The Gentle Rebel Podcast Why You Can’t Articulate a Five-Year Plan For Your Life
Where do you see yourself in five years?
Does that question fill you with excitement, or a quiet sense of dread?
We are wired differently.
For many people, myself included, the question is not difficult to answer because we lack imagination. It is difficult because it speaks a different language from our natural way of being. We are not compelled by any outcome-oriented approach to planning, conceiving, or measuring success. And yet this orientation is often treated as a default mode we should all operate within.
When the Five-Year Plan Feels Constricting Rather Than Motivating
“But everyone has a dream,” we might be told, as if struggling to articulate a five-year vision means we are hiding something from ourselves.
I have never been able to articulate a grand plan in the way this question assumes. I struggle to picture the future concretely, because it unfolds piece by piece. It always has. And I genuinely love watching how things emerge across different areas of life in ways I could not have foreseen.
What drives me is something quieter and steadier. A creative impulse. A desire to make things, to explore what might happen, to respond to what is in front of me, and to integrate what has come before. My life does not move in straight lines. It has grown around and within my values, with seemingly unrelated dots connecting in unexpected ways.
Maybe you relate to this?
“If you don’t know where you’re going, any road will get you there.”
This quote, inspired by Alice in Wonderland, reminds me of the five-year question. For some, it sounds like a warning. A demand to define the destination so the “correct” road can be chosen. For others, it feels like permission. A reminder that movement itself shapes direction, and that choosing a road does not require certainty about where it leads.
Two Approaches to Growing Life
There is research that can help us better understand this difference.
In an episode about Late Blooming, Kendra Patterson pointed to a study by David Galenson and Bruce Weinberg, who observed patterns in the careers of Nobel Prize winners in economics. They identified two broad orientations to creative innovation.
Some people are conceptual innovators. They work deductively. They begin with a clear idea and organise themselves towards it. In the study, these individuals often made their most significant contributions early in life, sometimes in their twenties.
Others are experimental innovators. They work inductively. Their contribution emerges step by step through trial, discovery, accumulation, and integration. Their most meaningful work often did not appear until their fifties. Sometimes later.
That is a thirty-year difference.
Experimental Thinkers and Emergent Direction
Experimental lives unfold differently. They need time, space, and patience. Decisions cannot be judged too early, and meaning emerges through lived experience rather than advance planning. These lives are not oriented towards a clearly imagined endpoint, but towards allowing something to take shape over time.
Our dominant culture tends to favour the conceptual orientation for obvious reasons. Goals are easier to measure than processes, and outcomes are more reassuring than slow inquiry.
So when more experimental people are asked to account for themselves in conceptual language, we can experience a disconnect. The five-year plan. Starting with the end in mind. Being asked to justify movement only if the destination can be named in advance.
We might learn to force an answer anyway, for fear of sounding vague and sketchy. Perhaps we adapt our path to fit the question, sometimes tethering ourselves to targets that outlive their purpose.
If You Can’t Articulate The Plan, You May Be Asking Different Questions
Experimental people tend to better orient around different questions.
Not “where do I want to get to?” but “does this path feel worth exploring?”
Not “how will I know I have succeeded?” but “what tells me I’m on the right path for now?”
This does not mean anything goes.
Our values provide an inner compass. A filter through which decisions pass.
Experimental consistency grows in relationship with deeper principles, even when they are not fully formed or easy to articulate. We sense them in how something feels. Whether it feels solid, expansive, and quietly right, even in the face of uncertainty.
That is very different from hit-and-hope searching.
An Unfinished Map
The problem begins when we are pressured to live by a map that does not match the territory of our own experience.
The Return To Serenity Island grew directly out of this recognition.
It was never designed to answer the question of direction. It emerged from understanding the difference between conceptual and experimental ways of moving through life, and from a desire to honour growth and change without forcing myself into a shape that did not fit.
The image of mapping an island felt natural. A way of imagining life not as something to optimise along a straight line, but as a living territory. An unfinished map with seasons, weather, history, and forgotten paths. A place where things fall away to make room for what comes next. Where time moves differently across the landscape, and where connections form quietly, often long before they make sense.
It has become a counterpoint to directive, outcome-driven models of goal setting. A place to reconnect with intuition, judgement, and possibility. To meet creativity not as a tool for achievement, but as a way of relating to life as something we are growing into, rather than something we are meant to complete.
The optional live sessions begin on Saturday January 24th 2026 and run for six weeks. You can find more information at serenityisland.me.
If you have any questions, feel free to drop me a message. I would love to hear from you if this sounds like something you would find helpful.
