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Jason Shen
Jason Shen
5 min read

With the exception of 2020 because, well, the world was super weird, I have made it a habit to publish a set of reflections on what I’ve learned in the past year. For instance, here’s 33, 32, and 31.

The third tenet of my resilience framework is “reflect”, which is about learning about yourself and the world around you. Especially after such a wild year, it’s especially worth taking the time to assess the world around us and extract insights to bring forward.

For my 35th birthday, I shared a Twitter thread of 10 lessons I’ve learned. Here on Cultivating Resilience, I’ve expanded on them. Would love to know if any resonate with you!

These are questions that comes up a lot in my job as a PM, but are relevant in any area of life. Often arguments that seem intractable are really just two people talking about tactics to solve different problems.

This came out of a podcast I was listening to about systems versus goals. The gist was that overly focusing on a specific outcome can be brittle (if you don’t get it, you’ve failed). Whereas focusing on systems and habits can enhance your luck, defined as the likelihood of any kind of positive event occurring.

This one is pretty simple and tactical. You can see some of my workouts on Twitter or Tiktok.

Another way to enhance your luck is to foster weak ties, by building new connections to interesting people who a bit outside of your normal circle. I really struggled to do this during the pandemic and this was a reminder to keep going. It applies both outside your company and also inside - when a reorg may mean you’re working with new people, it’s nice to already have some warm connections.

I’ve kept up a few habits like monthly calls and audio messages with friends during the pandemic and recently received 2 phone calls from friends out of the blue that were super lovely. Friends are the best.

As I’ve gotten older, I find myself working with people who are 10+ years younger than me. They’re all smart, savvy folks but they might not always know why the web and tech products are the way they are. And while I’m no internet historian, this was a reminder to share context on how the past influenced the present when seeking to build the future. (Screenshot is from last week’s piece on documents as interactive canvases)

This mindset doesn’t come naturally to me but in the last year, I’ve gotten much better at thinking bigger. What would I change about my product group, about my larger org. And that thinking has allowed me to advocate for changes when I an opportunity to do so.

There are so many layers to an organization - the official rules on how teams should run and careers operate, but under the surface, the informal rules are often a little different. (Sometimes they’re a lot different and generally speaking that sucks). But the final point to remember is that you still have agency on how you want to operate given your understanding of these rules.

This first came in really handy for PM interviewing, which especially in a remote environment requires you to really show how you think through talking out loud, white boarding or writing on the spot. But I’ve found it continues to be valuable in facilitating discussions at work.

This lesson comes from a reflection out of a book I’ve been reading called Dark Horse, which is about how people from nontraditional backgrounds succeed seemingly out of nowhere. One of the key ideas from that book is knowing yourself, what specific things drive you (the book calls these “micro motives”) and finding a workplace and position that fits that skillset best.

If you liked these lessons, I’d love if you could share this newsletter with a friend or like/retweet this thread!

Bonus Lessons That Didn’t Make the Top 10

  • You can take the founder out of the startup but you can’t take the startup out of the founder. I am the CEO of my life and my career - and I will never just hope my boss, my company, my industry will “take care of me”. That mindset has served me well.
  • Consistent communication and regular updates build trust and allow others to offer suggestions and answer questions.
  • Having energy and a great attitude is a huge advantage when figuring out who to work with.
  • In a chaotic situation, just start doing basic stuff that makes sense, learn from happens, and iterate. Moving faster means more feedback.
  • Words matter. If you can get your concepts into the public discourse and frame the ideas according to your thinking, you’re influencing in a powerful but subtle way.

Jason Shen Twitter

Founder, exec coach, and product leader help people foster the conviction to take bold leaps in their work and life—so they can get closer to what really matters.