10 Things I’ve Learned About Being A Freelancer: Part 2

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, I am including setting up 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. Here’s part 2.

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6. Be honest about who you are

In my January 2018 conversation with Mickey Smith, we explored his single-minded approach to creativity. Pic: Tozer

One of the most popular parts of my recent conversation with US snowboard broadcaster and journalist Tom Monterroso was when we discussed/confessed how we envied friends who’d dedicated themselves completely to one craft for the entirety of their lives. And about how we secretly feared that the fact we hadn’t done that meant our own creative efforts over the years where somehow less worthy.

In my case, I was thinking about my friend Ewan Wallace, the finest guitarist I know whose single-minded dedication to his craft has enabled him to carve an enviable career for himself as a session musician playing with the likes of Bonobo. Or Mickey Smith, another utterly single-minded creative who lives and breathes every project with an awe-inspiring intensity. Or my pal Schoph, who can go days without leaving the studio as he labours away on his complex, technical pieces.

Why is this idea of the solitary creative genius attractive? And why should it induce envy?

I’ve come to believe it has much to do with the stereotype of creativity that is fetishised in our culture. You know the one. The anointed creative with the pre-ordained talent. The artist in the garret who forgets to eat or wash as she quests away on her latest magical act of creative alchemy.   

These stories are beguiling. But it’s important to remember: they’re just stories (which Thomas Edison, for example, demolished with that old “…genius is one percent inspiration and 99 percent perspiration” line).

That’s why it’s important to be honest about what you actually are, and the type of work you’re actually good at, rather than succumb to the lure of these romantic imaginings.

Take Ewan, who I was fortunate enough to live with for over a decade. During that time, I watched with awe as Ewan devotedly and purposefully practised his playing for around four hours a day. Every single day. And he wasn’t just strumming along to Wonderwall. He was analysing his shortcomings, devising ways of improving his technique, finding people who were better than him to learn from, and striving constantly to improve.

Now, during that decade we lived together, I also played a lot of guitar. Did I improve? Sort of. Did I make the leaps and bounds he did? Not even close. And for years I beat myself up about this. What I didn’t realise or acknowledge at the time was that I was learning and advancing in other ways and on multiple fronts. Where Ewan focussed, I spun plates. After a while, I realised that my approach was also fine, and that even if I had the inclination to try Ewan’s way, my personality and way of working meant that I’d find it impossible. It was an important and liberating realisation.

I think the same thing now when I see people futilely trying to turn themselves into ‘creatives’ or ‘writers’ because it suits their own self image, rather than because it’s what they’re actually good at.

The problem with this bit of advice is that pretty much everybody in the world has to learn it empirically. Thanks to our old friend the ego, it can be a very difficult thing to admit.

So you’re probably quite likely to ignore this one. But I can guarantee that the sooner you learn this lesson, the happier your working life will be.

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The first piece I had published in a snowboarding magazine, summer 1996. Pic: me

7. Appreciate the power of the niche

Over the course of 25 years in the game, my own career as a journalist has come full circle, in a way that really reflects the changes that have taken place in the wider media landscape.

I got my first real ‘break’ (itself an extremely flawed concept) at the age of 19, when I had my first article published in Snowboard UK during that hellish 1996 summer. That led to some initial freelance work with Whitelines, before I was offered a job there as a staff writer right as I left University at the age of 21. Soon, I was having small pieces published in various European and international snowboard publication, such as Freestyler, Snowboarder and Transworld.

By any reckoning, it was a great start. And yet, looking back, I’m struck by how much I didn't really value this, instead seeing it as a stepping stone to a ‘proper’ career in journalism and the media. You know. ‘Real’ newspapers and magazines, like the Guardian, or the Times. I spent roughly the next decade attempting to use my experience in action sports media as a platform upon which to build a career for myself as a freelance travel and lifestyle journalist, while taking the other stuff very much for granted.

This quest was useful, obviously, and a lot of fun. It meant I learned many of rudiments of the freelance art I’m outlining here (not least how to blag endless free snowboard and surf trips, which I still consider an essential skill, and which I won’t be covering in this piece. Sorry, everyone).

