In praise of practical pessimism


Whenever I start work with a new client, I’m worried. But it’s the kind of anxiety that goes beyond simple self-doubt.

I’m primarily concerned about two things:

a)That I might miss a key bit of information in our sessions together that will give me amazing insight into their brand, meaning I end up getting their tone-of-voice wrong, and;

b)That they won’t like what I’ve written and can’t be bothered giving feedback. They’ll call me out in an email, stop talking to me, and refuse to go ahead with the project. They will curse me and I will never get a job in this town again, and then I’ll have to print off my old hospo CV and work for $15 an hour somewhere to be yelled at by mothers and chefs.

It’s a fairly poor way to look at things, and when I confess this fear of inferiority to other business pals, they often shower me with all manner of praises. Some which I take on, others which I discard. I’m a goddess – yes! I’m so smart – perhaps. I’m a great writer – sometimes. I’m perfect the way I am – NO.

This kind of negativity might sound like it’s entirely counter-productive. Who on earth builds a successful business based on mentally flagulating themselves? Aren’t we supposed to believe the hype on Pinterest and agree that no, nothing is stopping us, we must trust in the cosmic Buddha of self-employment to deliver us to happiness, and happiness is always a choice?

I disagree.

I don’t believe that positivity can save us.

Which is quite a bold and brazen statement to make as an entrepreneur. But I’ve noticed that one of the most common things to say to someone who’s fallen on hard luck is “Just think positively! Visualise your success! Yes, you can!”

Of course, optimism has its health benefits. According to many, many, many a study that you can find online, optimism helps you get over an illness or disease, decreases recovery time, and boosts your immune system.

But thinking positively isn’t always the silver bullet it’s lauded to be.

In fact, I’d argue – along with others way, way before my time – that a glass half empty approach might actually see you more successful, happier and safer in the long run.


Practical pessimism as a productivity hack

Let me say this frankly: thinking positively is not entirely productive.

Believing in yourself, while important in order to sell your ideas and persuade others, is not the only tool you should have in your arsenal.

We are told to elevate our thoughts, to raise our vibrations, to utter mantras in direct opposition to our circumstances, all in the name of attracting towards us what we truly desire.

But thought without foresight, and execution without preparation, are all recipes for disaster.

In their book The Power of Negative Thinking, psychologists Julie Norem and Nancy Cantor examined two groups of people: the strategic and pragmatic optimists, and the defensive pessimists. The pragmatic optimists took all measures to ensure their success, dreaming largely and envisioning the best possible outcome. On the other hand, the defensive pessimists envisioned all manner of throwbacks, regardless of previous successes.

The result? I’ll bet that you think the pessimists are wallowing in their own pity somewhere. And you’d be wrong.

“Before long, I began to realize that they were doing so well because of their pessimism… negative thinking transformed anxiety into action,” says Dr. Norem, a Psychology professor at Wellesley College.

And in fact, in one exercise, the pessimists were 30% more successful than their sunnier counterparts.

That’s not to say that optimisim is a fault. But blind faith is a smokescreen. When you impede your vision with nothing but hope, you fail to see the obstacles in the way. And there will always, always be obstacles in the way of a new venture. That’s not a negative thing, it’s just a part of life. And as one of my favourite people has previously said, the obstacle is the way.


Pessimism should not be debilitating

One part of that quote above stands out to me the most.

“Transforming anxiety into action.”

A consistently gloomy, debilitating anxiety or sense of despair isn’t productive pessimism – that’s nihilism

Productive pessimism means you’re thinking about possible throwbacks, and then making steps to counteract them.

It’s not in direct opposition to optimism, either. But it is different, in that it involves a certain degree of apprehension, and less confidence in definite success. Not less confidence in yourself per se, but less confidence in notions of good luck, the law of attraction and the catch-call of the new age entrepreneur, trusting the universe.

The best way to describe it is to use my own real life examples.


Negative belief:

During my client consultation, I’ll miss a key piece of information during our session, which will end up with me producing an inaccurate tone-of-voice or factually incorrect copy.


I’m hugely process-oriented so that nothing goes astray. I send a comprehensive worksheet to all of my clients beforehand, so that I can gather everything I need to know about them. I also send out a tone-of-voice document along with my content, outlining their voice values and why I think it applies to their copy.


Less chance of me not understanding what they need, and more of a chance of me delivering what they want.


Negative belief:

I’ve had clients before who can’t be bothered giving feedback and go AWOL. I’m often apprehensive about this happening again. If a person lacks communication skills, sometimes I assume that they’re going to go missing again and dodge their invoices.


I try to involve my client in the process as much as possible. Not only do they get to fill in a 15+ page worksheet at the start of our working together, but they also get an onboarding document, and access to a central hub where all our content will go. 

I also ask all of my clients to sign a Terms of Service Agreement before we commence working together. I know a lot of freelancers who work on the basis of ‘good faith’, but unfortunately, ‘good faith’ doesn’t pay the bills. My document outlines what I’ll do, when I’ll do it, and what’s required of my client. This includes resources they need to supply me with, and invoice terms.


By making them feel like they’re involved in the process, they’re more likely to be emotionally invested and give feedback.

There's also less of a chance that a client will get away with dodging invoices, because they've signed a legally binding document.

All of this might sound to you like common sense. And perhaps ‘pessimism’ is the wrong word to use in this context. The core message remains the same – safeguarding isn’t negative. It’s smart. Get outside of your comfort zone, yes. But in the long run, a bit of forethought never goes astray.

I'm Camilla Peffer, and I'm a Melbourne copywriter who creates engaging, results-driven content for fashion and lifestyle brands. From website copywriting, to fashion copywriting, content strategies and SEO audits, I've created clicks and conversions for the likes of Sportsgirl, Seed Heritage, CoYo, Ralph Lauren and Politix. Want to work together? Reach out! I'd love to hear about your next project.