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Dickie's Digest - The best podcasts and reflection questions from 2021
Keeping on the “best of 2021” recap trend, this week I’m sharing:
The 21 best questions to reflect on 2021
The best podcasts I listened to this year
Let’s dive in! And if you’re new here, be sure to subscribe:
21 Reflection Questions for 2021
My morning and evening journal sessions are a staple of my daily routine.
At night, it’s usually a brain dump of everything that’s on my mind so I can go to bed with a clear mind. And in the morning, it’s usually thoughts on the day ahead. But every once in a while, I’ll journal on a specific question.
And this habit has helped me develop the skill of collecting good questions.
I’ve started keeping a list of good questions I come across, grouping them by when they’d be relevant to me. I have questions to ask during a job interview, questions to ask someone I just met, questions to ask someone I look up to, etc.
As the year comes to a close, I block some time to dig into a longer list of reflection questions. This helps me think about the past year and gain clarity for the year ahead. And given it’s the end of the year and people have a bit of quiet time, I figured I might as well share my list!
You can find every question in this Twitter thread:
And Sachin Ramje took my thread and created an epic one-page visual with each question:
If you have some quiet time this week, I encourage you to pick a few of these and reflect on them in a handwritten journal outside of your normal working environment.
There’s something about doing this exercise by hand in a somewhat-unfamiliar place to break out of your normal routine.
If you find these questions helpful, hit reply and let me know! And also, I am thinking of sharing my list of good questions with anyone who is interested. So let me know if you want a copy when I make it public.
The Best Podcasts of 2021
Long-time Digest readers know I am a big fan of podcasts.
For the first ~70 editions of the Digest, I shared 4 or 5 podcasts I listened to that week, always on the hunt for something new and interesting. But in 2021, I tried to be more intentional with my listening, finding the podcasts I truly enjoyed and doubling down on them at a slower cadence. I did away with 2x speed listening and started enjoying the conversation instead of mining for information.
And that’s one of the biggest reasons I stopped writing the newsletter every week. I found myself listening and reading things only for the sake of finding content to share in the newsletter.
As I return to writing it, I’m thinking a monthly recap of only the highest-quality reads, listens, and finds is the best strategy. We’ll see how it goes - I don’t want to set anything in stone (like maybe it goes out on a Monday every week like this one!)
Now it’s been ~6 months since I shared the podcasts I’m listening to. So we’re overdue for a recap of what my go-to listens are.
Below you’ll find the shows I listen to just about every week, with some jumping-off episodes if you want to dive in.
In no particular order:
This was a new podcast for me new this year - but it ended up being the one I listened to most. It’s hard to summarize exactly what goes down in this podcast - other than it’s 2 dudes I look up to who are building cool businesses, talking about business ideas, and sharing their perspective, mistakes, lessons, and golden nuggets of life advice along the way.
Another weekly staple for me. It feels like you’re having a Friday-night dinner with 4 tech power players talking about the week’s big events. And this is 1000% where the future of media is trending - powerful people circumventing traditional media outlets and creating direct relationships with their audiences/fans/customers.
The perfect introduction to the podcast is their 2021 recap “Bestie Awards” from last week.
My most-listened-to podcast from 2020 was my second-most-listened-to in 2021. The Tim Ferriss Show had an absolute banner year with headline guest after headline guest.
Here are some of my favorites from this year:
This one is a must-listen for anyone building any kind of business or side hustle. It’s a no-nonsense business and entrepreneurial strategy podcast with every episode under 15 minutes.
Start with this one about never taking advice from your parents. Not that I necessarily agree (don’t worry if you’re reading Mom!) but he presents ideas in a way that forces me to question my preconceived beliefs, which is the best way to grow.
This is my go-to podcast for all things health - mental health, physical health, sleep, focus, energy - everything. Every episode is a 2-hour deep dive into a specific health topic, how it works, and how to optimize it in your everyday life.
This is not a “binge-worthy” podcast, but one you should space out over the course of ~6 months. Listen to one episode per week, take notes on it, and apply what you learned. I can point to at least ~10 upgrades to my daily and weekly routines that came directly from this podcast.
As a jumping-off point, start with this crash course on dopamine.
The last podcast in my weekly rotation is this always-fun roundtable with my friends Trung, Jack, and Bilal. It’s a recap of what’s happening in the world of web3, media, crypto, brands, markets, and the Twitterverse. The perfect mix of banter and insight from 3 smart guys that don’t take themselves too seriously.
Hop right in with this episode on Square becoming Block and the future of Twitter, then add it to your weekly routine.
Alrighty - that’s it for this week.
I’m always on the lookout for good questions and good podcasts, so hit reply and shoot them my way if you have any you think I’d like!
Next week I’ll share my favorite things I read and wrote this year, and make some predictions for 2022.
PS - I hope everyone had a great holiday. I cheffed up prime rib, Yorkshire pudding, roasted sweet potatoes, bacon-fried Brussell sprouts, and red-wine steakhouse-style mushrooms. Delish!