The Pros And Cons Of A Career In Freelance Writing

Freelance writing: An acquired taste, but it can make for an interesting and perhaps even secure employment option. Photo: By Negative Space on Pexels

Freelance writing is an increasingly popular career choice.

With the economic downturn eventuated by the pandemic having forced many companies to downsize, many are now turning to freelance writing as an effective way to make money online over the internet.

I’ve been working as a freelance content marketing writer for five years now — close on three of which have been full-time (my prior career was as an in-house marketing communications manager at technology startups).

I sometimes get asked what I think about freelance writing and whether I recommend that people get into it as a career. That’s a tricky question to answer and will probably be the subject of a later post.

In the meantime here are the good parts and not-so-good parts of the job itself.

Pro: It Can Be Varied Work

When it comes to learning how to work as a freelance writer, there’s a lot to learn. But if you want to pick up some of my knowledge for free, then check out my Medium publication, Freelance Writing, which dives deep into a lot of relevant topic areas.

But if I could make only two recommendations to those starting out they would be:

  • Get going with inbound marketing as soon as possible. In my opinion, it’s a lot more fun (and sustainable) than relying upon outbound techniques like sending out cold emails to drum up work. Having a real-life network to tap into helps enormously too. But don’t put all your eggs in one basket. Which brings me to:
  • As above, diversify as widely as possible. If you want to learn ‘how’ read the following post. There are a lot of ways when you put your mind to it.

One of the upsides of diversification is that — if you do it right — it should also make your day-to-day life a lot easier.

Working for only one client — besides usually being a terrible idea — also has a tendency to become really boring. I’ve made the same point about writing for only one small niche. So branch out — but not too far.

Diversifying your business can also give you access to a wide variety of clients in different industries and geographies.

Pro: Theoretically, It Can Be A Secure Way To Make A Living

Before you reach for the rotten vegetables to (virtually) pelt me with while screaming “freelancing? Secure? You idiot!” hear me out just for a moment.

It takes a lot of work to get to this point. I wouldn’t even say that I’m there myself yet, although I’m further along in the process than when I started out.

But I believe that if you plan your business properly you can get to the point at which you’re actually in a more secure position freelancing than your average employee.

How could that be so, you may be wondering with astonishment?

Your average employee is at the mercy of one organization. If you’re employed at-will then you can be let go for virtually no reason at all. But if you can diversify your freelance writing business (between clients, between passive and active income, between industries) you actually create a lot of redundancy in your business model. More redundancy than your average employee can muster.

If one client fires you, you may loose 1/6th of your income. But that’s a whole lot better than losing the totality of it. This is why pipeline development really matters too. You want to have a contingency for when stuff goes wrong.

Pro: If You Love Writing …. You’ll Get To Do Lots Of It

I think it’s safe to assume that the majority of people who get into freelance writing — or writing generally — do not do so for the money. When I got into student journalism, income was certainly not the driving factor on my mind.

Rather, they’re attracted to this profession, and way of working, because they love writing and find creativity rewarding.

And now I have to be honest for a moment.

I’m not always completely fulfilled by the kind of writing that I do for clients — particularly when it’s heavy on the content marketing side (I do a lot of thought leadership writing too).

This is where you have to make a decision between what’s more important to you: financial stability or professional fulfillment.

If you’re really craving fulfillment and the feeling that what you write makes a (positive) difference in the world then spending most of your energy in freelance journalism might make more sense. Although many on the journalism side of the divide would take issue with that notion.

On the other hand, there’s arguably a lot more work in freelance content marketing these days and picking a popular niche in that kind of writing might prove a more lucrative strategy over the long term.

Either way you’ll probably be doing lots and lots of writing (it kinda comes with the turf, ya know!?). But you can blend the kinds that you do in order to find the best mixture.

Cons: It’s Really Tough And Hard Work

Unless I’m doing something horribly wrong, there’s nothing easy about being a full-time freelance writer.

The hours can be brutal. We’re responsible for everything from getting the actual writing done to paying taxes and making sure that our clients get invoiced on the right day of the month (eventually many writers hire VAs for this kind of thing but at the start you’re more likely to be a one man band.)

Add to that the fact that the freelance writing market is extremely competitive — and seemingly always getting more so — and you can probably understand why there are days when I wonder why I don’t just do the easier thing and go get a job in an office.

Making a living as a full-time writer requires a lot of work and effort. Writing can be energy-sapping. If you also write for fun in your off hours — as many writers do — you can compound the mental exhaustion. But for many who really love writing, it’s still worth it in the end.

Cons: It Can Also Be Really Lonely

A lot of my work involves sitting in a home office, or coffee shop, and typing into a keyboard.

If that sounds kind of bleak to you then you might have a hard time making this work as a career.

This is one of the reasons why I think that networking with other writers — even if just over the internet — is vitally important.

It’s not just for the social aspect either.

Ideally every writer should have a strong referral network so that you have people to outsource work to if you hit capacity. Swapping ideas with other writers can be extremely useful and healthy too and I see nothing wrong with comparing notes about rates.

How else can you avoid becoming an unwitting hermit?

It’s obvious but having a good social life and ensuring you allocate plenty of downtime to recuperate makes a big difference too. It just might take a bit more effort than somebody who has a social group automatically created through the office water cooler.

The lifestyle of a full-time freelance writer is what I would call an acquired taste.

There are amazing perks to it — like being able to drop everything to go to the beach.

But equally I think that some of the supposed benefits — you have no boss! — are overstated. In reality, you’re still answerable to your clients.

I think that anybody getting into freelance writing should seek to diversify their income as quickly and as widely as possible.

Along with starting with a robust professional network this seems, to me, to be a key to success.




Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

Review: Bonsai is the best platform for freelance designers?

5 Profitable Gigs to Make Money On Fiverr

6 Side Hustles That Are Just Flat-Out Scams

Woman In Black Turtleneck Shirt Yelling

Two Contractual Pitfalls To Avoid In Your Next Freelancing Gig

Outsourcing IT Services: A Professional Company or a Freelancer?

Values of an independent agency

The 5 Best Newsletters to Subscribe to For Freelance Writing Success

6 Ways to Make $500 per Week Online

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Daniel Rosehill

Daniel Rosehill

Daytime: writing for other people. Nighttime: writing for me. Or the other way round. Enjoys: Linux, tech, beer, random things.

More from Medium

Keys To a Successful Freelance Writing Career

How a Bad Job and Core Desired Feelings Gave Me the Courage to Freelance Full-Time

The Freelancer’s Guide to More Shmoney

The Most Chaotic Writer In The World Shows You How To Choose A Writing Niche.