Traditional Linear Goal-Setting Versus Experimental Self-Development

I’ve always set goals. For the most part, linear goal setting has served me well: pick a target, map out the steps, and stick to the plan.

But over the past six months or so, I’ve been questioning that approach.

Linear goals can encourage binary thinking—success or failure, right or wrong... and don't get me started on perfectionism.

The irony isn’t lost on me. I’m a lifelong learner. I’ve spent over 15 years as an educator, helping others explore, reflect, and grow. Yet when it came to my own goals, I wasn’t really applying that same mindset. I was chasing outcomes rather than treating the process as something to learn from.

Now, I’m starting to think differently. I’m experimenting more. Setting goals but treating them as hypotheses. I'm trying things out, gathering data, and adjusting.

Even with goals that seem linear on the surface—like reducing weight for health reasons—I’ve found this experimental approach more sustainable. Instead of one fixed plan, I’ve tried different ways of eating, paying attention to what works for me. That’s the learning part I was missing.

My doodle captures that shift. The left-hand path is simple, clear, and focused but sometimes too rigid. The right-hand path is messy and full of questions and course corrections. I’m learning to value that mess.

I highly recommend Anne-Laure Le Cunff’s book Tiny Experiments, which has helped refine this thinking.

How do you approach goal setting? Is it something you use as a learning tool or something to tick off and move on from?

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