I’m a Freelance Writer Who Secretly Wants a 9-to-5

Why freelancing isn’t for everyone

I wrote a couple of weeks ago about how I quit my day job and started freelancing.

The majority of your responses were positive, and most of you felt inspired by my post. I did, however, receive one comment from an individual who felt I was bashing the 9-to-5 lifestyle and stating freelancing is a better life.

This is not what I believe at all, nor did I intend to convey this mindset. I secretly want a 9-to-5. I didn’t want the job I quit. It was toxic on all levels, left me in tears most nights, and I saw no future there.

Career vs. Job

I graduated from a business college. While I was in college, my professors stressed the difference between jobs and careers. At the time, I didn’t see the value of this topic.

Work was work, wasn’t it? Why did it matter if I was on a career path or simply worked a job to pay the bills? At the time, I knew I wanted to write, but I thought I wasn’t going to get to do it because it’s an impossible field to get into.

It took an entire decade out of college for me to realize I was wrong, I am qualified to have a career in writing, and it’s not as hard as I thought it was.

I realize now that I don’t want a job (unless it’s at a coffee shop or a store I love, to have a little extra jingle in my pocket). What I want is a career, and I want that career to be in writing.

Pros and Cons of Freelancing

Lately, I find myself gravitating towards 9-to-5 positions over freelancing positions. Don’t get me wrong, I love freelancing. There are many benefits to freelancing:

• You make your schedule.
• You can schedule an appointment without having to get approval from a boss.
• You can take an afternoon nap if you have a headache.
• You can take a trip without getting approval.

However, there are some serious disadvantages of freelancing–I’m not going to sugarcoat it:

• You have zero benefits. No healthcare, long-term disability, life insurance, etc.
• You don’t get paid vacation, so you need to find a way to make up your work when you’re on a trip to keep the funds coming in. (Or create income streams that generate funds while you’re away, but this takes time to set up.)
• You don’t have sick time, so if you get sick, it’s easy to fall behind.
• If you lose a gig, you’re not eligible for unemployment benefits.
• Freelancing requires a lot of hustling. Nothing is ever guaranteed. Your paycheck could be $2,000 one month and $500 the next. This makes it hard to budget.

I would not recommend anyone consider leaving their job to start freelancing unless you have a safety net. You either need a partner who makes a steady income, or you need to have a large sum in savings (at least $10,000).

I was fortunate to have both when I left my job, so I was in an ideal position to give freelancing a try.

Working from Home Doesn’t Mean Freelancing

I never set out to start freelancing.

My goal was always to work from home. My biggest reason for wanting to work from home? I hate driving.

The morning rush gives me extreme anxiety, and that’s not how I like to start my day. I like to start my day with a one-block walk to my son’s daycare, a smoothie or a cup of coffee, and sitting down at my desk to get to write or edit.

I live one block from my son’s daycare and two blocks from where he’ll go to elementary and middle school.

Having my home as my office makes it easy for me to be there for him when he needs me, not all over the city to rush to make it to his school events. He’s a quick walk or bike ride away–and I won’t have to deal with the school pick-up line!

My Mistake

When my first 1099 job ended my contract, apart from starting my Virtual Assistant business, I was applying to W2 positions.

But I was applying for the wrong jobs.

I was applying to work-from-home jobs like the ones I’d done in the past: customer service and administrative assistance.

I honestly had no answer to the, “Why do you want to work for us?” question.

The only answer I had was, “I need money, why else?”

I’m capable of doing these jobs, but they’re just jobs, and they’ll never be anything more to me. What I want is a career in the writing space.

Looking Forward

I am applying daily for W2 career writing jobs. I’m also applying to 1099 writing gigs. I don’t care what I do as long as I’m fine-tuning my writing skills and writing every day.

I have a million and one reasons for this, and I could talk all day about those. I’ll outline these reasons in future Medium posts, so follow or subscribe to me to read my stories.

My Biggest Challenge?

Social anxiety is my biggest challenge. I have PTSD from past work experiences and interviews. In-person experiences have been the most challenging.

Video call interviews aren’t as bad because I don’t have to worry about the interviewer judging my shoes. (I’m still traumatized from the time my mother-in-law criticized the shoes I wore to an interview.)

Speaking is also hard for me. I’m a writer, not a speaker (which is why I have no business in customer service.)

Final Comments

Freelancing is not for everyone–I’m not even sure it’s for me long-term. Writing is my passion, and that is forever.

I urge you to follow your passion, whether that’s through freelancing or a 9-to-5. You can do both (which is my end goal).

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