Dabblin' (Ricky Weekly #20)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

This is Ryan, a great man. Yesterday was his birthday. Happy birthday bro!

Thing on my mind:

I have a productivity system where I track my time in 25-min (Pomodoro) chunks, and at the end of each day I audit it to see how many chunks were productive chunks. If I get to 12, I’m happy. I fail all the time.

In the last few weeks during my daily audit I’ve also started asking myself to write down what “output” I was able to generate for the day because my brain is extremely sensitive to the input-to-output ratio getting too high, especially because these days we’re all drinking straight from the firehose.

So I define “input” as just whatever information or communication I consume. “Output” is whatever I put out there into the world and begins some sort of feedback loop. Ideally that feedback loop consists of more than just me, but depending on what it is sometimes just putting something out for myself is enough. This newsletter has become important to me because it’s output I can generate on a regular basis and my thinking gets refined from your feedback.

Pivoting this into a discussion on how I’m finding my next thing. Someone told me that I’m the busiest unemployed person she knows and that was funny to hear. I don’t think I’m that busy, but I just need to be generating output. But because I’m unemployed with a vague goal of finding my next thing, it’s hard to know what is the right output to work towards. So there were days where my desired output was “a framework for people to find their next thing,” which is kind of what this is 😂.

What I’ve found to be helpful is that I naturally don’t get too caught up in not knowing exactly what to do. Maybe it’s all the years of being startup founder. Instead, I dabble in a bunch of things. This newsletter is just me dabbling. Writing blog posts based on deep dives into my interests is dabbling. So is organizing events, advising companies, joining an accountability group, etc. Those are just the ones I feel okay saying because there were also some dabbling where I lost interest. Oh, standup comedy is not dabblin’ I’m so serious about that 🙃.

Dabbling somewhat aimlessly is useful because it still means generating output and feedback loops, which helps me get more precise about what it is I’m looking for. Dabbling also helps me get more out of all the input. You know how sometimes you read something and you’re like “omg, this is exactly what I’ve been trying to figure out” — that’s because a piece of information happened to meet your “prepared mind.” Dabbling prepares your mind and really helps you filter for signal.

David and I when we were building startups liked to call ourselves “heat-seeking missiles” because honestly doing a startup feels exactly like dabbling. You know your goal is “product-market fit” or “hyper growth” but you don’t actually know which output will get you there. You have some ideas but you don’t really know, so you just dabble, generate output, feedback loops, and try to identify the heat.

Piece of content I recommend:

The Peter Attia Drive: #68 - Marty Makary, M.D.: The US healthcare system—why it’s broken, steps to fix it, and how to protect yourself

One of my best friends Sid is a general surgery resident at UCSF so we talk about the healthcare system all the time. Talking to Sid is fun (and frustrating) because he is able to go through all that medical training while maintaining an “outsider” perspective, enough to clearly see and analyze the system for all of its flaws. This podcast is basically two famous “outsider” MDs talking to each other for two hours and I found it to be extremely fun (and frustrating) to listening to.

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My latest essay is called The arc of social