with your tips on how you manage to make it as a freelancer and whether or not you are living the dream—I would love to share people's personal insight in next week's column.

Sydney Gore’s
Hot List