How to go (and stay) Freelance: Five tips from Five years in

Going freelance - How to do it and stay freelance - Charlotte McMurray at Cameo Digital

5 years is the longest I’ve stayed in any single job. That’s perhaps not a huge milestone for a lot of people, but for me, it’s out of character and ever so slightly scary. I’m not really the type to stay doing one thing for all that long – more than a few years and I’m usually itching to shake things up and try something new. 

What’s even more surprising is that the more I’ve tried to shift my approach at Cameo, the more I’ve become convinced that I don’t really want to and that the way I set out five years ago remains a perfect fit for me. 

This all got me thinking about what kind of insider tips I might have for someone thinking of going freelance. Turns out, quite a few nuggets of insight really stick out and have done consistently since I took the leap back in 2016. So let’s get stuck in, shall we?

Going freelance: Five tips to get the most out of it

Freelancing isn’t the same as scaling a startup or growing a larger business, and often the advice out there just doesn’t fit. Not only do many established pieces of business wisdom not really apply to freelancers, they can also detract from the main benefits of the freelance lifestyle, making your business more time-consuming, more stressful and less profitable. Who wants to work more and earn less money?  

So, after five years, here are my top five tips for going freelance, maintaining your hard-earned freedom and making the absolute most of your independent life:

1. Don’t hustle. Ever.

Hustle is a way for rich people to convince you that they deserve to be rich, when in reality they’re just lucky. Hustle tells you that if you’re not as successful as them, that’s your fault because you didn’t work as hard (even though they probably didn’t work as hard as they say).

Hustle teaches you that if you want to succeed you should wake earlier, work longer and grind more in the pursuit of goals that you’ll burn out long before you achieve, because all the 4am yoga and 6am networking meetings have destroyed your executive function, and the crushing guilt of “not hustling hard enough” has trashed your mental health.

Anybody still talking about the value of hustle in 2021 is a sociopath and should be avoided at all costs. 

And that’s all I have to say about hustle.

2. Burn your plans!

I was always sceptical of planning. Maybe cutting my teeth in SEO was to blame for this. 

SMART objectives seemed like a parlour game – guess the number of sweets in the jar. I learned early on that uncertainty is the only certainty, and that any client or manager insisting on a “cast iron, guaranteed” set of ROI projections was probably a twat anyway.

5 years later, the experience of running my own business has completely failed to convince me of the value of planning and has completely vindicated my position on guaranteed ROI. And twats.

Long-term planning (I’m talking about “how do we reach our 15-year vision of being the market leader in vaguely-defined solutions?”-type planning, not “how do we get this project finished in 6 weeks so we can get paid?”-type stuff) is a terrible idea for freelancers. It promotes bad decision making because it pushes you to make decisions that look a bit like they might take you in the direction of your (completely arbitrary) plan, potentially leaving you blind to other, more interesting, opportunities. 

Long-term goals are also an awful idea because as a species we’re terrible at understanding what actually makes us happy. You might think you want a £5million company turnover within 5 years, or to be the global leader in your industry, or to drive a Tesla, or whatever else you can fit on the vision board your motivational coach told you to make.

In reality, even if you do achieve a goal like this, it almost certainly won’t make you as happy as you thought it would, and the act of visualising it will make you complacent and less likely to spot actual opportunities to better yourself. 

But you want to progress, right? It’s good to want to improve?

Of course, but there are better ways to do that.

Instead of SMART goals, go for incremental improvements. How could today be better than yesterday? How can this month be better than last? If the last set of mini-improvements worked, would more of the same be helpful tomorrow, or is it better to branch out in a different direction? 

Build a spiderweb, not a ladder, and take pleasure in looking back at where you started, not forward to what you think you should be aiming for.

3. Avoid people who “see your potential”

As you build your reputation as a freelancer you’ll probably come across quite a few of these types.

They usually want you to come work for them full time, set up a division of their business and “do what you do best” while they handle all the difficult legal stuff, like, y’know, owning the company and distributing the profits. 

It’s a pretty clear “thanks but no thanks” when you put it like that. Nobody goes freelance to end up back in the rat race under a different guise. The trouble is that corporate culture tends to teach you that it’s an amazing stroke of luck to have somebody who wants to take you under their wing and help you make something of yourself. This conditioning can leave you open to making decisions that undermine the freedom and autonomy that make the freelance life so rewarding. 

We’re taught that a mentor is something to be cherished, and that’s not untrue, but many of these people aren’t mentors. When they say they see fantastic potential in you, what they mean is that they see the fantastic potential for you to make them money, or a fantastic opportunity to neutralise you as a potential competitor.

Watch out for: amazing benefits that disappear after the first conversation (“directorships” which are job titles, not actual legal directorships, “dividends” which turn into “performance-based profit-share bonus schemes”, or which are swept under the rug because “the tax is too complicated”); any structure where you keep doing what you’re doing right now, except that somebody else owns part or all of it; or anybody who wants you to come into a “business partnership” who then expects to be able to set your targets.

