Insights: What I’ve Learned About Being A Freelancer - Part 1
Lessons learned in the 25 years I’ve spent pissing about for a living and trying to avoid getting a proper job.
I realised recently that I’ve been a freelancer my entire working life. And yes, as my definition of being a freelancer is not having a boss, I am including the years spent running our agency All Conditions Media in this.
So I decided to write down ten things I’ve learned in that time, in the hope it might be useful to anybody thinking of embarking upon the freelance life themselves.
1. You must enjoy your work
Let’s start with a really obvious one: you must have a genuine appetite for whatever work you’re about to base your career around.
Why? Because, while it can be hard to remember when you’re fired by the romance of an idea, and fantasising about that exciting new life you’re imagining for yourself, it is one of life’s immutable laws that absolutely everything - performing open heart surgery, playing at Wembley Stadium, flying a helicopter - becomes routine after a while. (Why else would all rock stars, at some point, end up writing a record about how devastatingly difficult it is being a rock star?)
Professionals understand this. They also understand that the act of (sorry everybody) ‘doing the work’ means turning up day in/day out, when the glamour has long faded, there’s a stack of bills on the table, and the latest Damoclean deadline looms over you.
But how can you truly know if you’ll love the work when you’re at the beginning of your freelance career, have got no outlets, and are wondering how to get started?
The answer is simple. Forward movement, of any kind. Even just making a tiny decision that changes your current situation in some imperceptible but important way counts. If you ask me, this simple act, in whatever context, is the entire ‘point’ of life. Even a single, solitary step counts.
So make that first move, and just do … something. Anything. Which could mean writing your first article. Or taking that first photograph.
I was lucky enough to find the work I wanted to do early. I was 14 when I decided I wanted to become a journalist. One of my Mum’s friends was a producer on a local late night TV show called Granada Upfront, which was presented by local broadcasting legend Tony Wilson. So I asked this friend to take me along to see an episode being recorded so I could meet and interview Tony, which I then submitted to the school magazine. Hooray. My first published article.
The next year, I learned that a bloke called Dino Davie, at the time one of the only British cyclists to have forged any kind of professional career, was living down the road from me. I still can’t believe I did this, but I got his number out of the phone book (lol), rang him up, persuaded him to let me interview him, and submitted it to the school magazine. (Hilariously, given that they had to literally browbeat kids into writing anything for that magazine, they rejected it, thus teaching me another important early lesson about the vagaries of the freelance life).
A couple of years later, when I had my foot in the door at Whitelines, I found myself on a family holiday in Florida, during which we visited all the state’s amusement parks. To pass the time, I reviewed each rollercoaster I went on, which I then submitted to Chod the editor when I got home. (Hey, magazines used to publish that type of thing in the ‘90s. And yes, this one got rejected too).
I’m sure you get the point.
It’s also important to remember that you need to nurture this urge for your entire career. Yesterday, I was in the shower when I had an idea for a blog about how to become a freelancer. Today, I sat down and started writing it, partly because I knew I’d enjoy the process of trying to marshal it all into one coherent thread. And so it goes.
In any area of life, forward momentum is critical. You’ll soon learn whether you love it enough to make it a job. Start today, and make it a habit.
2. You need to understand the rules
When you embark upon a career as a freelancer, a huge part of the early phase is spent trying to work out the rules of the game. The problem is that not all of these rules are obvious. Solving this puzzle is as much as part of the freelance life as the actual work part. Fortunately, some of these rules are universal, whatever the discipline.
This one could take up an entire article on its own, so for now I’ll just concentrate on a couple of the basics, from the perspective of somebody who has pitched hundreds of ideas as a writer, and who these days gets pitched every single day, by people who want to work with my agency All Conditions Media, or by people who want to work with me on the podcast.
The first of these rules is - when pitching somebody, you need to work out how to make their job easier, and communicate this to them in a way that makes your case unarguable. The best example I can think of here came from Fina Charleson, the producer who edits my podcast each week and who is now a valued friend and colleague.
Fina’s pitch was simple - 'I will take the most tedious, soul-destroying part of this gig and do it for you in a simple, affordable and efficient way. This will free you up to concentrate on the parts of the process you actually enjoy'.
Thanks Fina. Where do I sign up?
Here’s another one - make it relevant. This is so crashingly obvious I can’t believe it needs to be pointed out but, judging from the sheer number of inappropriate pitches I get every single day, it does.
You really, really need to make sure the idea you’re offering your recipient is relevant to them. This involves research, time and care; which communicates to the person on the receiving end that you’ve paid them the compliment of taking the time to understand what it is they do.
