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In 2014, I got abruptly laid off from a job I had just started six weeks before. I was briefly devastated (six weeks isn’t even really enough time to fuck up), and then relieved (the place was toxic, I wrote about that here) and then…
I had an idea!
I had always done some freelance writing on the side, here and there, and I really loved it. I already had a project or two lined up. What if I could give it a go, full time? It seemed like a pipe dream, but also like a dream. What did I have to lose? If it didn’t work out, I could always find another full-time job.
I gave myself a year. I also need to say I am incredibly privileged. I graduated college without debt, which is a huge financial leg up (thank you mom and dad), and I didn’t have anyone to support besides myself. Sure, I lived in one of the most expensive cities in the world. (Love you forever, NYC!). But I was just about to move into a friend’s lovely apartment in Hamilton Heights, which would mean a big cut in my rent, and my work with a cheese company meant a lot of free samples of very fancy cheese.
Since then, I’ve had a few full-time jobs, which came from freelance clients that wanted to hire me full-time. I don’t regret them, but I really love working for myself. I love the freedom it allows me on any given day, the opportunity to explore different kinds of projects with different people, and the chance to dig into my passions. In pre-pandemic times, I loved getting to travel.
Of course, the freelance life also comes with challenges. It’s been a learning curve. I’m still learning all the time. Here are some things I wish I knew way back in 2014:
Pay your Quarterly Taxes
Or else you’re in for a serious bill on Tax Day. I had a sort of breakdown year one—I thought I was being so organized with my finances, and then BAM. Pro tip: QuickBooks Self-Employed is well worth the $12.50/month. I track all my expenses, and it automatically categorizes the business-related bills and estimates how much quarterly tax I owe.
Also, taxes aren’t fun, but I remind myself that paying taxes is a positive thing, because it means I’m making money!
It’s a Small World
Most of my work has come from referrals, one thing leading to the next. I’ve spent a lot of years doing work I feel proud of and delivering on time, the simplest things that help me stand out and build my reputation over time. Then when somebody asks Ms. Marketing Guru if she knows a copywriter, or Ms. Editor if she knows a food writer, hopefully they say, “I have just the person for you!” and that person is ME. This still feels like magic happening, and it happens over and over again. Sometimes somebody I met or worked with years ago will randomly reach out with a new project. I think of my work and my relationships as planting seeds. Which leads to:
Have Some Patience
I am so awful at patience! But all of this takes time. Sometimes, a lot of time. Deep breaths.
Ask for More Money
If a client offers to pay you $200, ask for $250. The worse thing that can happen is they say no. But you’ll never know if you don’t ask!
It’s Always Worse in my Brain
Just the other day, I looked at a sprawling Google Doc from a new client and realized my breathing was getting all ragged and my palms getting sweaty. My brain said, “OMG this is an infinite, insane amount of work and you’ll never be able to handle it.” But one thing at a time, one little section at a time, I’m working my way through. Like Anne Lamott said, “bird by bird, buddy. Just take it bird by bird.” (Also, they’re paying me hourly, so…a lot of work isn’t all bad.)
I Am a Way Tougher Boss than Anyone Else
When it comes to me, at least. I’m unrelentingly hard on myself. Another Ann Lamott quote: “Perfectionism is the voice of the oppressor, the enemy of the people. It will keep you cramped and insane your whole life.” Who needs this? I’ve come to realize that reading something over 17 times is counterproductive. I try to read anything over two or three times, then call it a day.
Rest Is Essential
I’ve definitely internalized whatever part of American culture that says productivity = worth. But I know in my bones it isn’t true. This is one I’m still very much working on. One of the reasons it’s so great to be a freelancer in the first place is that if you need or want to spend the day wondering through the Brooklyn Botanical Gardens or heading to every cheese shop you can find or binging on Tana French novels in bed, knock your socks off.
Every day is not going to be this way, but there’s no big brother that says you must have your butt in the chair, working away, Monday - Friday, 9 - 5. (If that was what you wanted, you could get yourself a full-time job. There’s nothing wrong with this, it’s just not some universal law.) I’ve learned I do my work best in bursts of focus, then I need a break for my brain. Maybe a walk. A latte.
Anyway, you’re your boss, employee, colleague and all the rest. So be a compassionate boss, employee, and colleague to yourself. You deserve it!
I want to hear your freelance stories. I hope you have a beautiful week!
Here I am in Athens in 2016, on a work trip to write about olive oil. (How lucky am I?!)