I also made many, many mistakes that make me cringe to this day; most of which were linked to me having way too high an opinion of myself as a writer, and failing to tailor my pitches correctly as a result.

While all this was going on, the internet was (to put it kindly) upending the business models of the very media titles and institutions that I so venerated as the type of ‘real’ outlet a shithot hack like me ought to be working for.

It happened quickly, too. I remember pretty clearly when I realised just how quickly, and how it was going to decimate our industry. I was on a press trip with a group of fellow travel writer friends, one of whom had just lost his job as Travel Editor at one of the UK’s foremost nationals. “One of the reasons I got into journalism in the first place,” he lamented, “…was because I thought it would be a job for life. That was five years ago!”

Within a couple of years, almost all of my freelance journalist pals had either quit, retrained or gone in-house. The few who are still at it are on the hustle 24-7. As this change occurred, I was able to fall back on my surf, snowboarding and action sports work, which protected me from these changes and enabled me to continue having a career.

The lesson? There’s power in the niche. Sure, at the start I thought my putative career as an action sports writer would be a mere stepping stone to greater things. In the end, as I belatedly realised, this specialism was … actually my career.

Life is what happens when you’re busy making other plans, and all that.

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My podcast work station, just after I cleaned the shed. Pic: me

8. Understand your rituals

“If in doubt, tidy the studio” - Brian Eno

There’s nothing like a sturdy work deadline to bring out every last quirk of your psyche. My own deadline rituals follow a pattern that appears to be ingrained in me so deeply, on some primordial, Freudian level, that it would take a therapist to unpick.

First, I tidy up. Yep. Apparently, this is very common. In my case, it appears to have a cleansing, scouring affect on my right-brain. Or, it could just be me fucking about and finding endless things to do instead of the actual thing itself. Whatever the reason, it suddenly becomes essential that I painstakingly organise the Tupperware. Yes, in the words of the immortal Paul Calf, when it’s deadline time, “the canal’s never been so clean”.

How long this phase lasts usually depends on the gravity of the deadline. I used to justify this behaviour internally by telling myself that I was artificially creating the situation on some unconscious level because “I work better under pressure”. Now this is obviously total bollocks, as anybody who has experienced the blissful feeling of virtuousness that comes with finishing a project way earlier than the deadline will understand (more of which later).

These days, after mulling this behaviour over for around 30 years, I’ve reached the conclusion that it is nothing more complicated than an extension of the behaviour I outlined in part one of this piece: me being terrified that my internal creative bluffing has finally been discovered. So to avoid facing this terrifying prospect, I erect roadblocks of my own making, which I must then dismantle before I can get started.

What does it mean? Fook knows, to be honest. What I do know is that I next move onto stage two of the ritual: spending any number of hours writing one, possibly two, and sometimes even three to-do lists. Seeing the work written down and mapped out in this way gives me a way of tackling it.

With this is done, and when I know I absolutely cannot put it off any longer, I move on to the final phase: getting up stupidly early and getting cracking. And when I say early, I mean 5am. Or even earlier, if it’s a particular whopping deadline. Why? Because I know I work best in this pre-dawn mid-state. Nothing more, nothing less.

Absolutely everybody has their own idiosyncratic behaviours when it comes to creative work. Hell, there’s an entire industry dedicated to understanding them and, if necessary, dismantling them. (Look up The Artist’s Way by Julia Cameron, or The War of Art by Steven Pressfield, for example).

You can’t avoid them. So you might as well understand them. It’ll help, believe me.

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“Just another day at the office LOL amirite?” A lovely day touring with my pals at Patagonia, January 2018. Photo: Hannah Bailey

9. Embrace the tedium

Here’s something those ‘Another day at the office!!!’ Instagram posts of people working on laptops from a trapeze next to Victoria Falls never mention about freelance life: there’s a LOT of admin involved.

When you go freelance, you’re not just expected to do the work part. You have to do everything else as well: accounts, book-keeping, HR, marketing. All of it.