Irrelevant pitches tell the recipient, on an extremely basic level, that you can’t do your job properly. If you can’t be bothered working out what type of work an agency actually does, for example, why on earth would that agency hire you as a consultant?
Understanding basics like these will at least give you a platform for success. Taking the next step requires tenacity, creativity and a lot of practise until you get to Fina-like levels of pitching greatness. In the meantime, you will receive plenty of rejections. Which leads me to the next two very important lessons.
3. Learn how to take feedback
If you ask me, one hallmark of a professional is somebody who can take feedback like … well, a pro. Sounds simple, right? But my own experience is that this is one of the most difficult things to learn. Even now, after 25 years, it can catch me out.
When it comes to creativity, rejection is as inevitable as the sun rising each morning. And as a freelancer, you will need to learn how to take rejection in the right spirit.
(At one point early on in my career, I wrote down the words ‘Thicker skin developing daily’ on a piece of paper, which I stuck to my monitor. Did it help? Not really. But it was a useful reminder not to take things personally when I received yet another rejection).
One reason it can be so difficult to accept rejection is because ego is such a key driver of creativity. All creative work, when you think about it, is really the creator sticking their hand up and asking the world to notice them. I don’t think this is a particularly profound insight. But it is true. And when you are mustering up the courage to start in the first place, it becomes particularly important.
Why? Because creativity often involves a form of self-deception, during which you rely on your ego to overcome the imposter syndrome that is telling you not to bother in the first place, because it won’t be good enough.
The irony, of course, is that once you’ve stuck your head above the parapet, you’ve put yourself in a position to have that imposter syndrome confirmed to you. How? By the horrific possibility that somebody you’re desperate to impress (the editor you’re hoping will commission you, for example) might tell you what your work isn’t good enough.
That’s why, when you’ve poured your heart and soul into something creatively important to you, rejection from can be so hard to take.
The thing to remember is: while for you, it is very personal indeed; for this bearer of bad news, it isn’t.
Of course, you’ll always come across dickheads who use this power negatively (like the English teacher who used to edit the school magazine, who used to shout ‘How’s Dino Davie?’ at me in the corridor).
But these are rare. Most of the time, the people who deliver this bad news are just like you. They’re just trying to do their job to their best of their ability, and are looking for freelancers (which could be you!) who can help them do that.
The best way to subsume your ego, and take your medicine in the right spirit? Think of it as a free lesson on how to make your work better, and make sure you heed it so that your next piece of work is even better.
Whatever you do…
4. Don’t be a dick
“Being kind is often more important than being right. More often than not, being right can win the short term game. Being nice is the only way to win the long term game.” - Nathan Gallagher
This one is really important, and something my pal Nathan covered brilliantly in his interview in Jonathan Weaver’s excellent book The Anti-Blueprint Project.
Enjoying working with somebody is a critical part of the freelance game, and one of the simplest things to stack in your favour. One of the reasons I work so well with Owen Tozer, for example, is that the basis of our working relationship is that we really like hanging out together, and use work as an excuse to do so.
I’ve even started business relationships based upon nothing more substantial than the fact that I like the other person and really want to work with them.
Nobody in the world is immune from this factor. I realised this about a decade ago, when I was working on a project with somebody extremely famous, and we were looking to raise money to help get it off the ground. Here was a guy at the absolute top of his game, working with some of the biggest brands in the world. It looked like an open goal. “Ask my sponsors,” he said. “They’ll definitely help us”.
Imagine my surprise, then, when I spent the next six months being completely ignored by all of these sponsors. At first, I assumed it was me. Then, when I did manage to book in a few pitches, I assumed it was because they didn’t like the idea.
About six months later, I was with a friend and was explaining the entire situation to him. “Ah yeah”, he replied. “I heard about that. It’s nothing to do with you or the project. It’s him. They all think he’s a total dickhead and nobody wants to work with him. He’s only still there because he’s been on their books for so long. I’d drop it if I where you, because it’s never going to happen. And you’re starting to annoy people”.
Recognising good advice when I heard it, I did just that. But it confirmed an important lesson. Nobody likes working with a dick. Even now, I’m convinced that a big part of most ‘cancellings’ (yawn) is an individual’s, er, dickhead chickens (one mixed metaphor I’m going to proudly own, so don’t @ me) coming home to roost, rather than any great point of principle.
You can also be nice/none-dickish in the other direction. For example, when rejecting somebody’s pitch. Social media is full of snarky, self-important journalists posting things like ‘Hey everyone! Look at this SHIT pitch I just received from this PR! What a bellend!’
