How To Overcome Fear of Failure | Tim Ferriss Fear-Setting Exercise

In this YouTube video, I share my favourite journaling exercise from Tools of Titans by Tim Ferriss: Fear-Setting.

This is a journaling exercise that helped me overcome the fears I had around quitting my full-time job for blogging. If you have fear around any kind of life decision, big or small, this exercise will help you by having you get super clear on exactly what that fear is and see how the outcome you’re scared of is most probably reversible and temporary. I hope this exercise helps you! And I’ve written out the questions from the fear-setting exercise below so it’s easy to follow along!


To make the most of Tim Ferriss’ fear-setting exercise, reflect on the below questions while focusing on a big (or small) decision that you’ve been struggling to make. I also recommend handwriting your answers as you’ll be able to access deeper and more meaningful thoughts than if you type out your answers (just my experience)!

The following questions are from Tools of Titans by Tim Ferriss, I highly recommend getting his book because it’s FULL of amazing exercises like this! Here they are:

Q1 – Define your nightmare, the absolute worst that could happen if you did what you are considering. What doubt, fears and “what-its” pop up as you consider the big changes you can – or need – to make? What would be the permanent impact, if any, on a scale of 1 to 10? Are these things really permanent? How likely do you think it is that they would actually happen?

Q2 – What steps could you take to repair the damage or get things back on the upswing, even if temporarily?

Q3 – What are the outcomes or benefits, both temporary and permanent, of more probable scenarios? What would the impact of these more-likely outcomes be on a scale of 1 to 10? How likely is it that you could produce at least a moderately good outcome? Have less intelligent people done this before and pulled it off?

Q4 – If you were fired from your job today, what would you do to get things under financial control?

Q5 – What are you putting off out of fear? Usually, what we most fear doing is what we most need to do. That phone call, that conversation, whatever the action might be – it is fear of unknown outcomes that prevents us from doing what we need to do. Define the worst case, accept it and do it.

Q6 – What is it costing you – financial, emotionally and physically – to postpone action? If you don’t pursue those things that excite you, where will you be in 1 year, 5 years and 10 years? Inaction is the greatest risk of all.

Q7 – What are you waiting for? If you cannot answer this question without resorting to the BS concept of good timing, the answer is simple: You’re afraid, just like the rest of the world. Measure the cost of inaction, realise the unlikelihood and repairability of most missteps and develop the most important habit of those who excel and enjoy doing so: action.


Tim Ferriss is someone I find insanely inspiring because he’s willing to try different things and share his experiences to the advantage of others. I’ve learned SO much from Tim Ferriss. And if you’re interested in finding out more about him, here are the best ways to do it:

I hope you find this fear-setting exercise helpful! If you give it a try, please let me know in the comments!

Sam xx

A journaling exercise to overcome fear of failure from Tim Ferriss' book Tools of Titans. A must-watch video for millennials and twenty somethings who are scared to make a big life decision.

Author: Sam Brown