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🐙 How I do Tim Ferriss' famous "Fear-Setting" exercise with ChatGPT

The most powerful exercise to handle business challenges

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Greet from the deep,

It’s Ole from the AI Solopreneur here.

Today, you’ll learn:

  • Why I write out my fears every month

  • How doing Tim Ferriss’ “Fear-Setting” exercise will drastically improve your business decisions

  • How you can use ChatGPT to do “Fear-Setting”

Let’s d-d-d-d-dive in! 🤿

Why “Fear-Setting” is Tim Ferriss’ most powerful exercise

“I do an exercise called “fear-setting” at least once a quarter, often once a month. It is the most powerful exercise I do.”

Tim Ferriss, 2017

Out of the 1,000s of reflection exercises out there, “Fear-Setting” is the only one I keep coming back to.


Because it’s incredibly useful and liberating.

Fear-Setting works by clarifying what you fear right now, and then leaning into your fears:

  • What, exactly, the worst thing that could happen if everything went wrong?

  • What are the outcomes or benefits of the best & worse case scenario respectively?

  • What are you putting off out of fear?

The reason why this works so well is because identifying our fears helps us find the things we’re putting off to stay comfortable.

This doesn’t only feel incredibly liberating…

…but it’s also a massively useful protocol for your business.

Because Fear-Setting helps you validate your opportunities from a more rational perspective, it helps you choose better risks.

And you don’t have to take it from me:

“Fear-setting has produced my biggest business and personal successes, as well as repeatedly helped me to avoid catastrophic mistakes.”

Tim Ferris, 2017

Appears like the only catastrophic mistake Fear-Setting couldn’t help Tim avoid is wearing this damn hat in every video… I can’t stop laughing at it:

In either case, I’ve done Fear-Setting every once in a while for 1 year, and I recently discovered that ChatGPT could help me guide the exercise.

I use 3 prompts:


  1. Defining the nightmare scenario

  2. Flipping the worst-case scenario: What’s the most realistic outcome?

  3. Creating an action plan to act on my fears

I grew my Twitter from 0 to 100k in 65 days using my AI content systems

Now I’m creating a course, the AI Audience Accelerator.

It will teach you:

  • How to create a week's worth of content in 1 hour

  • How to create Content that sounds like YOU

  • AI Systems that skyrocketed my growth

I will launch in around 2 weeks.

How to use ChatGPT to do a guided fear-setting exercise.

How to use the prompts:

  • Use the below 3 prompts in the same chat.

  • Prompt 1 requires your input for [CONTEXT] and [YOUR FEAR]

  • You don’t need to make any changes to prompt 2 & 3 because they are follow-up instructions to ChatGPT.

Prompt 1: Defining the nightmare scenario

This prompt lets ChatGPT elaborate on the worst thing that could happen if your fear became true and EVERYTHING went wrong:

I want to do my monthly fear-setting exercise. I want you to write out the worst case scenario that could occur if my fear became true. Let's start with defining the fear. 

My current fear is that [EXPLAIN YOUR FEAR]


Could you help me elaborate on the "nightmare scenario", the worst thing that could happen if everything went wrong?

Now, look at the nightmare scenario: Is it as terrible as you expected?

Prompt 2: Flipping the worst-case scenario: What’s the most realistic outcome?

This prompt inverts your nightmare scenario to highlight the potential benefits of acting on your fears.

Okay, now that we have defined the fear, let's try to reverse it. 

What could be the potential benefits if I face this fear and take action? 

What could be the potential consequences if I don't?

Compare the benefits to the nightmare scenario:

This should make you see the great upside in acting on your fears.

Prompt 3: Creating an action plan to act on your fears

Now that you’ve decided to act on your fears, this prompt gives you an actionable plan so you can get started asap:

Great, now that we have defined and reversed the fear, it's time to take action. 

Could you help me create a plan with specific goals and steps to overcome this fear?

Example: My Fear-Setting results

Here’s GPT-4’s nightmare scenarios for my upcoming product launch and what would happen if everyone stopped being interested in AI:

Wrap up


  • How Tim Ferriss’ Fear-Setting exercise works

  • Why setting your fears helps you make better decisions

  • How to use ChatGPT for Fear-Setting

Fear-setting is great…. My only fear this weekend:

Not being smart enough to understand the art I was looking at in a museum in Rome….

What do you think about my sophisticated art-expert pose? Did I pass the test?

If you liked this newsletter, I strongly suggest you check out Tim Ferriss’ blog article on Fear-Setting to get an even deeper overview.

Keep diving,


P.S. This Newsletter topic was a bit different. Please let me know if you like it.

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