And there’s no way around it: a lot of this stuff is dull as fook. It’s also the aspect of freelance life that confirms that yes, you really have left the safety net of regular employment behind. There’s nothing like filling that first tax return, and realising how little money you earned during that first year, to confirm that you really are out on your own now. Perhaps that’s why so many people find it so weirdly daunting, and cite it as the main thing that’s stopping them from taking that first step into the freelance realm.

I can empathise. In the early years, I made every single administrative mistake in the book. Then I made some more, just for good measure.

Unopened letters piled up by my front door (OK, I still do this). Receipts were stuffed into obscure corners. Tax deadlines sailed by. To be honest, I didn’t give it much thought. Then, one day, that mythical and terrifying scenario that every freelancer dreads actually happened: the taxman came calling.

There followed a surreal and extremely unpleasant few months during which every aspect of my working life was pored over by a dour, sceptical tax inspector who didn’t like my approach to the administrative aspect of freelance life one little bit.

There were dark mutterings about how not keeping proper records was actually against the law, and tangible outrage at the very concept of a ‘snowboard journalist’. “Admit it”, he said at one point. “You just want to go on holiday all the time”. (He had a point there, now I come to think about it).

By the end of this process, I had a £6k tax bill to pay, and a new found respect for the importance of keeping on top of the admin.

True, this is a worst-case scenario. But I came to realise: by ignoring this stuff, you’re just artificially adding more stress, on a subliminal and psychically damaging level, to a lifestyle that can already be pretty stressful.

Another reason it is so stupid to ignore this stuff is because it’s an area where, with the help of a decent accountant, you can take simple actions that enable you to take full advantage of your freelance life - and relieve some of the financial stresses that are another huge part of going freelance.

The solution? Embrace the tedium, and get your head around the admin.

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10. Start with the trickiest task

“He felt the satisfaction and leisure of the man who has organised so well that he is astride of time” —R. C. Sheriff

I love that quote. Because I LOVE the feeling it describes. And because, like all the best lines, it describes an essential truth or feeling that I recognise, but have never quite been able to articulate in the same way. (Art, I believe they call that).

Another reason I like this quote so much is because it is also further evidence to me that my old self-deception about working ‘better under pressure’ is a load of old rubbish. And because it helps me cope with one of the key truths about freelance working life I briefly outlined in the point above: there’s a lot of shit to get through.

I learned long ago that, for me, there’s a pretty simple way of tackling this mass of work while achieving the above feeling (those rituals again): writing one of those massive to-do lists I described earlier. And then starting with the item I’d really like to put off the longest.

I’m not going to claim this as some incredible insight or (vomits) ‘life hack’. I’m pretty sure Tim Ferriss mentions this exact point in The Four Hour Work Week. But it works.

And yet, this is advice I very frequently fail to follow myself. I can’t count the number of times I’ve written that to-do list, only to keep ignoring two or three longer-term items that pretty soon assume Gorgon-like levels of fear and trepidation in my mind.

Sometimes, they can lurk there for weeks (this is usually when I decide to clean the garage, or start re-organising my bookshelves based upon spine colour).

Come to think of it, there’s one of these little bastards on my to-do list right now: ’Sort merchant account on Amazon for Looking Sideways Vol. 1’.

At the time of writing, this little shit has been malingering at the bottom of my master to-do list for around 4 weeks. It symbolises everything I hate about the freelance life: dealing with a faceless institution I know are going to rip me off, having to get my head around a new e-commerce system, wondering how the fook I’m going to link it to my fulfillment company. Which means I’m going to have to speak to Kris, the guy at my fulfillment company who nearly drove me to tears of frustration when we initially launched the book. And so on.

So like a spoiled teenager soiling his own clothes just so he can piss his Mum off by not doing the washing, I continue to ignore it.

The ridiculous thing is that once I start, I know I’ll breeze through it and unleash the feeling of virtuousness which R. C. Sheriff captures so well.

Right. That’s it, I’m going to do it as soon as I’ve finished this sentence. Well, after I’ve cleaned the freezer, that is...