Why You Should NOT Freelance as a Writer

Lots of people, upon finding out that I freelanced as a writer for about four years, ask how to make it work for them. I usually tell them it’s a terrible idea and that they should steer clear.

Yes, I will not lie, I had a bad time as a freelancer. Part of this, of course, was battling mental illness, but I think the stress and lack of structure really didn’t help.

I primarily used the site Upwork, which has the benefit of handling the money aspect for you so you don’t have to chase your clients down to get them to pay you. However, the site also has many downsides, which I will address below.

Here are some reasons you should NOT freelance:

The pay is not good.

Unless you are unusually savvy, you will start out with clients who want you to work for CHEAP. This is especially true if you decide to use Upwork, which markets itself to entrepreneurs who aren’t looking for experts.

Also, many clients will pay by the project rather than by the hour. This doesn’t sound so bad until you realize you’ll need to do your own research, adding time to your project. Even when you’re given what seems like a fair wage, there are often unforeseen hiccups that can extend a project’s time commitment, and you will not get reimbursed for those.

Getting out of this low-pay rut requires a significant amount of luck OR enough savings to be able to be discerning from the get-go.

You often don’t get to decide what you write about.

If you use Upwork, you will be applying to jobs where your clients already know what they want. While you may be able to nail down an area of expertise, your topics will usually be decided for you. (You will probably still have to do your own research.)

If you would prefer to write an article about something you care about and then sell it, you will probably make more money per article but sell them less frequently.

Income is not consistent.

Even if you’re making pretty good money, you will have highs and lows. This can make it hard to budget and save.

Likewise, time commitment is not consistent.

Sometimes, a client will need something urgently, or you will get more clients, and your workload will be huge. Other times, you will be ready to work, but have nothing available to work on. This feast or famine can be really stressful.

You constantly have to be selling yourself and looking for new jobs.

If you don’t like job hunting, freelancing is not for you. You must be constantly on the look out for new clients and new opportunities, and many people find this draining.

There are no worker protections or benefits.

Worker protections and benefits have been hard-won in the last two centuries, and when you freelance, you get none of them. With freelancing, there is no minimum wage. There is no healthcare. There is no Paid Time Off.

It’s hard to work alone.

When you go to a physical workplace, you will almost always have coworkers that share in the camaraderie of the grind.

I often use a strategy called body doubling, but that doesn’t happen in freelancing unless you MAKE it happen by teaming up with other people with similar work.

You have to motivate yourself because there’s no structure.

When you freelance, you don’t have a boss or a teacher to make sure you’re working steadily— or at all. You get up in the morning and YOU have to make the decision to sit down to work. This can be really tough. Often, freelancers struggle with procrastination.

If you are REALLY good at waking up at the same time every day and sitting down to work at the same time every day, you will probably have an easier time than I did. My schedule was all over the place, and I was just as likely to be working at 2am as at 2pm. I had absolutely no structure to my life, and my mental health definitely suffered for it.

You will OWE taxes come tax season.

When you work a regular job as an employee, taxes are automatically taken out of your paycheck, and you get a large portion back when you do your taxes each year. As a freelancer, you would have to keep track of your money and save your own taxes, to then pay the government what they are owed. It’s not fun.

It’s hard to relax when your home is your workplace.

Unless you have an extra bedroom whose door you can shut, you’re going to be looking at and worrying about your work even in your “off” hours. Trying to sleep in the same room as my desk really stressed me out.

Reasons you SHOULD freelance:

You’re totally serious about a career in copyediting and you like internet marketing.

If you are 100% dedicated to a marketing and/or copyediting career, then freelancing might be your cup of tea.

It’s not the same skillset as any creative writing you may have done, even for publication. The fundamental aspects of copyediting are different and have different goals. You may often be asked to dabble in social media and/or graphic design. If that sounds like fun, I think you should seriously consider a freelance writing career!

How To Start Writing Poetry

You want to write poetry, but you don’t know where to start.

There are two components to the art of poetry, the writing part and the reading part. The writing part is the part where you actually DO it. The reading part is how you get better. We’ll cover both here.

For the record, I have been through a lot of formal education in the art of both reading and writing poetry, so I know a thing or two about how it is taught. I don’t agree with absolutely everything that was part of my training, but also there were some good takeaways, which I will impart to you here for free!


A. Some Notes on Permission

My first point here is that you do NOT need anyone’s permission to start writing poetry. You do not need to get a degree or even take a class. You do not need to Google it. You do not even need MY permission.

Secondly, your poetry does not have to be for anyone else. It doesn’t have to be “good,” it doesn’t have to be “publishable.” What matters is that you had fun and expressed yourself. (Yes, there can definitely be a type of satisfaction in getting really good at a craft and sharing your art, but that’s not what we’re talking about today.)

Really, you don’t need me at all.

However, I CAN help you get started. You will probably have an easier time and put less pressure on yourself if you don’t expect your poems to spring fully-formed from your brain. Instead, there is a trick for first drafts called Freewriting.

B. Freewriting

Freewriting is a little bit like dreaming. You set pen to paper (yes, usually analog writing is recommended) and you write literally anything that comes to mind. Yup, anything. It doesn’t have to make sense, it doesn’t have to be good or profound or true or anything else in particular. Don’t edit or cross anything out. Being fully uninhibited during the freewriting process takes practice, and it’s something I’m still working on myself, but I recommend giving it a try anyway and seeing what happens.

After you’ve filled a page or two, take a break and let your work breathe for a few minutes. Get up and do something else. When you come back to it, reread what you’ve written and highlight or underline what’s interesting. Maybe you made up a weird turn of phrase that you like, or you really nailed how you feel in a certain situation.

After you’ve selected the most interesting parts of your freewriting session, you can use the lines and phrases like fridge magnets to construct a poem. Don’t be shy: throw out or fill in absolutely anything you want.

Revise as much or as little as you want. Sometimes it feels great to get the accuracy that comes with editing, while other times it can feel stifling. Read it out loud to yourself if you want. Do exactly what you want to do at all times in your poetry journey. It’s YOURS.


If you want to get better at poetry and expand your capabilities, I highly recommend reading poetry. Luckily, this is not as intimidating as it might sound.

In my personal opinion, it can be important to read more modern poets, from the last 70 years or so. For one thing, their work is often more accessible. For another thing, there is more diversity in the demographics of the writers and their subject matter. Thirdly, if you’re super serious about writing to publish, it will show you current trends in the poetry world.

A. How To Read Poetry

What is the best WAY to read poetry? There isn’t one. Focus on getting as many words into your brain as possible at first— you can analyze later as your instincts get honed into skills. Soon you will notice meter and slant rhymes and all that other stuff, but for now you can just read for enjoyment.

You may want to try reading your favorites out loud to hear how things sound. This may add another layer to what you already liked about the poem!

You may also want to buy your poetry books so you can write notes or highlight in them.

B. Reading Suggestions: Where To Start

(I had fun with these suggestions, but that doesn’t mean these aren’t good places to start!)

If you’re queer and you’re not shy about the sexual, read Allen Ginsburg.

If you like nature and Abraham Lincoln, read Walt Whitman.

If you care about Black Power, read Nikki Giovanni.

If you’d like something accessible and easily digested, read Rupi Kaur.

If you love nature and enjoy feeling at peace, read Mary Oliver.

If you’re sad and feeling kind of feral, read Sylvia Plath.

If you like rhymes, read Robert Frost.

(Everyone should read Joy Harjo.)