The Optimistic Musings of a Pessimist

Happy Things Friday: 21 August

Friends, at various points this week I was pretty sure I was going to collapse to the ground like a ragdoll! Nothing objectively hard happened, but it felt like a perfect storm of busy…

Kathleen Paley on Early Retirement: Life After BigLaw

I am so excited to welcome today’s guest.

Eagle-eyed readers might recall that Kathleen Paley has actually visited here before!

Last year, Kathleen joined me for a conversation about gratitude, minimalism, frugality, and financial independence….

Guest Post, Frugality, Minimalism, Time Management
Aug, 20, 2026
34 Comments

11 Recent Frugal Wins

I cut Indy’s hair and trimmed Belle’s. He wanted a taper fade and he got… a haircut. But it doesn’t look half bad, he’s content with it, and it saved me both a trip…

Frugality
Aug, 19, 2026
24 Comments

What Long-Term Family Travel in Europe Was Really Like

Long-term family travel sounds like an extended vacation, but our 110 days in Europe included plenty of ordinary life alongside the adventures.

There were extraordinary adventures (so many of them!!)… but there were also groceries,…

I’m on The Reframe! Talking 110 Days in Europe, Our Budget + More

For anyone curious to hear my voice (or some approximation thereof; does anyone else feel self conscious about hearing their own voice on audio???), I’m on a podcast today!

Earlier this summer, Kathleen Paley invited…

Euro Adventure, Frugality, Guest Post, Podcast, Travel
Aug, 17, 2026
19 Comments

Happy Things Friday: 14 August

We’re at the halfway point in the month and I’ve been getting texts and seeing posts all week from friends in different parts of the world writing about their kids going back to school….

Packing for Long-Term Travel: What Worked for 110 Days in Europe

When I first wrote about our plan to spend months exploring Europe, one detail received some extra attention: the fact that we were each taking a single (small, wheeled) carry-on suitcase and one backpack…