Here are fourteen hard fought freelance lessons I’ve learned as a full-time freelancer of fourteen years (and a freelance advocate of twelve years via the Freelance Jungle). I’m sharing them so the newbies don’t have to learn the hard way and the other long haul freelancers can add theirs to mine.

Let’s do this, shall we?

1. There is no Us and Them

Like most things in life, freelancers come into this looking for their tribe. Which is admiral and worthy because (to be quite frank) it often rains shit and we need each other to get through. But some people move the tribe thing into tribal territory. They decare for the white knights of freelance good (their tribe) there must be a collective enemy (not their tribe). And it takes the form of all kinds of things:

  • Freelancer VS Client
  • Freelancing VS Traditional Employment
  • Companies of One VS Those That Scale
  • Freelancers Who Meet in Person VS Those That Don’t
  • Freelancers Who Use eBidding Sites VS Those That Don’t
  • Freelancers With Degrees VS Self-Taught
  • Freelancers Who Follow This Guru VS Freelancers Who Follow a Different Guru
  • Freelancers Who Say Freelancer VS Those Who Don’t
  • Freelancers Who Are Creatives VS Those That Don’t See Themselves That Way

Eventually, it all come downs to: My freelance tribe VS the other freelance tribe over there.

But there is no real Us and Them. And the sooner we stop looking for our personal villain and just embrace the community’s diversity, the better off we’ll all be.

2. Look after your best asset – you

A lot of freelancers love their work and get to follow their passion. And some do follow their passion – right off the damn cliff. The workaholism and “freelance is all I need” rhetoric tells us one thing – burn out will slay you one day.

It doesn’t matter how much you love freelancing, if you don’t rest, you will burn out.  You wouldn’t run your car day and night forever on cheap fuel in tiny doses. So, don’t do it to your brain.

3. In service does not mean in servitude

“The customer is always right, in matters of taste” – Harry Selfridge.

What Selfridge meant was if someone wants to wear an ugly sweater, at a certain point, you’ve got to let ‘em buy it. He didn’t mean that clients are always correct in their opinion or assumptions. Or that they know something we don’t.

Understanding that to help someone sometimes means challenging them, offering them alternatives and not doing exactly what they say is part of freelancing. There’s a difference between servicing a project and being in servitude to the people running it.

4. The closer you are to your core capabilities, the happier you will be

The hardest part of freelancing is arguably everything else you need to do to make sure you get to make the art you wanted to make.

Freelancers wear many hats. The more we get dragged away from our core offering by marketing, admin, social media, accounting, client management, networking, technical support, business development, and all the other hats, the less time we have to stretch our creative legs.

Whether you outsource, develop a taste for certain aspects, hack your responsibilities, automate, or find a new spin on how to do these things, the main priority is to stay connected with what you like to do more than anything.

5. Nobody freelances like you 

Learning from other freelancers is great. Learning when to pick what it listen to is even better. Don’t let another freelancer try to tell you how you freelance isn’t right. Chances are, they have no clue either.

You’ll find what’s right for you if you remain choosy instead of imbibing everything they’re selling. And developing your own style of freelancing can be freeing and empowering.

6. You need a financial goal

Freelancing revolves around asking people to pay you what you are worth, pay you on time, and not treat you like some brainless, bottomless cup at Seven Eleven. Understanding what you need to earn to thrive and to back yourself any time someone tells you otherwise is a key to your financial advocacy and survival.

7. Doing too much only confuses clients

Clients want to see what they asked for reflected in the work they receive. And we might sometimes fall for the temptation to add more work in. But most of the time, clients just want to see what they asked for. Your extra bells and whistles aren’t necessary – or wanted – most of the time. And the rejection of that extra mile people pleasing stuff is bound to sting more than if you just did the scope and met the delivery.

8. It’s your bloody business

Want to work three days a week or work a small number of hours every day? Feel the need to meet every prospect over coffee or send every prospect to Zoom? Don’t want to offer more than one service or want to offer all kinds of wonderful things? Want to always be available or never ever give your phone number out to anybody?

It’s your bloody business. Play it the way you feel it.

Just remember that no matter what you do, consistency is key.

9. Beware the client’s office politics

In freelancing, even if we’re popular and likeable, we’re temporary. And the transient nature of the way we work means that someone else’s workplace political situation may end badly for us. It means that no matter how much a client bitches about their colleague, we’ll get nowhere if we agree. And our lack of power means that when it’s time for heads to roll, ours is often the easier target.

10. There’s joy in curiosity

Yes, there is a lot to learn as you freelance. But there is also a beautiful joy in learning new things and the time spent experimenting. Part of what we do as freelancers is engage with new concepts and ideas regularly. The more you do it, the lower your stress will be, the more confident you’ll feel, and the more skilled you’ll become. So, embrace it.

11. You will cringe later at early stage you

Freelancing is a learning-by-doing scenario. No amount of boil-in-the-bag class will teach you exactly what it is like to be in the freelance saddle. You will learn a lot of stuff the hard way. It will also mean that the naïve confidence we all come into freelancing with looks a little silly once we’ve been at it a few years. But that doesn’t mean you shouldn’t try because other freelancers are more established. Or that old blogs, assumptions and marketing is evil because it makes you cringe. Part of growing as a freelancer is looking back and saying, “what was I thinking?!” In fact, it’s proof you’re going in the right direction.

12. Freelance Gatekeepers aren’t Freelance Gods

Humans have a very boring habit of deciding because something isn’t to their taste, it shouldn’t be for your taste, either. We’re prone to scarcity and the desire to protect our patch. We assume our version of best practices or ethical behaviour is the gold standard.

Humans are snobby, judgemental, immature, and protective sometimes. And unfortunately, it leads to things like freelance gatekeepers.

But like everyone else that has an opinion on what you should do and who you should be, remember this:

It’s your arse on the line, not theirs. They won’t suddenly rush to your aid or help you face any negative consequences of their advice. They probably won’t be at your funeral.

So, you do you, boo.

13. Don’t build empires on shifting digital sands

While it’s tempting to leverage platforms, tie your business worth to followers, and think you are Top of the Pops based on analytics, none of it means anything if you don’t have somewhere else for your clients to land.

Social media accounts get hacked with alarming regularity. Social media platforms can close or fall out of favour. Heck, even SEO can cut out the creators and start bypassing you to serve their own content.

But if you have your own space (website, newsletter, shopfront etc), at least you’ve still got something to work with.

14. Freelancing is a challenging (but rewarding) career

Tech bubble bursts, eBidding sites, GFCs, pandemics, natural disasters, inflation crisis, AI threats, big tech pivots – we’ve seen them all in the last fifteen years. That will not change. The world is in a state of flux. There will always be another problem just around the corner.

But what we can do as freelancers is keep talking to each other and ourselves. We can keep working through the problems we face and try to find opportunities. And find a way to be happy with the work we do.

There will always be another series of external challenges to take on. And there will always be freelancing to fill the gaps and ride the waves.

What helps freelancers survive is their ability to adapt and change.

You can’t stop these things from happening by yelling at them. You cannot ignore them. You can either learn the new Tik Tok, outpace AI, or consider your other options.

But don’t get hit with the arrow of change and feel the sting only to keep twisting it in position by refusing to acknowledge it exists. Get inventive!

I’d love to hear from freelancers on what your lessons are – especially if you’ve been at it longer than me!

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