New career announcement! Finding structure through serendipity (Part 3)

Exciting announcement: I will teach a First Principles of Investing course for On Deck Investing (ODI) and coach ambitious, entrepreneurial learners 1-on-1 this fall! This is the tale of how everything serendipitously came together and where I plan to go from here.

To begin, you should know that I spend a lot of time writing.

Beyond essays like these and various emails, I write many notes and plans for myself.

By and large, I get to choose when I write. As a result, I’m fortunate to have many days and evenings where I enjoy long stretches of uninterrupted deep work.

Writing is meditative. I feel like I’ve become a better structured thinker and communicator. I feel like I’m thinking more clearly and more methodically.

But It’s really hard for me to tell for sure. How do I get feedback on whether I’m becoming a better thinker? How do I test a nebulous hypothesis like that?

After all, for over a year, I’ve worked from home, with no boss and unlimited flexibility to explore.

Sounds great right?

Well, there is a saying: “Creativity needs constraints.” Over the past year of exploration, I’ve felt the need for some self-imposed constraints. 

So I sought out structure. Or perhaps more accurately, structure found me through serendipity. 

In late 2020, I thought, “I’ve been writing online for three years, maybe I’ll build a start-up related to my passion.”

I discovered Stew Fortier – who was building a paid community of online writers called Foster. I reached out and Stew was kind enough to share his insights. I ultimately did not start a company in this space, but I did join the Foster community.

Foster has been a great experience. Not only did it help me improve my writing, but it also provided structure and human connection during the pre-vaccine era of lockdown and isolation.

Through Foster, I met two people—Kyla Scanlon and Tom White, who were working with another paid learning community. They were launching a brand-new program called On Deck Investing (ODI).

Investing has had a profound impact on how I think. So I joined ODI’s inaugural cohort as a founding fellow.

I’ve always wanted to try my hand at teaching investing, so I volunteered to teach a group session for ODI in July 2021. I organized everything I knew, simplified it into first-principles, converted those insights into 30 PowerPoint slides, and repeatedly practiced my delivery.

I spent an enormous amount of time—dozens of hours—in preparation for a one hour presentation.

I invested all this effort with little expectation of getting anything in return. I did so not only because I have a passion for investing, but also because I’ve always enjoyed teaching. I suspected that I had what it takes to do well in a post-graduate classroom format, and ODI provided the perfect opportunity for me to test that hypothesis.

Fortunately, my presentation was very well-received. One follow-up conversation led to another, and as a result, I’m now helping ODI in a part-time, paid capacity— developing curriculum, leading group learning sessions, and coaching members 1-on-1.

I’m excited for what lies ahead as this particular role aligns well with my strengths and interests while critically affording me the flexibility to continue exploring. In the near future, I plan to ramp up coaching, and I also plan to build my own private, membership-based community of curious learners. 

Just to think – I would not be in this position if it wasn’t for starting my little blog 3.5 years ago.

Such is serendipity, such is life!

This is part 3 of a 4-part series. For more context, read part 1: Learning to explore and part 2: Entrepreneurial reflections via explorationNext, part 4:  Always happy, never satisfied


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September 14th, 2021

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