To make sure you’re not letting the excitement of being chosen lead you to act against your own best interests in the long-term, be aware of “pick me” tendencies in your own behaviour. We’re taught that it’s a wonderful thing to be sought out and headhunted, and, particularly if you’re a woman, you’re taught that refusing these generous offers makes you arrogant and ungrateful.

Neither of these things are true. Don’t let the fear of offending people push you to give up your autonomy.

4. Learn to use your “negative” traits

Closely related to “pick me” anxiety. 

We (by which I mean largely, but not exclusively, women) are taught from day one to be nice, and humble, and quiet, and appeasing. The trouble is that in business that’s not always possible or advisable. There are plenty of people out there who’ll happily step over others if they can see they’re not prepared to make a fuss.

When you’re working for yourself there will be times when you’ll need to be arrogant, and petty, and angry, and vindictive. There’ll be times when you need to be cold-hearted and selfish. There’ll be times when you need to be nasty.

Or, to word that more accurately: there’ll be times when you need to have confidence in your opinions, advocate for your own interests, and draw appropriate boundaries with people who treat you badly. There’ll be times when you need to prioritise your own needs over others’ wants. And there’ll be times when people will react badly to that, and you’ll have to accept that you’re not responsible for regulating their emotions.

From our earliest years, we’re taught that self-preservation and self-respect are negative traits (usually by having them labelled as “selfish”) and that we should unlearn them at all costs. This is completely untrue. Your ability to advocate for yourself, and to effectively utilise those “negative” traits, is absolutely critical to your success and your sanity.

So, learn to embrace the bits of you that you’re told are undesirable when something isn’t quite hitting the mark for you. Fire that client. Decline that request for proposal. Stick to your guns on that day rate.

Be arrogant, bitchy, bolshy and selfish, and do it well.

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5. Work less

If the pandemic has taught us anything as a society, it’s that work is not the be-all-and-end-all we thought it was. We work too hard as a society, and we put far too much emphasis on our work as a measure of our personal worth. 

For some, the pandemic has proven how little our jobs actually matter. If you’re in a professional position, you’ve probably noticed by now that your work really doesn’t have a critical level of importance compared to people who drive lorries or treat sick people or serve food.

It also turns out that a lot of the stories we were told about how we needed to work were also untrue. It turns out that “essential” office attendance wasn’t so essential after all, and that as long as we can turn in the required work at the end of the week, nipping to the post office or taking a few hours to sit in the garden isn’t the end of the world either. 

That’s not to say that work isn’t important: keeping ourselves occupied is good for us, and even “non-essential” work can be productive, useful and rewarding. But for most of us, the world is not going to end if you’re not at your desk 9-5 every day, no matter how much some managers might throw around comments about “commitment” and “team players”.

People who only think about their work are rarely interesting people. Moreover, people with stuff going on outside of work tend to be able to bring a much wider range of perspectives and approaches to bear on their jobs when they are working, so they usually perform better. 

So as a freelancer, take advantage of the “free” part: finish early. Indulge your hobbies. If you don’t have any hobbies, find some. Grow plants, or go LARPing. Take days off when you’re not feeling it and read books that have nothing to do with your work. Remember that one day, sooner than you think, you and everybody you know will be dead, and nobody (NOBODY!) will care about that report. 

Don’t listen to the voices that tell you that you must grow your company, or that putting in extra hours make you more “committed”. Get good at gauging when you’ve done enough, and get good at stopping when you hit that point. Then go and do something else. Something that makes you a better and more interesting person. 

Staying freelance in the face of “proper business” creep. 

If my LinkedIn feed is anything to go by, the pandemic has inspired yet another wave of digital freelancers to break out on their own, and with good reason. 

With remote work now the standard and demand for digital specialists high, it makes sense for experienced digital bods to cut out the middle man, moving on from pressurised agency environments to enjoy more autonomy. For stressed-out agency (and also in-house, who seem to be jumping on the bandwagon too recently) types, freelancing means choosing their own clients and setting their own working hours and methods, not to mention taking their fair share of the profits generated by their efforts. 

Despite loving the way I work right now, however, one of the biggest challenges I’ve had to contend with as a freelancer is the nagging feeling that I should turn my freelance approach into a “proper business” –  one with employees and offices and growth plans and all that grown-up stuff. 

I’ve gone through a couple of (relatively minor) phases of experimentation with “doing stuff properly”, driven by everything from too much work to pandemic panic to too much time spent listening to other people’s opinions. 5 years in, I’m more convinced than ever that that’s a bad idea, and I’m more convinced than ever that freelance is where I’m happiest and where I’ll stay. 

Like every point in this blog post, the bottom line here is that it has to work for you. Some people want to grow their one-person freelance venture into something bigger and that’s great for them. Some people want to run a business that pays the bills and complements their lifestyle, giving them free time and headspace to pursue other interests. Both are fine.  

The key thing is following your gut and doing what you perceive to be right for you, not what society pushes you towards.

Seriously considering going freelance? You can discover more freelance stories from the wider Cameo team here.

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