Cultivating serendipitous moments

I’m on holiday in Japan with my wife.

Before arriving, we planned an itinerary for the first few days of our trip. For the second half, we kept it free and easy and decided to figure out what to do on the fly.

We would pick a location, take a train there, and walk towards whatever looks most interesting.

It’s been magical. We stumbled upon countless hidden gems—unique shops and incredible food we’d never have discovered otherwise.

If we had a fixed itinerary, we would have relied on lists of “top places to eat” or “must-visit places” and missed out on so much.

This experience reminded me of the value of sometimes not having a plan to increase the chances of serendipitous moments happening.

I remember once I had to attend a networking event that my boss had committed to but had to miss due to an emergency.

I showed up without any expectations. I decided to enjoy the evening and have fun.

Somehow, I walked away with meaningful conversations and business leads who eventually became clients.

I genuinely feel that if I went in with an agenda to make a sale, I would turn off whoever I spoke with.

Sometimes, the best results come from leaving space for the unknown to unfold.

Today’s Prompts

1 - Self-reflection

When did you last let go of a rigid plan and discover something unexpected?

2 - Planning

What areas of your life could you benefit from a more relaxed, exploratory approach?

3 - Quote of the day

“What people call serendipity sometimes is just having your eyes open.” - Jose Manuel Barroso

4 - The 'If you don’t have time’ Prompt

What is one thing you normally do that you will do at a different time today?

Get the most out of your journalling:

• Choose one prompt: Focus on just one prompt each day to avoid feeling overwhelmed.

• Be brutally honest: Reflect openly and honestly. This is your safe space to explore your thoughts and feelings.

• Take your time: Sometimes it takes a few days to clarify your thinking. Here’s permission for you to take your time to unravel a prompt and not take on any new ones during that time.

• Journal your way: Whether you prefer writing, audio recording, or video, choose the method that suits you best.

• Don't stress about streaks: If you miss a day, don't worry. You can always revisit a previous prompt.