If at first you don’t succeed, try and try… until when?

We’ve all heard the saying, “if at first you don’t succeed, try and try again”, but how do we know when we’ve tried enough, and when to admit defeat? This is a question I’ve asked myself repeatedly since ditching my day job and deciding to try and make it as a freelance writer. I mean, fuck, just writing the words “freelance writer” seems dumb; a preposterous venture to even start with. Like, who do I think I am? Stephen fucking King?

But I did decide to start, and now, nearly three years later, I am still left questioning whether it has all just been a massive error in judgment and if I am indeed a massive failure. I certainly haven’t attained a level of success that means something to me, though others might look on and think that just having a go is a success in itself. I’d have to disagree with that, but then again, I have ridiculously high standards.

It has been my experience thus far, that working as a freelancer can be a seemingly endless cycle of disappointment: People making promises they don’t or can’t keep, companies offering hourly rates barely above minimum wage (if any rates at all), competing with 19 year-old uni graduates with fucking Masters Degrees in digital this and that. The list goes on.


Obviously it’s not all doom and gloom — the flexibility is awesome. Nothing better than having only yourself to answer to, and being able to 100% manage your own time. And when you have a pretty amazing existing network of people who actually believe in you and give you a shot, well, that’s a really nice feeling.

On the flipside, there’s no one to blame but yourself when things go to shit. Like when your network dries up and you have to look externally, that’s when things start to get tough and you automatically start questioning your worth. External people don’t know, or care about you. You are a disposable commodity, easily cast aside without so much as a ‘nice to meet you’.

It’s the question of worth that’s really plaguing me here — how many times do you cry over that lost lead? Or a flaky company that promised you the world and delivered nothing? Or the fact that you’re alone all day every day with no one to bounce ideas off? How many nights do you lay awake wondering what else you can do to get ahead? How much is too much? When is it time to pack it all in and just get a goddam day job?

It’s all these questions that keep me awake at night; that are slowly chewing away at my sanity. On the surface I feel as though I could probably just give up right about now, but there’s a teeny tiny part of me that refuses to quit, and I think maybe it’s trying to tell me not to roll over just yet. What do you think, dear readers? How do you measure success?


Peta. x