The Difference Between Planning Life and Living It

My ride with Pink Hat Guy - Johno Verity

I had a brilliant conversation recently on Safe Harbour with Johno Verity.

You might know him as the bloke in the pink hat cycling around London at dawn, sharing stories, history, observations and little musings about life.

He’s built a huge audience doing exactly that, with over 287,000 followers watching him ride through quiet streets before the city wakes up.

And what I loved about our conversation was this:
Underneath the humour, the pink hat, and the London dawn rides, there’s a man asking really interesting questions about life, creativity, getting older, and what it means to do things your own way.

Somewhere in the middle of our ride around Stroud, this question came up:

Are you a pilgrim or a tourist in your own life?

One Story

A tourist wants the plan.
The booking.
The itinerary.
The safe route.
The certainty of where they’re sleeping that night.

A pilgrim moves differently.
A pilgrim trusts the road a little more.
They don’t need the whole map.
They’re willing to meet what comes.

And that really hit me.

Because I think a lot of men in midlife become tourists in their own lives.

Everything gets planned.
Managed.
Controlled.
Kept safe.

Career.
Money.
Family.
Responsibilities.

And none of that is wrong.

But at some point, life can start to feel more like maintenance than adventure.

You’re doing everything properly.
But you’re not quite feeling alive in it.One Shift

Here’s the reframe that changes everything: Awareness isn’t the finish line. It’s the doorway.

Seeing the pattern isn’t the work, naming the truth isn’t the work, and even understanding why you feel the way you do isn’t the work. Those are invitations.
Real change begins when awareness is followed by honesty, structure, and a decision to stop circling the same thoughts alone.

Most men don’t get stuck because they’re unaware; they get stuck because they mistake insight for action.

One Shift

Here’s the shift.

A lot of men aren’t lost because they don’t have enough structure.
They’re lost because they’ve stopped trusting themselves to walk without certainty.

They want the next chapter to come with guarantees.
A clear path.
A perfect decision.
A risk-free move.

But life doesn’t usually work like that.
Especially not in midlife.

Sometimes the next version of you only appears once you start moving.

Not recklessly.
Not by blowing everything up.
But by taking one honest step toward something that feels more alive.

The tourist waits until everything is organised.
The pilgrim starts walking.

One Challenge

Ask yourself:

Where in my life am I waiting for certainty before I move?

Is it a conversation?
A project?
A decision?
A change you keep circling but never quite start?

Then ask:

What would one pilgrim step look like?

Not the whole journey.
Just one step.

Send the message.
Book the call.
Go for the walk.
Start the thing.
Say the truth out loud.

You don’t need the whole map.
You just need to stop standing still.

Because sometimes clarity doesn’t come before movement.
Sometimes clarity is what movement gives you.

The full conversation with Johno is worth your time.

▶ Safe Harbour with Johno Verity

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Listen on your commute. Or your lunch break. Or that walk you keep meaning to take.