The Gentle Rebel Podcast

The Gentle Rebel Podcast


327 | The Impossible Question

March 23, 2021

Have you ever been asked where you see yourself in five years?

How did you respond? How WOULD you respond you were asked today?

I struggle to think in long term abstractions. I think I always have done. But I never understood why for me and for many, this might be an impossible question to answer.

In the previous podcast I spoke with Kendra Patterson about burnout, late blooming, and the differences between Conceptual and Experimental people. These topics are all interlinked, and might shine a light on the struggles many of us experience.

There is a common assertion in the personal development world that you should "begin with the end in mind". But what if the end is not that simple?

For many of us, our deepest desires are not end points. They are inexplicable moments and feelings, brought about by an openness to a life of slow meandering and repeat blooming. Along an evolving and experimental pathway of incremental steps?
A Lot Can Happen in Five Years
If you search for "begin with the end in mind", almost every result tells you to define your destination so that you can draw a straight efficient line between where you are and that desired point in the future. Many articles on the subject carry a shaming spirit. If you can't say where you'll be in five years then there's something wrong with you.

What if we can't really know where we're going until we get "there"? And our route to joy is the journey itself...experimenting, moving, joining dots, and building experiences that take us in all manner of unexpected direction.

This is not an easy path to justify in our modern world. Society likes nice neat roadmaps and linear processes from "problem to solution". But by trying to squeeze ourselves into these boxes, we neglect our natural orientation and preferences.

What if some people have no idea where they want to be in five years time, not because they refuse to dream; but because life just doesn't work like that for them?
The Stories We Tell Ourselves
The relationship we have with our core underlying traits, informs the story we tell ourselves about ourselves. And this is especially significant if society prefers and promotes one approach or trait over others.

Society celebrates people who followed a conviction about what they wanted to do with their life from an early age. Those who "pursued their passion" with unwavering drive and determination.

We say “follow your dream”, with the unspoken assertion that everyone has one. A tangible concrete thing that we were born to do with our life. And for some people this idea idea of "finding their purpose" or knowing what they were "meant to do" with their life, is exciting and enjoyable.

But for others it can be a huge source of underlying anxiety. And it can underpin the story we write for ourselves, based on what we're taught to believe about the right way to be. We might let life happen to us, as we accept that we're failures, drifters and perennial underachievers.
A Different Way of Being
But what if the success for people like that, was found in the heart of the journey itself? What if joy was not the dream of getting to the destination, but it was discovering, exploring, and experimenting along the way?

And what if that approach to life wasn’t seen as time wasting, procrastinating, and unfocussed; but actually key ingredients to your success as a human being?

And what if you could begin to accept yourself in all that messy beauty? And even find a way to make it work in practical, intellectual, and emotional ways.

When I look back at my own life I see this so clearly. I’ve never been one for long term conceptual goals, and I used to beat myself up for not sticking with things, getting distracted, and allowing projects to veer away from their original intent.

But stepping out of that self-judgement and away from the critical inner ego, I can see that all of the things I’m most proud of in my life so far,