Plan paradox

Following a plan is how I used to thrive. It reduces the cognitive load by eliminating the question of “what should I do now” at every given moment. More than that, it reduces anxiety about whether I’m doing the right thing. It also shuts off any doubt about whether the thing I’m doing has any results whatsoever.

A plan always starts with the person I’d like to become. I then dissect what this person values in life, what behaviours those values entail, and how they translate into everyday activities. This ensures that by following the plan, I’m doing “the right” thing. Since the plan is always for multiple weeks, months, or even years, I don’t get to worry about the immediate results of each individual activity. I can just evaluate their compound effect at a later checkpoint or at the end of the plan.

So why have I avoided having a plan in the last few years? Every time I ask myself, the short answer is usually fear. The fear of accountability.

Accountability discourages me because I know I’ll fall off the wagon eventually. And it’s so easy to be hard on myself, thinking I let myself down. But as Coach Bennett says, “plans are written in pencil”, they allow room for adjustments. A plan is just a guide, helping to consistently do the things that matter to me. Consistently, not constantly. No life plan will ever be executed perfectly to the word, and it’s about time for me to finally accept this.

Starting a plan is a heavy baggage. It comes with incredibly challenging emotions attached to it. At the start is when I’m the furthest from the goal. And the plan does a beautiful job at highlighting exactly that gap between me and who I’d like to become. It shows me every bit of myself I need to let go of and reveals how much I’m lacking of the things that are supposed to make up for everything I’m leaving behind during the process. Withdrawal from what I’m used to is the smaller problem for me. The shame I feel when I look into this mirror is what really frightens me. But again, I should rather be focusing on the positive, which is that I’m inching closer to a more fulfilling future.

Until I internalise looking at the bright side, the paradox stands: The more I’m in need of a plan, the less likely I’ll start one. That’s because I hate facing the truth – and the feeling of shame that comes with the realisation – of how far I am from my ideal self.

Not facing my flaws to avoid the shame and withdrawals coming with the change seemed like a fair trade when I pretended my life is OK. But it wasn’t. I felt anxious and miserable way too often. A recent situation opened my eyes to the why; I wasn’t present. I was trying to rush ahead and live the future. That equals living in an illusion which results in unreasonable and unrealistic expectations that cannot be met. The disparity between the illusion and the reality always results in disappointment and misery.

Once I accepted the reality for what it is and stopped focusing on how things should be, or where I’m supposed to be, I suddenly became calm and collected. Being content in the present moment also brought joy to every task at hand. Then I realised that this might be the biggest superpower of a plan.

Even though a plan builds towards a future image of mine, it keeps me grounded in the present. It stops me from comparing what I’m doing to all the other activities I could be doing instead. This makes it easier to get into the flow and enjoy anything. Joy is key in supporting me in the early phases of the plan until all the new behaviours become habitual.

Only the disciplined ones are free in life. ¹

And here is the second paradox. It can seem like a plan turns everything into a dry, joyless, robotic, almost “chore-like” execution that’s also very rigid. But in reality, by being able to fully immerse myself in a task reduces the misery and increases happiness instead. And when I attend consistently, I don’t feel guilty taking a day off.

1: Eliud Kipchoge, Oxford Union Q&A

Friday, 6 March 2026