about Rainn Wilson … and this newsletter
Why am I starting a newsletter?
About Rainn Wilson
A few weeks ago, I was perusing Apple News when I came across a familiar face. It was Dwight Schrute from The Office.
Immediately, the article featuring Dwight’s face caught my eye. I wasn’t used to seeing Dwight in the news. I decided to take a closer look. Turns out the article wasn’t about Dwight or even about The Office. It was about the actor playing Dwight, Rainn Wilson, and his new TV show, a travel docu-series called Rainn Wilson and the Geography of Bliss.
The article talked about how even after being on one of the most successful TV shows of all time, Rainn felt it was not enough and was deeply unhappy. This new show was his chance to just walk the earth, visiting the world’s happiest places, the least unhappy places, and anywhere else where he might find a clue about what makes him unhappy, and what he can do about it.
Now, while I am not an almost 60 year old award winning actor who, after a decade long career working on one of the greatest TV shows of all time, is getting paid by a network to create a show about my midlife crisis, I am a 25 year old who, after 3 years into his first job, left this aforementioned job and is not getting paid by a network to write a newsletter about getting through his very own personal quarter-life crisis.
In his show, Rainn shares his story of trying to understand himself through understanding others. But the show is not about him recounting how he figured it out. Instead it is a live play by play of him putting himself out there and sharing his thoughts before, during, and after an experience. He doesn’t talk down to us, he takes us with him on this crazy journey where, so far, he has done a cold plunge into the Atlantic with a group of Viking women in Iceland, followed a rock star into someone’s home for a ‘home concert’ while in Bulgaria, as well as sat through a meditation in Thailand.
This is what I want to do with this newsletter. I want to share my journey, as it unfolds, of discovering what the big bad world out there is like. I am hoping that by learning more about it and the different people within it, I can learn more about myself and what makes me happy, and if I’m really lucky spark some inspiration in you about what might make you happy as well.
About this newsletter
Rain released the first five episodes of Rainn Wilson and the Geography of Bliss on May 18th, 2023. That is around the time that I left my job as a Product Manager and decided that, instead of jumping into another job, I would take a mini-sabbatical to figure out what I wanted to do with my life. It was scary and completely off the script of the life I had planned out for myself and was following up until now: High School, College, Product Manager, Founder, Early Retirement. But it was also really exciting as it was my chance to fully let go of the narrowed focus that comes with running down a path and embrace being completely open to any new path, such as the path of creating this newsletter. With this newsletter, I’m hoping to just follow my curiosity and experiment with all kinds of different ideas and formats. That being said, there are three key reasons why I’m creating this newsletter:
I want to share my story, and hear yours
So, what happens next? What do the days look like when you aren’t working a 9 to 5 or when you are in Japan? What exactly does it mean to find yourself, what does the day to day of that entail for me? I want to take you along my journey and share what I’ve been able to take away from it.
I know that hearing about the experiences of others who re-invented their life through time off the traditional path such as Paul Millerd in his book, The Pathless Path, Matt Yao’s newsletter Game of One, or Rolf Potts in his book Vagabonding, were incredibly helpful for me in taking the leap of faith and considering lifestyles I had never imagined before. I’m hoping to add my experiences to the mix too and encourage you to share yours as well, so we can all hear and learn from each other’s stories.
I want to share what I’m learning
I’m interested in a lot of topics: work, life, travel, fun, happiness, culture, society, politics & governance, TV (I really love TV, it’s how I relate to a lot of stuff), food, reading, dance, writing (obviously). I am trying to get more comfortable putting my thoughts online through personal essays, and I’m really curious what you think, what is resonating with you, what is definitely not resonating with you. Some of the places I go to get my fill of new ideas are my favorite YouTube channels (Wisecrack, Cinema Therapy, Sisyphus 55), as well as newsletters (The Elysian, Wait But Why, The.Ink | Anand Giridharadas), and even podcasts (The Ezra Klein Show, Spark & Fire, On Being, Deviate with Rolf Potts). I’m hoping to spread the ideas that have really worked for me, whether I thought of them myself or I found them somewhere else.
I also want to grow my knowledge and skills in different areas: product, data science, entrepreneurship, public policy, animation, music, and more. As I grow, I want to share what I’ve learned.
I want to build things, and get your feedback
I want to take on new projects such as building a Chat GPT assistant to help me plan my day or creating an animated short film. I’m also hoping to put everything I’ve learned into practice and see what happens, such as curating my own information diet or building a new practice around deep work. I want to get your thoughts on my projects, habits, and experiments and hear what you’re thinking of trying next.
At this point, it is probably becoming clear that this newsletter has a lot going on, but I finally feel ready to start on this journey and see where it goes.
Just like Rainn with his show, I’m not sure what my future holds or what the future of this newsletter is. But if you’re a little lost like me, if the feeling scares you a little, and excites you a lot, then just know we’re in this together. If nothing else, this newsletter is my way of keeping in touch.
Good luck and talk soon!