Becoming a Freelancer: 5 Things to Do Before Quitting Your Day Job

Becoming a Freelancer
Dena Landon

By Dena Landon | Dec 4th, 2018

For years I’d wanted to control my schedule and work for myself. I tried teaching dance full-time and made less than twenty thousand dollars that year. One year I set up a children’s clothing business, another I sold knitting bags. Nothing quite stuck until I started turning my love of writing into a freelance and search engine optimization business.

It wasn’t intentional. After a nightmare situation in which I felt my son was unsafe, I had to quit my job, drive cross-country and land back in Minnesota with nothing. Luckily I had a place to stay, but no plan and no job. In the month that it took me to find a contracting gig I started turning the part-time writing I’d done on the side into a full-time reality.

And I loved it. I dropped by my son’s school and cheered him on during his fundraising run. I could go to yoga class in-between writing articles. Work from home in my pj’s. Ignore make-up and do laundry in my 500 unit building on Tuesday morning when all the machines were free. Freelancing life suits me.

I think that the reasons so many single moms strike out on their own is simple – the corporate world isn’t set up for moms, period. And it’s even worse if you’re parenting without a partner.

When I first had my son I worked at a major corporate bank in a group run by three men. All of their wives were stay-at-home moms. I remember trying to explain to my boss how daycare charged late fees. It was one of our last meetings before I went out on maternity leave.

“I won’t be able to work late if my husband can’t pick up the baby.”

“Why not?” my boss asked.

“Because if I’m late I’m charged $15 per minute.”

“What? That’s ridiculous. No, you have to be able to work late during the busy season.”

Not only could he not grasp that I couldn’t work late, he also couldn’t grasp that I had no family able to drop everything to care for my child. I’m forced to live in a state where I have no familial ties and yet the general population stays put. I’ve lost track of the number of times I’ve had to explain that, no, grandma can’t come pick him up. His aunt lives in Seattle. And traffic sucks so I’ll be late. Now that I’m divorced, and can’t ask a spouse to pick up my son, I’m truly on my own.

“Life is unpredictable; no one knows that better than a divorced woman.”

With bosses who don’t understand, corporations that consider themselves women-friendly just because they employ women, and the overwhelming amount of emotional labor and childcare that falls on women’s shoulders – freelance life started to look pretty good to me. It probably does to many single moms. If you can handle the ups and downs and the uncertainty, it can’t be beat for offering the flexibility to both parent and work.
I’m not freelancing full-time yet, though I’m making enough money that I could. Unfortunately, I still have legal bills to pay off. I temp as a contractor to fill in during slow months. If you’ve toyed with the idea of freelancing or contracting instead of showing up for a 9 to 5, here are some tips to make it work:

Build a savings account first

In July I made ten grand. No joke. And then the next month my main client decided to go on hiatus and I made…two grand. Barely enough to cover rent. I was incredibly grateful that I’d built my savings account before striking out on my own.

“If you’re going to make it as a freelancer you need discipline and time management skills, and a lot of drive. Single moms have all that in spades. “

While conventional wisdom says that you should have three to six months of expenses in savings, I advise building up more than that. If you lose a main client, it can take time to find one or more clients to replace them. Plus, what if something else goes wrong while your income takes a dip?

My car broke down mid-September. It needed four grand in repairs but it wasn’t even worth a grand. I’d known I needed a new car soon but had been putting it off. Even though I’d just come back to contracting, I hadn’t received a full paycheck yet. The new car’s down payment came from savings.

Life is unpredictable; no one knows that better than a divorced woman. If at all possible, make sure you have a cushion before handing in your resignation letter. And when you do need to draw down on the savings, try to repay it as soon as possible. I repaid the money I’d taken out for rent the next month.

If you’re going to make it as a freelancer you need discipline and time management skills, and a lot of drive. Single moms have all that in spades.

Diversify your client base

July taught me a valuable lesson. Having one client who makes up over 50% of my income just wasn’t a good idea. I hustled like mad that month, bringing on three new clients and sending out over ten applications a week. My new goal is to never rely on one client for more than 20% of the monthly income I need to survive.The client who halted production in August came back in September with more work. I was lucky in that I’d found a client for whom I could do as little or as much work as I wanted, so I wasn’t too swamped. In addition to diversifying your client base, try to build in that flexibility.

Diversify your offerings

At first, I wrote only in the parenting and divorce space. I quickly realized that it limited my client base. Plus, I worried that I’d burn out writing and coming up with new ideas in one area. So I decided to diversify.

I enrolled in a search engine optimization course at Coursera. If you could complete all five college classes in a month it was free, after which they’d charge me. Guess how hard I worked to get them all done before I had to pay?

Once done, I added analyzing websites for SEO, providing content marketing plans for small businesses, and scheduling and sharing content to my product offerings. And shortly thereafter landed a client in that space.

Build Slowly

I also recommend building slowly. While I built my freelance business, and am still building it, I worked full-time. I wrote at nights and on the weekends. Yes, it was exhausting, but I kept my end goal in sight.

In a way, we divorced women have it lucky in this respect. Because I had weekends and some nights “off,” I could come home from the day job and log-on. If you’re going to make it as a freelancer you need discipline and time management skills, and a lot of drive. Single moms have all that in spades.

Give yourself a few months, or longer, to learn how you work without supervision. To discover how long it really takes you to accomplish a task or complete a project. To get faster at some tasks, make mistakes when your rent doesn’t depend on it, and have the freedom to screw up.

Obtain credit before quitting

Banks don’t like extending credit to people whose job doesn’t deposit a bi-weekly paycheck into their account. Access to credit helps out on rainy days. Even with a savings account you might find yourself in a situation where you can’t or don’t want to pay cash.

A friend of mine has been writing professionally for years. She has an open line of credit on her house “just in case.” It’s not drawn on, but it’s there for unexpected emergencies. Look at it this way; you may never need the credit, but knowing that it’s there will help you sleep better at night.

Life has no guarantees. Marriage has no guarantees. If you’ve been thinking about making a change, you can do it successfully with some planning and hard work. Freelancing isn’t for everyone, but if you can make it work and you’re the type of person who needs flexibility in their lifestyle, it’s guaranteed to make you happy. My only regret is that I didn’t do it sooner.

Dena Landon

Dena Landon

Dena Landon's bylines have appeared in The Washington Post, Good Housekeeping, Salon and more. The proud mom of a boy, she specializes in parenting and divorce.


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