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Are You Already Living Your Worst Case Scenario?

by Thomas Despin September 26, 2018

Are You Already Living Your Worst Case Scenario?

This afternoon, an old friend I didn’t meet for years texted me asking for advice about a work situation he was facing.

I led him through “the worst case scenario” questions I use to make my own choices on a daily basis.

I read about this “trick” for the first time 5 years ago, and consistently applied it whenever I was facing a challenging choice since then.

It became so natural to me that I sometimes forget that a lot of people never heard of it.

Here is the conversation:

Often we are stuck to make a decision because we are afraid of what would happen if we fail.

I get it, it’s natural.

But what often happen is that we just stick to the initial fear without digging further and asking ourselves the right questions.

Here are some of the ones I ask to myself on a daily basis:

  • Let’s say my project fail miserably, what exactly would happen?
  • Would I be able to recover from it?
  • How? What would I specifically do?
  • How likely am I to be successful? to fail?
  • How great would a success feel out of 10?
  • How does the current situation feel out of 10?
  • How bad would a failure feel out of 10?

By rationalising and specifically addressing the fears, we manage to put them into perspective and realise how much of a risk we are actually taking.


I used this when I planned to travel the World on a bicycle and sleeping in a tent.

I had no money and no solid plan to make any.

I ended up cycling through 18 countries on 2 continents in 14 months before flying to Bali where I am now settled for the past 2 and a half years.

My worst case scenario was that if I failed I would just have to go back home and find the first job I could find to make money.

The will I had to see the world on my own and face myself on the way was way higher than the risk I was taking in my opinion back then.

So I went on the road, and whenever things went wrong, I did what any human being does when he has no other option: I figured out.

I was 23 years old.


Today, I am 27 years old and live in Bali where I recently became officially a resident.

I also own my own clothing brand, develop the Hustlers Villa, open my first co-working café in 3 weeks.

Next month, I will fly to another region of Indonesia called Sulawesi where I am about to buy a small virgin island to develop it into an eco-retreat called Reconnect.

All of this often scares me, and my learning curve is so steep that it sometimes feels like a wall in front of me.

I feel like I don’t have the skills, or the money, or the charisma needed to lead those projects.

And I probably don’t have them.

But when I write my worst case scenario and have a look at what would happen if everything goes wrong, I become aware that what would be the worst for me would be to not even try.

I failed several times. 
And some other times I gave up before.

I always recovered.

Actually, each one of the failures I faced was deeply associated as a lesson and used to bounce back straight away.


Just think about it, it will cost you 10–15 minutes of your time to ask you those questions and become aware of the actual risk you are about to take.

But don’t stay in a position where you already live the worst case scenario that you are so afraid to live in case you fail.

Most of the time, doing nothing is the worst that could ever happen to you.

Much love from Bali ❤

Thomas Despin
Thomas Despin

Founder of doyou.co & hustlersvilla.com


You do you, we do us.