How Long Should I Struggle with my Freelance Writing Business Before Giving Up?

I gave up a secure job to become a full-time freelance writer four years ago. This decision felt so right at the time, but if I’d known how tough it would be, I probably wouldn’t have been so eager to make the leap.

I’m still passionate about my career, and I don’t even mind the struggle – it’s just the fear the struggle might be in vain that keeps me awake at night.

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Is it Normal to Be Still Struggling After Four Years?

I saw a steady increase in my earnings for my first two years working as a freelance writer/blogger but then I hit a plateau. Unless something miraculous happens in the next couple of months, I’ll have earned less in 2013 than I did in 2012. I expect there to be ups and downs in my business, but it’s hard not to worry when the overall trend is downwards.

There have been months where it’s been a close thing, but I do always earn enough money to pay the bills. I’ve also enjoyed long periods when I’ve been making a decent amount of money. There is so much I enjoy about the freelance life, and I’m grateful to be at least surviving – it’s just I never expected it to be so hard for so long.

I’ve become obsessed with stories of people who struggled for years before finding success. I love the idea of the hero’s journey – the years of hardship followed by great reward. I do get some comfort from these biographies, but I’m not sure how applicable they are to my own experience.

My yo-yo journey as a freelance has been so messy, and it often feels like I’m going backwards instead of forwards. I sometimes can’t tell if this is all normal or a sign from the universe that I should just give up.

Why I’m Not Going to Give Up

It would be so nice to see some evidence that I’m making progress towards a stable income, but all I can do is to keep pushing forwards. Giving up just isn’t an option for me– I’ve sunk too much of myself into this project. It is the first time in my life I’ve been willing to fully commit to something – maybe I’m deluding myself, but I have to believe this passion to continue means something.

The thing that gives me hope is the knowledge this struggle has made me a better person. It has done wonders for my humility, and it has made me appreciate all the good things in my life. It is hard to take things for granted when you are worried you might go bankrupt at any second.

There other thing that reassures me is that I’m not struggling because I’m repeating the same mistakes – I learn from the hard times, and I change my approach going forward. I’m sure that so long as I keep improving my game, there has to be a point where it all becomes easier.

How Long Should I Struggle with my Freelance Writing Business Before Giving Up?

Maybe there is a point in the struggle when we should just call it a day but how do we know when we’ve reached this point? How can we give up when there is always the possibility of success being around the next corner?

What do you think?


  1. I think in Thailand, you have the ultimate safety net of falling back on teaching, which will cover ones main bills, then keep pushing the freelance writing on the side, which tops the income up. Of course this means working more hours, and having less free time, however it may take the financial worry away. Teaching covers the bills, writing is the bonus money. Whilst this may not be an ideal situation, when one has a wife and young family, it ensures a standard of living until the writing picks up again. Having an option like this, the fall back of teaching again, whilst keeping the writing dream alive, should minimize the worry.

  2. Talen

    Paul, I’ve averaged about the same freelancing this past year as 2012 but only because I have a few clients that pay extremely well, everyone else seems to be paying less because they are getting less. It is a struggle at times but being in Thailand makes a lot of things easier such as food prices and housing.

    • It’s good to hear you managing to hold your own Talen. Things are cheaper in Thailand for sure – in some ways it would be easier for me if I was back in Ireland because I could always make good money by doing the occasional nursing shift.

  3. I’m making more this year than I did in 2012, but only because I worked just 6 months in 2012 🙂

    Overall I think I’m probably in a similar situation to you though. I have a couple clients who pay well and the work is regular. I probably make enough to survive in the U.S., so as you might imagine life is pretty good in Thailand. I will need to move the game up in the next few years though because school for Alivia will become more expensive I think.

    Certainly don’t give up, you have built up a nice income and I’m guessing that you could bring in new clients if you had to.

    • Thanks Steve. I like what you say about upping your game – I think that’s the only way. I do expect things to begin picking up for me again soon. I’d just to like to get back up to a good income and maintain it.

  4. Have you heard of Seth Godin? He wrote a book called The Dip, and it’s about this topic you are wrestling with, when to give up and when to keep going.

    As I’ve gotten older (555) I’m more into compromise. I don’t want you to give up because I’m in a similar boat, but I understand the reality of it too, and I don’t think compromising will make you less of a writer or one that “gave up”.

    But hot damn, Jesus, don’t go back to teaching…let’s hope it doesn’t get that bad.

    • Thanks Lani, I don’t mind compromising, but I just can’t find a way to compromise that wouldn’t put me in a worse situation than I am now. I’ll have to check out that Seth Godin book – thanks.

  5. Jim

    Hi Paul , you know , reflecting on some of my experiences in situations like this , I ask does it have to be all or nothing ?

    I mean , I have heard there are many hours English teachers spend between lessons – planning ( cough…).
    Why not change the way you play the game , not giving up the goal , but modifying the strategy.

    How many hours are spent writing for a decent return and how many hours for very little ? Could you be more selective and take on less work , but get more for it .
    Work which could be done in addition to planning a next lesson as an English teacher .

    Then you could enjoy the security of a pay cheque , and the bonus of higher rewards for less writing.

    It may also help to make you feel your efforts are more valued by others .

    Whatever you do , keep the vids and blogs coming , I really enjoy and look forward to them.

    All the best , Jim.

    • Hi Jim, the problem is my high paying jobs are nearly always large orders – they require full-time work. I could have a client contact me today and provide me with enough work to keep me going for a few months. The problem is that eventually the project ends, and I’m scrambling to find a new large order. Ideally, I’d have about three clients offering me a moderate amount of work because this way I could have always have something going on – what happens in reality is a client offers me a large order, I can’t afford to turn it down, and I’m left fully dependent on one client for most of my income.

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