📕Issue #52 - My Biggest Learning & Limitation

The most effective learning unit, a double-edged sword, and my self-sabotage

👋🏻 Hi! I’m Charlene Wang. I can make your life a little better with coaching and community. I’m writing a book to break the model minority stereotype. LivingOS Newsletter is my musings on moments and transitions in life. Grateful to have you here ❤️

Today is a special day.

It is my brother’s birthday (remember Dear Warren) and the 188th day of my daily writing project.

I started my daily writing project at the start of the pandemic. Looking back on what I did in the first 66 days, I’m glad to report that I have delivered on all the promises and hired a team to scale each initiative. I’m grateful for everyone who believes in LivingOS before we were able to articulate the brand. After weeks of user research, conversations, and introspections, we have got the clarity we need for the next steps.


Here is my biggest learning… 🤩

Team is the most effective learning unit.

This may be counterintuitive to the way we used to think about work. We all know the importance of getting things done and exceeding key objectives, but we don’t often associate work with cultivating tribal knowledge and building on each others’ insights.

Earlier this year, my intuition told me that I could empower my team to do a lot more. To help them reach the next level, I decided to share my early thoughts and walked them through the entire creation process. After all, exposure determines awareness.

I began to share my second brain. Some part of my second brain is structured with hyperlinked tables and topic forests, but a larger part of my brain is just stream of consciousness. There are many unstructured thoughts, shorthands, and half-baked stories. While I am turning these notes with my creative projects, I have learned that it’s unrealistic to get through them. Hopefully, someone on my team could pick up these nuggets and put it to good use.

However, my second brain was equally, if not more, overwhelmed by the amount of knowledge in my digital 🧠. To solve this challenge, I took on a project to create a third brain for team knowledge management:

As you can see, the third brain replaces the confusion with clear status, outcome, and ownership. Such structure is essential to share knowledge in a fully distributed team.

I can go on and on to talk about how to optimize teamwork, but I figure out that you would be more interested in what I’m going to share next.


And here’s my biggest limitation… 🤯

Spoiler’s alert: It’s a double-edged sword.

I have talked about how writing helped my iterate fast, learn a ton, and get a better sense of my core business. However, I have found that my daily writing is getting in the way of success.

Crazy right? While I still love every aspect of my daily writing practice, I began to realize that it is no longer the best way to invest my time and energy.

The daily writing practice has become my self-sabotage.

Why? Here’s a simple math: It takes me four hours to write one article. If I replace that investment with coaching, I would get $2000 instead. Or if I replace that with relationships, I would get even more quality time with Chris, which is priceless!

The good news is that there are 30+ draft articles in queue and many more in my second brain, so there will be more than enough high quality content in the short term. In the long term, we might replace the daily newsletter with a weekly deep dive and shift the free version to monthly.

Bottomline: The weekly newsletter will stay, free or paid, because I’m having so much fun writing it ❤️

If you want to get more exclusive life-hacks, you can subscribe to the new (!) premium newsletter. As special offer, you will get access to our effective communication workshop next Monday!

Releasing my self-sabotage… 💪🏻

Remember that when things are going great, fear might stop you from doing what you need to do next. I used to reject these signals and brute force my way through. After all, it takes a lot of courage and awareness to get over the chicken in our head. Fortunately, my coaches are kind enough to call me out of my BS.

Today I want to end with Steven Pressfield’s piece in The War Of Art: “The problem is we’re thinking like amateurs. Amateurs don’t show up. Amateurs crap out. Amateurs let adversity defeat them. The pro thinks differently. He shows up, he does his work, he keeps on truckin’, no matter what.”

The struggle with self-sabotage is part of our journey.

How are you stepping into the next grand vision of your life?


🎁 Gifts

If you haven’t watched my talk show with Grace, you are missing out…

It’s so good that I immediately rewatched it after.

Curious about how Christina Qi built a billion dollar hedge fund from her dorm room? Sign up for the talk show next week!


P.S. - As part of the LivingOS 2.0, we are launching a 6-week, 10-person small group coaching program to upgrade your life toolkit. There are 3 spots left for the first cohort. Send your worthy inquiry if you want to learn more 😉

P.P.S. If you like this newsletter, don’t forget to ‘heart’ it on Substack ❤️