Are you cut out to freelance? 5 ways to tell

by Rachel Smith
19 September 2022

Updated Sept 2022

In all the years I’ve been freelancing, I’ve seen a lot of colleagues dip a toe in the freelance world, and just as quickly jump out like a scalded cat and get back into an office job as soon as they possibly can. I’ve answered countless questions from friends and colleagues on how to make it work, how to stay motivated, whether there’s enough work out there. And after watching many accomplished journos either try it and thrive (or crash and burn), I know for a fact that not everyone is cut out to freelance.

Here are the five tell-tale signs you’ve got what it takes.

1. You’re prepared for your finances to change drastically

Something I heard over and over from colleagues who abandoned freelancing to return to the ‘safety’ of an office job was, ‘I couldn’t handle the unpredictable cashflow – I need a regular paycheck’. I totally get that. Freelancing, especially at first, can be treacherous financially until you get into a rhythm of regular work and if you haven’t started out with regular gigs under your belt (or have a partner with a steady income), things may be hairy for a while. Also on money: you need to become very good at talking about it, setting fees and negotiating constantly. Knowing what to charge and working out which work/clients you need to chase in order to make a decent living is a huge part of whether you’ll succeed or fail.

2. You’ve already been freelancing on the side

If you’ve been building your freelance business while working full-time, this tells me you’re realistic about how it’s going to be, and you know the importance of having some work / contacts in place before you move into freelancing full-time. When the novelty of your first week at home wears off, it can be a massive shock to the system realising your new job is no cakewalk and you’ve got to hustle if you want to eat. Much better to have started hustling while you’re still earning a wage.

3. You’ve got a bulging contacts book…

… of editors and potential clients, and you’re not afraid to hit them up for work with regular pitches or emails to see if there’s something you can do for them. A huge part of freelancing is the ability to put yourself out there again and again. To pitch, even when you don’t hear back or get knocked back. To be always on the look-out for potential work or new clients. Being able to confidently hand over a business card or sell yourself. It’s very, very different from sitting at a desk and having certain pages to write each week or being assigned a list of stories to write after the weekly editorial meeting.

4. You’re good at motivating yourself

Are you? Really? Be honest with yourself about this one. Do you need an editor breathing down your neck? It’s fine if you do; some people only operate best under the structure of an office. And, the best freelancers I know all have systems in place; they pitch regularly and track their pitches, they meet up with editors face to face, they don’t leave deadlines until the night before. Temptations – to put a load of washing on, hit the gym, watch a daytime cooking show – are plentiful when you work from home, and while of course you can shoehorn a lot of that into your day when you’re well organised, if you’re NOT organised enough to knuckle down and work, those temptations can eat up the hours. And before you know it, a week’s gone by and you’ve got zero bucks to show for it.

5. You’re quite solitary

Okay, so many might disagree with me on this one, but I have seen quite a few colleagues abandon freelancing because they just got too lonely. They craved the buzz of an office and liked working as part of a team – it drove them. Freelancing is the opposite. You work alone for the most part and you’ve got to LIKE doing that. You’ve got to crave that peace and quiet and not feel like you’re missing out. Of course, it’s important to take steps to be social and network, but ultimately you’ve got to want and need that solitary space in which to create.

Do you agree with our points above? When did you realise you were cut out to freelance (or that it wasn’t for you?)

Rachel Smith

7 responses on "Are you cut out to freelance? 5 ways to tell"

  1. Kate McMahon says:

    I agree to an extent about the solitariness of freelancing, but I work out of a coworking space that solves that side of things for me. And, although I am a soloist, I’ve noticed others starting businesses as partners or teams, which is almost the opposite of solitude!

    1. Rachel Smith says:

      Interesting Kate – I’ve had other freelancers ask me to join with them in co-working spaces but I’ve never actually done it. Sounds like the best of both worlds; the camaraderie of other soloists around you, yet you’re still your own boss, can set your own times etc.

  2. pip harry says:

    Such great tips! I’ve been freelancing for 9 years and I’ve recently been mixing working from home with a few part time days in an magazine office on a day rate. That’s been fun to get some steady income and break the lonely/talking to walls. I’ve also been able to learn some new systems and skills.

    1. Rachel Smith says:

      I’ve often been tempted by 2 or 3-day a week jobs with the chance to freelance on the other days. I’ve never actually gone for one but in lean times, it always looks like a very attractive prospect. Never say never I guess 🙂

  3. Great tips! I love the buzz of an office and do go through periods where I really miss it, but I thoroughly enjoy the freedom of running my own (solo) business. I’ve found it really important to supplement work colleagues for other freelancers – especially those who work in similar areas – who I can catch up with regularly.

    1. Rachel Smith says:

      I do regular catch-ups with colleagues too. It’s sanity-saving!

  4. clairemchow says:

    Another quality. You’re PROACTIVE. It’s the only way to make freelancing work!

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