A foggy rural road curves into the distance, its cracked asphalt and faded centerlines leading into thick morning mist. Overgrown grass lines the edges, and a faint utility pole stands in the background. The soft, diffused light creates a calm, subdued atmosphere, evoking a sense of quiet motion and uncertainty.

I Don’t Make Plans Anymore

March 31, 20255 min read

I realised something recently.

I don't think I'm a planner anymore.

Not in the way we usually talk about it. Not in the "what's your five-year vision?" kind of way.

That used to feel like the responsible thing.

Set goals. Map the path. Stay on track.

But I've stopped living like that. And I only just noticed.


Plans Made Me Feel Like I Was Doing the Right Thing

There's something very reassuring about having a plan.

It gives you structure. It makes you feel prepared. It creates the impression of momentum - like you're in motion, heading toward something defined.

And for a long time, that worked for me.

Career. Relationships. Life decisions.

I had frameworks. Next steps. Timelines.

But somewhere along the way, I started seeing how often things didn't play out the way they were supposed to.

How much energy we spend protecting plans that no longer make sense.

And how hard it is to admit when the path you chose isn't the one you're still meant to be on.


Plans Have a Shelf Life. Most of Us Just Don't Admit It.

I've seen it happen quietly.

People following plans long after the context changed.

Staying in jobs because they were part of the trajectory.

Staying in relationships because they fit the version of the future they'd imagined.

Holding onto ideas - not because they still made sense - but because they were written down at some point, and it felt wrong to let go.

And I've done the same.

More than once.

Not because I couldn't feel the shift - but because there's something about a plan that makes you believe you're supposed to see it through.

Until it becomes obvious you're not.


Be Honest: Who Is Where They Thought They'd Be 5 Years Ago?

Think about it. Among your friends, colleagues, or even yourself – how many people ended up exactly where they planned to be five years ago?

That promotion you were certain about? That relationship? That city you thought you'd live in?

Life rarely follows our carefully crafted scripts. And that's not a failure – it's just reality.


So I Stopped Needing a Plan

I still care about direction.

I still have intent.

But I no longer believe that scripting the future is the way to secure it.

Life doesn't play out in straight lines.

It bends. It collapses. It opens unexpectedly.

And trying to control it through detailed planning, I've found, is often just a way to distract yourself from the discomfort of not knowing.

So now, I make fewer fixed decisions.

I stay closer to what's true in the present.

And I move when it makes sense to move.

Not because I've given up. But because I've seen how much effort goes into holding still what was never going to hold.


Planning Gave Me Comfort - but Not Control

This is something I think a lot of people feel, even if they don't say it out loud.

Planning is comforting.

It gives us something to point to when things feel uncertain.

It helps us feel like we're ahead of the problem.

But I've come to believe that's a story we tell ourselves.

Control is thin.

The real world doesn't respond to our spreadsheets.

Jobs vanish. Markets shift. People walk away. Priorities change. You change.

And the more tightly you hold the plan, the more fragile you become when it breaks.


What I Do Instead: Pattern-Awareness in Practice

I pay attention.

I look for what's actually happening - not what was supposed to happen.

Here's what this looks like in practice:

Opportunity filters: Instead of a rigid five-year plan, I have three questions I ask when something new presents itself: "Does this align with my values? Does it create more possibilities than it closes? Does it feel alive rather than just logical?"

Engagement signals: I've developed an internal awareness of when I'm genuinely engaged versus when I'm just going through the motions. Without formal tracking, I notice when something consistently creates resistance or feels hollow - that's information I pay attention to rather than pushing through because "it's part of the plan."

Context over commitments: When making decisions, I prioritize the current context - what's true about my situation, resources, and knowledge right now - rather than commitments I made based on outdated information. This means sometimes walking away from things that once made sense but no longer do.

This isn't instinct. It's not guesswork. It's trained awareness.

And it's a skill, not a vibe.

I don't wait to be certain.

But I do wait until something feels real enough to act on.

I don't drift.

I orient.


The Freedom of Letting Go

What I've seen - over and over - is that sticking to the plan when the reality has changed doesn't make you resilient. It makes you stuck.

And I don't want to live stuck.

I'd rather adjust quickly than follow a story that no longer fits.

Even if it's messier. Even if it doesn't look like progress to the outside world.

Because at least it's real. At least it's now.


I Don't Think I'm a Planner Anymore. I Don't Think I Need to Be.

I haven't stopped thinking ahead.

But I've stopped pretending the future can be engineered through willpower.

I don't need to hold life in place anymore.

I just need to hold myself steady in it.

That means I'll still get caught out sometimes.

There will be turbulence.

But I'd rather meet it with presence than illusion.

Plans can break.

But attention holds. Awareness holds.

The ability to stay aligned with what matters - that holds.

And for where I am now, that's enough.

Paul Littlejohn is a visionary leader and leadership advisor with over three decades of experience spanning military aviation, global corporations, and academia. As the founder and CEO of Wingman Executive, Paul leverages his unique background to deliver transformative results for senior leaders and organisations worldwide.

Paul Littlejohn

Paul Littlejohn is a visionary leader and leadership advisor with over three decades of experience spanning military aviation, global corporations, and academia. As the founder and CEO of Wingman Executive, Paul leverages his unique background to deliver transformative results for senior leaders and organisations worldwide.

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