Mastering the mind game of freelancing

Over recent weeks I’ve had an article published on the website of the most prestigious public broadcaster in the world and also had numerous pitches I’ve sent to far less esteemed media outlets ignored. I’ve seen my business account balance wax to over $8,000, only to wane to $2.78 seemingly moments later. I’ve had strangers make the effort to leave flattering comments on articles I’ve posted on LinkedIn. I’ve also had a commissioning editor I had a years-long relationship with abruptly decide she could no longer be bothered responding to my emails. I’ve felt overwhelmed by the volume of work I had to complete one week and found myself twiddling my thumbs the next. I’ve freaked out about having a major client depart while simultaneously fantasising about all the coin I could make if a potential new client took a shine to me.

I relate all this not in an attempt to harvest either admiration or pity but to illustrate that freelancing is, in large part, a mind game. Many novelists like to remind themselves and others of Isak Dinesen’s sage advice – “Write a little a little day, without hope, without despair”. Dinesen (real name Baroness Karen Christenze von Blixen-Finecke) did alright for herself, churning out books including Out of Africa and Babette’s Feast in what was a presumably a Zen state of equanimity. If I had one piece of advice to give to freelance content providers, it would be to write as much as possible every day, without hope and without despair.

Here are some lessons I’ve learned the hard way about maintaining a level-headed perspective in the face of freelancing’s triumphs and tragedies.

Accept that you will be rejected 99 per cent of the time

I once wrote an article about a pricey dating coach. As far as I could surmise, he didn’t do much other than take his male clients to a nightclub and force them to keep approaching women. Did these men experience a mounting sense of failure, futility and self-loathing as they were brushed off and, on occasion, cruelly mocked by their female targets? Undoubtedly, they did. But as the dating coach forcefully explained to me, you don’t get to experience sweet success without spending many hours chowing down uncomplainingly on the excrement sandwich of rejection.

I usually only approach organisations that have advertised that they are in the market for content. On average, maybe one or two of those approaches will result in the organisation getting back to me. Of those ‘warm leads’, no more than one in 10 turns into a solid client that provides me with an ongoing revenue stream. Of those solid clients, 10 out of 10 will at some point decide they have no further need of my services.

But, as the dating coach might put it, so what?

If you approach 500 organisations every year and five of them end up commissioning around $1700 of work a month, that one per cent success rate translates to a six-figure annual revenue stream. Yes, it would be nice if you could pocket the money without having to step in front of a firehose-blast of knock-backs, but I’m yet to meet a freelancer who’s worked out how to pull that off.

Resist succumbing to either desperation or hubris

The two mental states that get investors into trouble are greed and fear. Hence Warren Buffett’s oft-quoted counsel to “be fearful when others are greedy and greedy when others are fearful”. The two mental states that get freelancers into trouble are desperation and hubris. Hence my advice to freelancers is to attempt to retain some humility when things are going swimmingly and hold on to some self-respect when they are going disastrously.

Let’s start with the perils of hubris.

After months/years/decades of grinding away, it finally seems you’ve made it. In fact, you’re in such heavy demand that you start to believe it’s no longer an efficient use of your valuable time and exceptional talent to engage in pedestrian activities. Activities such as checking your work (surely some hack sub-editor can take care of that?). Or responding to emails from clients (don’t they understand how busy and important you are?). Or meeting deadlines (given how scintillating your copy is, surely you don’t have to be governed by the same timetable as lesser mortals?). And now you’re doing so well, maybe you also ditch some of those loyal but humdrum customers so you can devote more time to all those upmarket clients that soon will be offering you top dollar to work for them.

Even if you haven’t been guilty of believing your own publicity at some point (and it’s a rare creative type who hasn’t), you can predict how this morality tale ends.

Of course, desperation can also lead to bad business decisions. When the inbox stops pinging, it’s easy to start panicking. This is counter-productive given that reeking of desperation is just going to make it even more challenging to attract good (or even bad) clients. Taking on jobs you are ill-suited for, or lowering your rates, or emailing contacts incessantly to beg for work rarely turns out well over the longer term.

By all means, get out there and shake the trees but always act like you’re negotiating from a position of strength. Remember that just like the busy periods, the quiet times never last.

Know thy limitations

Freelancing comes with some impressive upsides (i.e. no commute, dress code, fixed working hours, boss, office politics or corporate bullshit), especially for those of us who value our autonomy.

That noted, not everybody is cut out for the never-ending peaks and valleys of self-employment. If you’ve given the gig economy a red-hot go and discovered you don’t cope well with loneliness, instability and rejection, there’s no shame in returning to working arrangements that you find more amenable.

You’ll rejoin the ranks of wage slaves with a greater appreciation for what employers offer their staff. You will have acquired skills from running your own business that make you a more capable and promotable employee. Most importantly, you won’t die wondering whether the grass is greener on the other side of the livelihood fence.