When challenged, they always defend this transparently thirsty behaviour as a gallantly yet reluctantly offered public service. Sure, lads. (Even more damningly, as content it is about as interesting as somebody complaining how many emails they get. Newsflash: everyone in the developed world gets a lot of emails.
So don’t be that guy. It just makes you sound like a dick. Instead, try sending back a polite note saying, ‘Thanks for the pitch and interest, but it isn’t for me.’ Who knows? They might go away, think about it, and come back a few weeks later with something you really can’t ignore. They might even up being important to your career. Why? Let’s find out…
5. You’ll need a network
It is an inescapable fact that success in any endeavour requires a network. It is another inescapable fact that the answer to the question ‘How do you meet the right people?’ is different for everybody.
Consider, by way of example, the cabinet of the government of the United Kingdom. At the time of the September 2021 reshuffle, 60% of incoming ministers went to Oxford or Cambridge, compared to 7% of the general population. You’ve only got to look at some of the clowns in charge right now to know that this had nothing to do with merit, and everything to do with their network.
Whether we like it or not, accidents of birth, access to pre-existing networks, and the weight of often nefarious historical trends all have a huge influence on our path through life.
That’s why successful and/or privileged people making Molly Mae or Kirstie Allsop-esque ‘We all have the same 24 hours in a day/You can achieve anything if you work hard enough’ arguments are so tone-deaf. It is also one key reason why diversity and inclusion is such an important topic, and why I focus on it so heavily on the podcast.
Personally, I think it is fundamentally dishonest to suggest otherwise. (If you disagree, I recommend watching the above clip of Martin Luther King above, in which he deftly and definitively demolishes the standard meritocratic argument that people have been wheeling out since the dawn of time).
So with all that said, and assuming you’re coming at this from a standing start - where to begin?
I’m just going to talk about my own situation here. I was born into a lower-middle class family in Manchester in the mid-1970s. Thanks to the 11-plus (double lols) I went to a state grammar school, and was told from an early age I was a bright kid who should aim high. Looking back, even this simple affirmation was enough to give me the confidence to embark upon the quixotic path I eventually followed. Again, very obviously, this isn’t the case for everybody. (And not everybody’s Mum is mates with Tony Wilson’s producer).
All that said, it’s still a long way from there to the incredibly weird job I’ve ended up with. Uttering the words ‘Snowboard journalist’ would certainly have got me laughed out of the 1992 Stretford Grammar School careers night.
One of the key ways I achieved this was by building the network that still serves me today. I started early, and I started the old fashioned-way: by contacting as many people as I possibly could in the hope that they would notice me.
One example springs to mind. It was 1996, the summer of Euro 96 and Football’s Coming Home, and I’d just graduated from University. I’d been evicted from my house, dumped by my girlfriend, and was so skint I was working at McDonald’s in Sheffield City Centre.
The place was so rough we had a panic button under the counter that could instantly summon a police riot van. I go so much shit from the customers that I ended up changing my name badge to ‘Ted,’ so at least it was funny when they started threatening me. Yes, it was the most depressing summer of my life.
But it was also the summer I’d had my first article published in a real magazine. And been paid the same amount of cash I was being paid for two weeks spent being called Ted by pissed idiots, which was the real eye-opener.
This was the glimmer of hope that I needed. So every day, during my lunch break, I’d go to WH Smiths, grab five magazines, and write down the Commissioning Editor’s name and mailing address. Then, every night, I’d go home and HANDWRITE THEM A LETTER full of article ideas which I’d then stick in the letterbox the next day. Yes, this was how we did it before everybody had email.
I did this for months. During that time, I received one solitary reply. Yes, one.
This was from a journalist called Kate Spicer who was working for a long-lost women’s magazine called Minx. Kate, bless her kind heart, replied with a note saying to look her up next time I was in London. A few months later, when I was down in London working for TSA at the Ski Show, I took her at her word. These days, Kate is a proper big shot journo but I never forgot her act of kindness, which was enough to keep me going when I really had no idea where to start. And yes, we’re still in touch.
This is another reason why I do my best to pay it back now when people contact me for advice, pitch me irrelevant ideas, or message me on Instagram asking if they can pick my brains for ten minutes. Often I’m too busy. But if I have the time, I usually will.
Why? Because 25 years ago, it was enough to keep me going, and a crucial part of building the network that everybody needs to succeed.
Eh up! Great little series Matt, some words of wisdom I perhaps needed to hear starting out again on a new road
Hi Matt, I was trying to find my own substack account and found this, perhaps you can repay the favour (not that you owe me one) and help Granny master this new platform