One of the first 30-day challenges I recall completing successfully was in November 2016. It was a new-to-me experiment, which I dubbed the “eat at home challenge” — at that time, I was going to fancy restaurants so frequently that it didn’t feel special anymore and I wanted to interrupt that pattern. A 30-day challenge seemed like a good way to do that.

I spent a month looking up new recipes, digging through my cupboards for long-forgotten cooking tools, and puttering around my kitchen. Even though the challenge was (ahem) challenging, it was worth the effort — not only did I save lots of money, but I also started viewing even simple meals out as special treats again. And somehow, cooking became less stressful and tedious.

The eat at home challenge got me curious about what else might be fun to try for 30 days. I experimented with a capsule wardrobe challenge, a yoga challenge, a no-news challenge. I didn’t think there was anything unusual about this until someone tweeted me in 2019.

This article kinda reminded me of you (not in a critical way). Your thoughts?

The link took me to a New York Times article entitled, “Why Is Silicon Valley So Obsessed With the Virtue of Suffering?” The article is behind a paywall but it talks about the prevalence of stoicism among Silicon Valley executives. The author’s premise is that people choose to make themselves miserable when they ought to be “living their very best lives.”

Now, I don’t identify as a Stoic, and I’ve never studied stoicism, not even a little bit. But some of the experiments in the article sounded familiar — silent meditations, cold showers, and generally seeking out discomfort have all piqued my curiosity in the past.

When I read the article, I had just finished my very first 30 days to spring deep cleaning challenge, so naturally I wondered: Is that what people think I’m doing with my 30-day challenges? Self-imposed suffering? I’ve thought about this intermittently over the years and even rambled about it during my 2022 vlogmas (which is, ironically, a 30-day vlogging challenge that I do almost every December).

Over the years, I realized I do 30-day challenges for three very idiosyncratic reasons:

1. They help me connect with my true self. One thing I’ve noticed in the past decade of doing 30-day challenges — when I interrupt my existing patterns of thought and behaviour, I make big changes in my life. My tidying challenge transformed my relationship with stuff. My gratitude journal changed how I see the world. My morning pages experiment led to a 5-years-and-counting daily practice that helps me regulate my emotions. With each 30-day experiment, I learn a little more about my authentic self and gain a little more confidence to trust in my decisions.

2. They give me perspective. As I’m revisiting the New York Times article (thank you to the person who sent it to me!), something else struck me. I want to challenge myself and do uncomfortable things — because the juxtaposition helps me appreciate the ease and comfort in my life even more. There was a time when I took a lot of things for granted — things, money, people — and I don’t ever want to go back. Instead, I choose to be more mindful in all areas of my life, making conscious choices and appreciating the little things. My 30-day challenges contain many moments of self-reflection to help me do that.

3. They’re fun (for me). I enjoy 30-day challenges immensely so it took me a while to realize they’re not universally fun. 😅 And even though some of my challenges involve an aspect of deprivation, I don’t view them as being deprivation. While I may experience the ups and downs that inevitably come from doing hard things, I’m certainly not miserable or suffering. In fact, I look forward to my 30-day challenges. They contribute to me “living my very best life.”

I’m a true believer in 30-day challenges. There might come a time when I experiment with not doing them for a while but this is not that time. Instead, I’m overjoyed to invite you to join my newest and shiniest challenge: 31 Days to 2025.

This is a fun little challenge to take us through the last 31 days of the year. It starts on December 1st and it’s completely free to join. I’ll be posting a mini exercise every day on a secret page on my website. Each exercise will involve an aspect of tuning in to yourself.

As I’m drafting up the challenge, a huge theme that’s emerging is letting go of urgency and perfection. If that sounds like something that might be helpful as we move into the new year, I’d love for you to join me.

This month’s reflective questions

What does “living your very best life” mean to you? How might someone else’s interpretation of this question differ from yours?

A note for next month

Since I’ll be participating in 31 Days to 2025 next month, I won’t be sending out my regular newsletter on December 23rd. Instead, I’ll be sending out weekly check-in emails to the people participating in the challenge. Please sign up for the challenge if you’d like to see me in your inbox in December. And yes, I’ll also be vlogging every day. 😉

Excitedly counting down,