159: Sitting in Silence

159: Sitting in Silence


I'm headed to a meditation retreat that started today!

Cultivating Resilience is a weekly newsletter about rebounding from setbacks and reinventing the future—by 3x founder and executive coach Jason Shen.

I'm on silent retreat! I wrote this letter and the one next Saturday ahead of time. Further updates to come upon my return.

We all are familiar with the benefits of physical activity: cardio, strength, and stretching are all important ways we can move our bodies to keep them limber, strong, and powerful. When we get past the "should's" and "ought's" and actually go on that run, lift those weights, or hit that yoga pose, it feels good.

Similarly, there's been a lot of exploration of mindfulness and meditation as ways to support our mental health, it's become a part of language "live in the present" and formed the basis of at least one billion dollar startup.

Unlike my very consistent routine of physical activity, I must confess to be a sporadic meditator.

In high school, I would sit quietly with my eyes closed and try to focus on my breathing as a way  settle my nerves and perform better under pressure in gymnastics competitions. It helped (I think?) and over time I could manage my excitement without an ongoing practice.

Over the years, I've subscribed to Headspace, bought a brainwave sensing meditation device (no joke), and have been an occasional attendee of a weekly 45 minute meditation sit hosted by a dear friend. But nothing's ever stuck.

And I think there's a simple reason why: I don't feel particularly better after I meditate!

After a great Crossfit workout, my mood and energy are lifted for hours if not days. But a 10 or even 30 minute meditation simply doesn't seem to do much for me. Which makes it hard to invest in when life is short and the days are packed.

That said, many of my friends swear by the longer week-long meditation retreat, where you sit for 5 to 8 hours per day (with breaks, meals, and dharma talks). There's apparently a saying that you make progress on your meditation practice during retreat, and you try to maintain it during your day-to-day life.

I've never felt like I could take a week long break that's not like a "vacation" or more standard holiday before my sabbatical. So here we are.


PS: I'm hosting a live virtual discussion about the emotions, complexities, and mechanics of leaving your job on July 12th and I'd love for you to join me.

049: Retreat (Scotch & Bean)

Wow, it's been a while since my last Scotch & Bean huh? Dang.

What's on deck this week:

  1. 📣 Live Convo on Leaving Your Job (Wed July 12)
  2. 🎧 Mindfulness Edition (#019)—revisiting a deep dive from 2020
  3. ✏️ Mindful Elementary—NYC Schools to teach mindfulness
  4. ☁️ Where'd You Go?—Mind wandering can be good for you
  5. 👁️ Mildly Anti Buddhist—five loving and relatable critiques Buddhism

📣 Leaving Your Job (Live Convo: 7/12)

Reminder that I'm hosting a live virtual discussion about the emotions, complexities, and mechanics of leaving your job. Have you tended to mic drop, quiet quit, or burn the place down? Will you leave your contact info? Ping the coworkers you like directly? Never speak to them again? Let's talk about it.

The Art of Farewell: Saying Goodbye At Work - Interintellect
In a world where job-hopping has become increasingly common and remote work blurs the lines between personal and professional relationships, saying goodbye can be an emotional and complex endeavor. From acknowledging the challenges… Continue reading The Art of Farewell: Saying Goodbye At Work

Average (the most common type, characterized by high levels of extroversion and neuroticism and low levels of openness)
Self-centered (high in extroversion and low in conscientiousness, openness, and agreeableness)
Reserved (low on extroversion, neuroticism, and openness, and high on conscientiousness and agreeableness)
Role models (high on every big 5 trait other than neuroticism)

🎧 Mindfulness Edition (#019)

I thought I might revisit a piece I first wrote in 2020, with a deep dive into the app war between Calm vs Headspace, the brainwave sensing Muse headset, and some wise words from monk Pema Chodron.

MC#019: The Mindfulness Edition
5 takes on Calm app, Headspace, neurofeedback and meditation

✏️  Mindful Elementary

Mayor Eric Adams recently announced that every public school studen will be required to learn mindful breathing for 2-5 minutes each day. On one hand, major validation for breathwork and mindfulness. On the other hand, feels like maybe a cheap way to check a "mental health" box for students.

☁️ Where'd You Go?

Mindfulness and meditation are all about ignoring the random thoughts that float through your mind and maintaining awareness on the present moment. But as this NatGeo piece points out, are benefits to mind wandering too—it's a form of subconscious creativity and insight formation. And it too needs time to incubate. I'm sure I'll do some mindwandering during my many sits this week.

We need to become relaxed enough mentally in order to not try to be productive or reach some goal. With habitual activities we engage in with some regularity, we don’t feel guilty about letting our minds wander—that’s when the mind can reach new places.”
The science of why you have great ideas in the shower
It has nothing to do with getting clean—and everything to do with your state of mind.

🙊 Mildly Anti-Buddhist

To avoid overhyping this retreat, here's a great set of 5 "mildly anti-buddhist essays" from Sasha Chapin's substack.

Personally, after years of going down the meditative path, life is enormously nicer, but the problems of existence are far from over. I am still capable of making bad decisions that hurt myself and others. I am still capable of wasting my potential and making myself miserable.


Thank you for being a member of Cultivating Resilience. This newsletter has spread almost exclusively by word of mouth. Would you help share it with a friend or two who might also enjoy it?

Recent Issues

158: Meta Lessons—Managing Achievers
This week I unpack 5 concepts Meta taught me about managing high achievers: expectations, calibrations, showing care, HPMs, and alignment.
157: notes from vibecamp
In Week 2 of my sabbatical I attended vibe camp—a self-described “ingroup burn / unconference / summer camp” in it’s 2nd year of existence.
156: Steve’s Patience + Wildfire Smoke Gear
Admitting you don’t know what’s next, using AI to spice up headlines with emoji’s, and gearing up for a smokey summer