Reaching 100 days feels like a milestone.
Not because everything is finished —
but because everything starts to feel real.
The Shift from Dreaming to Deciding
Early planning is full of ideas.
This phase is different:
- narrowing options
- setting timelines
- making decisions that shape everything else
The Unexpected Challenges
Some parts of planning don’t match expectations.
For us, South America has been more complex than anticipated:
- fewer points options
- higher flight costs
- less predictable routing
Planning requires adjusting assumptions.
Decision Fatigue Is Real
Planning across months and countries means:
- constant research
- repeated trade-offs
- balancing cost, time, and experience
At some point, progress matters more than optimization.
Living with Uncertainty
Even at 100 days out, not everything is finalized.
And that’s okay.
Leaving space allows for:
- flexibility
- spontaneity
- better decisions later
Finding Enjoyment in the Process
Not every moment of planning is fun.
But there are moments where it feels like building something meaningful.
That part is worth paying attention to.
100 days isn’t the end of planning.
It’s the beginning of commitment.
And that feels different.

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