What Would This Look Like If It Were Easy?

Daniel Riley
3 min readMar 27, 2020
Photo by LumenSoft Technologies on Unsplash

Tim Ferriss had a series of existential questions when he reached the age of 40. He had experienced book rejections, huge book success, had learnt several languages and had seen a number of his friends die. He realised that most of his life’s planning revolved around what he wanted to have accomplished by the age of 40 — nothing with regards to after.

So, as is the case for many people at this age, a mini mid-life crisis started to ensue. Difficult questions would surface and although they were important, Tim didn’t know how to approach many of them, nevermind answer them.

Were my goals my own, or simply what I thought I should want?

How much of life had I missed from underplanning or overplanning?

How could I be kinder to myself?

How could I better say no to the noise to better say yes to the adventures I craved?

How could I best reassess my life, my priorities, my view of the world, my place in the world, and my trajectory through the world?

The thing is, Tim is no stranger to difficult situations and decisions. Whether the dilemma be a personal one, a business one, a relationship one or one in any other walk of life, there is always one question that he leans back on to clarify his thoughts.

What would this look like if it were easy?

It may seem like an overly simplified question, but that is entirely the point. Far too often, we convince ourselves that things need to be difficult and that if we aren’t in some sort of mental or physical turmoil, then we are doing something wrong or not trying hard enough. As a result, we can sometimes actively seek out the path of most resistance and intentionally make things more complicated than they need to be.

Quite often though, we are able to solve problems simply by rewording them. As the famed author Dr Wayne Dyer once said: “When you change the way you see things, the things you see change.” This is what this magical question can do. It allows you to take a step back and see if there is an easier path that you are missing or avoiding for some reason.

Tim had a mission to answer all of those mid-life crisis questions but had no answers. He was stuck, and…



Daniel Riley

Passionate about personal development in mind, body and finance. You can also find me at https://danielriley.blog/