The Freelancer’s Myth

Sarah Weiler
5 min readJan 30, 2020

(This is a blogpost I wrote in Summer 2018 and never published. Last night I was speaking to a friend about this very topic so thought it was time to get it out there.)

June 2018: This morning a message dropped into my inbox from a friend saying, ‘hey love, don’t suppose you have any calming words for a lass who just went freelance and is feeling very wobbly about the whole thing?’’

Well yes, I do.

But this ‘lass’ could easily be me. I’ve been feeling somewhat wobbly myself of late and I’m starting to see why.

At first when you become self-employed you’re just so happy you’ve got all the freedom. It’s bliss. I can do anything with my day! No-one is telling me what to do! I can go to a yoga class at 11am on a Monday morning. I can skip in the park!

But here are some things that quickly creep in….

Money anxiety


Fear of the impending space

Feeling guilty for not being ‘’productive’’

Feeling exhausted even though you haven’t technically ‘’done anything’’ and people are asking how come you’re so tired when you seem to have so much fun

Feeling like you don’t have a ‘job’ and therefore no identity

Feeling like you don’t fit into society’s blueprint of a normal functioning human

Being able to take a holiday whenever you want but not ever feeling like you’ve done enough to deserve one

Exhaustion from lack of routine and having to motivate yourself every day

Knowing that the answer to all of the anxiety is SLEEP but feeling like you’ve already slept too much and judging this very basic human need.

In these moments you remind yourself of all the things you wanted when your were in an unfulfilling full-time job:

Autonomy and creative space.

Getting up in the morning and having control over our day

Being in charge of our time and responsibilities

Being able to meet a friend for a 3 hour lunch during a heatwave or being able to take 5 weeks off to walk in Spain without it not affecting anyone.

SURELY once you leave your job and get all those things you wanted you should be happy, right?

But these things are only half of the story, and after a while a strange thing happens: you start to crave all the things that full time work gave you:

A regular income.

Someone telling you what to do (read: guidance/clear goals)

Someone holding you accountable

Measurement of success and milestones

Feeling like you are needed somewhere

Positive feedback

Structure to your day

Community of people around you


But this is confusing, because you hated full time work, right? What is going on?

What I’ve realised is this: we are just substituting one problem for another.

In an attempt to have more autonomy and less micro-managing you suddenly gain scary amounts of responsibility and zero support.

You wanted a little more space in your week and suddenly gain FULL TIME BLANK CANVAS.

You don’t want to be locked to a routine, and then suddenly find yourself with f*ck all structure to your day.

These are EXTREMES — and neither serves us.

I flung all rigidity out of the window when I quit full time work.

I associated routine, structure and regularity with BEING IN A BORING SOUL DESTROYING 9–5. I avoided anything that remotely resembled a ‘normal’ job. I turned my nose up as soon as commitments became predictable. I saw a regular pay-cheque as cheating on my creative dreams.

And yet at the same time I looked at friends in ‘real’ jobs and envied that they were needed there. That someone cared if they didn’t submit something on time. That they were sent on development courses by their bosses. That they spent Friday nights drinking with their colleagues.

It was a strange realisation — I had shunned ‘real work’ so much, but hadn’t actually inquired which parts of it were actually worth keeping.

We need a healthy mix of routine and spontaneity, regularity and irregularity, structure and chaos in our lives— the magic is in knowing the dosage that keeps us alive.

I got to know my own mix of ingredients:

I wanted to choose and direct my own projects, but still have accountability with them. (Cue — get a coach).

I wanted to have spacious days to be creative and follow my flow, but I didn’t want to have weeks on end of nothingness. (Cue — have a few well-paid projects that kept me focused, and allow myself to play the rest of the time).

I wanted to have a regular income, but I didn’t want to have a regular job. (Cue — work out how much I actually needed each month, transfer it as a salary, but be open to how that money comes in.)

By choosing to be freelance I had said yes to a lot of important values: adventure, space, joy, creativity. But these could not be supported if I didn’t keep some of these other ‘full time work’ things in place.


The opposite of a 9–5 job is not NOT EARNING REGULAR MONEY



No, It is about choosing how you earn your regular money, knowing it doesn’t have to translate to sitting behind a desk.

It’s about choosing a routine that works for you — getting up at a time that suits you and having your genius stream of consciousness flow state at 1am if that’s your jam.

It’s about choosing the people you bring into your life to support you, guide you and ask you powerful questions, rather than trying to do it all yourself.

So ask yourself the following questions:

  1. What routines do I need so I can feel free?
  2. What structures do I need to give constraint for my creativity?
  3. What financial stability to take pressure off and allow me to be present with the things that light me up?
  4. What guidance and mentorship do I need in order to flourish alone?
  5. What accountability do I need in order to make progress with the projects I care about?
  6. What milestones or goals do I need to put in place to give me that extra push?



Sarah Weiler

I’m a multi-passionate TEDx speaker, writer, coach, framework-fanatic, quitting researcher & ukulelista/composer. //