3 Tough Lessons After 6 Months of Freelance Writing

What I’ve learned after quitting my ‘normal’ job


Alexander Boswell

3 years ago | 7 min read

Click, click, click, sip, click, make an annoyed face, click some more, make notes, click, get more coffee, sanitize my hands, click... If you repeat those actions long enough, you’ll have a pretty good idea of my experience working in a 9–5 office during a global pandemic.

There I was, in August 2020, sitting at my desk with yet another (pretty terrible) coffee and the lunch I could only eat at my desk, with the same thoughts running through my head.

“If I could dedicate all of my working hours to writing, what could I achieve? Would I even be able to support myself financially? Would I enjoy it?”

You’ve probably had those thoughts a few times yourself.

There was a permanent job opening at the place I was working (as a temp), which I had applied and interviewed for, but these thoughts were nagging me like a small child at my leg.

I couldn’t put them off any longer, so after making sure I’d saved up enough to support myself another two months, I withdrew my application and handed in a resignation notice instead.

I know you might be wondering, “why the heck would you reject a stable job during such a crazy time?”

The answer is loaded with a set of privileges I’m lucky to have, but simply because I believe not trying would have been my biggest regret. I figured it would be more convenient for me if it worked out. Which, thankfully, seems to be the case.

I dove head-first into freelance writing in September 2020 and started my Ph.D. in October. Now six months on, I feel like I can offer you some advice if you’re thinking of starting your freelance writing journey.

#1 Freelancing takes up more time than you think

Like many people, the laptop lifestyle was pretty alluring (even if I couldn’t travel quite yet). The popular notion is that you have an idea, quit your job to pursue it, then magically, the money will appear to allow you to work only 4-hours a week.

That, my friend, is not the reality — at least not in the six-month time-frame for me (nor for many other freelancers I know).

There are a few tasks and job roles outside of the act of writing you need to consider to make freelancing work out for you.

The little business tasks you have in your draw can quickly lead up to days of work if you’re not careful, especially when you start bringing clients into the mix. You don’t leave behind activities like emailing/Slack, Zoom meetings, and a work schedule in the office; they’ll come with you.

However, since you’re now running your own business, you’ll also need to think about business banking, bookkeeping, tax, contracts, sorting out your own benefits (insurance and such), and in my case, at least, web development/maintenance.

These activities take a lot of time and learning if you’re new to them.

What you can do about it

The best advice I can give is to automate as much as you possibly can or find tools that’ll make your life a little easier and save you time.

Use accounting software like Quickbooks, Freeagent, or Xero linked to your business bank account to help you manage your bookkeeping.

I personally use Quickbooks after trying all of them as I’ve found it more user-friendly. At the end of my week, I spend about 15–30 minutes uploading my receipts from email and approving transactions/invoices.

I also use Bonsai to help me create and store contracts, as a CRM (Customer Relationship Management), and for invoicing international clients. This one has saved me a ton of time and stress over whether I have the right legal wording etc.

Another solution can also be to hire an assistant to help you with these tasks, if you can afford one, to take them off your plate completely. Though, I’d still advise you to learn these tools and processes to make sure you’re on the same page as your assistant.

#2 Marketing your services can be hard

I pretty much live and breathe marketing, it’s what I study academically, and it’s what I write about for clients most of the time nowadays.

Yet even I still struggle to market myself as a freelance writer. Again, marketing yourself to potential clients or publications takes a lot of time and effort, particularly in the beginning if you have little to no reputation to lean on.

One of the main stumbling blocks you might come across is establishing a niche for yourself.

You might already have one. If so, you go, Glen Coco! But when I started freelancing, I took pretty much anything I could get. I wrote about retail, facial recognition, employment laws, transport, and of course, marketing.

The trouble with this ‘shotgun method’ of trying to hit lots of places at once is you don’t build a reputation in those spaces, and people don’t remember you. Think about it from the client perspective, say you wanted to hire a writer to create content for your e-commerce site, and you had two options:

Writer A whose portfolio is scattered with articles in unrelated industries, one or two on e-commerce, or Writer B, whose portfolio consists almost entirely of e-commerce writing, who’d you pick? Likely Writer B.

