I’m gazing out the window at the glorious sunshine. The temperature is cool, the sky blue and the weather perfect for a run. I look at the time. It’s 4 pm. Ugh, another hour and a half to go. I can’t focus on what I’m doing because all I can think about is how great it’s going to be when I get outside even though the sun is going to start slipping away. It sucks.


When I started freelancing full-time, it was because I wanted the freedom to work on my own terms, on the hours and days I wanted to, complete work that interested me and make my own decisions about what kind of clients I worked with.

If someone told me I had to work 9–5 in a specific office one more time, I was going to scream. The nature of my work is time zone and location agnostic. Sure, I need to be able to talk to clients and stakeholders during their working hours but aside from that, the blinking cursor on the blank page couldn’t give a toss what time it is. Freelancing gave me a way to unshackle myself from inefficient and arbitrary limitations.

All good. But then this is what happened.

What happens when you don’t make a plan

As every self-employed person knows, there’s a certain level of simmering fear deep under the surface of your soul. What if no one pays me? What if I’m never good enough to makes ends meet? What if people think I’m slacking?

And what do we do in the face of fear? We cling to the things we know. What do we know?

The 9–5.

After a couple of years of freelancing full-time, I found myself questioning why I was putting myself through so much stress. I had work and clients and, on the face of it, it was all work I liked. So why did I find myself scrolling through job ads and wondering if I should make a return to employment?

It took me six months to work it out.

There I was, sat at my desk staring out the window at the sunshine. I swear it had rained for weeks. If only I could just switch off my laptop and head out the door.

And look, I know this sounds a little stupid, but that’s when it hit me.

OH WAIT. I CAN.

Be a better boss

I took the afternoon off work last week because my hayfever was so bad I couldn’t think in a straight line. I’d battled with it all morning and when I finally made the decision to just stop, it was revolutionary.

Imagine a boss who, no matter how terrible you feel, won’t let you take the afternoon or day off. Imagine if they berate you, make you feel guilty and threaten you with never working again.

I mean…you’d quit, right?

I am, hands down, a terrible boss to myself.

In my last employed role, in the few times I felt ill, my manager would always say, ‘why don’t you go home? Don’t worry about work, just go home and relax’.

When I finally remembered that I was absolutely in charge of my time and what I do with it, my happiness at work changed in a split second. The flexibility and autonomy was the reason I went freelance in the first place. So why, when I could actually take control of my time, did I immediately start working 9–5 and taking less time off and fewer holidays?

Here’s the thing.

When I went freelance full-time I never made a plan. I already had work coming in and I had a (sort of) plan for getting more clients and progressing my business, but I never made a plan about how I would work. I didn’t know what working policies I would have or how much time I would give myself off. None of that. Why would I need to? I’m my own boss!

Yeah, a f**king tyrannical one.

The funny thing is this: I fully believe that when bosses don’t encourage their employees to take sick days when they’re sick, to take time off when they say they need it off (for whatever reason) and to take holidays, the business will suffer.

After all, how can you have a thriving business when your staff are stressed, oppressed and run down? How can you expect them to produce their best work when they’re not feeling remotely their best?

A major reason I became self-employed is because I hate this kind of patronising, dehumanising disrespect.

And then I turned around and behaved in exactly the same way to myself.


Want to get all my advice on working as a writer? Head to my new Youtube Channel, The Writer Diaries, and subscribe to get a ton of tips: https://bit.ly/3uQPWh3


The bottom line

When you work for yourself, you get to be the best boss in the world. Sure, that means building a business that has enough money coming in to pay you what you want, but it also means building a happy, high morale workplace, even if the only person working there is you.

At the end of the day, you wouldn’t want to do business with a company who treated their staff like shit. So why will people want to work with you when you can’t even give your one employee an hour off to go for a run in the afternoon sunshine? When you make them feel terrible for taking a sick day? It’s so painfully simple I can’t believe it’s taken me this much time to realise it.

Making a plan

So, I’ve made a working plan that dictates how I treat my staff (me) and create a positive working environment. It’s based around why I went freelance in the first place and what makes me produce the best work I can for myself and my clients.

(I’m a writer specialising in the outdoor and adventure industries, FYI.)

It includes these things:

  • Take sick days whenever you need to; you can’t work well if you’re feeling grotty.
  • Prioritise health: take time to eat good food away from your desk; take regular breaks to stretch your vision and walk around; go swimming, running and cycling in the working day if you want to and can’t outside the working day; take a meditation break — it improves focus every time
  • You can’t write about adventures if you don’t go on any. Go on adventures.
  • Start work at 8 or 10 whenever you want to, stop being so obsessed with the number 9.
  • Invoice fortnightly because it feels so good
  • Freelance success means taking time out to do whatever you want to regularly. Freelance failure means staying chained to a desk and an ideology that doesn’t belong to you. Forgive yourself for choosing success.
  • Attend networking meetings, they always make you feel good.
  • Hell, just do what feels good.

Why are you freelancing?

As a writer, I know it’s important to figure out the point of what you’re writing before you start and keep bringing the text back to that purpose. And yet, I’ve forgotten to do it in my business.

So, from now on I’ll be regularly asking myself if what I doing is aligning with why I’m freelancing.

I wholeheartedly suggest you do the same.

Have you gone self-employed only to become a tyrannical boss? If so, what are you going to do about it? If you have any tips or thoughts, share them below, we all need to hear them!


Want to get all my advice on working as a writer? Head to my new Youtube Channel, The Writer Diaries, and subscribe to get a ton of tips: https://bit.ly/3uQPWh3