Imagining the Worst Might Be The Best

The hard choices – what we most fear doing, asking and saying – are very often exactly what we need to do. How can we overcome self-paralysis and take action?

In his short, practical Ted Talk (which has almost three million views), entrepreneur and author Tim Ferriss encourages us to fully envision and write down our fears in detail. He uses a simple exercise he calls fear setting to put fears under a microscope.


Because it works.

Fear setting took Ferriss from stressed, depressed and feeling trapped to successful entrepreneur and author. He calls it a recipe for avoiding self-destruction, self-paralysis and emotional free fall. It’s also the technique that has helped him make all of his best business decisions.

The theory behind the fear setting exercise comes from Stoicism.

In 300BC, a philosopher named Zeno of Citium lectured while on a painted porch (a stoa) and his teachings later become known as Stoicism. Stoic philosophy asserts that wisdom comes from happiness and judgement should be based on behaviour, not words. Stoics believe that we don’t control and cannot rely on external events – only on ourselves and our responses to given situations. They remind themselves how unpredictable the world is, how brief human life is. Stoicism teaches its followers to be strong and in control of themselves. It doesn’t teach complicated world theories – it’s mostly about overcoming destructive emotions and focusing on what we can control and act on.

What’s really great about it, as a philosophy, is that it’s practical. It is not a theory designed for endless debate – it’s about getting things moving. Doing. It’s a tool, not just a theory. Therefore, Stoicism lends itself extremely well to dealing with fear, since the goal with fear is generally to move past it or to act in spite of it.

To put all this philosophy in a more practical context, let’s get back to Tim Ferriss’ story. Fear setting is what changed his life when things looked quite grim…

A young friend had recently unexpectedly died of pancreatic cancer. Ferriss was working 14-hour days in a financially successful business that relied only on him – and was therefore unsaleable. His girlfriend, the woman he thought he’d marry, had left. And he was relying on chemical stimulants to keep it all together. He says, “It was a disaster and I felt completely trapped.”

In the search for a way out, Ferris bought a book on simplicity that contained a quote from Seneca, a famous Stoic.

“We suffer more often in imagination, than in reality.” Seneca


That led Ferriss to Seneca’s other writings and eventually the Stoic version of fear setting. In simple terms, the idea is to visualise the worst case scenario of the thing/situation you fear in great detail.

Ferriss needed a written version, so he created the fear setting exercise. He talks about the time in his life detailed above, during the middle of which he received an invitation to visit and stay with a friend in London. He hadn’t been on holiday in four years and knew he needed to go, not least because he had to either remove himself as a bottleneck from the business or shut it down. He was in desperate need of some rest and a great deal of perspective, but terrified of going on the trip.

So he used fear setting to help him look closer at his fears and make a decision.

Here’s what that looked like, as described by Ferriss in the Ted Talk…

Fear setting is a three page exercise.


Page One

Page one looks like this:

At the top of the page, write ‘What if I…?’ and underneath that create three columns titled ‘define’, ‘prevent’ and ‘repair’.

Column one – define – is the place to detail your fears. Be very specific about the worst case scenarios you’re imagining. Look for 10-20 answers to the ‘what if’ question.

With reference to the trip to London, Ferriss gives two examples:

“It will be miserable and raining and I’ll have a miserable, crappy time and the whole thing will have been a waste.”

“I’ll get a letter from the IRS and I’ll miss it and get audited.”

Column two – prevent – is designed to look at what you could do to prevent the worst case scenario happening, or at the very least decrease the likelihood of it occurring.

For Ferriss and his trip to London, that meant daily use of techniques designed to stave off depression and changing the mailing address he had on file with the IRS to his accountant’s so he couldn’t miss anything.

Column three – repair – gives you the space to look at what you could do to repair the damage, or who could you ask for help, if the worst case scenario did occur.

Ferriss planned to go to Spain and get some sun on the beach and/or contact a lawyer to ask for advice on dealing with an audit. He says, “Ask yourself if anyone less intelligent or less driven than you has ever figured this problem out. Chances are the answer is yes!”


Page Two

The idea on page two is to look at the possible benefits of attempting the thing you fear.

Ferriss says ask yourself, “What might be the benefit of an attempt or partial success? If I tried, might I build confidence, develop skills, find financial or emotional benefit?”

He recommends spending 10-15 minutes exploring the answer to those questions.


Page Three

On page three, take the time to write detailed answers to this question:

‘What is it costing you – financially, emotionally and physically – to postpone action?’

Ferriss says, “Humans are very good at considering what might go wrong if we try something new, but we don’t often consider the atrocious cost of the status quo.”


Ask yourself, ‘If I avoid this action or decision (and others like it), what might be the cost of that in six months, twelve months or three years?’ ‘How will I feel having allowed circumstance to impose itself upon me?’

Ferriss says that for him, the picture page three painted was terrifying…“I was self-medicating, my business was about to implode and my relationships were failing.”

As a result of completing the fear setting exercise, he realised that inaction was no longer an option and committed to taking the trip to London. Here’s a short excerpt from a blog Ferriss wrote about the subject…

“As soon as I cut through the vague unease and ambiguous anxiety by defining my nightmare, the worst-case scenario, I wasn’t as worried about taking a trip. Suddenly, I started thinking of simple steps I could take to salvage my remaining resources and get back on track if all hell struck at once. I could always take a temporary bartending job to pay the rent if I had to. I could sell some furniture and cut back on eating out. The options were many. I realised it wouldn’t be that hard to get back to where I was, let alone survive. None of these things would be fatal—not even close. Mere panty pinches on the journey of life.

That is when I made the decision to take the trip and bought a one-way ticket to Europe. I started planning my adventures and eliminating my physical and psychological baggage. None of my disasters came to pass, and my life has been a near fairy tale since. The business did better than ever, and I practically forgot about it as it financed my travels around the world in style for 15 months.”

Ferriss says that he can trace all of his biggest wins and disasters averted back to doing the fear setting exercise about four times per year. “It’s not a panacea, some of your fears will be well founded,” he adds, “but don’t conclude that until you’ve put them under a microscope.”

He finishes the talk by sharing the story of a modern day Stoic he’s done some studying with, who he quotes…

So, that’s fear setting in a nutshell. It’s a fantastic technique for creating action when you’re feeling stuck. It won’t make all of your hard choices easy, but it might just make some of them easier.

And as Ferriss says, ‘The biggest challenges we face will never be solved with comfortable conversations – with ourselves or other people.’ 

Watch the Ted Talk here 

For more information on Tim Ferriss, go to his website