What you can do about it

In terms of establishing a niche, one of the best bits of advice I’ve ever received was to make a list of your dream companies/brands to write for and see what they all have in common. For example, let's say your list looked a little like this:

  • Glossier
  • Skin+Me
  • Clinique
  • Botanics
  • The Soap Co.
  • Lush

It’s pretty obvious you’ll want to be focusing on building yourself up as a beauty writer. However, how niche is too niche? You could narrow this down even further by being a writer for sustainable beauty brands. If your list has more range to it, still try to find commonalities (this is how I found my niche of B2B SaaS marketing).

When you’ve got a better idea of your niche, you can craft a portfolio targeting those types of companies on your dream list.

When I got started, I used articles I’d published in Better Marketing (in fact, I still use a few of them) to help build a portfolio to use on Fiverr and my website when I didn’t have any articles published outside of Medium.

Just remember to share friend-link folks. It’s pretty cringy when you send a link, only for that link to be paywalled, and your potential client can’t see it.

#3 Networking is ridiculously important

You might argue that networking is a part of marketing, and I wouldn’t disagree with you. However, I felt it deserved its own breakdown/advice because the bulk of my work (and general life as a freelancer) has come from networking.

A little while ago, I published a piece here on Medium titled Why It’s So Important to Network with Other Freelancers’.

This article talks about this particular point in more detail, but I’d add to them here that networking, of course, isn’t limited to other freelancers. Your dream companies, and others you might not have considered, will also have watchful eyes on social media.

The tough part is, for me, despite being a marketer, I’ve never been particularly active on social media in terms of creating content and engaging as myself.

Maybe you’re like me, a lurker. Someone who has plenty of social media accounts but only passively consumes the content, rarely showing any meaningful engagement.

Naturally, as a freelancer, you’re going to have to step out of your comfort zone to put a spotlight on yourself. It makes it a lot easier for your potential clients (and freelancer friends!) to see you.

By making an effort to share more value on social media (Twitter is my platform of choice — @alexbboswell), I managed to build high-quality relationships with people involved in my niche, which did end up leading more clients my way.

What you can do about it

When you become active in your scene, people start to take notice. Try to make sure what you’re putting out into the world truly benefits others.

You can share pithy versions of your best advice or findings on your topic, respond to other people doing the same (adding your own value, preferably), and simply providing boosts of motivation.

The key here is not expecting monetary benefits from networking (though it can happen). It’s about sharing value with your community.

A good example of this in action at the time of writing is the #ship30for30 trend, where writers (of all kinds) share short atomic essays on topics of their choice every day for 30 days.

While the cost to join the live cohort is a little out of reach for lots of people, there’s nothing stopping you (or I) from taking that idea and doing it for yourself.

Final thoughts

Going from (seemingly) secure employment to freelancing can be a huge jump to make, and before I did, I wish someone would have given me some more heads up for what I was getting myself into. I hope by reading this, I’ve helped you bring yourself down to Earth a bit.

That being said, freelance writing has also been the most rewarding working experience in my life so far. I’ve learned a ton of new skills, built relationships I highly value, and developed a stronger sense of belief in myself.

Also, if you’ve been considering going freelance but don’t feel comfortable quitting your job, it’s totally okay to freelance part-time (I think most people do).

Technically, I freelance part-time because I’m also doing a Ph.D. You’ll just need to be aware of the sacrifices you’ll be enduring to make that dream a reality (bye, bye, Netflix).

So while I’ve learned some tough lessons, by doing so I’m able to pass those experiences onto you, so you can learn from them too.


Created by

Alexander Boswell

Alexander Boswell is a Business Ph.D candidate specialising in Consumer Behaviour and uses this knowledge as a freelance writer in the Content Marketing and B2B SaaS space. Find him on Twitter @alexbboswell or his website







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