Are you cut out to be a freelancer? Does that nudge hurt? Freelance tough love comes in many forms. It is created with each question or comment that brings you crashing back to earth. It’s there when you know and the client knows what you’ve given them isn’t that great. It’s born when you give it your all and the client still rejects it.

You face so many waves and pains, you are responsible for so many things.

You will have to give yourself your own version of freelance tough love on occasion. That includes drowning out the din screaming “are you cut out to be a freelancer?”

What a terrible question to ask on a freelance website, right? Well, maybe. Let’s not tap-dance in the petunias. Freelancing is a tough gig. You will ask yourself if freelancing is the right thing for you at regular intervals throughout your career. Sometimes, it will be really hard to push past that sensation of sinking into the mire.

Purpose- pffft! Profit- bahaha. Pro-activity? Well, it’ll be sucked into procrastination.

All these things and more will melt away without warning. The life of a freelancer is full of sharp edges and moments you simply don’t see coming.

Well, here’s the tough love speech you need if you’re going to love your freelance career.

Your friends and family (even your romantic partner) won’t be able to relate most of the time. Even if they freelance or work in small business, there is no guarantee. Their attitude towards your work can influence you to drop your prices, accept shitty work and feel isolated.

There is still stigma associated with freelancing. Some people will assume you can’t play well with others. Others will think it means you suck at your job. Or that you’re some kind of weird non-grown up trapped in a grown up body. Or whatever else they invent as your problem on the day.

That stigma can and will colour the way clients will treat you. They’ll assume you only barely live above the poverty line. Or you have some kind of personality problem they need to navigate. Or you’re somehow inferior to them and their career.

You will suffer from Imposter Syndrome.There will be times when you doubt your own credibility and ability. This is especially true at moments where clients are difficult. Or when you’re trying to develop new offerings and expand your business. It will feel as though you’ve walked out on a tight wire without a way to clamber back.

It’s not all beer and skittles.We all skirt close to bankruptcy and feel pressurised as we chase unpaid money.  You can be terrified of the tax department if you exceed your earnings in a year and haven’t left enough money aside come tax time.  You could be threatened with legal action or having your reputation ruined. We’re not immune from being sued. You’ll most definitely face competitive freelancers, some of whom can be almost crazy to deal with at times. You might get distracted by cute ideas and get taken off your path both financially and in terms of your overall goals. You will be worried about work-flow management. And generally take on some pretty damn serious hits. Many of which will keep you awake at night.

Beyond testimonials and the odd kind email, freelancing is a thankless job.Sometimes it will feel like the only time you hear from people is if they want to complain. Remember, celebrity status and parades of appreciation are rare for freelancers. Anger, criticism and unhelpful advice however…

Customers are irrational.You can do a brilliant job only to find the client wants you to rework every single aspect of a project. Sometimes, you’ll need to push for common sense. Sometimes, you’ll have to let it go. You’ll need to pick these battles wisely. It’s hard to balance a tightrope pulled taut by pleasing the customer, having work you are proud of, and preserving your sanity.

You will screw up, be wrong and make a mess of things on occasion. No freelancer is perfect. You’ll need to apologise, make amends and move on. You have to ditch the good girl syndrome at the door because it will only torture you and the people around you.

Freelancing is isolating.You work alone most of the time. You’ll deal with clients that nobody else has experience with. Getting out and about (to co-working joints, shared offices, out of client offices, networking events etc) is essential.

Value is in the eye of the beholder.Get used to having to justify your approach. Stand firm behind your quotes, your rates, the time you take to do things, and the quality of your work. Even if you are super amazing, you’ll still have to explain the value you bring to the projects you are hired to do.

You can also read more about whether you are cut out to be a freelancer via my blog.

What makes a good freelancer? 

You have to be adaptable and learn on-the-fly to stay competitive. You also need to be confident enough to face off with those moments where everything turns to hell.

Smart freelancers abide by the 3 things rule as explained by Neil Gaiman, where you need to be:

  1. Easy to work with (easability)
  2. Good at what you do (ability)
  3. Reliable (reliability)

You can have 2 out of these three things and still get work. But if you are an arrogant person who doesn’t deliver on time, or not that great at the work and unable to meet deadlines, freelance life will be incredibly difficult.

So why would you want to be a freelancer if it is this hard?

You can thrive as a freelancer and build a career that leads to some great opportunities. Freelancing is ideal for certain people. Usually the kind that look at the points below and think “hey, that’s me!” in high volume:

  • You find a day job is often a place where you think “I know a better way to approach this for the customer” with a positive outlook (as opposed to cynicism)
  • Hard work, long hours and putting your bum on the line is something you already do
  • You want to balance other life goals (such as parenting, travelling, writing a book etc) with having a career
  • You like having a career that you are proud of; and know the kind of commitment that requires
  • Making your own decisions and leading instead of following is something you already do and do well
  • Providing guidance to others is both a love and a talent
  • Office politics, group-think and ‘design-by-committee’ have always bugged you on some level
  • The idea of “wherever I lay my laptop, that’s my office” not only appeals, it suits the lifestyle you currently (or want to) lead
  • You’re a self starter who doesn’t need to rely on someone else to prod you to get on with the job
  • You’re passionate about what you do and willing to keep learning and practising your craft

So are you cut out to be a freelancer in the true sense of the word?

Only you know the answer to that. But now is as good a time as any to write down your reasons for being a freelancer. Knowing why you freelance is what helps you get through the tough times. And it helps you identify your freelancing wins along the way.


Whatever you decide, it’s a decision only you can make. And that’s part of the beauty of it all. Your risk, your rewards.

What would you say if someone asked you if you were cut out to be a freelancer? Do you have your own freelance tough love masquerading as self-talk?


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