“Do all freelancers dream of Sisyphus? (Or am I mythtaken?)”

At no point in my long career of being called various things has anyone ever accused me of being highly cultured. While I can spot the difference between cannelloni and a Canaletto, I can’t deny my entire knowledge of opera starts and finishes with Bugs Bunny or that I thought, “Out, damned spot!” was Lady Macbeth shouting at her dog.

But if I’m more a culture tit than vulture, why would a troglodyte like me have recurring dreams of the Greek legend of Sisyphus?

Before these started a few years ago, I knew exactly two things about Sisyphus. One, he was the chap cursed to roll a big rock up a hill every day for eternity, only to see it roll back down again. And two, I can’t say or type his name without snickering. (Sissy!)

Clearly this was insufficient, so I did some research.


His story’s told in the Odyssey by Homer (not that one). Sissy Face was the son of Aeolus (ancestor of the Aeolians) and the father of Glacus (patron saint of eye diseases.)

He was extremely clever and crafty as all hell. He died twice, handcuffed Death and locked him in a cupboard, stiffed the ferryman on his fare across the River Styx and populated Corinth with people grown from mushrooms.

I was fairly sure mushrooms were going to be involved in this story at some point.

No one seems to know why exactly he was given the big stone to roll up the hill, but it’s generally seen as some comment on the futility of existence and the absurdity of the human condition.

So that’s nice.

When I started having these dreams, I’d just gone freelance for the first time, and Sissy Pants would show up almost nightly. He’d heave the big rock up the hill, and sure enough, down it would go. As a struggling freelancer with no clients and a rapidly dwindling bank balance, metaphors were the last fucking thing I needed.

But as my customer base grew and my bank account could at least dare to believe it might return to the black one day, the dreams of mythological Greek mushroom farmers faded away.

So, why come back now?

Apart from being a little heavy handed with the parmesan on my pizza the night before, why would I possibly start dreaming about this depressing pile of drivel again? Like I said, I’m not one for the classics—even though I did go to Cambridge. (Sorry, no — I’ve been to Cambridge).


I’m sure most people hit periods of existential angst from time to time, but I’ve started to wonder if those of us who work for ourselves have fewer defences against it. Being a freelancer can certainly feel like the up-est of all uphill battles sometimes. The struggle of finding and keeping quality clients can still be overwhelming even now.

Early on in my career, I made the rookie error of concentrating all my efforts on my first big client, and pretty much gave up marketing myself. When the inevitable happened and they decided to go ‘in another direction’, my rock rolled its arse all the way back down to square one again.

It was enough to set me up for some serious late night sessions of ‘is this really what I want to do anymore?’ when all my hard work could be discarded so easily. Was it worth all the effort?


But in a rare moment of clarity (when I ran out of wine) the basic flaw in my thinking struck me.

I wasn’t Sisyphus. And I wasn’t Sisyphus for one very good reason:

My rock wasn’t rolling down to the bottom of the same mountain.

My rock was rolling to the top of one mountain…

and then down the other side.

The land lays a little higher over there. All the lessons I’d learned from pushing my rock, all the new information I’d taken in, all the problems I’d solved weren’t magically lost at the end of the day. I wasn’t starting from scratch.

I was starting just a little bit closer to the summit of my next mountain.

I had momentum.


Gaining momentum in a freelance career is a bugger. In fact, it’s a bit of an arse in everything. Ever tried to push start a car?

Yes, losing my main client hurt. A lot. But the work I’d produced during my time with them now made an excellent addition to a portfolio I could use to go hunting for other clients. All the people I’d dealt with along the way knew my name, we were connected all across social media and when it was time for them to move onto new companies, they remembered me and gave my rock a gentle nudge.

Life is a series of these peaks and troughs and they don’t go away just because we wish they would. Darius Foroux talks about the magic of momentum here.

Finding my next clients was difficult. Almost as difficult as the first time. But now I knew slightly better where to look. I knew slightly better what to say. I had samples to back up any extravagant claim I might make.

It was all a very very tiny bit easier.

I won’t say that now, my days of rock pushing are behind me. Sometimes it gets heavier and the mountain seems steeper. But I’ve got some better developed glutes to give me some leverage now, as well as a spotter or two I can call on when things get on top of me.


So, why the dreams again? Well, I’m facing another mountain, and it’s a big one. The early stages of building a business (called Accountsify, since you ask) are where the most effort is needed, and where the most setbacks are felt. Getting heard above all the noise takes a lot of pushing. But now at least, I have the knowledge that the pushing pays off.

Every now and again, I get to a summit. It might only be the summit of a molehill—drafting an email newsletter, scheduling a meeting—but I still get a slightly better view from up there. I’m still better off than I was and it’s a molehill that doesn’t have to be climbed again.


I’m pretty sure that’s where my brush with Greek mythology will end. I think I’ve learnt enough to see me through and the world of academia can struggle on without me. Hopefully, I’ll get some decent night’s sleep now too.

But I’m going to finish with a quote by Albert Camus from his essay The Myth of Sisyphus (because I read the entire Wikipedia page on it, and that totally qualifies me) in case these constant ups and downs set you thinking it’s not worth all the effort:

“The struggle itself towards the heights is enough to fill a man’s heart.”